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Tech Salescraft: Tom Dunlop, Founder & CEO at Summize

Tech Salescraft: Tom Dunlop, Founder & CEO at Summize

August 12, 2021

James Hounslow:

Hello, and welcome to the latest episode from Tech Salescraft. Our mission is simple - we want to bring you exclusive insight from some of the brightest and most influential minds in the tech sales scene. We want this podcast to be your weekly go-to for inspiration, and if this is your first time listening to the show, please subscribe to keep up to date with all the latest releases.

Welcome to the latest episode from Tech Salescraft, and today, I'm delighted to be joined by the founder and CEO of start-up firm, Summize, Tom Dunlop. Tom, welcome.

Tom Dunlop:

I'm here. It's good to be here with you today.

James Hounslow:

Awesome. Today, we're going to be talking about Summize's journey from inception through to where they are, and the future, and what it holds, but as a way of getting started, Tom, could you just give our audience a brief background as to who you are?

Tom Dunlop:

Yeah. No, of course. I guess depends on how far back you want to go, but I think what I started on the road to become was actually an athlete. In many ways, my path has been very varied. My early career was all about... I say athlete in the loosest term. It was badminton, so make your own judgment, but we-

James Hounslow:

Great sport.

Tom Dunlop:

It's a great sport. I agree. I agree. Very timely with the Olympics and everything on as well. I was very much got on the GB program. Not bragging, but I was the number one in England, in Europe-

James Hounslow:

Nice.

Tom Dunlop:

…and was very much going on the I'm going to be an Olympian. I'm going to go into sport in some way and did my degree at the same time as that. My last choice was to do law, and I had five other courses that were very much sports-related. I just thought, "Oh, I'll give this law thing a go. It could be good backup if I don't manage to get to the Olympics." I'm kind of glad I did because then the rest of my career was very much centred around that legal side.

Then after university, I went to law school. I then probably carried on as a full-time professional badminton players whilst doing my law degree and law school, and then made the choice really that I think badminton was not going to be the route. It wasn't quite as glamorous as probably what I thought as a junior, and it certainly wasn't paid very well either, hence the legal route came through.

After there, really I guess I did start a business up when I was in law school as well. That was an online comparison site for solicitors. All the GoCompare’s were very popular at the time. Then did that for a little bit, but then fell into sports agency. In my view, I was like, "This is perfect. I'm going to be combining my law and my sport, represent footballers and Olympic athletes, do sports management," which was in many ways... There was parts of it that was as glamorous as you probably think, but then there's a lot of parts that were definitely not and quite a shady world.

That's when I switched over to the legal because the guy who set up was a former lawyer. We set up a law firm. I trained as a solicitor, qualified, and really the next few years, my life was then being an in-house lawyer. I very much centred to or kind of gravitated towards the tech world. I was the GC and legal director of a few different fast-growth tech and SaaS businesses. Really that was then the use case that propelled me into founding Summize.

James Hounslow:

Nice.

Tom Dunlop:

There's a brief potted history.

James Hounslow:

Summize, who are you, and what do you guys do, and who do you service?

Tom Dunlop:

Yeah, I mean the background that I just talked about I guess is relevant to what we do. The product really was born out of my I guess frustrations or problems with just spending my life reviewing contracts really. Contracts, I think everyone can agree are, one, very long, two, very boring, and probably sales guys' worst nightmare when it gets towards the end of a deal, and they have to get it over line quickly. When you're spend every day reviewing them, they're just very manual and very time-consuming.

With Summize, the product, what we aim to do... the first thing that we did was we were able to summarize contracts, hence the name. The core technology is that we take a long contract, and we can create an instant summary of it and pull out the key points. That was the core technology, which were great in a few different use cases, whether that's reviewing multiple contracts in one go. We went through a number of acquisitions, so that was very useful for that context.

Then also for if someone asks you to do a quick red flag review, you can do that very quickly. That's the core technology behind Summize, and then we've branched out from there now, and we look at how we can connect so many business users to the legal team. We have things like the Microsoft Word add-in. We have Teams and Slack integrations. The best way to think about that is you can almost ask a question of your contract to the Teams, "How do I end my contract with whoever," and it'll go, and find the answer, and give you the answer back through Teams. That's our next iteration of how the product will work. It's basically to make contracts easier for legal teams.

James Hounslow:

Interesting. Where are you on your journey? Have you taken funding? Do you class yourself a pre-seed, seed series A?

Tom Dunlop:

Boom, and we're kind of between seed and series A is the best way to describe it. We did take pre-seed investment from I guess a combination of a VC, Maven, and an angel. We then proved out a prototype. We then sold that first iteration of the product, got further money, which I kind of class as then that seed round to just build, get some salespeople into the business. We're now about 55, 60 customers and mainly UK, but have some in the US, and Australia, and one in Canada. Now, we're kind of starting, I guess, that more scale-up journey looking towards a series A probably Q2 next year.

James Hounslow:

Nice. How many people do you have in the business today?

Tom Dunlop:

We've got 19 full-time heads at the minute.

James Hounslow:

Now, you started the business in Manchester, which is one of the tech hubs within the UK, but I'm sure a large part of your customer base, I could be wrong, would definitely be London with what you guys are doing. What was the reason behind Manchester? Did you do any research to decide that Manchester was the right place?

Tom Dunlop:

Yeah. I mean it's been an interesting, I guess... I mean because prior to setting up Summize, I guess even me from a... looking for jobs as an in-house counsel of tech businesses, naturally, London has a much higher concentration of the tech businesses. What I found over recent years at actually UserZoom, which was where I was last at, which is a fast-growth tech business... They were headquartered in Silicon Valley. They chose to open one of their European HQs in Manchester, and we started to get this influx of... Amazon opened up a tech hub here, and we get these businesses that have started to open up in and around Manchester.

Then we have direct flights that were from Manchester to San Francisco, which we never used to have, and so I think that the past five to 10 years, there's been this gradual focus on Manchester becoming more of a hub for, say, US companies, both from a travel and infrastructure perspective, but also from a talent perspective, you started to get people that... cheaper cost of living, and obviously, the universities are good. That meant that there wasn't as much competition for roles as well because the concentration of tech businesses in London, you can actually recruit high-quality people from the Manchester area. I definitely had it in my mind as to where's the concentration of talent, but also where's the concentration of customers and how could we potentially service international customers as well from the space.

I think that I kind of arrived at the conclusion that certainly at this stage that we're at, I know a lot of the tech businesses. I've worked in a lot of them, so I had a lot of contacts for talent. Our whole dev team is from a company I used to work at that meant that that wasn't an issue. Then, obviously, we launched I guess the product at the start of the pandemic, so I think in terms of where our customers are, that became a lot less relevant once everyone moved to this kind of remote world. So Manchester's served us well.

There's a lot of investment in the area and there's... from a VC perspective, but also in terms of the buildings popping up left, right, and centre, and different hubs being created. Yeah, I'm glad that we stayed in Manchester, and I can only see it growing from strength to strength if I'm honest. It's a good place to be at the minute.

James Hounslow:

When I speak to VCs and founders who've seen an exit, they talk about the early days, that it normally takes about three iterations of the product before you have the product that people want to buy. The quicker you get to that point, the better. As a founder, you come in with a great idea that you think's going to work. Now, you're coming from a slightly different perspective is that you've seen a problem, and you're providing a solution to a problem, whereas a lot of founders will have a conversation with someone, and they'll see something, and think, "Right, this actually could work in that sector." Did the first iteration of what you wanted to do... Is that what the clients are seeing today or how many iterations have you gone through, and how quickly did you get those changes?

Tom Dunlop:

I think it's a great point because I think it applied equally even though I am essentially the customer as well as the vendor in many ways, but what was interesting and one thing I actually... It's not a regret, but in terms of an emphasis that I would put on really in those days is not to be as defensive of the product or to certainly gain as much customer feedback as you possibly can because we created our version one of the product, which created summaries of contracts, but it was a platform. It was a web-based product. Really when people saw it, they immediately assumed it would be for multiple contract reviews, so a project review. It was kind of shoehorned into a use case that was where it was born from, but, ultimately, I'd be like, "Well, no, you could use it for this. You could use it for that."

I think sometimes you've got to really look at your products and look at that customer feedback to go, "Well, why wouldn't they use it for a particular use case, and what's stopping them?" It might be something as simple as it doesn't send me email notifications or it doesn't integrate with a particular product. I think that sometimes you're so concerned about selling the product and getting that initial traction so you can get to the next phase that you don't iterate enough in the early days. We were quite lucky that we had a very strong development team that I knew and I'd worked with before, and I had friends in the industry that I could bounce it off that we iterated a number of times.

I mean I think if you ask my co-founder, Dave, yeah, the early days were quite rough for him because the bar was quite high, and we changed our mind or pivoted left, right, and centre for the first six to probably 12 months really I mean in terms of what we actually did. I'd say only really now, we've got a very, very clear vision as to what the product does today, and also what it will do, and exactly what customers that serves. Yeah, it is a process you go through.

James Hounslow:

When did you know you were ready to offer it to a client?

Tom Dunlop:

I think there's two different sides to that. There was one, which we allowed customers to use it for free to get that feedback for a particular use case, and then I think once you know you've kind of... I mean there's a great book that I read quite early on called Impossible to Inevitable that was by the founders of SaaStr, but they did this book. I mean it's almost like they talk about the first 10 customers being at arms' length, being that's where all your focus is on is getting these first 10 customers to pay for it, and also about nailing your niche, and really getting one use case down to the point where you know it solves it, and you know that people will pay for it.

For us, that use case was multiple contracts in the system and create summaries for it. At the point that we knew that the product did that and we trialed that with the customer, we then went to other customers that had that problem, and we sold it on that basis. We knew that at that point, the alternative was very manual and costly, so we could charge for it. I think that was the point that we focused solely on that one particular use case, how we solved it, and then we made our first sales on that basis.

We've broadened out since then, but I think it's really important, certainly on those initial sales, to really, really focus in the specific value and the problem you're solving to be able to justify people paying money for it. I think that's what we did quite well, but then we did branch out quite quickly given COVID probably stopped a lot of project reviews happening. It was one of those where we pivoted quite quick, but it was good for the other customers.

James Hounslow:

How did you feel as a founder having to be that salesperson? Was it you that was going out, doing those initial pitches?

Tom Dunlop:

I did all the initial pitches. I think what was interesting about the early... I say the early days. We're still very much in the early days, but was I could pick the use case, understand their use case, and speak to them in almost a conversational way rather than a pitch straight away, so I think the actual demo part of I guess the sales process. In terms of the ability to get straight to the use case, almost satisfy the typical kind of sales methodologies that you're doing in terms of use case, and budget, authority, everything. I could get to that very quickly because I'd worked there. I did it. It was my problem, so they probably had the same thing.

I think where I soon realized that I was not very good was, well, what happens next. I just didn't control a sales lifecycle. So we showed loads of people. We got loads of great feedback. Demos were great. Use case was spot-on, and then it was kind of like, "Well, what now?" It was that next bit of, well, how are we controlling that customer to make sure they sign on a given day. That was the bit that I probably found the hardest, but also something I just hadn't done before that meant that bringing in a proper sales leader was obviously very important and opened up my eyes up as well about how many things you can do at that part of the sales lifecycle.

James Hounslow:

At what point did you decide that you were ready to hire a salesperson, and what was the first hire? Was it a salesperson or a sales leader?

Tom Dunlop:

Hire, we did. Well, I guess we hired five SDRs. We went for the junior, and pretty much all of them were recent guides. They might have six months' experience. Would I do that again? I don't know. Not as heavy with recent grads. I think what we didn't account for that... We had loads of keen, I guess energetic individuals that would hit the phones or hit LinkedIn or do my book. In terms of actually training them on what you need to do, and managing them day-to-day, and really being on top of the KPIs... Obviously, I was still responsible for the product really as well, so I think we went quite heavy on the junior side.

It wasn't until we hired I guess a sales leader, which was probably nine months after that really we got that organization that meant that we could get an actual predictable revenue model. I think we were kind of grabbing deals. We had the machine that put... I say it was a machine. It wasn't as effective as it could have been, but we were having the demos being put in the top. I was doing them, and then collectively, we'd try and chase them down. We'd grab deals left, right, and centre, and it felt very much like that.

It wasn't until we hired a leader on top of those, by then it was three or four, that we actually got some proper... I guess that process and were using HubSpot at the time as our CRM, and we still are, but using that more effectively that we actually felt, "Oh, we've got something that's quite predictable now, where I know that we'll do X number of deals, X number of revenue." That was so refreshing from my perspective rather than I guess a little bit of chaos really to start with.

James Hounslow:

Was it like an SDR or manager that you brought in or an actual SaaS sales leader who was doing the selling themselves? They-

Tom Dunlop:

Yeah. I guess right now, we're going through a transition from that to bringing in actually a CRO, so like a full sales leader as such. When we hired, first of all, it was sales manager, so player-manager, so really we did that with someone who'd been a salesperson for a number of years, not a load, but I'd say four or five years. They'd just taken that first step into management, so they might be a regional manager or they might manage four other AEs. At that point, we hired that person because we knew they could sell, which was important, but then, secondly, they had a bit of experience of managing people. It didn't have to be massive amounts of people, just three or four, so that kind of player-manager role was our first hire, which was absolutely right for where we were at the time.

James Hounslow:

What made you decide to go down to SDR and then a player-manager route? Some organizations will go to get a couple of just good AEs, account executives in just to go out and get themselves up to a couple of million annual recurring revenue. What insight did you look at, or did you get advice to say, "Get an SDR team in play, and then get a player-coach in?"

Tom Dunlop:

I mean with the AEs, I think a lot of them... If you want good AEs, they're also used to having an element of demos being given to them or leads being provided to them. I think at the point that we hired the SDR, we didn't have any leads. It was me going out to friends really, so we needed to build up just some form of lead generation in whatever form it was that would mean that we can actually make an AE effective. I think you've got lots of different personalities as to what makes a good AE. I think some people can be very self-starting and don't mind picking up the phones and generating X number of leads, but that might still only be five a month or something like that. They don't want to be spending all their time doing lead generation.

And our chairman was a sales guy who turned entrepreneur, and which founded and sold two software companies, so he was advising a little bit as well. I think it was more let's get some people in who can work out who's receptive, who isn't, start building up more of a predictable lead generation engine. Then we bring in the AE, player-manager person who can then start to really convert them and guide them onto where they should have been. That was kind of the idea behind it.

James Hounslow:

Interesting. Then once this player-coach came in, then you talked about that's when you introduced HubSpot as a CRM, which is obviously a great tool, because I guess you probably haven't got a fully functioning marketing department just yet either, and there's some great content that you can put into the HubSpot suite, which helps you to create that function. You mentioned that that's where you found the repeatable process. How did you stumble onto that, and how long did it take once this person arrived?

Tom Dunlop:

I mean one thing that's good about who we brought in, Dan, was that he came instead, and the first thing he did was look at how are we tracking anything that we're doing. I have the free version of HubSpot, which is pretty basic, so we upgraded HubSpot pretty quickly within the first month to have more of a sales and marketing side of the product. That allowed us to really open up the functionality we needed to track the deal stages. We created our own, I guess, funnel and the different stages of the sales cycle. We then would be able to create the dashboards and be able to monitor it. We then could create target lists of customers that we can go after.

We had Sales Navigator as a tool LinkedIn Sales Navigator, and we then got Lusha as an add-in. Again, I didn't do it, so I can't say how we did, but we found a way to link Lusha to HubSpot. Within the first, I'd say, two to two and a half months, we had HubSpot with a good dashboard reporting tool, a solid sales cycle that we were dragging and dropping the deals through. Then in terms of where they were finding the leads, we actually were effectively using Navigator to kind of target our ICP. We didn't really have an ICP before the sales leader came in as well. Then with the combination of Lusha and Navigator pushing into HubSpot meant that the engine is just working, and it was very visible and transparent rather than the black hole of what's going on with these leads. That really was pivotal in us to be able to understand I guess why. We are quite a, I'd say, data-driven organization as such, but we definitely look at... I think it's essential that you have to have that information to be able to get to predictable revenue.

James Hounslow:

100%. I think a lot of people are worried about saying that they're a data-driven business, but sales is data-driven 100%. There is obviously the sales element side of it, but data tells you the story about what you need to go and do. You mentioned there that you may not necessarily do exactly the same thing if you had your time again. Did you decide to go and find this kind of player-coach or did the stars align, and someone knocked at your door at the right time that you thought, "Ah, let's give this a go?"

Tom Dunlop:

I guess in some ways, we didn't really know what we were looking for. I think we went out to market to look for a sales leader. We knew we wouldn't get, in some ways, the CRO level. We didn't want that either because we felt it's far too early, and you want someone who is going to roll the sleeves up. If I was a previous sales leader, I think it would have been slightly different, but I think because I have limited sales experience, having someone who can actually do the selling was important, but we went out and said, "Look, we don't really know what we need, but we know we need someone who has at least managed a few people. Ideally, it's not been too long since they were actually selling, but they're senior enough to actually manage people." We did see a range of potential people.

Yeah, it was a little bit of a stars aligned, where the person we recruited was actually recruiting with the same recruiter for his team, and they ended up being tipped off about this, and actually came, and joined us to set up everything from scratch really. Yeah, it wasn't specific we were looking for, but I think we had an idea that type of person, and I'd definitely do that again. That wasn't something I'd change.

James Hounslow:

Timing-wise, if you had your time again, would you bring this person in earlier, or did they come at the right time?

Tom Dunlop:

I think they probably came at the right time because I think what we did for a few months was work out... We didn't have the ICP at that point, but we'd done the market research essentially to understand where that was. I mean the difficulty with that tool was I mean every business has contracts, so in some ways, we could sell it to every business. It was working out was it law firms, is it in-house legal teams, is it SMEs.

I think that just getting your team of bright, kind of enthusiastic SDRs to just go and test it with all of those helped us refine where it really fit. Then when you plug that kind of player-manager into it, it just means that they go, "Right, you've gone all that bit. That's fine. I can take what you've done and make it into a machine rather than having to start that process from scratch." Accidentally, I think the timing was very good. Wasn't necessarily achieved, but I think I would do that bit the same way.

James Hounslow:

Where are you at at the moment in terms of annual recurring revenue?

Tom Dunlop:

We're in a runway of the late hundreds of thousands basically. We're pushing on the door to try and get above the million mark, and that's our next goal really to get to. It's important for you to reach that point before obviously series A and touch on that scaler phase.

James Hounslow:

Once you hired this player-coach, what did it do to your day-to-day role? Could you shift it elsewhere? Were you still putting the same amount of time into sales? What happened once this person arrived?

Tom Dunlop:

Actually, we talk about there's these two things that happened within the first three months. The first was... because I used to do every demo and every deal basically. So the first one was I wasn't involved with the deal at all. It was an American company, a pharma company that I could hear the demo going on, and it was the player-manager plus an SDR. I could hear them talking and asking questions. Almost like listen in on the glass, thinking, "Are you answering these right?" Almost didn't want to let go of that control. Then they closed this deal, and I knew about it, but I didn't get involved at all. There's that realization that was like, "Wow, that's great. I didn't have to get involved."

Then about a month or two later, we had a new SDR that we brought in that had prospected a particular in-house legal team, and then the SDR that was on that original call... It was sort of them filling in this junior AE role, so we promoted him to actually do the demos. All of a sudden then, we had the new SDR with that junior AE. They prospected and closed a deal without me or Dan involved. Just in the space of three months, we went from me being involved in everything to actually I didn't have any involvement, and then neither did Dan. I was almost two steps removed from it, so it really did change my day-to-day.

I wouldn't say freed up as such, but in terms of focus, it definitely wasn't on demos. It definitely wasn't on what is this deal up, why aren't we doing what... We need to send this email. I could look at bit higher level and think more about I guess other elements. Because I am basically the product manager in many ways as well because that's where my background is, it did give me more time to then focus more on the product side of it than just sales. Yeah, it was a really interesting journey we went on, but those three months, those two stages that we went through was great.

James Hounslow:

So here's an interesting question for you then. When we spoke about bringing this person in, you mentioned there that you didn't have a sales background, and perhaps if you had, you may not have needed to bring him in so early. I've seen and I've heard through talking to people that when founders hold on to sales for longer than necessary, it takes off the focus elsewhere. So how much value do you think particularly in the fact that you're A game is product, not sales, and you've been able to put more time into product than into an area that isn't your strong point?

Also, VCs talk often about the companies that really kick on that series A is where they have a repeatable sales process that doesn't involve the founder. The founders will always have some aspect in sales, and they'll always be a bit in there, but it's not reliant on them. How much value do you think that's given to you and the product, and the business not actually being the person trying to drive sales?

Tom Dunlop:

I think it's huge. I mean because I'm the same way. When I listen to... where would it be? The podcasts or the usual things that you listen to when you're, "How do you start and get to the first whatever of revenue?" A lot of people say, "Well, you should always get to at least a million without a sales lead. That just should be a given," and so I was a bit reserved about bringing somebody in so early because I almost felt like this goes against a lot of the advice I've heard. It's almost like since then in the past, I don't know, 12 months that I've actually heard the opposite, which is that people like, "No, you should bring in CROs a lot earlier. Bring in sales leaders a lot earlier."

I mean I can only speak, I guess, from my experience. The ability to be confident that we have a sales machine without me involved and without me having to drive it, without me having to explain the use case every time and... because it's almost like a cheat code. If I get involved in the sales process, I come in, and within five minutes, I know exactly the problem. I know exactly where the product fits, which is great, but at the same time, that's not scalable.

I think the sooner you can prove out that other people who don't have your background can do the same with the product and can drive it to a sale, it's got to be more attractive to VCs. It's got to actually get you to revenue quicker. I think in the long run and if you want to genuinely scale up quicker, the sooner you bring someone in, the sooner you get that machine going, the better in my view.

James Hounslow:

Yeah. Everything's going super well. You've gone through a few iterations probably of the SDR teams and who they are. You've got the leads coming through. You've got somebody on board who is doing business for you, promoting an SDR into kind of an AE position. Everything's going really well. Revenue's going in the right direction. You've done something interesting, and you've gone for a CRO much earlier than a lot of people. In my view, 100% the right thing to do.

Why did you guys do it, and really importantly, it's delicate, but how did the player-manager take it? Because a lot of start-ups do a very bad thing, and that's promise the world to everybody who comes in, and that they're going to be X, Y, and Z, and come in now as a senior salesperson, and you'll be the CEO by the time we exit out. There's a lot of questions in there, but I think it's really important. What made you go for a CRO pre-series A, and how did you handle that conversation with your player-coach?

Tom Dunlop:

Yeah, I mean it 100% is a delicate kind of situation you've got to think long and hard about. I think the two things that happened was, one, we very much went out selling to the mid-market is the best way to describe it. We had smaller legal teams, smaller law firms. I think there was a moment where we... I'm not going to say we dragged to the enterprise, but there was certainly, obviously, the relevance of the product. It felt like it was better than all other products, but bigger companies.

So we hired a more senior AE, so more, I guess, enterprise AE, not in the traditional sense of the cybersecurity software, like extreme enterprise, but certainly a bigger deal person. It just became clear that the player-manager approach of a mid-market team didn't lend itself well to managing then someone who was actually same level, if not more experienced in the sales side. Kind of almost like instead of earlier on taking the manager route, they just continued on the sales route and wanted to be a salesperson.

I think when you start to branch out and almost have different focus areas, where you've got someone who needs to have their own sale process that's more enterprise, someone who's managing sales process that's more mid-market... We also have a marketing team now. We have, I guess, two or three people in marketing that are looking in there. It started to feel a little bit not disjointed, but it started to feel like we're kind of going three silos here. We've got a sales area of enterprise, which is not doing their own thing, but they didn't have as much guidance because the person we brought in didn't have that experience.

When we were chatting as, I guess, a board, it was very much like, "Well, to take us to the next level and to show that we can serve enterprise, we've got a predictable revenue machine with the mid-market, and we've got this marketing, I guess, machine that starts getting leads and really get us out there, we need just a commercial leader." Again, it comes back to your first point. I recognize that I'm not someone who has years and years of experience in leading sales marketing teams. Again, it may have been different had I been that person, but I think because I recognize that, it was another iteration of I don't need to be spending my time daily really in the weeds on the sales marketing side. That's kind of why we did it.

The honest answer... We did think it would take six to nine months to hire the right person because it's very hard to find that sort of VP of sales, CRO of sales, who could come in at this stage and is the right fit. It just happened that we actually managed to find someone that I guess had grown with a software company, I guess the VP of EMEA when he exited, actually founded his own business, and lives in the Northwest, lives in Manchester. So it was a great fit. A member of the board already knew him as well, so that kind of made sense, and it is someone that could help us in the US, has experience with moving to the US and being in Boston for three years.

So there was a solely different aspect to why that made sense and why it was the next iteration that we could go to a series A and say, "We've already got this in place. We know exactly where we're going to go into the US. We know exactly the enterprise model versus corporate versus marketing. That's already set out. We've got three machines now." That's important for us to get that in place prior to series A, so that when they're giving us the money, they're giving it to people who've been there and done it before and know that it's a safe investment rather than wondering about it after the event. That's, I guess, the why and the how.

Then I think, yeah, in terms of how the player-manager took it, it's always a difficult conversation. I think we tried not to do the same mistake as what a lot of people do. We promise the world. It was very much, "Look, you're coming in at this level, but there are two or three levels above this position. There's VP. There's SVP. There's CRO. At some point, there will be someone who comes in." I think because we did that, it made it easier.

I think it was generally the way it's received is, "Yeah, get it. Yeah, and completely get the rationale now." I think it's earlier than what anyone thought, so I think that's the hardest bit. Ultimately, because we don't have a bigger organization structure, there's not an obvious managerial role available really. It's just be a sales guy for a while. Then you'll have to go back to a managerial role. That's really how we pitched it.

It was received okay. It was received in a kind of understanding way, and time will tell. I think, yeah, in terms of the decision as to the why, I think it absolutely made sense, and I would still do that every day.

James Hounslow:

Three of the biggest challenges that a founder like yourself will face throughout is acquiring the right talent, getting the right VC, and acquiring clients. You're now head down. You know exactly what you need to achieve to get to the biggest milestone for you guys, which will be series A funding. How much are you thinking and planning for life post-series A? Because, particularly on the sales side, you seem to have been all right in finding the people that you want, but it's a critically difficult marketplace to scale sales teams.

Once you get to series A, a large part of your scale will be on the customer acquisition side. There will be obviously some into development, but by the time you're a series A, you'll kind of know where you are with the product of where it is, and a lot of these successful exit-ers have talked about the difference from businesses that go from A to B is the processes you have in place and the sales talent you bring on board. Do you have enough time to think about post-series A at the moment, or is it, "Once we get there, then we'll think about it? I wish I could do it before, but I just don't have time."

Tom Dunlop:

Yeah, there's a couple things in there, which I think one of them was about the right investors at the right time. I think one other thing that was quite good that we had from the start is I'd got... who's called Charlie Sharland. He was the founder of AppSense, which is where I used to be the GC. He came on as chairman, and he's grown companies to 100 million-plus revenues. That means he already knows the post-series A world. They raised 70 million from Goldman Sachs, so in many ways, the reason why we've done a lot of this stuff early is because we've got that mind.

So in terms of scaling out sales team, hiring a CRO or VP that has the connections that has been there and done it before that has led a sales team in a different organization that's exited means that a lot of the time, he can go, "Look, I've got 10 AEs here that I can just bring in tomorrow. It's known. It's trusted. I've got the context. They've been there and done it before. I've been there, and they trust me." We did with the development team early on to get the right product, and I think that's worked amazingly well.

I think, yeah, in terms of post-series A, it's another reason why getting a sales leader in earlier is better because now we can say to the series A investors, "Well, we've already got it figured out. We know the specific neighbourhood in Boston that we want to open up an office. We've already got a whole network of people over there that we could recruit. We've got a whole network over here that we could recruit. Just give us the money, and we'll make it happen." I think that feels like such a confident position to be in going into the series A investors than saying, "Don't worry. We'll work it out."

I think that you can get away with that at seed because I think, a lot of time, it's all about backing the founders, and they'll work it out, but I think if you get to series A and beyond, that's no longer good enough. It's like, "No, we need to know exactly what you're going to do." That's why we've done what we've done.

James Hounslow:

It sounds like you've done some really good planning. What does it look like post-series A? How much are you scaling? You've mentioned Boston a few times, so when are you heading there? What does it look like?

Tom Dunlop:

Yeah, we have a concept of pods if that's the best way to describe it. We talked a bit before about the mid-market and the enterprise, so we have, well, corporate or enterprise. At the moment, we have two pods as it were, which is an SDR, a junior AE, and an AE. What we basically mapped out is what we need for an enterprise pod, the cost of it versus what they should be producing, demos, and deal size, and also the corporate pod.

Really post-series A is basically... I mean we could go through the minutia, but I think it's basically some corporate enterprise pods in the UK that focus on a specific market and verticals, then really focusing on the first pod being enterprise over in the US for a specific in-house vertical. Then we'd basically tag on... It goes to corporate. Then it goes to private practice, like law firms. It's kind of scaling up in this kind of pod model from... more in the UK. There's a lot more in the UK focused, but then having one in the US. Then we'll add two more in the US and then three more in the UK. When it becomes that predictable, both on the enterprise side and mid-market side, you can quite easily see how you can just add new ones on.

I think that's really the plan post-series A. It's still really heavily outbound in terms of our go-to-market. It's not going to switch to be more inbound for a little while after that, but it's very much I guess getting this scalable pod model, one in the US, closely followed by a second and a third, and then equivalent in the UK.

James Hounslow:

Scary stats out there that only 20% of businesses that receive series A will go on to get to series B. Do you think about that at all or are you... put that to the back of your mind as unimportant, and you just try particularly from a professional athlete's background, where high performance is... You don't worry about the result. That will take care of itself. The continuous improvement on what you're doing or have you got that doubt of that 20% in your mind?

Tom Dunlop:

I never think about that in terms of some element of failure rate. I think it's one of those things that it is exactly the athlete mentality. It's just an inevitability in my view. It's not a question of if we'd fail at any particular point. It's more of a case of how far do we want to go. The only thing in the back of my mind right now is post-series A, I do think because we're in a market that's, one, very active, but, two, we could be a enhancement to large document or contract management systems because we extract information from contracts, and we make it usable, and we connect it to other tools... So naturally, in the back of my mind is I think we're going to be faced with decisions to make after series A. I think we'll have a point where we will get approached because of the technology that we have and because it lends itself so well to those bigger players.

At the same time, this market's massive, and no one's won yet. The only part of the contract lifecycle that's kind of been won is the eSignature piece, which is they're at a billion revenue with DocuSign for eSignatures. So I'm thinking, "Well, we do the rest of the contract lifecycle, and I think we do it in a way, which means it's very future-proof. It's very chatbot-focused, voice-focused, Q&A, integrating with all the day-to-day tools." I think the fact that we do that means there is no reason why we can't get to that level.

So it's going to be one or the other, and the honest answer is right now, I'm not kind of not concerned about it. As I say, it's more now about getting predictable revenue, predictable sales process, the product to where I want to get it to. I have no doubt that one or the other will happen. It's just we'll make that decision at that time.

James Hounslow:

Yeah, I don't know. I'm maybe putting it out there, but knowing your background, I don't think you'll sell out early. I think you'll try and see how far you can drive it because if it can go alongside, it's about taking it as far as you feel you can take it before you go the other way. I think that option will always be open to you, so awesome. Just-

Tom Dunlop:

Just an interesting thing just on that. Just very quick on that one. I worked with an entrepreneur when I was a legal advisor, and he's worth about 300 million or something at the minute. One of the biggest things he said to me at the start was, "Life's all about the journey. It's not about the destination as a thing." I mean it's almost a well-known concept. At the same time, he was like, "I did the thing where you get to the top of the mountain. I bought private jets. I got helicopters, almost like that moment that you think that you're all striving towards." He was like, "I was bored, and I had to get back and just do something."

I think there's a lot of that in me at the minute that I already kind of know that, that I couldn't just sit there, and almost no matter what the exit was, I'd need to be doing something. Yeah, I totally agree. I think in the back of my head, I think we'll have some interesting conversations in the next couple of years, but at the same time, I'm hopefully young enough to see this out for a long time yet. Yeah, we'll see.

James Hounslow:

Before I let you go, if you had somebody in front of you now who had an idea, they're looking to start a tech business, what one bit of advice would you give to them that you've learned that you would change if you had the chance to within your own organization if you started again?

Tom Dunlop:

I feel like this is a long-winded answer, but I always think that... There's no such thing. I did a post actually yesterday about there's no such thing as an entrepreneur. I think one of the first things people need to do if they want to start a business. Now, I think an entrepreneurial mindset is very much just day-to-day life, get in the habit of always thinking of a better way of doing what you're doing. It could be in the house or it could be in work, whatever it might be. The reason I say that is because I've so many friends that come up with these ideas, and it's because they were on the train, and they saw something about Facebook and thought, "I can build a better social media platform." Maybe, but that's not resulting from a problem that you've personally suffered. That's just an idea that's come out of the blue.

I think first thing is if you get into that mindset, you'll stumble across an idea, but the great thing about that is that it's something that you've genuinely incurred the problem of because you're thinking about it as a result of what you're doing, which sets you up in a much better position than just randomly pursuing ideas.

Then I think after that, one I think I've always been conscious of is to actually at least get to prototype phase. Whatever it is that you do, don't just talk about it. The sooner you can get something in front of someone... It could just be a design. On Figma, you can build a prototype, a clickable prototype. You could maybe even pay a web consultant something to actually just deliver you a prototype. The sooner you can get that into a user's hands and get them to genuinely feedback whether they'd use, whether they wouldn't, and it's something visual and works, the better because then you can look at investment at that stage. You don't have to have loads of proof points and clients.

Yeah, two things really, which is getting to that entrepreneurial mindset as soon as you can because it'll lead to better ideas. Then, second, once you've got an idea that you've genuinely suffered the problem of, at least push it to prototype stage, and try and get that early-stage feedback, and ideally someone who says, "I'll pay you a notional amount to use that on a day-to-day basis." Then I think at that stage, you're in a very good position to potentially get investment or to look at other options that can get it going.

James Hounslow:

Awesome. Tom, thank you very much for giving up your time today and sharing your journey. I think you're doing absolutely the right things. I think you're doing it the new way, which is kind of the new way of particularly in the UK and Europe, and I think you'll set yourselves up for the success. Definitely keen to follow you guys and the journey and see when you get to that real big landmark of series B funding.

Tom Dunlop:

Yeah. Thanks for your time. It's been good to chat.

Tech Salescraft: Tom Dunlop, Founder & CEO at Summize

By
August 12, 2021

James Hounslow:

Hello, and welcome to the latest episode from Tech Salescraft. Our mission is simple - we want to bring you exclusive insight from some of the brightest and most influential minds in the tech sales scene. We want this podcast to be your weekly go-to for inspiration, and if this is your first time listening to the show, please subscribe to keep up to date with all the latest releases.

Welcome to the latest episode from Tech Salescraft, and today, I'm delighted to be joined by the founder and CEO of start-up firm, Summize, Tom Dunlop. Tom, welcome.

Tom Dunlop:

I'm here. It's good to be here with you today.

James Hounslow:

Awesome. Today, we're going to be talking about Summize's journey from inception through to where they are, and the future, and what it holds, but as a way of getting started, Tom, could you just give our audience a brief background as to who you are?

Tom Dunlop:

Yeah. No, of course. I guess depends on how far back you want to go, but I think what I started on the road to become was actually an athlete. In many ways, my path has been very varied. My early career was all about... I say athlete in the loosest term. It was badminton, so make your own judgment, but we-

James Hounslow:

Great sport.

Tom Dunlop:

It's a great sport. I agree. I agree. Very timely with the Olympics and everything on as well. I was very much got on the GB program. Not bragging, but I was the number one in England, in Europe-

James Hounslow:

Nice.

Tom Dunlop:

…and was very much going on the I'm going to be an Olympian. I'm going to go into sport in some way and did my degree at the same time as that. My last choice was to do law, and I had five other courses that were very much sports-related. I just thought, "Oh, I'll give this law thing a go. It could be good backup if I don't manage to get to the Olympics." I'm kind of glad I did because then the rest of my career was very much centred around that legal side.

Then after university, I went to law school. I then probably carried on as a full-time professional badminton players whilst doing my law degree and law school, and then made the choice really that I think badminton was not going to be the route. It wasn't quite as glamorous as probably what I thought as a junior, and it certainly wasn't paid very well either, hence the legal route came through.

After there, really I guess I did start a business up when I was in law school as well. That was an online comparison site for solicitors. All the GoCompare’s were very popular at the time. Then did that for a little bit, but then fell into sports agency. In my view, I was like, "This is perfect. I'm going to be combining my law and my sport, represent footballers and Olympic athletes, do sports management," which was in many ways... There was parts of it that was as glamorous as you probably think, but then there's a lot of parts that were definitely not and quite a shady world.

That's when I switched over to the legal because the guy who set up was a former lawyer. We set up a law firm. I trained as a solicitor, qualified, and really the next few years, my life was then being an in-house lawyer. I very much centred to or kind of gravitated towards the tech world. I was the GC and legal director of a few different fast-growth tech and SaaS businesses. Really that was then the use case that propelled me into founding Summize.

James Hounslow:

Nice.

Tom Dunlop:

There's a brief potted history.

James Hounslow:

Summize, who are you, and what do you guys do, and who do you service?

Tom Dunlop:

Yeah, I mean the background that I just talked about I guess is relevant to what we do. The product really was born out of my I guess frustrations or problems with just spending my life reviewing contracts really. Contracts, I think everyone can agree are, one, very long, two, very boring, and probably sales guys' worst nightmare when it gets towards the end of a deal, and they have to get it over line quickly. When you're spend every day reviewing them, they're just very manual and very time-consuming.

With Summize, the product, what we aim to do... the first thing that we did was we were able to summarize contracts, hence the name. The core technology is that we take a long contract, and we can create an instant summary of it and pull out the key points. That was the core technology, which were great in a few different use cases, whether that's reviewing multiple contracts in one go. We went through a number of acquisitions, so that was very useful for that context.

Then also for if someone asks you to do a quick red flag review, you can do that very quickly. That's the core technology behind Summize, and then we've branched out from there now, and we look at how we can connect so many business users to the legal team. We have things like the Microsoft Word add-in. We have Teams and Slack integrations. The best way to think about that is you can almost ask a question of your contract to the Teams, "How do I end my contract with whoever," and it'll go, and find the answer, and give you the answer back through Teams. That's our next iteration of how the product will work. It's basically to make contracts easier for legal teams.

James Hounslow:

Interesting. Where are you on your journey? Have you taken funding? Do you class yourself a pre-seed, seed series A?

Tom Dunlop:

Boom, and we're kind of between seed and series A is the best way to describe it. We did take pre-seed investment from I guess a combination of a VC, Maven, and an angel. We then proved out a prototype. We then sold that first iteration of the product, got further money, which I kind of class as then that seed round to just build, get some salespeople into the business. We're now about 55, 60 customers and mainly UK, but have some in the US, and Australia, and one in Canada. Now, we're kind of starting, I guess, that more scale-up journey looking towards a series A probably Q2 next year.

James Hounslow:

Nice. How many people do you have in the business today?

Tom Dunlop:

We've got 19 full-time heads at the minute.

James Hounslow:

Now, you started the business in Manchester, which is one of the tech hubs within the UK, but I'm sure a large part of your customer base, I could be wrong, would definitely be London with what you guys are doing. What was the reason behind Manchester? Did you do any research to decide that Manchester was the right place?

Tom Dunlop:

Yeah. I mean it's been an interesting, I guess... I mean because prior to setting up Summize, I guess even me from a... looking for jobs as an in-house counsel of tech businesses, naturally, London has a much higher concentration of the tech businesses. What I found over recent years at actually UserZoom, which was where I was last at, which is a fast-growth tech business... They were headquartered in Silicon Valley. They chose to open one of their European HQs in Manchester, and we started to get this influx of... Amazon opened up a tech hub here, and we get these businesses that have started to open up in and around Manchester.

Then we have direct flights that were from Manchester to San Francisco, which we never used to have, and so I think that the past five to 10 years, there's been this gradual focus on Manchester becoming more of a hub for, say, US companies, both from a travel and infrastructure perspective, but also from a talent perspective, you started to get people that... cheaper cost of living, and obviously, the universities are good. That meant that there wasn't as much competition for roles as well because the concentration of tech businesses in London, you can actually recruit high-quality people from the Manchester area. I definitely had it in my mind as to where's the concentration of talent, but also where's the concentration of customers and how could we potentially service international customers as well from the space.

I think that I kind of arrived at the conclusion that certainly at this stage that we're at, I know a lot of the tech businesses. I've worked in a lot of them, so I had a lot of contacts for talent. Our whole dev team is from a company I used to work at that meant that that wasn't an issue. Then, obviously, we launched I guess the product at the start of the pandemic, so I think in terms of where our customers are, that became a lot less relevant once everyone moved to this kind of remote world. So Manchester's served us well.

There's a lot of investment in the area and there's... from a VC perspective, but also in terms of the buildings popping up left, right, and centre, and different hubs being created. Yeah, I'm glad that we stayed in Manchester, and I can only see it growing from strength to strength if I'm honest. It's a good place to be at the minute.

James Hounslow:

When I speak to VCs and founders who've seen an exit, they talk about the early days, that it normally takes about three iterations of the product before you have the product that people want to buy. The quicker you get to that point, the better. As a founder, you come in with a great idea that you think's going to work. Now, you're coming from a slightly different perspective is that you've seen a problem, and you're providing a solution to a problem, whereas a lot of founders will have a conversation with someone, and they'll see something, and think, "Right, this actually could work in that sector." Did the first iteration of what you wanted to do... Is that what the clients are seeing today or how many iterations have you gone through, and how quickly did you get those changes?

Tom Dunlop:

I think it's a great point because I think it applied equally even though I am essentially the customer as well as the vendor in many ways, but what was interesting and one thing I actually... It's not a regret, but in terms of an emphasis that I would put on really in those days is not to be as defensive of the product or to certainly gain as much customer feedback as you possibly can because we created our version one of the product, which created summaries of contracts, but it was a platform. It was a web-based product. Really when people saw it, they immediately assumed it would be for multiple contract reviews, so a project review. It was kind of shoehorned into a use case that was where it was born from, but, ultimately, I'd be like, "Well, no, you could use it for this. You could use it for that."

I think sometimes you've got to really look at your products and look at that customer feedback to go, "Well, why wouldn't they use it for a particular use case, and what's stopping them?" It might be something as simple as it doesn't send me email notifications or it doesn't integrate with a particular product. I think that sometimes you're so concerned about selling the product and getting that initial traction so you can get to the next phase that you don't iterate enough in the early days. We were quite lucky that we had a very strong development team that I knew and I'd worked with before, and I had friends in the industry that I could bounce it off that we iterated a number of times.

I mean I think if you ask my co-founder, Dave, yeah, the early days were quite rough for him because the bar was quite high, and we changed our mind or pivoted left, right, and centre for the first six to probably 12 months really I mean in terms of what we actually did. I'd say only really now, we've got a very, very clear vision as to what the product does today, and also what it will do, and exactly what customers that serves. Yeah, it is a process you go through.

James Hounslow:

When did you know you were ready to offer it to a client?

Tom Dunlop:

I think there's two different sides to that. There was one, which we allowed customers to use it for free to get that feedback for a particular use case, and then I think once you know you've kind of... I mean there's a great book that I read quite early on called Impossible to Inevitable that was by the founders of SaaStr, but they did this book. I mean it's almost like they talk about the first 10 customers being at arms' length, being that's where all your focus is on is getting these first 10 customers to pay for it, and also about nailing your niche, and really getting one use case down to the point where you know it solves it, and you know that people will pay for it.

For us, that use case was multiple contracts in the system and create summaries for it. At the point that we knew that the product did that and we trialed that with the customer, we then went to other customers that had that problem, and we sold it on that basis. We knew that at that point, the alternative was very manual and costly, so we could charge for it. I think that was the point that we focused solely on that one particular use case, how we solved it, and then we made our first sales on that basis.

We've broadened out since then, but I think it's really important, certainly on those initial sales, to really, really focus in the specific value and the problem you're solving to be able to justify people paying money for it. I think that's what we did quite well, but then we did branch out quite quickly given COVID probably stopped a lot of project reviews happening. It was one of those where we pivoted quite quick, but it was good for the other customers.

James Hounslow:

How did you feel as a founder having to be that salesperson? Was it you that was going out, doing those initial pitches?

Tom Dunlop:

I did all the initial pitches. I think what was interesting about the early... I say the early days. We're still very much in the early days, but was I could pick the use case, understand their use case, and speak to them in almost a conversational way rather than a pitch straight away, so I think the actual demo part of I guess the sales process. In terms of the ability to get straight to the use case, almost satisfy the typical kind of sales methodologies that you're doing in terms of use case, and budget, authority, everything. I could get to that very quickly because I'd worked there. I did it. It was my problem, so they probably had the same thing.

I think where I soon realized that I was not very good was, well, what happens next. I just didn't control a sales lifecycle. So we showed loads of people. We got loads of great feedback. Demos were great. Use case was spot-on, and then it was kind of like, "Well, what now?" It was that next bit of, well, how are we controlling that customer to make sure they sign on a given day. That was the bit that I probably found the hardest, but also something I just hadn't done before that meant that bringing in a proper sales leader was obviously very important and opened up my eyes up as well about how many things you can do at that part of the sales lifecycle.

James Hounslow:

At what point did you decide that you were ready to hire a salesperson, and what was the first hire? Was it a salesperson or a sales leader?

Tom Dunlop:

Hire, we did. Well, I guess we hired five SDRs. We went for the junior, and pretty much all of them were recent guides. They might have six months' experience. Would I do that again? I don't know. Not as heavy with recent grads. I think what we didn't account for that... We had loads of keen, I guess energetic individuals that would hit the phones or hit LinkedIn or do my book. In terms of actually training them on what you need to do, and managing them day-to-day, and really being on top of the KPIs... Obviously, I was still responsible for the product really as well, so I think we went quite heavy on the junior side.

It wasn't until we hired I guess a sales leader, which was probably nine months after that really we got that organization that meant that we could get an actual predictable revenue model. I think we were kind of grabbing deals. We had the machine that put... I say it was a machine. It wasn't as effective as it could have been, but we were having the demos being put in the top. I was doing them, and then collectively, we'd try and chase them down. We'd grab deals left, right, and centre, and it felt very much like that.

It wasn't until we hired a leader on top of those, by then it was three or four, that we actually got some proper... I guess that process and were using HubSpot at the time as our CRM, and we still are, but using that more effectively that we actually felt, "Oh, we've got something that's quite predictable now, where I know that we'll do X number of deals, X number of revenue." That was so refreshing from my perspective rather than I guess a little bit of chaos really to start with.

James Hounslow:

Was it like an SDR or manager that you brought in or an actual SaaS sales leader who was doing the selling themselves? They-

Tom Dunlop:

Yeah. I guess right now, we're going through a transition from that to bringing in actually a CRO, so like a full sales leader as such. When we hired, first of all, it was sales manager, so player-manager, so really we did that with someone who'd been a salesperson for a number of years, not a load, but I'd say four or five years. They'd just taken that first step into management, so they might be a regional manager or they might manage four other AEs. At that point, we hired that person because we knew they could sell, which was important, but then, secondly, they had a bit of experience of managing people. It didn't have to be massive amounts of people, just three or four, so that kind of player-manager role was our first hire, which was absolutely right for where we were at the time.

James Hounslow:

What made you decide to go down to SDR and then a player-manager route? Some organizations will go to get a couple of just good AEs, account executives in just to go out and get themselves up to a couple of million annual recurring revenue. What insight did you look at, or did you get advice to say, "Get an SDR team in play, and then get a player-coach in?"

Tom Dunlop:

I mean with the AEs, I think a lot of them... If you want good AEs, they're also used to having an element of demos being given to them or leads being provided to them. I think at the point that we hired the SDR, we didn't have any leads. It was me going out to friends really, so we needed to build up just some form of lead generation in whatever form it was that would mean that we can actually make an AE effective. I think you've got lots of different personalities as to what makes a good AE. I think some people can be very self-starting and don't mind picking up the phones and generating X number of leads, but that might still only be five a month or something like that. They don't want to be spending all their time doing lead generation.

And our chairman was a sales guy who turned entrepreneur, and which founded and sold two software companies, so he was advising a little bit as well. I think it was more let's get some people in who can work out who's receptive, who isn't, start building up more of a predictable lead generation engine. Then we bring in the AE, player-manager person who can then start to really convert them and guide them onto where they should have been. That was kind of the idea behind it.

James Hounslow:

Interesting. Then once this player-coach came in, then you talked about that's when you introduced HubSpot as a CRM, which is obviously a great tool, because I guess you probably haven't got a fully functioning marketing department just yet either, and there's some great content that you can put into the HubSpot suite, which helps you to create that function. You mentioned that that's where you found the repeatable process. How did you stumble onto that, and how long did it take once this person arrived?

Tom Dunlop:

I mean one thing that's good about who we brought in, Dan, was that he came instead, and the first thing he did was look at how are we tracking anything that we're doing. I have the free version of HubSpot, which is pretty basic, so we upgraded HubSpot pretty quickly within the first month to have more of a sales and marketing side of the product. That allowed us to really open up the functionality we needed to track the deal stages. We created our own, I guess, funnel and the different stages of the sales cycle. We then would be able to create the dashboards and be able to monitor it. We then could create target lists of customers that we can go after.

We had Sales Navigator as a tool LinkedIn Sales Navigator, and we then got Lusha as an add-in. Again, I didn't do it, so I can't say how we did, but we found a way to link Lusha to HubSpot. Within the first, I'd say, two to two and a half months, we had HubSpot with a good dashboard reporting tool, a solid sales cycle that we were dragging and dropping the deals through. Then in terms of where they were finding the leads, we actually were effectively using Navigator to kind of target our ICP. We didn't really have an ICP before the sales leader came in as well. Then with the combination of Lusha and Navigator pushing into HubSpot meant that the engine is just working, and it was very visible and transparent rather than the black hole of what's going on with these leads. That really was pivotal in us to be able to understand I guess why. We are quite a, I'd say, data-driven organization as such, but we definitely look at... I think it's essential that you have to have that information to be able to get to predictable revenue.

James Hounslow:

100%. I think a lot of people are worried about saying that they're a data-driven business, but sales is data-driven 100%. There is obviously the sales element side of it, but data tells you the story about what you need to go and do. You mentioned there that you may not necessarily do exactly the same thing if you had your time again. Did you decide to go and find this kind of player-coach or did the stars align, and someone knocked at your door at the right time that you thought, "Ah, let's give this a go?"

Tom Dunlop:

I guess in some ways, we didn't really know what we were looking for. I think we went out to market to look for a sales leader. We knew we wouldn't get, in some ways, the CRO level. We didn't want that either because we felt it's far too early, and you want someone who is going to roll the sleeves up. If I was a previous sales leader, I think it would have been slightly different, but I think because I have limited sales experience, having someone who can actually do the selling was important, but we went out and said, "Look, we don't really know what we need, but we know we need someone who has at least managed a few people. Ideally, it's not been too long since they were actually selling, but they're senior enough to actually manage people." We did see a range of potential people.

Yeah, it was a little bit of a stars aligned, where the person we recruited was actually recruiting with the same recruiter for his team, and they ended up being tipped off about this, and actually came, and joined us to set up everything from scratch really. Yeah, it wasn't specific we were looking for, but I think we had an idea that type of person, and I'd definitely do that again. That wasn't something I'd change.

James Hounslow:

Timing-wise, if you had your time again, would you bring this person in earlier, or did they come at the right time?

Tom Dunlop:

I think they probably came at the right time because I think what we did for a few months was work out... We didn't have the ICP at that point, but we'd done the market research essentially to understand where that was. I mean the difficulty with that tool was I mean every business has contracts, so in some ways, we could sell it to every business. It was working out was it law firms, is it in-house legal teams, is it SMEs.

I think that just getting your team of bright, kind of enthusiastic SDRs to just go and test it with all of those helped us refine where it really fit. Then when you plug that kind of player-manager into it, it just means that they go, "Right, you've gone all that bit. That's fine. I can take what you've done and make it into a machine rather than having to start that process from scratch." Accidentally, I think the timing was very good. Wasn't necessarily achieved, but I think I would do that bit the same way.

James Hounslow:

Where are you at at the moment in terms of annual recurring revenue?

Tom Dunlop:

We're in a runway of the late hundreds of thousands basically. We're pushing on the door to try and get above the million mark, and that's our next goal really to get to. It's important for you to reach that point before obviously series A and touch on that scaler phase.

James Hounslow:

Once you hired this player-coach, what did it do to your day-to-day role? Could you shift it elsewhere? Were you still putting the same amount of time into sales? What happened once this person arrived?

Tom Dunlop:

Actually, we talk about there's these two things that happened within the first three months. The first was... because I used to do every demo and every deal basically. So the first one was I wasn't involved with the deal at all. It was an American company, a pharma company that I could hear the demo going on, and it was the player-manager plus an SDR. I could hear them talking and asking questions. Almost like listen in on the glass, thinking, "Are you answering these right?" Almost didn't want to let go of that control. Then they closed this deal, and I knew about it, but I didn't get involved at all. There's that realization that was like, "Wow, that's great. I didn't have to get involved."

Then about a month or two later, we had a new SDR that we brought in that had prospected a particular in-house legal team, and then the SDR that was on that original call... It was sort of them filling in this junior AE role, so we promoted him to actually do the demos. All of a sudden then, we had the new SDR with that junior AE. They prospected and closed a deal without me or Dan involved. Just in the space of three months, we went from me being involved in everything to actually I didn't have any involvement, and then neither did Dan. I was almost two steps removed from it, so it really did change my day-to-day.

I wouldn't say freed up as such, but in terms of focus, it definitely wasn't on demos. It definitely wasn't on what is this deal up, why aren't we doing what... We need to send this email. I could look at bit higher level and think more about I guess other elements. Because I am basically the product manager in many ways as well because that's where my background is, it did give me more time to then focus more on the product side of it than just sales. Yeah, it was a really interesting journey we went on, but those three months, those two stages that we went through was great.

James Hounslow:

So here's an interesting question for you then. When we spoke about bringing this person in, you mentioned there that you didn't have a sales background, and perhaps if you had, you may not have needed to bring him in so early. I've seen and I've heard through talking to people that when founders hold on to sales for longer than necessary, it takes off the focus elsewhere. So how much value do you think particularly in the fact that you're A game is product, not sales, and you've been able to put more time into product than into an area that isn't your strong point?

Also, VCs talk often about the companies that really kick on that series A is where they have a repeatable sales process that doesn't involve the founder. The founders will always have some aspect in sales, and they'll always be a bit in there, but it's not reliant on them. How much value do you think that's given to you and the product, and the business not actually being the person trying to drive sales?

Tom Dunlop:

I think it's huge. I mean because I'm the same way. When I listen to... where would it be? The podcasts or the usual things that you listen to when you're, "How do you start and get to the first whatever of revenue?" A lot of people say, "Well, you should always get to at least a million without a sales lead. That just should be a given," and so I was a bit reserved about bringing somebody in so early because I almost felt like this goes against a lot of the advice I've heard. It's almost like since then in the past, I don't know, 12 months that I've actually heard the opposite, which is that people like, "No, you should bring in CROs a lot earlier. Bring in sales leaders a lot earlier."

I mean I can only speak, I guess, from my experience. The ability to be confident that we have a sales machine without me involved and without me having to drive it, without me having to explain the use case every time and... because it's almost like a cheat code. If I get involved in the sales process, I come in, and within five minutes, I know exactly the problem. I know exactly where the product fits, which is great, but at the same time, that's not scalable.

I think the sooner you can prove out that other people who don't have your background can do the same with the product and can drive it to a sale, it's got to be more attractive to VCs. It's got to actually get you to revenue quicker. I think in the long run and if you want to genuinely scale up quicker, the sooner you bring someone in, the sooner you get that machine going, the better in my view.

James Hounslow:

Yeah. Everything's going super well. You've gone through a few iterations probably of the SDR teams and who they are. You've got the leads coming through. You've got somebody on board who is doing business for you, promoting an SDR into kind of an AE position. Everything's going really well. Revenue's going in the right direction. You've done something interesting, and you've gone for a CRO much earlier than a lot of people. In my view, 100% the right thing to do.

Why did you guys do it, and really importantly, it's delicate, but how did the player-manager take it? Because a lot of start-ups do a very bad thing, and that's promise the world to everybody who comes in, and that they're going to be X, Y, and Z, and come in now as a senior salesperson, and you'll be the CEO by the time we exit out. There's a lot of questions in there, but I think it's really important. What made you go for a CRO pre-series A, and how did you handle that conversation with your player-coach?

Tom Dunlop:

Yeah, I mean it 100% is a delicate kind of situation you've got to think long and hard about. I think the two things that happened was, one, we very much went out selling to the mid-market is the best way to describe it. We had smaller legal teams, smaller law firms. I think there was a moment where we... I'm not going to say we dragged to the enterprise, but there was certainly, obviously, the relevance of the product. It felt like it was better than all other products, but bigger companies.

So we hired a more senior AE, so more, I guess, enterprise AE, not in the traditional sense of the cybersecurity software, like extreme enterprise, but certainly a bigger deal person. It just became clear that the player-manager approach of a mid-market team didn't lend itself well to managing then someone who was actually same level, if not more experienced in the sales side. Kind of almost like instead of earlier on taking the manager route, they just continued on the sales route and wanted to be a salesperson.

I think when you start to branch out and almost have different focus areas, where you've got someone who needs to have their own sale process that's more enterprise, someone who's managing sales process that's more mid-market... We also have a marketing team now. We have, I guess, two or three people in marketing that are looking in there. It started to feel a little bit not disjointed, but it started to feel like we're kind of going three silos here. We've got a sales area of enterprise, which is not doing their own thing, but they didn't have as much guidance because the person we brought in didn't have that experience.

When we were chatting as, I guess, a board, it was very much like, "Well, to take us to the next level and to show that we can serve enterprise, we've got a predictable revenue machine with the mid-market, and we've got this marketing, I guess, machine that starts getting leads and really get us out there, we need just a commercial leader." Again, it comes back to your first point. I recognize that I'm not someone who has years and years of experience in leading sales marketing teams. Again, it may have been different had I been that person, but I think because I recognize that, it was another iteration of I don't need to be spending my time daily really in the weeds on the sales marketing side. That's kind of why we did it.

The honest answer... We did think it would take six to nine months to hire the right person because it's very hard to find that sort of VP of sales, CRO of sales, who could come in at this stage and is the right fit. It just happened that we actually managed to find someone that I guess had grown with a software company, I guess the VP of EMEA when he exited, actually founded his own business, and lives in the Northwest, lives in Manchester. So it was a great fit. A member of the board already knew him as well, so that kind of made sense, and it is someone that could help us in the US, has experience with moving to the US and being in Boston for three years.

So there was a solely different aspect to why that made sense and why it was the next iteration that we could go to a series A and say, "We've already got this in place. We know exactly where we're going to go into the US. We know exactly the enterprise model versus corporate versus marketing. That's already set out. We've got three machines now." That's important for us to get that in place prior to series A, so that when they're giving us the money, they're giving it to people who've been there and done it before and know that it's a safe investment rather than wondering about it after the event. That's, I guess, the why and the how.

Then I think, yeah, in terms of how the player-manager took it, it's always a difficult conversation. I think we tried not to do the same mistake as what a lot of people do. We promise the world. It was very much, "Look, you're coming in at this level, but there are two or three levels above this position. There's VP. There's SVP. There's CRO. At some point, there will be someone who comes in." I think because we did that, it made it easier.

I think it was generally the way it's received is, "Yeah, get it. Yeah, and completely get the rationale now." I think it's earlier than what anyone thought, so I think that's the hardest bit. Ultimately, because we don't have a bigger organization structure, there's not an obvious managerial role available really. It's just be a sales guy for a while. Then you'll have to go back to a managerial role. That's really how we pitched it.

It was received okay. It was received in a kind of understanding way, and time will tell. I think, yeah, in terms of the decision as to the why, I think it absolutely made sense, and I would still do that every day.

James Hounslow:

Three of the biggest challenges that a founder like yourself will face throughout is acquiring the right talent, getting the right VC, and acquiring clients. You're now head down. You know exactly what you need to achieve to get to the biggest milestone for you guys, which will be series A funding. How much are you thinking and planning for life post-series A? Because, particularly on the sales side, you seem to have been all right in finding the people that you want, but it's a critically difficult marketplace to scale sales teams.

Once you get to series A, a large part of your scale will be on the customer acquisition side. There will be obviously some into development, but by the time you're a series A, you'll kind of know where you are with the product of where it is, and a lot of these successful exit-ers have talked about the difference from businesses that go from A to B is the processes you have in place and the sales talent you bring on board. Do you have enough time to think about post-series A at the moment, or is it, "Once we get there, then we'll think about it? I wish I could do it before, but I just don't have time."

Tom Dunlop:

Yeah, there's a couple things in there, which I think one of them was about the right investors at the right time. I think one other thing that was quite good that we had from the start is I'd got... who's called Charlie Sharland. He was the founder of AppSense, which is where I used to be the GC. He came on as chairman, and he's grown companies to 100 million-plus revenues. That means he already knows the post-series A world. They raised 70 million from Goldman Sachs, so in many ways, the reason why we've done a lot of this stuff early is because we've got that mind.

So in terms of scaling out sales team, hiring a CRO or VP that has the connections that has been there and done it before that has led a sales team in a different organization that's exited means that a lot of the time, he can go, "Look, I've got 10 AEs here that I can just bring in tomorrow. It's known. It's trusted. I've got the context. They've been there and done it before. I've been there, and they trust me." We did with the development team early on to get the right product, and I think that's worked amazingly well.

I think, yeah, in terms of post-series A, it's another reason why getting a sales leader in earlier is better because now we can say to the series A investors, "Well, we've already got it figured out. We know the specific neighbourhood in Boston that we want to open up an office. We've already got a whole network of people over there that we could recruit. We've got a whole network over here that we could recruit. Just give us the money, and we'll make it happen." I think that feels like such a confident position to be in going into the series A investors than saying, "Don't worry. We'll work it out."

I think that you can get away with that at seed because I think, a lot of time, it's all about backing the founders, and they'll work it out, but I think if you get to series A and beyond, that's no longer good enough. It's like, "No, we need to know exactly what you're going to do." That's why we've done what we've done.

James Hounslow:

It sounds like you've done some really good planning. What does it look like post-series A? How much are you scaling? You've mentioned Boston a few times, so when are you heading there? What does it look like?

Tom Dunlop:

Yeah, we have a concept of pods if that's the best way to describe it. We talked a bit before about the mid-market and the enterprise, so we have, well, corporate or enterprise. At the moment, we have two pods as it were, which is an SDR, a junior AE, and an AE. What we basically mapped out is what we need for an enterprise pod, the cost of it versus what they should be producing, demos, and deal size, and also the corporate pod.

Really post-series A is basically... I mean we could go through the minutia, but I think it's basically some corporate enterprise pods in the UK that focus on a specific market and verticals, then really focusing on the first pod being enterprise over in the US for a specific in-house vertical. Then we'd basically tag on... It goes to corporate. Then it goes to private practice, like law firms. It's kind of scaling up in this kind of pod model from... more in the UK. There's a lot more in the UK focused, but then having one in the US. Then we'll add two more in the US and then three more in the UK. When it becomes that predictable, both on the enterprise side and mid-market side, you can quite easily see how you can just add new ones on.

I think that's really the plan post-series A. It's still really heavily outbound in terms of our go-to-market. It's not going to switch to be more inbound for a little while after that, but it's very much I guess getting this scalable pod model, one in the US, closely followed by a second and a third, and then equivalent in the UK.

James Hounslow:

Scary stats out there that only 20% of businesses that receive series A will go on to get to series B. Do you think about that at all or are you... put that to the back of your mind as unimportant, and you just try particularly from a professional athlete's background, where high performance is... You don't worry about the result. That will take care of itself. The continuous improvement on what you're doing or have you got that doubt of that 20% in your mind?

Tom Dunlop:

I never think about that in terms of some element of failure rate. I think it's one of those things that it is exactly the athlete mentality. It's just an inevitability in my view. It's not a question of if we'd fail at any particular point. It's more of a case of how far do we want to go. The only thing in the back of my mind right now is post-series A, I do think because we're in a market that's, one, very active, but, two, we could be a enhancement to large document or contract management systems because we extract information from contracts, and we make it usable, and we connect it to other tools... So naturally, in the back of my mind is I think we're going to be faced with decisions to make after series A. I think we'll have a point where we will get approached because of the technology that we have and because it lends itself so well to those bigger players.

At the same time, this market's massive, and no one's won yet. The only part of the contract lifecycle that's kind of been won is the eSignature piece, which is they're at a billion revenue with DocuSign for eSignatures. So I'm thinking, "Well, we do the rest of the contract lifecycle, and I think we do it in a way, which means it's very future-proof. It's very chatbot-focused, voice-focused, Q&A, integrating with all the day-to-day tools." I think the fact that we do that means there is no reason why we can't get to that level.

So it's going to be one or the other, and the honest answer is right now, I'm not kind of not concerned about it. As I say, it's more now about getting predictable revenue, predictable sales process, the product to where I want to get it to. I have no doubt that one or the other will happen. It's just we'll make that decision at that time.

James Hounslow:

Yeah, I don't know. I'm maybe putting it out there, but knowing your background, I don't think you'll sell out early. I think you'll try and see how far you can drive it because if it can go alongside, it's about taking it as far as you feel you can take it before you go the other way. I think that option will always be open to you, so awesome. Just-

Tom Dunlop:

Just an interesting thing just on that. Just very quick on that one. I worked with an entrepreneur when I was a legal advisor, and he's worth about 300 million or something at the minute. One of the biggest things he said to me at the start was, "Life's all about the journey. It's not about the destination as a thing." I mean it's almost a well-known concept. At the same time, he was like, "I did the thing where you get to the top of the mountain. I bought private jets. I got helicopters, almost like that moment that you think that you're all striving towards." He was like, "I was bored, and I had to get back and just do something."

I think there's a lot of that in me at the minute that I already kind of know that, that I couldn't just sit there, and almost no matter what the exit was, I'd need to be doing something. Yeah, I totally agree. I think in the back of my head, I think we'll have some interesting conversations in the next couple of years, but at the same time, I'm hopefully young enough to see this out for a long time yet. Yeah, we'll see.

James Hounslow:

Before I let you go, if you had somebody in front of you now who had an idea, they're looking to start a tech business, what one bit of advice would you give to them that you've learned that you would change if you had the chance to within your own organization if you started again?

Tom Dunlop:

I feel like this is a long-winded answer, but I always think that... There's no such thing. I did a post actually yesterday about there's no such thing as an entrepreneur. I think one of the first things people need to do if they want to start a business. Now, I think an entrepreneurial mindset is very much just day-to-day life, get in the habit of always thinking of a better way of doing what you're doing. It could be in the house or it could be in work, whatever it might be. The reason I say that is because I've so many friends that come up with these ideas, and it's because they were on the train, and they saw something about Facebook and thought, "I can build a better social media platform." Maybe, but that's not resulting from a problem that you've personally suffered. That's just an idea that's come out of the blue.

I think first thing is if you get into that mindset, you'll stumble across an idea, but the great thing about that is that it's something that you've genuinely incurred the problem of because you're thinking about it as a result of what you're doing, which sets you up in a much better position than just randomly pursuing ideas.

Then I think after that, one I think I've always been conscious of is to actually at least get to prototype phase. Whatever it is that you do, don't just talk about it. The sooner you can get something in front of someone... It could just be a design. On Figma, you can build a prototype, a clickable prototype. You could maybe even pay a web consultant something to actually just deliver you a prototype. The sooner you can get that into a user's hands and get them to genuinely feedback whether they'd use, whether they wouldn't, and it's something visual and works, the better because then you can look at investment at that stage. You don't have to have loads of proof points and clients.

Yeah, two things really, which is getting to that entrepreneurial mindset as soon as you can because it'll lead to better ideas. Then, second, once you've got an idea that you've genuinely suffered the problem of, at least push it to prototype stage, and try and get that early-stage feedback, and ideally someone who says, "I'll pay you a notional amount to use that on a day-to-day basis." Then I think at that stage, you're in a very good position to potentially get investment or to look at other options that can get it going.

James Hounslow:

Awesome. Tom, thank you very much for giving up your time today and sharing your journey. I think you're doing absolutely the right things. I think you're doing it the new way, which is kind of the new way of particularly in the UK and Europe, and I think you'll set yourselves up for the success. Definitely keen to follow you guys and the journey and see when you get to that real big landmark of series B funding.

Tom Dunlop:

Yeah. Thanks for your time. It's been good to chat.

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