How to sell to lawyers in 2026

When I joined Summize as the first sales hire nearly six years ago, the legal tech market looked very different to how it does now. In many ways, the last six years have been about growth – not just for Summize, but for Contract Lifecycle Management (CLM) as an industry and for how legal teams think about technology. Having sold into the UK, Europe and the US and having worked with everything from early-stage legal teams to global enterprises, here are a few of the biggest lessons I’ve learned across the way.  

1. The CLM market has evolved – but not evenly

One of the biggest things I’ve noticed is how differently the CLM market has developed depending on geography. In the UK and wider EMEA region, a lot of my early sales conversations were about education. Legal teams weren’t always clear on what CLM actually was and many were first-time buyers. General Counsels often didn’t have a dedicated technology budget which meant they had to make a strong business case internally. The conversation wasn’t just about legal efficiency, but about how contracts impact revenue, risk and the wider business as well.

The US was different. CLM was already more established as an industry and legal teams often knew what they were buying, but that brought competition as a new challenge. Legal teams were often replacing an existing tool or looking for something better, which meant positioning Summize as a second-generation CLM in a far more crowded market. As the space has grown, so has the number of startups, point solutions and overlapping solutions.  

That shift means sales in legal tech today demands a lot more than just a surface-level product pitch – and this is where myself and Summize are seeing the success!

2. Domain expertise isn’t optional anymore

As the market has matured, buyers have become more sophisticated, and selling CLM now relies on having an understanding of the realities of different industries. We sell to all kinds of verticals, from big tech to sports teams to software to finance, but selling to all of them looks different.

Recently, I’ve worked with a lot of medical device and pharmaceutical organizations, who deal with huge volumes of contracts, highly specialized supply chains and intense regulatory scrutiny. They often have two extremes at once: complex, bespoke agreements that require meticulous review, alongside large volumes of standard agreements like NDAs. That’s where AI and structured contract data can really add value, but you have to understand the full context they’re operating in.

The key lesson is needing to understand how a business and their teams function, the risks they carry, the rewards they’re chasing and the role legal plays in making that possible. Without that, it’s almost impossible to sell legal tech credibly.

3. What makes a good salesperson

80% of being successful in sales is hard work – it’s non-negotiable. It’s cliché to say, but the more you put in, the more you get out. But once those basics are in place, the real difference comes from how much you genuinely care. I’ve learned that when you actually care about how a business and the person or team you’re speaking to operates and what they’re going through, they open up! They’ll talk about their pressures, their frustrations and what success genuinely looks like to them.

Listening properly is critical. A lot of salespeople try and plug a gap which they can’t necessarily always fill. The best salespeople are honest with both the customer and with themselves. If you can’t genuinely say you’re the best fit for someone’s needs, it’s better to acknowledge that than push something that won’t deliver value.

4. People buy from people – especially in the age of AI

No matter how advanced technology has become, relationships still win. Buyers are so inundated with emails, LinkedIn messages and automated outreach, so it means you’ve got to cut through the noise by being personable.

I always tell my sales team to focus on connection first. Whether it’s a cold call, LinkedIn message or an in-person meeting, the goal is to just be memorable and personable. If you can make someone smile, you’ve already set yourself apart. Get to know the people you’re talking to, whether that’s how long they’ve been in the role, how fast the company is growing, any exciting news or even just their hobbies and interests.

Human connections matter more than ever as AI becomes a bigger part of sales and tech, but trust and rapport can’t be generated. You never want someone to think “Oh no, I’ve got to speak to Harvey again.”

5. Advice for sales professionals starting out in legal tech

Sales development can be some of the hardest roles. It’s getting told no hundreds of times a day, thousands of times a week, but it’s where you really earn your stripes.  

The biggest piece of advice I’d give to new sales colleagues is to enjoy it. If you take rejection personally, the role can quickly become overwhelming. Sales has highs and lows, and learning to ride that wave is part of the job. Having the right team culture also helps enormously – friendly competition, shared wins and a sense of humor make a tough role far more sustainable.

Most importantly, remember you’re speaking to humans. Try to bring something positive to someone’s day. It’ll make your conversations so much more meaningful and the results will follow.

Almost six years in, legal tech continues to evolve, and so does the way we sell it. But the core principles are still the same: work hard, understand your customer deeply, be honest about fit and remember that behind every deal is real people.

Meet more of our people and find out more about Summize by clicking below.