Mark Oshry

Mark, tell us about your career history and expertise

My entire career has been in a post-sale capacity at software companies, even before the term “customer success” was popularized. I started out implementing software and training customers on how to solve real business problems using technology. From day one, my role was about helping people get value from products.

I’ve worked across a number of different industries over the years. Early on, I worked in the public sector with school administrators and teachers. I then moved into financial technology, working with traders and portfolio managers – two very different customer profiles. More recently, I worked in  revenue enablement, supporting salespeople, marketers and operations teams.

Across four software companies, I’ve always been customer-facing and post-sale. As SaaS and subscription models became more established, customer success as a function really started to take shape, and that’s where I found my long-term home. What’s been consistent throughout is a focus on helping customers achieve outcomes and building relationships that last.

What first attracted you to Summize?

I was introduced to Summize’s CEO Tom Dunlop and the rest of the leadership team through a mutual connection, as Summize was scaling quickly in the US and looking for the right leadership presence in Boston. From the very first conversations, it was clear this was a team I could see myself working with.

For me, it’s always been about the people and the culture. Meeting the leadership team, it was obvious they were aligned, unified and clear on what they were trying to build. There was no disconnect between vision and execution, and that’s something I really value.

The legal tech space itself was a bonus. It’s an underserved market with a huge opportunity, but what ultimately drew me in was knowing this was a leadership team I could get behind and a mission I could be genuinely motivated by.

What does it mean to be SVP of Customer Success at Summize?

Customer success is about owning the entire customer journey – from implementation through to renewal and growth. That means making sure customers achieve quick time-to-value, clearly understand their use cases and feel confident taking ownership of the platform.

My role is to make sure our team is consistently educating customers on what’s possible with Summize, keeping them informed about the roadmap and helping them solve real business problems. When customers are successful and see genuine value, growth becomes a natural outcome.

While I spend my time thinking about strategy and scale, it’s also important to stay close to customers. You can’t improve the customer experience if you don’t experience it yourself. Being involved directly helps make sure we’re always looking at the business through the customer’s eyes.

What do you find most interesting about the legal tech space?

Before Summize, I didn’t have deep experience in legal tech, but I had worked with in-house legal teams and saw first-hand how understaffed and under-resourced they often are. At the same time, legal teams are becoming increasingly strategic to the business, particularly in SaaS environments.

What really resonated with me was the pain around contracts. In customer success, we deal with contracts constantly – clauses, renewals, amendments, SLAs – and finding that information across multiple documents can be incredibly painful. Seeing how Summize allows users to ask natural language questions and get clear answers was a real lightbulb moment.

Legal tech is also an interesting challenge, because legal teams are understandably risk-focused. Adoption can take time, but when you show how contract lifecycle management (CLM) technology can save hours of manual work and help lawyers become better business partners, the value becomes very clear.

What does the future look like at Summize, and what are you most excited about?

What excites me most is how much opportunity there is to continue building a world-class customer success function as Summize scales. As our customer base grows, we’ll evolve how we support them through smarter segmentation, better processes and more tailored experiences based on customer size, geography and industry. Longer-term, that opens up opportunities to specialize, verticalize and build deeper expertise across the team. A customer success organization where teams support customers with similar needs is more efficient and ultimately delivers a better experience.

I also see customer success as a major growth driver for the business. As long as we continue to make customers genuinely successful – supported by strong product innovation – Summize is very well positioned for the next phase of growth. If customers describe us as trusted advisors who help them solve real problems, we’ll know we’ve got it right.