A conversation between Walid Koleilat, VP of Product & Design at Alexi, and Heidi Ram, Product Practice Lead at The Product Recruiter.
At The Product Recruiter, we spend a lot of time with founders who have reached an inflection point. The product works. Customers are engaged. Expectations are rising. And the question then becomes: who will lead product from here?
To explore what it really looks like to step into that role, Heidi Ram sat down with Walid Koleilat, VP of Product & Design at Alexi, who was hired as the first Product Manager two years ago. Since joining, he has built the product and design function and helped expand product-market fit as the company scaled.
Walid shares what founders can expect, how the role evolves beyond initial assumptions, and what makes the founder–product partnership work.
I’m a senior AI product and growth leader who has spent about 15 years building B2B products in highly regulated industries like financial services and legal.
I started as a founding engineer, then moved into management consulting at a Big4 firm, and eventually returned to startups where I’ve built product and design organizations at high-growth companies.
Today I’m VP of Product & Design at Alexi. I joined as the first PM and built the product and design function from the ground up.
At Alexi, we build AI automation for law firms. You can think of it as Claude meets Zapier for legal workflows. We help lawyers automate research, document analysis, and other complex tasks.
What excites me most is seeing how quickly even traditionally conservative industries like legal are embracing AI. Lawyers are building their own tools and adapting faster than most people expect, and it’s exciting to help enable that transformation.
Alexi had just reached product-market fit with its legal research product and had closed its Series A. The team was growing, a board had formed, and expectations shifted from “does this work?” to “how do we scale?”
At the same time, AI technology was evolving rapidly, which meant product-market fit wasn’t static. We needed to continuously refine the product as models improved.
When I joined, there were a few parallel challenges:
It was a classic post-Series A moment where the company had proven value and now needed to build systems that could scale.
Founders often hire a product manager to execute against immediate priorities, like shipping the next version or scaling a roadmap. But once you’re inside, you realize that sustaining growth requires building the underlying system that allows the company to move faster over time.
At Alexi, that meant not only delivering the next version of the product but also evolving how the organization operated. We needed tighter feedback loops between product, sales, and marketing, faster decision-making, and a deeper connection to customers.
The product became part of the broader system, not just a set of features.
It’s a partnership, and it requires an intentional transition. Founders have usually built the first version of the product themselves. Letting someone else take ownership is emotionally difficult because the product is deeply personal.
In my experience, the relationship works best when three things are clear:
1. Explicit decision rights: There should be clarity on scope, responsibilities, and how decisions are made.
2. Public alignment: Even when there are private debates, founders should visibly support the PM in front of the team.
3. Recognition that letting go takes time: It’s natural for founders to jump back into decisions out of habit. Working through that transition together builds trust.
At Alexi, we spent a lot of time aligning on vision and context so I could carry that forward while earning trust.
Start by defining the problem you want this person to solve. Sometimes founders feel pressure from boards or advisors to hire, but clarity on outcomes matters more than timing alone. Ask yourself what should change in the business if this hire is successful.
Beyond experience and skills, three factors are critical:
Trust: Can this person carry the vision and make sound decisions when you’re not in the room?
Chemistry: You’ll be working through hard problems together, so mutual respect and shared values matter.
Passion: They should be genuinely curious about your customers and the problem space.
Once you hire, give them context, clarify decision rights, and support them as they lead. That’s what allows the role to have real impact.
