A conversation between Ron Benegbi, Founder & CEO of Uplinq Financial Technologies and Heidi Ram, Product Practice Lead at The Product Recruiter.
Hiring your first product manager is one of the most consequential decisions a founder will make. Done well, it can unlock focus, momentum, and clarity. Done poorly, it can slow the business at a moment when every decision matters.
To unpack what first-time founders should really expect, Heidi Ram sat down with Ron Benegbi, a serial entrepreneur and CEO of Uplinq Financial Technologies, to talk candidly about when he hired his first PM, what he looked for, and how that hire changed the trajectory of the company.
I’m a multi-time founder. I’m also an immigrant. My family came to Canada in the early 1970s with very little. My father started his first small business with a $5,000 loan from a Toronto bank in 1973, which at the time was a huge opportunity. Watching my parents run small businesses shaped everything for me, especially seeing firsthand how hard it was to access capital and manage cash flow.
That experience is deeply tied to Uplinq’s mission. We help financial institutions make smarter small business lending decisions using advanced data and credit decisioning models. But our story isn’t “AI built in a basement by PhDs.” We took a product that had been built and tested over 15 years and repurposed it into a modern fintech platform. That gave us credibility with banks from day one, because while the company was new, the technology wasn’t.
Uplinq was incorporated in April 2021, and honestly, even early on I was already thinking about product leadership. I knew that given the market we were going after and the complexity of what we were building, product would be critical.
A few months in, around late summer 2021, we made a strategic pivot. Nothing unusual for a startup, but meaningful enough that it forced us to slow down and really rethink the product direction. Around that time, my co-founder joined. He’s the technical brain behind the company.
That was the inflection point. We were about to invest real time getting the product right, and it became obvious we needed someone whose full focus was product.
Before making the permanent hire, I actually brought in a very senior product consultant through the MaRS ecosystem here in Toronto. That gave us short-term support while we went through a proper hiring process for our first full-time PM. In hindsight, that bridge was incredibly valuable.
A lot.
We sell a very complex product to banks. It impacts how they think about credit, risk, and regulatory compliance. Our product doesn’t make lending decisions, but it absolutely influences them, which means we sit under regulatory scrutiny. That’s very different from most fintech products.
When we defined what we were looking for, three things really mattered:
What surprised me was realizing that almost no candidate perfectly checked all three boxes. Even the person we hired had gaps in two of the three areas. That forced us to make conscious trade-offs.
The question became: do we keep looking, or do we hire someone strong enough overall who fits culturally and grow from there? We did the latter and it was absolutely the right hire for us at that stage.
We decided that fit and upside mattered more than perfection.
The person we hired was more senior and more expensive than we initially planned. That’s not a small decision for a venture-backed startup. But when we weighed cost against impact, it made sense.
They left a very secure role at a large company to join a no-name startup. That alone told us something about their mindset. They weren’t perfect on every requirement, but they were strong enough where it mattered and culturally aligned with how we work.
In an early-stage company, cultural misalignment can be devastating. One person out of sync can slow everything down.
In very real ways. Within the first year, we had a strong product demo, which was critical for us. We sell data through APIs, and that’s incredibly hard to demo without a thoughtful product layer. They were also exceptional at conferences and events, better than I was. Not selling directly, but engaging people, building comfort, and representing the product well.
Most importantly, they freed up my time. As a CEO, that’s everything. I could focus on sales, partnerships, finances, and operations while trusting that product was moving forward with clarity. It was absolutely the right hire at the right moment.
