Hiring your first PM is one of the most consequential decisions a founder will make. Get it wrong, and you'll spend years untangling the damage. Get it right, and you'll wonder how you ever shipped without them.
John, VP of Product based in New York City, has lived this from both sides, repeatedly. A domain expert in AI-enabled CRM and CX products, he's been the first product hire at multiple companies, stepping in where there was no roadmap, no process, and a founder who needed a real thought partner, not just an executor.
In this conversation with Heidi Ram, Product Practice Lead at The Product Recruiter, John pulls back the curtain on what the first PM role actually looks like inside a SaaS startup; what founders get wrong when hiring for it, how the dynamic really works day-to-day, and why the founder-PM relationship can make or break a company's trajectory.
My path into product was not traditional. I actually started in marketing. Early in my career I thought I would be creating advertising campaigns and working on big brand moments. But I ended up getting pulled into the world of B2B SaaS and eventually transitioned from running brand marketing into running product.
A lot of my early experience focused on the real estate industry. We were building websites, SEO tools, and property search tools that helped realtors manage the influx of leads they receive when listings go online.
That was really where I started to understand platforms, CRM systems, and how the different pieces of a SaaS business connect together.
The company was about fifteen people at the time and the founders trusted the team to figure things out. Over the course of about seven or eight years we ended up growing the business four times over.
From there I joined another zero-to-one startup, which is something I’ve done multiple times. That company was building a CX CRM platform in New York. Over four to five years we grew the business to roughly $60M before it was acquired by Meta.
After that, AI was suddenly showing up in every product conversation. I eventually joined a voice AI company in hospitality where we were building technology to handle restaurant phone calls for reservations, catering, and menu questions.
At that stage the product was being built almost entirely from scratch. Every few weeks things were evolving and changing. It was a really exciting time to be working in product.
One example happened when I transitioned internally from marketing into product. The company was originally an agency doing branding, websites, and marketing for a range of clients. We worked with schools, nonprofits, and a few other industries.
As a marketer I had access to a lot of the business data. One morning I was having breakfast with the founders and pointed out something interesting: roughly 60 percent of our revenue was actually coming from real estate clients.
That insight started a broader conversation about whether the company should focus entirely on that vertical. That shift eventually led us toward building a product instead of just providing services.
At the time none of us had deep SaaS experience. We were used to contracts, hourly billing, and project work. Now we were talking about charging customers monthly for access to software.
So the early work was figuring out:
As we started bringing in new customers every week, the product function naturally expanded. That’s when I started learning things like writing requirements, running customer research, and thinking about how to scale ideas beyond the “coolest idea in the room.”
What really mattered, though, was building something customers loved enough that they would keep using it and tell others about it.
One common misunderstanding is that product is just project management.
Some founders think the job of the PM is simply to execute a roadmap that the founder has already defined. That can work in certain situations, but the real value of product is broader than that. A strong product leader looks at problems across the business.
If you’re introducing a new product line, for example, that might impact pricing, onboarding, support, or professional services. Product should be thinking about those implications and working cross-functionally across the company.
The best product hires operate like business operators. They break down problems, align teams around solutions, and help the organization move forward.
In my career I’ve been pulled out of traditional product work and asked to solve problems in areas like CX, sales, or data. That flexibility is especially important in early-stage companies where everyone is wearing multiple hats.
Founders are deeply invested in the product. It’s their idea and often something they’ve sacrificed a lot to build. Because of that, they sometimes develop blind spots. That’s not a negative thing. It’s often what allows founders to push through difficult moments and keep moving forward.
The product leader’s role is to introduce balance. Sometimes that means creating productive tension. For example, a founder may want to pursue a new direction immediately. A product leader might say: “I love the idea, but we have a critical problem that needs attention this quarter.”
That back-and-forth can actually create stronger alignment. When there is trust between the founder and product leader, those discussions help clarify priorities and build a shared understanding of what the company should focus on next.
Don’t over-index on process. Early-stage founders sometimes assume they need someone who will immediately introduce product specs, Jira workflows, and formal roadmaps.
Those tools are useful, but they are not the most important thing at the beginning. What matters more is finding someone who shares your passion for the problem and genuinely cares about the customer.
If you hire a product person who speaks about the business and the customer instead of just features, you are probably hiring the right person. The processes and frameworks can always be taught later. Passion for the problem and comfort working in ambiguity are much harder to teach.
Hiring your first product manager isn't just a staffing decision, it's a strategic one. As John's experience makes clear, the right PM brings more than process to the table. They bring conviction, customer empathy, and the ability to hold productive tension with a founder without losing trust. Whether you need someone to take your napkin sketch to MVP, or a seasoned operator who can think across the entire business, the fit has to be right.
