From Fit to Scale: Hiring the Right Product Leader for Growth

Founders will eventually hit a point where product decisions can no longer live in their heads or calendar. Features start slipping, teams lose clarity, and go-to-market stalls because no one is connecting what’s being built to what actually drives growth.

That’s when the question surfaces: Is it time to hire a product leader?

Bringing in a first Head of Product or CPO is one of the most pivotal leadership hires, but it’s also one of the hardest to get right.

To help unpack what makes a great product leader, and when to hire one, we sought the advice of Jonathon Schuster, an AI/ML and data product executive who’s built and scaled product orgs from Series A through C. His superpower? Turning raw data into revenue and helping founders grow without losing product-market traction along the way.

With product leadership roles spanning across SaaS and Data-as-a-Service (DaaS) companies like LiveRamp, Bombora, and Unacast, he has firsthand insight into how founders can hire the right product leader to unlock their next stage of growth.

And when he’s not building and scaling product orgs? Jonathon is pushing limits in a different arena: he’s completed 47 marathons and is training for his first full Ironman. He notes the parallel between the difficulty of building a startup and the day-in-day-out of training for endurance events.

In this conversation, Jonathon shares:

• How to know you’re actually ready for a product leader
• Why most founders over-index on vision and under-value GTM
• The two biggest myths he sees in startup product hiring

Start by complementing—not replacing—the founder’s strengths

“I’m not the Head of Product you bring in to reinvent the wheel,” says Jonathon. “I’m the one you bring in once you’ve found some fit and need to align and grow.”

For founders considering their first product leader, Jonathon advises taking a hard look at what skills or capacity the business is missing, not just hiring a generalist to “own product.”

In his experience, there are two common scenarios where a founder might benefit most from a VP Product:

1. Scaling the founder’s vision.
   As the team grows, founders can’t be everywhere at once. A strong product leader can help evangelize the founder’s insights internally turning that deep domain expertise into priorities, roadmaps, and clear communication.

“Founders don’t scale,” he says. “They need someone who can be the voice of the Founder’s vision to the rest of the org.”

His biggest piece of advice: “Ensure that the hire has exceptional communication skills, especially at amplifying someone else’s vision.”

2. Exploring new growth areas.
   When a company is branching into new markets or verticals, the team needs to learn fast and build without perfect information. That requires a product leader who knows how to ship in ambiguity and adapt quickly.
   
   “They don’t need to have hit a home run in a new space,” Jonathon notes, “but they do need to know how to evaluate, test, and learn.”

His advice: “Ensure that the hire has experience crafting products in unknown/new spaces.”

GTM thinking is the product superpower most founders overlook

One of Jonathon’s core strengths is applying go-to-market thinking to every stage of product development. 

In a world where build velocity is accelerating, he cautions that speed without strategy isn’t enough. 

“We’re in the middle of a massive sea change in terms of the kinds of companies out there in the tech space and growth for growth’s sake is no longer an option. Profitability, free cash flow, EBITDA positive are the phrases of the day, and none of those things happen unless the products sold are purchased and used.”

Especially in today’s profitability-driven climate, product leaders must bring a commercial lens to the table. That means understanding not just what to build, but see the whole process from end-to-end. And with the emergence of Gen AI and vibe coding, build velocity is moving along faster than ever. 

“We can release more alphas and betas than ever, but it only matters if we’re shipping the right things—things that sell.”

What most founders misunderstand about hiring product leaders

There are two myths Jonathon sees crop up repeatedly when it comes to product leadership hires:

1. The “Steve Jobs” fallacy
   Many founders hope there’s a visionary out there who will fix all their product problems and while that person probably does exist, there’s likely only one or two of them in the world, and the organization probably doesn’t need that. While vision is important, it’s no replacement for the day-to-day leadership and communication that actually moves teams forward.
   
   “What it probably needs is someone who builds trust, sets up a strong process, and helps the team execute—step by step.”
   
   
2. Big tech = guaranteed success
   Hiring out of FAANG (or MAANGM, as he jokingly calls it) might seem like a smart bet, but it doesn’t always translate. Those environments often come with structure, resources, and stability that smaller startups don’t have.
   
   “If the company doesn’t look like that today or won’t in the immediate future, it’s worth questioning if a person from that background can help a Founder actually operate and grow the business the way it's expected to grow in the next few years.”

Jonathon sees product leadership as a partnership with the CEO. One rooted in shared goals, constant communication, and clarity on what success looks like. Every founder starts with a mission to solve a problem. A Product Leader's job has always been to help scale that solution.

TL;DR

✅ Hire for complementarity, not replacement
The first product leader should extend a Founders strengths and cover their blind spots—not “own product” in a vacuum.

✅ Look for GTM fluency
The best product leaders think beyond features. They understand how to build things that sell and scale.

✅ Don’t chase visionaries or big-name résumés
Don’t chase a Steve Jobs or a FAANG veteran—lookf for someone who builds trust, process, and real momentum.

✅ Think partnership, not delegation The founder–CPO relationship works best when rooted in shared goals, constant communication, and mutual respect.