Head of Product

Retirable is a mission-driven, New York-based fintech that helps everyday Americans retire with financial confidence through professional retirement advice, wealth management, and banking. We're the bridge between where Americans are today and the confident, well-funded retirement that they deserve.

The problem is staggering: 12,000 Americans retire each day and less than a quarter have ever seen a financial planning professional. That's millions of hardworking Americans aged 55+ heading toward retirement underfunded, underprepared, and unnecessarily stressed.

At Retirable, we're tearing down traditional barriers to world-class retirement advice. We don't sell products, we build relationships. We don't push portfolios, we craft personalized roadmaps to financial freedom. This isn't just FinTech. This is about fundamentally reshaping how America retires—one person, one plan, one confident future at a time.

The Role

We are hiring our Head of Product to be a senior, hands-on operator who will own the product roadmap end-to-end. You will report directly to the CEO and partner closely with the CTO and engineering team to ship.

This is a player-coach role with the player dial turned all the way up. You will write the strategy, prototype the next feature, sit with engineering to ship it, and then write the launch post. You will build the team underneath you over time, but for now you are the team.

What You'll Own

Product strategy & roadmap. Define what we build, why, and in what order. Translate Retirable's mission into a sequenced set of bets that move retention, advisor leverage, and AUM.

AI in the core product. Lead the integration of AI across the client experience and the advisor / retirement / investment back office. Streamline the workflows our advisors run today, automate what shouldn't be human, and make every advisor more effective.

Engineering leverage. Help our engineers 2x their output without 2x'ing headcount. Bring AI-first development practices, prototyping tools, and tight feedback loops to the team.

Hands-on shipping. Bias toward working prototypes over PRDs wherever it makes sense.

How You Work

AI-first by default. You assume AI is part of the answer, not an add-on. You use it daily in your own workflow and you push the team to do the same.

Commercial instinct. You think about CAC, LTV, conversion, and unit economics as naturally as you think about UX.

Prototypes over PRDs. You'd rather show than tell. A working demo beats a 10-page spec, and you can produce either one when the situation calls for it.

High velocity. You optimize for shipping. You break work into small pieces, you ship something every week, and you iterate based on what users actually do.

Hands-on, not hands-off. You are still in the work. You write the spec, you draft the copy, you QA the build, you watch the user session.

What You Bring

5–10 years in product, ideally with at least one tour at an early-stage startup where you owned a meaningful surface end-to-end. Bonus points for fintech, wealth management, or anything advisor-adjacent.

Demonstrated AI fluency. You have shipped AI-powered features in production, not just prompted ChatGPT.

Strong design and engineering taste. You can sit with a designer and an engineer as a peer, not just a stakeholder.

Comfort with regulated environments. We operate as an SEC-registered investment advisor. You don't have to be a compliance expert, but you need to respect the guardrails and ship within them.

Nice to Have

Experience building tools used by financial advisors, RIAs, or any back-office operator.

A CFP, Series license, or genuine interest in personal finance and retirement.

Founder or founding-team experience.

A portfolio of side projects, prototypes, or products you've shipped on your own.

Why This Role

Direct line to the CEO and a real seat at the strategy table from day one.

A massive, underserved market — most retirees still don't have access to good advice, and AI is the unlock.

Greenfield: you will define the product function, the marketing function, and how AI shows up in both.

Leverage: every feature you ship reaches retirees who genuinely need it and advisors whose work you can make 10x better.

The Details

Location: On-site New York.

Compensation: $190K–$250K base + meaningful early-stage equity.

Reports to: CEO. Partners closely with the CTO.

Type: Full-time, individual contributor (for now — team-building comes next).