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Salary: USD 190,000 - 250,000 / annual
Retirable is a mission-driven fintech based in New York that democratizes retirement planning and wealth management for everyday Americans aged 55+. The company addresses a critical market gap: 12,000 Americans retire daily, yet fewer than 25% have ever consulted a financial planning professional. Retirable bridges this gap by combining professional retirement advice, wealth management, and banking services to help underserved retirees build confidence in their financial futures.
As Head of Product, you will own the complete product roadmap and strategy, reporting directly to the CEO. This is a hands-on, player-coach role where you will define what the company builds, why, and in what order. You will translate Retirable's mission into a sequenced set of product bets focused on retention, advisor leverage, and AUM growth.
Key responsibilities include: (1) Product strategy & roadmap—defining the product vision and sequencing bets that move core metrics; (2) AI integration—leading the deployment of AI across the client experience and advisor/retirement/investment back office to streamline workflows and automate non-human tasks; (3) Engineering leverage—helping the engineering team 2x output without proportional headcount growth through AI-first development practices and tight feedback loops; (4) Hands-on shipping—prototyping features, working closely with engineering to ship, and writing launch communications.
You will build a product team over time, but initially you are the team. You are expected to write specs, draft copy, QA builds, and review user sessions. The role demands an AI-first mindset—you use AI daily in your own workflow and push the team to adopt it. You balance product thinking with commercial instinct, understanding CAC, LTV, conversion, and unit economics. You favor working prototypes over lengthy PRDs and optimize for weekly shipping cycles.
Required experience: 5–10 years in product management, ideally including at least one early-stage startup role where you owned a meaningful product surface end-to-end. Demonstrated AI fluency with shipped AI-powered features in production (not just ChatGPT prompting). Strong design and engineering taste to collaborate as a peer with both disciplines. Comfort operating in regulated environments—you don't need to be a compliance expert, but you must respect SEC guardrails and ship within them.
Bonus qualifications: experience building tools for financial advisors, RIAs, or back-office operators; CFP, Series license, or genuine personal finance/retirement knowledge; founder or founding-team experience; a portfolio of side projects or self-shipped products.
The opportunity is significant: direct access to the CEO and a seat at the strategy table from day one; a massive, underserved market where AI unlocks advisor productivity and client access; greenfield scope to define the product function, marketing function, and AI's role in both; and leverage—every feature you ship reaches retirees who need it and advisors whose work you can make 10x more effective.
