Boldin delivers a collaborative financial planning solution to consumers, enterprises, and financial advisors with innovative software, embedded digital coaching, and educational content. @boldin
Based on AI technology, the comprehensive planning and modeling engine considers thousands of scenarios, enabling individuals to do holistic accumulation and decumulation planning at scale. The solution provides strategic outreach to plan participants that improves employee satisfaction for plan sponsors (employers) and enables financial service organizations to better retain assets and drive revenue. The NewRetirement platform was voted best retirement solution by both Forbes and the American Association of Individual Investors (AAII).
At Boldin, we believe financial confidence should be accessible to everyone. Money decisions shape our lives, yet too often people are left without the clarity or tools they need to make informed choices. We exist to change that.
Boldin is a comprehensive financial planning platform that helps people understand their financial picture, make smarter decisions with their money and time, and plan for the future with confidence.
With over $20M raised and strong momentum, Boldin is entering a pivotal phase of growth. This is an opportunity to join a mission-driven team and help shape the future.
About This Role
We are hiring a Senior Product Manager to own retention and engagement for PlannerPlus, our subscription product. Acquisition brings people to Boldin; you make sure they stay, return, and keep getting value for years — because their plan keeps getting better and their confidence keeps growing.
Your mandate is bigger than reducing churn. Today, Boldin is the best DIY financial planning tool on the market, and our most engaged users are planning enthusiasts. The next chapter is bringing CFP-level capabilities to everyone: making sophisticated planning so delightful and approachable that a much wider market can build, trust, and act on a real financial plan.
You will own the experience that makes that possible — from the moments a subscriber feels clarity, confidence, or relief, to the habits that bring them back, to the depth that keeps them for a decade. This is a senior, high-accountability role with real ambiguity. You won’t inherit a perfectly scoped roadmap; you will form a strong point of view from customers and data, hold it firmly until something better comes along, and move without waiting for certainty that isn’t coming.
Key Responsibilities
- Own retention end-to-end. Define the retention metrics that matter, understand why subscribers stay and why they leave, and fix root causes — in the product, not just the cancellation flow. Ensure growth upstream translates into customers who are durably better off, not top-line gains lost to churn.
- Drive meaningful engagement. Identify the engagement signals that actually predict long-term retention, then design toward them. Build the rituals and return moments — plan check-ins, life-event updates, progress milestones — that make Boldin a habit, not a one-time exercise.
- Bring CFP capabilities to everyone. Partner with Design, Engineering, and our financial planning experts to translate professional-grade planning (tax strategy, drawdown, Roth conversions, insurance, estate basics) into experiences everyday people can understand and act on — without dumbing down the modeling that makes Boldin trustworthy.
- Broaden the market through delight. Make the planning experience approachable for people who would never call themselves “planners,” while preserving the depth our power users love. Balance education, friction, and simplicity thoughtfully.
- Run customer-driven discovery. Spend real time with customers — many of them older than you, at emotional moments in their financial lives. Synthesize qualitative insight with quantitative signal, and turn it into focused bets with clear success criteria.
- Be rigorous about measurement. Run experiments that answer important questions, not just easy ones. Use cohort, funnel, and lifecycle analysis to sharpen judgment — not outsource it.
- Tell the story. Bring executives, Design, Engineering, Marketing, and Data along with a clear narrative of ongoing subscriber value. Raise the bar for how the whole organization thinks about retention, engagement, and customer outcomes.
KPIS + Targets
- Trial Cancels
- Subscriber Churn
- Engagement Metrics (DAU/WAU/MAU)
Qualifications
- 5–8+ years of B2C product management experience with clear ownership of retention, engagement, or lifecycle outcomes, preferably in personal finance
- Experience with subscription products and a deep understanding of subscription economics
- Good product sense, strong point of view, low ego — you form opinions from customers, data, and experience, and engage in direct, respectful debate to get to the best answer, not to win
- Highly competent and self-directing — you know what to do without being asked and own your domain
- Data and analytical rigor: fluent in cohort, funnel, and experiment analysis; comfortable making hard calls with imperfect information
- A good storyteller and a highly collaborative partner across Design, Engineering, Data, and executives
- High empathy for people unlike you — in this cause most likely people older than you; you understand financial decisions are emotional and human, not just analytical
- Genuine passion for personal finance and our market
- Soul for startup culture: you thrive in ambiguity and deliver high output without sacrificing quality
Preferred: experience making complex or expert-domain products accessible to mainstream audiences; background in fintech or alongside CFPs/advisors; fluency with modern AI tools
Salary
$150,000 - $178,000 DOE
We want to be as inclusive as possible in our hiring process. If you don’t have 100% of what we’re looking for, but feel like you’re pretty close to growing into the role — please still apply. If a candidate has only 80% of the skills but a fantastic attitude and perspective, they might be the perfect fit.
Boldin values the unique perspectives and contributions of all individuals and we strive to foster a diverse and inclusive culture. We encourage applications from individuals of all backgrounds, including and not limited to people of any race, ethnicity, or national origin, individuals with differing abilities, members of the LGBTQ+ community, veterans, gender minorities, women and people from underrepresented communities.We are committed to providing reasonable accommodations for applicants with differing abilities throughout the recruitment process. If you require any accommodations, please let us know, and we will work with you to meet your needs. We are committed to fostering an environment where everyone can bring their authentic selves to work. If you are comfortable doing so we invite you to share your preferred pronouns in your application.
