← PeakHealth / Product Manager
candidate_questions / art_joRzI86aLXE
Interviewer
Stephanie Tilenius is the CEO and Founder of Peak Health, having launched the company in January 2025. She brings an extraordinary pedigree: VP of Commerce & Payments at Google (Google Wallet, Google Offers, Google Shopping Express), SVP/GM at eBay overseeing a major marketplace turnaround, GM of PayPal Merchant Services (scaled from zero to a multi-billion dollar business), and co-founder of PlanetRx — an online pharmacy that IPO'd in 1999. She also founded and ran Vida Health for 12 years, a digital health company, giving her deep firsthand experience in consumer health product-building. As CEO and interviewer, she will likely probe product vision, 0-to-1 execution instincts, AI fluency, consumer product taste, and healthcare domain understanding. Shared context with the candidate includes: both have founded and shipped consumer-facing AI products (Streamio/Fintellect vs. Vida Health/Peak Health), both have deep technical backgrounds paired with business/product leadership, and both have experience in health-adjacent domains.
Questions to ask them (20)
| category | question | why |
|---|---|---|
| interviewer_experience | You co-founded PlanetRx in 1998 — one of the earliest online pharmacy and disease management companies — and now you're building Peak Health. What did you learn from that first attempt at reimagining healthcare delivery that's directly shaping how you're architecting Peak Health today? | Demonstrates deep research into her career arc, invites reflection on hard-won lessons, and signals genuine curiosity about the company's strategic DNA — not just its current state. |
| interviewer_experience | You ran Vida Health for 12 years before founding Peak Health. What was the moment or insight that made you say 'the next company needs to be built differently' — and how does the longevity + AI angle represent a fundamentally different thesis than what you pursued at Vida? | Shows you've done the homework on her full journey and surfaces the strategic pivot logic — critical for understanding what Peak Health is actually optimizing for vs. prior attempts. |
| interviewer_experience | At Google you built Google Wallet and Google Offers from scratch, and at PayPal you scaled Merchant Services from zero to a multi-billion dollar business. When you think about applying that 0-to-1 consumer product muscle to healthcare, where do you find the biggest translation challenges — and where does it actually transfer cleanly? | Connects her Big Tech consumer product background to the healthcare context, surfaces her mental model for what's hard about this space, and positions the candidate as someone who thinks in frameworks. |
| role_team_dynamics | For this PM role, what does a genuinely successful first 90 days look like to you — not just ramp activities, but a concrete outcome or artifact that would make you say 'yes, this person gets it'? | Clarifies the real bar for early success and reveals whether the role needs immediate execution or a longer discovery phase — critical for evaluating fit and setting expectations. |
| role_team_dynamics | The JD mentions owning both consumer product vision and AI automation systems for care delivery — those can be two very different product muscles. How do you see those two workstreams being balanced right now, and is there one that's more urgent given where the company is? | Surfaces prioritization reality vs. the idealized JD, and signals that the candidate has read carefully enough to notice the potential tension between consumer UX and clinical/ops automation. |
| role_team_dynamics | How is the product team currently structured relative to engineering and clinical? Is this PM role expected to be the first dedicated PM, or are there others — and how does product decision-making flow between those functions today? | Reveals team maturity, whether this is a solo PM situation or a team, and how much political navigation will be required — all critical for evaluating the actual scope of the role. |
| role_team_dynamics | Given that your Chief Longevity Officer has a large public following and your Founding Medical Director comes from Peter Attia's practice, how does clinical opinion factor into product prioritization? When clinical instinct and product/data signals diverge, how does the team resolve that? | Healthcare PMs live or die by their ability to navigate clinical stakeholders. Understanding the power dynamics early is essential — and it shows the candidate is thinking about real execution challenges. |
| technical_environment | The JD emphasizes AI-forward product thinking and owning AI automation systems for care. What does the current AI stack look like — are you building on top of foundation model APIs, fine-tuning proprietary models, or something more bespoke — and where do you see the biggest technical leverage points for the PM to influence? | Signals genuine technical depth and helps the candidate understand whether the AI work is primarily integration/orchestration (like the candidate's multi-agent work at Streamio) or deeper model-level work. |
| technical_environment | For the EMR and clinical data layer, are you building on top of an existing platform like Elation or Canvas, or is there a proprietary clinical data model being developed? How much of the PM's work will involve navigating EMR constraints vs. greenfield product surface? | EMR integration is one of the most painful constraints in digital health product work. Understanding the architecture early signals domain sophistication and helps evaluate the actual complexity of the role. |
| technical_environment | The JD mentions prototyping with AI tools and running quick A/B tests. What does the current experimentation infrastructure look like — is there a feature flagging system, analytics pipeline, or is this something the PM would help build out from scratch? | Reveals the maturity of the data/experimentation stack, which directly affects how much time the PM will spend building infrastructure vs. running experiments — important for setting realistic expectations. |
| culture_working_style | You've led large organizations at eBay and Google and also co-founded companies — you've seen both ends of the autonomy spectrum. How would you describe the working style you're cultivating at Peak Health: how much latitude does a PM get to set direction vs. how much alignment with you and the CTO is expected before moving? | Directly surfaces the autonomy/alignment balance from the person who sets the culture — critical for a candidate evaluating whether this is a 'build and show' or 'align then build' environment. |
| culture_working_style | When a PM has a strong product conviction that conflicts with what engineering says is feasible or what the clinical team says is appropriate, what does healthy disagreement look like on your team — and can you give me an example of how that's played out recently? | Tests for psychological safety and reveals the actual conflict resolution culture — especially important in a company where clinical authority can easily override product judgment. |
| culture_working_style | Peak Health is still early-stage. How do you think about the balance between moving fast on consumer product iteration and the higher stakes of healthcare — where a bad experience isn't just churn, it's a patient outcome? | Surfaces the CEO's philosophy on velocity vs. rigor in a regulated, high-stakes domain — and signals that the candidate is thinking about the unique responsibility that comes with health products. |
| growth_development | You've written publicly about putting consumers in control of their healthcare — going back to your 2014 LinkedIn article. As someone who's been thinking about this problem for over a decade, what do you think is the most important thing a PM joining Peak Health today needs to learn or unlearn coming from outside healthcare? | References her published thinking to show genuine research, and invites mentorship-framing — revealing what she values in PM development and what blind spots she's watching for. |
| growth_development | For a PM who performs exceptionally well in this role, what does the growth path look like — is there a VP of Product or Head of Product role on the horizon, or is the expectation that this person grows into a broader leadership seat as the company scales? | Directly assesses career trajectory and whether the company has thought about PM leadership development — important for a candidate with 12+ years of experience evaluating long-term fit. |
| strategy_vision | The JD describes Peak Health as rebuilding the U.S. healthcare model from sick care to preventive care. In the near term — say the next 18 months — what are the two or three product bets that you believe will most define whether that vision is real or just positioning? | Forces specificity on strategy and reveals whether the CEO has a crisp product thesis or is still in discovery — critical for evaluating whether the role has clear direction or requires the PM to create it. |
| strategy_vision | Longevity as a category is getting crowded fast — Function Health, Hone, Lifeforce, and others are all competing for similar consumers. What's the moat you're building at Peak Health, and how does the AI layer specifically create defensibility that a well-funded competitor can't easily replicate? | Shows competitive awareness and pushes for strategic clarity on differentiation — a question a strong PM should be asking before joining, and one that signals the candidate thinks like a business owner. |
| strategy_vision | You're simultaneously a Venture Advisor at AI Fund and building Peak Health. How are you thinking about the intersection of those two roles — are there AI capabilities or partnerships coming out of AI Fund that could accelerate Peak Health's roadmap? | Surfaces a potentially important strategic resource that isn't publicly discussed, and shows the candidate has read the full profile carefully — could reveal partnership or technology advantages. |
| shared_context | I've been building multi-agent AI orchestration systems at Streamio — coordinating specialized agents across health, insurance, and financial domains — and I'm curious how you're thinking about agentic AI in the clinical workflow at Peak Health. Are you exploring agents that can act on behalf of physicians or patients, or is the current focus more on AI-assisted decision support? | Directly connects the candidate's hands-on multi-agent work to Peak Health's AI roadmap, establishes technical credibility, and opens a substantive product conversation with the CEO. |
| shared_context | PlanetRx was one of the earliest attempts to bring pharmacy and disease management online — and I've been thinking about similar distribution challenges building Fintellect and Streamio in regulated-adjacent spaces like finance and health. What do you think the regulatory and trust environment looks like for longevity care in 2025 vs. what you faced in 1999, and how is that shaping your go-to-market approach? | Creates genuine peer-level dialogue by connecting the candidate's own 0-to-1 experience in regulated consumer spaces to her founding story, while surfacing important go-to-market context. |
Conversation starters
- I went back and read your 2014 LinkedIn article — 'Tomorrow's Healthcare Puts Consumers in Control Like Amazon for Shopping' — and it struck me how much of what you wrote then is still the unsolved problem. I'd love to hear how your thinking has evolved from Vida to Peak Health.
- I noticed you co-founded PlanetRx back in 1998 — one of the first online pharmacies — which means you've been working on this consumer health access problem for over 25 years. That's a rare kind of conviction. I'm curious what keeps pulling you back to this space.
- I've been building multi-agent AI systems for health and financial workflows at Streamio, so when I saw Peak Health's AI-forward positioning I was genuinely excited — I'd love to compare notes on where you think agentic AI actually moves the needle in care delivery vs. where it's still mostly hype.
⚠ Handle carefully
- Vida Health's 12-year run ending in December 2025 — it's unclear whether the company wound down, was acquired, or is still operating. Avoid implying it was a failure or asking directly why it ended; if it comes up, frame it as 'lessons carried forward' rather than probing the outcome.
- The overlap between her Venture Advisor role at AI Fund and her CEO role at Peak Health — this dual role could imply divided attention or that Peak Health is partly an AI Fund portfolio experiment. Avoid framing questions in a way that implies distraction or conflict of interest; approach it as a potential strategic asset instead.
- Team size and funding stage — Peak Health launched in January 2025 and the team composition is not publicly detailed. Avoid questions that could expose skepticism about whether the company is sufficiently resourced; frame resource questions around prioritization and roadmap rather than headcount or runway.