← PeakHealth / Product Manager
candidate_questions / art_WTHTMdEiJ-0
Interviewer
Stephanie Tilenius is the CEO and Founder of Peak Health, having launched the company in January 2025. She brings an extraordinary pedigree: co-founded PlanetRx (IPO'd in 1999), founded and ran Vida Health for 12 years, held VP/SVP roles at PayPal and eBay, and served as VP of Commerce and Payments at Google where she built Google Wallet, Google Offers, and Google Shopping Express from scratch. She is also a Venture Advisor at AI Fund and sits on multiple public and private boards. As the founder and CEO conducting this interview, she will likely probe deeply on 0-to-1 product instincts, consumer product taste, AI-forward thinking, and cultural fit. Shared context with the candidate includes consumer product at scale, marketplace/platform thinking, and a shared thread of building AI-powered products from the ground up.
Questions to ask them (20)
| category | question | why |
|---|---|---|
| interviewer_experience | You built Vida Health over 12 years and now you're founding Peak Health — what did you learn from that journey that's most directly shaping how you're architecting Peak Health's product from day one? | Shows deep research into her background, invites her to share hard-won lessons, and signals you're thinking about institutional learning rather than just the shiny new thing. |
| interviewer_experience | At Google you built Google Wallet and Google Offers essentially from scratch inside a large organization — how does that 0-to-1 experience inside a big platform inform the way you think about building a consumer health product at a startup where the constraints are totally different? | Anchors in a specific chapter of her career, demonstrates you've read her profile carefully, and surfaces her philosophy on 0-to-1 product development — directly relevant to the role. |
| interviewer_experience | PlanetRx was an online pharmacy that IPO'd in 1999 — decades before digital health was mainstream. What's different about the consumer readiness and regulatory environment now that makes you confident the timing is right for Peak Health's integrated longevity care model? | Connects her earliest founding experience to the current venture, shows historical awareness, and opens a rich strategic conversation about market timing. |
| role_team_dynamics | What does success look like for this PM role at 30, 60, and 90 days — and what's the single most important thing you'd want this person to have shipped or decided by the end of month three? | Classic but essential signal-gathering on expectations, pace, and what 'good' looks like early — critical for evaluating fit and setting yourself up to succeed. |
| role_team_dynamics | The JD mentions owning both consumer product vision and AI automation systems for physicians — how are those two workstreams currently staffed and balanced, and is the expectation that one PM owns both indefinitely or that this role seeds a future team? | Surfaces scope clarity, hiring roadmap, and whether this is a 'do everything' IC role or a seed for a product org — critical for workload and career planning. |
| role_team_dynamics | How does the PM role interface with the clinical team day-to-day — is the Chief Longevity Officer or Founding Medical Director directly in the product loop on feature decisions, or does clinical input flow through a defined process? | Healthcare PM roles live or die on the clinical-product interface. Understanding the actual workflow reveals how much of the job is stakeholder navigation versus pure product execution. |
| role_team_dynamics | What's the biggest product challenge the team is wrestling with right now that this hire would be expected to step into immediately? | Cuts through the polished JD to understand the real, messy problem — and signals you're not afraid of hard problems. |
| technical_environment | The JD calls out familiarity with EMR platforms specifically — which EMR or EHR is Peak Health built on or integrated with today, and how much of the PM role involves working within that system's constraints versus building around or on top of it? | EMR integration is a major technical and regulatory constraint in digital health. Understanding the stack signals technical depth and helps assess the real scope of the role. |
| technical_environment | Where is the AI layer in the product today — is it primarily in the care workflow for physicians, in the consumer-facing experience, or both — and what's the current tooling stack the engineering team is using to build and iterate on those AI features? | The JD emphasizes AI-forward product ownership. Understanding where AI actually lives today versus where it's aspirational is critical for scoping the real work. |
| technical_environment | How does the team currently handle rapid experimentation — A/B testing, feature flags, analytics — and is there existing infrastructure for that or is building that infrastructure part of what this PM would own? | The JD explicitly calls out A/B testing and data diving. Knowing whether the tooling exists or needs to be built changes the nature of the role significantly. |
| culture_working_style | You've led large organizations at eBay and Google and also founded companies — how would you describe the decision-making culture you're building at Peak Health, particularly around how much autonomy a PM has to make calls versus bringing you into the loop? | Founder-led companies can range from highly autonomous to founder-bottlenecked. Understanding her operating style is essential for evaluating day-to-day working conditions. |
| culture_working_style | When the clinical team and the product team disagree on a feature direction — which will inevitably happen — how does Peak Health resolve that tension? | Healthcare product management uniquely requires navigating clinical authority. Understanding the conflict resolution model reveals organizational maturity and potential friction points. |
| culture_working_style | What does the team's current cadence look like — sprint cycles, product reviews, how often you're in the product details as CEO — and how do you see that evolving as the company scales? | Signals how hands-on Stephanie is as a product CEO (which, given her background, is likely very hands-on) and helps the candidate understand the real working rhythm. |
| growth_development | You've scaled from IC contributor to SVP to founder multiple times across your career — for a PM who joins Peak Health at this stage, what's the realistic growth path if they execute well, and how do you think about building a product org around this initial hire? | Anchors the question in her own career trajectory, signals ambition without desperation, and gathers real information about upside. |
| growth_development | Given that you're also a Venture Advisor at AI Fund, are there opportunities for the product team to engage with that broader AI ecosystem — whether through exposure to other AI companies, research, or tooling partnerships? | Shows awareness of her full portfolio, signals intellectual curiosity about AI, and surfaces a potentially unique development opportunity that wouldn't exist at most companies. |
| strategy_vision | The positioning is 'longevity AI services and platform' — how do you think about the platform play long-term? Is the vision to be a direct-to-consumer care brand, an underlying platform others build on, or both? | Platform versus product is a fundamental strategic question that shapes everything about the PM role. Understanding the long-term architecture vision is critical. |
| strategy_vision | The JD mentions peptides, diagnostics, Rx, and integrated care — that's a broad surface area. What's the sequencing logic for what gets built first, and how do you think about the product bets that will define Peak Health's first two years? | Surfaces prioritization philosophy and strategic clarity — and tests whether there's a coherent roadmap or a wide-open greenfield that could become chaotic. |
| strategy_vision | Rebuilding U.S. healthcare from sick care to preventive care is a massive mission — what's the specific wedge that Peak Health is using to get consumers to change behavior, and how does the product reinforce that behavior change over time? | Behavior change is the hardest problem in consumer health. This question signals product sophistication and opens a rich conversation about the core product thesis. |
| shared_context | I've been building AI-powered consumer products across health, finance, and real estate at Streamio and Fintellect — one thing I've wrestled with is the tension between AI-generated personalization and the trust consumers need to act on health recommendations. How is Peak Health thinking about building that trust layer into the product experience? | Directly connects the candidate's own 0-to-1 AI product experience to Peak Health's core challenge, demonstrates genuine domain thinking, and invites a peer-level strategic conversation. |
| shared_context | You built PayPal Merchant Services from zero to a multi-billion dollar business by deeply understanding the merchant's workflow — I'm curious whether you're applying a similar 'understand the physician's workflow first' lens to how Peak Health is designing the care-side product experience for doctors and clinicians. | Draws a specific parallel between her PayPal operator-side experience and the physician-side product challenge at Peak Health, showing you've connected dots across her career in a way most candidates won't. |
Conversation starters
- I went deep on your PlanetRx story — co-founding an online pharmacy that IPO'd in 1999 is remarkable, especially given how early that was for digital health. I'd love to hear how that experience shaped your conviction about what Peak Health could become.
- I noticed you've been on the Seagate board for over 12 years while simultaneously founding and running Vida Health — that's an unusual combination of deep operator and board-level governance experience. I'm curious how wearing both hats has shaped how you think about building companies.
- I built a multi-agent AI orchestration framework at Streamio that coordinates workflows across health, insurance, real estate, and financial markets — so I've been living the 'AI-forward product' challenge you're describing at Peak Health. I'd love to compare notes on where AI actually moves the needle in consumer health versus where it's still more hype than reality.
⚠ Handle carefully
- Vida Health's 12-year run ending in December 2025 — it's unclear whether that was a wind-down, acquisition, or pivot into Peak Health. Avoid implying it was a failure or asking directly why it ended; let her characterize it if she brings it up.
- The breadth of the role (consumer product vision + AI automation + physician tools + PRDs + data + design) could signal an under-resourced team or unclear scope — probe this carefully through the 30/60/90 and team structure questions rather than directly challenging whether the role is scoped reasonably for one person.
- Stephanie is clearly a very hands-on product CEO given her background — avoid any framing that implies you'd want significant autonomy from founder oversight early on, as that could read as a red flag to a founder who will likely want to be deeply involved in product decisions at this stage.