Product Manager

Company Description Smirk Health is building the AI-powered healthcare benefits infrastructure for the modern workforce. More than 90 million Americans — freelancers, part-time, seasonal workers, and 1099 contractors — either don't have health insurance or can't afford to use it. ACA marketplace plans exist, but when you're making $600/week, high deductibles can make you functionally uninsured. Traditional employer-tied healthcare was never built for this workforce. Our platform, anchored by the Smirk Wallet™ and Ailene™ AI care concierge, unifies coverage, payments, and care navigation into one intelligent, portable system delivered with radical clarity. We have the nation's largest collection of freelancers and Fortune 20 customers in the pipeline, Chubb as our carrier partner, and CHROs from Starbucks and McDonald's advising us. Seed-stage, post-product, post-traction, and accelerating — we're building the growth engine that will define a new category at the intersection of healthcare, AI, fintech, and the future of work. Role Description Full-time, remote-first role operating on Central Time. Works as peers with product, engineering, and marketing leaders from Lemonade, Venmo, and Instacart, and collaborates directly with the founders. As Product Manager, Growth at Smirk, you'll own the full funnel — from the moment someone discovers us to the moment they rely on their coverage. Your job is to remove friction, run experiments, and move the metrics that get more people covered and keep them covered. Seed-stage means real ownership, ambiguity, speed, and execution, with outcomes prioritized over optics. What You'll Own Acquisition, activation, and retention across the Smirk product — identify where people drop off and ship the changes that fix it A rigorous experimentation program: form hypotheses, design tests, read the data, and make the call — building a culture where we learn in days, not quarters The funnel metrics that matter — conversion, activation rate, retention, CAC, LTV — using them to find the biggest levers and prioritize what ships next Onboarding optimization, so people go from "interested" to "covered" with as little friction as possible Lifecycle strategies — re-engagement, habit formation, and upsell — that keep members active and confident in their coverage Direct collaboration with the founders to shape what we build and why Shipping quickly, learning quickly, and keeping the loop tight Qualifications 7+ years of product management experience, with meaningful time in growth, lifecycle, or PLG roles at a consumer company Proven track record improving acquisition, activation, and retention through experimentation — not just launching features, but moving metrics Built 0→1 products that shipped to real users and scaled, or led major growth initiatives with measurable impact Strength in consumer-facing products that simplify complex decisions — healthcare, fintech, insurance, or marketplaces Fluent in funnel analytics, A/B testing, and experimentation platforms Comfortable across both B2C and B2B2C growth motions Strong grasp of growth metrics (CAC, LTV, conversion, retention, payback) and the ability to translate data into a prioritized roadmap Build and ship with AI-native workflows Strong judgment about which details matter most, and the ability to make sharp tradeoffs with limited resources and tight timelines Default to experimentation over debate — run the test, read the data, make the call Strong taste paired with humility, and genuine care for the people on the other side of the screen Clear communicator across engineering, design, marketing, and executive audiences Able to work on Central Time Bonus Points Healthtech, insurtech, fintech, marketplace, or embedded distribution experience Familiarity with portable benefits, ICHRA, or nontraditional workforce models Seed or Series A startup experience Hands-on experience building onboarding flows, activation loops, or PLG systems Experience scaling growth inside regulated or multi-stakeholder ecosystems Compensation & Benefits Competitive base salary Meaningful early-stage equity with significant upside Health coverage through Smirk Health 401(k) Flexible PTO How to Apply Send your resume and a brief note to [email protected]. No formal cover letter required. Tell us: A growth experiment or funnel improvement you're most proud of — what you tested, what you learned, and what moved Why improving healthcare access for the modern workforce matters to you We read everything. Smirk Health is an equal opportunity employer committed to building a diverse and inclusive team reflective of the workforce we serve.