Head of Retention

Polymarket is the world's largest prediction market, where millions of people trade on real-world outcomes across politics, economics, sports, and culture. The platform processed over 21 billion dollars in trading volume in 2025 and is rapidly becoming a trusted alternative news source globally. Built as a peer-to-peer marketplace with no house edge, Polymarket aggregates diverse opinions into transparent, market-based probabilities that reflect what people actually expect to happen next.

Polymarket operates in a competitive and rapidly growing space where retention has become a fundamental business challenge and company-level priority. The prediction market category is gaining mainstream adoption, and the company is scaling its operations to capture this momentum. Like many high-growth platforms in fintech and trading, Polymarket faces the challenge of converting one-time users into long-term active participants—and that gap is exactly where this role focuses.

You will be hired as Head of Retention to build and lead a retention organization from the ground up. This is a leadership role where you own the entire function, including lifecycle management, CRM operations, retention analytics, and incentive strategy. You will design the team structure, make hiring decisions, and establish the operating model. There is no existing playbook; you will create it. Your work will sit at the executive level, influencing product roadmaps and company scorecards directly.

What you'll do

• Design and build the retention organization from early stage into a complete function, determining hiring timelines, what to build internally, and what to source from external partners.

• Own active-trader retention metrics at 30, 90, and 180-day intervals and lifetime value growth as company KPIs, reporting directly to the CEO and executive leadership on cohort performance, churn signals, and incentive return on investment.

• Develop and defend the retention incentive budget with Finance, using incrementality testing to make evidence-based decisions on spend allocation and ROI.

• Coordinate Markets, Growth, Product, and Brand teams around retention strategy for major event moments like elections, playoffs, and cryptocurrency moves, ensuring acquisition and retention align.

• Secure Engineering and Data roadmap commitments for retention infrastructure, including tools like Braze, Customer.io, and Amplitude, along with triggers and data pipelines the team needs.

• Establish company-wide messaging rules covering frequency caps and channel priority to balance retention efforts with user experience and competitive demands for attention.

• Partner with Legal and Compliance to establish retention guardrails around CFTC regulations, state eligibility requirements, and contact permissions.

What you'll bring

• A minimum of 10 years working in retention, lifecycle management, or CRM, with at least 5 years in team leadership and direct experience managing managers.

• Proven track record building or scaling a retention organization at a high-churn consumer business in sports betting, fintech, streaming, or comparable categories.

• Experience owning retention or incentive budgets with full ROI accountability, including presenting incrementality study results to Finance and executive teams.

• Strong analytical capability to challenge models, design incrementality tests, and communicate results clearly to non-technical audiences.

• Experience influencing C-suite strategy on retention, beyond simply reporting metrics.

• Background working in regulated industries with knowledge of compliance constraints on user communications and promotional activities.

• Genuine interest in markets, sports, politics, or cryptocurrency, since the product is event-driven and success requires deep engagement with trader interests.

Nice to have

• Direct experience in sports betting or prediction markets, with understanding of bettor churn patterns and re-engagement drivers.

• Operating experience in CFTC-regulated or similarly regulated environments.

What they offer

• Competitive salary and equity package.

• Unlimited paid time off.

• Comprehensive health, vision, and dental coverage.

• 401k matching.

• Hardware setup including MacBook Pro, display, and accessories.