Head of Retention

About the Role

Polymarket is the world's largest prediction market, and retention is one of the most important unsolved problems in the business. Traders come in for elections, crypto moves, and playoff runs, then go quiet. The gap between a one-time depositor and an active, long-term trader is where this role lives. You will build and lead the team that closes it.

The retention org today is early. You will design the structure, make the hiring calls, and build the operating model from the ground up, including lifecycle, CRM operations, retention analytics, and incentives. You will manage through managers, own the incentive P&L with Finance, and be the voice of the retained trader in executive forums. This is not a role for someone who wants to inherit a playbook. The playbook does not exist yet.

This hire matters because retention is now a company-level priority, not a marketing function. Active-trader retention and LTV are going into the company scorecard. The person in this role will sit in leadership reviews, shape product roadmaps, and make the call on where incentive dollars go. If you have built a retention org at a high-churn consumer business, know how to run incrementality tests, and want to work on a product that is genuinely hard to retain users on, this is the job.

What You'll Do

• Build the retention organization from an early-stage team into a full function, including lifecycle, CRM operations, analytics, and incentives, and make the calls on when to hire, what to build in-house, and what to bring in from partners.
• Own active-trader retention at 30, 90, and 180 days and LTV growth as company-level KPIs, and report cohort performance, churn signals, and incentive ROI directly to the CEO and exec team.
• Set and defend the retention incentive budget with Finance, using incrementality data to make the hard calls on when spend is and is not worth it.
• Align Markets, Growth, Product, and Brand around a single coordinated plan for major event moments, including elections, playoffs, and crypto events, so acquisition and retention move together.
• Negotiate roadmap commitments from Engineering and Data for the triggers, tooling, and data infrastructure the retention team needs to operate, including Braze, Customer.io and Amplitude.
• Own messaging rules across the company, including frequency caps and channel priority, to resolve competing demands for user attention and protect the trader experience.
• Work with Legal and Compliance as a peer to set retention guardrails covering CFTC rules, state eligibility, and contact permissions, so the team can move fast inside clear limits.

What We're Looking for

• 10 or more years in retention, lifecycle, or CRM, with at least 5 years leading teams and direct experience managing managers.
• A track record of building or scaling a retention org at a high-churn consumer business, in sports betting, fintech, streaming, or a comparable category.
• Experience owning an incentive or retention budget with full ROI accountability, including presenting incrementality results to Finance and executive leadership.
• Strong analytical judgment: you can challenge a model, design or read an incrementality test, and explain the results clearly to people who are not specialists.
• Experience presenting to and influencing a C-suite on retention strategy, not just reporting metrics.
• Experience leading in a regulated industry, with working knowledge of compliance constraints on user communications and promotions.
• Genuine interest in markets, sports, politics, or crypto, because the product is event-driven and the team needs to care about what traders care about.
• (Plus) Direct background in sports betting or prediction markets, with familiarity with how bettors churn and what actually brings them back.
• (Plus) Experience operating in a CFTC-regulated or similarly regulated environment.

Benefits

• Competitive salary & equity
• Unlimited PTO
• Full Health, Vision, & Dental coverage
• 401k match
• Hardware setup: new MacBook Pro, big display, & accessories