Director / Senior Director, CRM & Lifecycle Marketing

Fliff unpacks sports gaming into social, free-to-play games for all types of sports fans. We've built a social sports gaming experience that allows users to compete for leaderboard positioning, to achieve badges and build their status within the game.

We are pioneering play-for-fun sports gaming, with our flagship social sportsbook experience that includes sweepstakes promotions and loyalty rewards. We provide sports fans with fun, engaging, and free-to-play alternatives to real money gaming.

Fliff is redefining the sports gaming experience by blending the fun of social play with the thrill of real-money competition. What began as a pioneering social sportsbook has evolved into a multi-vertical platform that is the fastest growing brand in sports gaming. As we continue to expand, we’re building a world-class ecosystem of sports gaming experiences that span social, sweepstakes, and real-money formats — giving every type of fan a way to play, compete, and connect.

The Role:

We’re looking for a top-tier CRM & Lifecycle leader with deep real-money gaming / gambling experience to own how we keep players active, engaged, and coming back to Fliff.

This person will:

Build and lead our CRM function end-to-end — from strategy to hands-on execution — across email, push, in-app, and other owned channels.

Leverage cutting-edge data, segmentation, and experimentation tools to maximize retention, frequency, and LTV.

Bring a deep understanding of iGaming / sports betting / casino user behavior, regulation-aware messaging, and VIP/rewards dynamics.

You’ll partner closely with Product, Data, Acquisition and Growth, and Creative to build an ecosystem of always-on programs, experiments, and personalized experiences across millions of sports fans.

• Strategy & Ownership
• Own the CRM & retention strategy across the full player lifecycle: acquisition handoff, onboarding, activation, engagement, VIP development, reactivation, and win-back.
• Define north star and operational metrics for lifecycle (D1/D7/D30 retention, WAU/MAU, session and pick frequency, ARPU, churn, reactivation rates, LTV).
• Build a clear program roadmap balancing always-on journeys, sport-seasonality (NFL, NBA, MLB, etc.) and big tentpole / marquee events.

• Lifecycle Programs & Campaigns
• Design, launch, and optimize lifecycle flows including:
• New user onboarding & education (how Fliff works, dual currency, rewards, risk & responsible play messaging).
• Activation drives to get first deposit-equivalent / first pick / first parlay / first streak.
• Daily/weekly engagement programs (missions, streaks, challenges, leaderboards, promotions).
• VIP & loyalty programs: tiers, benefits, bonus structures, and personal concierge-style communications.
• Churn prevention and win-back for lapsed and at-risk players, with clear incrementality and control groups.
• Build sports-calendar-driven CRM (game days, playoffs, tournaments, tentpole events) that feels native to how real bettors/fans watch and sweat games.
• Develop triggered and behavioral messaging based on actions like first pick, bet size milestones, big win/loss, risk patterns, and abandoned betslip/pickbuilder moments (where applicable).

• Advanced Data, Segmentation & Tooling
• Own the segmentation strategy:
• Value tiers (VIP, high-value, mid, casual)
• Product preferences (sport, market type, pick formats)
• Lifecycle stage & cohort
• Risk indicators and bonus sensitivity
• Partner with Data Analytics to:
• Build and activate predictive models (churn risk, value propensity, reactivation likelihood, bonus abusers, etc.).
• Translate them into live segments and CRM treatments.
• Use modern tools to operationalize segmentation and personalization, such as:
• Custom Data Platforms
• Data warehouse 
• Analytics platforms (e.g.,Mixpanel)
• Establish a rigorous testing culture (A/B, multivariate, incrementality testing, holdouts) across offers, creative, cadence, and channels, and publish clear learnings.

• Channel & Technology Management
• Own day-to-day execution in our CRM platform (e.g., Optimove):
• Journey and canvas design
• Trigger and event setup
• Templates, personalization, and dynamic content
• Real-time messaging (game starts, live sweat, results)
• Drive channel best practices for a real-money gaming context:
• Deliverability & list hygiene
• Frequency caps and fatigue management
• Preference centers and responsible communication
• Ensure best-in-class creative in partnership with design/content:
• Strong hooks and urgency
• Clear offer / promo explanations
• Compliance-friendly copy that still feels fun and native to sports bettors.

• Real-Money Gaming Context, Compliance & Risk
• Work with Legal, Compliance, and Operations to:
• Ensure all lifecycle communications align with real-money gaming / sweepstakes regulations, age gating, state-level nuances, and responsible gaming guidelines.
• Help define VIP and high-value treatment strategies that balance LTV growth with responsible play.

• Cross-Functional Leadership
• Partner with:
• Acquisition / Growth to ensure downstream retention performance is built into acquisition strategies and creative.
• Product & UX to align in-app surfaces (modals, inboxes, banners) with CRM journeys.
• Data on dashboards, cohorting, and experiment readouts.
• Build and lead a small but highly capable CRM & retention team (managers, ops specialists, analysts) as the function scales.

• Within 12–18 months, success looks like:
• Significant lift in early-life retention (D7/D30), WAU/MAU, and pick frequency per active user.
• Improved activation funnel from install → account creation → first real-money-style pick behavior.
• Measurable incremental uplift in LTV through lifecycle and VIP programs, validated with proper control and holdout frameworks.
• A clear testing and learning framework with a constantly prioritized backlog and published learnings.
• Fliff’s CRM function is seen internally as a core profit and LTV engine, not just the team that sends emails and push notifications.

• Must-Haves:
• 10+ years in B2C CRM / Lifecycle / Retention marketing as a leader and builder of departments, with at least 4–5 years owning strategy at Director+ level.
• Deep experience in real-money gaming / gambling (sports betting, iGaming, gambling, casino, social casino, DFS, or closely related categories) with a clear understanding of:
• Player behavior and motivations
• Bonus/offer mechanics
• VIP dynamics and lifetime value
• Regulatory and responsible gaming constraints in communication
• Hands-on experience with modern CRM platforms (Optimove) plus data tooling:
• CDP + data warehouse + reverse ETL
• Event-driven segmentation
• Real-time and batch campaigns
• Proven track record driving retention and LTV through:
• Sophisticated segmentation
• Triggered journeys
• Structured experimentation
• Strong analytical chops:
• Cohort analysis, incrementality, and experiment design
• Ability to partner with Data/DS and work from SQL / BI dashboards.
• Ability to operate at two altitudes:
• Set vision and roadmap
• Go hands-on to ship campaigns, troubleshoot data flows, and iterate quickly.
• Excellent communication and storytelling skills, especially with non-CRM stakeholders and execs.
• Genuine passion for sports and sports betting culture; you “get” how bettors think, talk, and engage.

• Experience launching or scaling CRM programs in multi-state or multi-jurisdiction environments.
• Prior ownership of VIP, loyalty, or rewards programs within gaming or real-money-like products.
• Experience leading small, senior-heavy CRM teams and influencing broader orgs (Product, Creative, Ops).

• Competitive compensation package, including base salary, benefits, and equity.
•  Unlimited/flexible paid time off.
•  Medical, dental, vision, and generous parental leave.
•  Employee-sponsored 401(k).

• $500 work-from-home stipend + equipment.
• Fully remote work environment.
• Professional development opportunities.
• High-ownership, collaborative culture.

#LI-Remote

We are a multinational company with our headquarters based in Philadelphia, and offices in New York, Austin, and Sofia, Bulgaria. Wherever we are in the world, we pride ourselves on being a close-knit, focused team that is welcoming and friendly, and the work that we do is always interesting and rewarding. Wherever we are in the world, we pride ourselves on being a close-knit, focused team that is:

Welcoming and Friendly

We want to reflect the diversity of the cities we serve. By creating an inclusive culture where everyone can thrive, we’ll make Fliff better for employees and customers alike.

Lively and Creative

We respect and value each other’s ideas, experience and expertise. There is no such thing as a bad idea; only ideas that are executed and ideas that are discarded after consideration.

Stimulating and Rewarding

We know bright minds love a challenge, and we understand your desire to see your hard work pay off. We’ll make sure your daily tasks align with your career ambitions as we grow together.

Equal Employment Opportunity Statement

Fliff is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Join Our Team!

If you're ready to be part of an exciting, innovative, and dynamic team, apply now to help shape the future of sports gaming with Fliff.

IMPORTANT NOTICE: The privacy and security of applicant information is paramount and we take fraud attempts very seriously. Please note that Fliff will never ask for payment or personal financial information during the application process. All of our legitimate job opportunities can be found on our official career site (https://www.getfliff.com/careers). Please be cautious of communications and links that come from non-company email addresses (@getfliff.com), social media messaging platforms or unsolicited phone calls.