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.

Key Responsibilities:

• 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.

What Success Looks Like:

• 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.

Qualifications:

• 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.

Nice-to-Haves:

• 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).

Benefits:

• 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).

Perks:

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