Head of VIP & Loyalty

Location: Remote (North America Preferred)

Reports To: General Manager, The Boss

About The Boss

The Boss is a fast-growing online gaming company redefining how players engage with casino entertainment. We combine a world-class game portfolio, data-driven decision making, innovative player experiences, and a relentless focus on customer satisfaction to build a differentiated gaming platform for North America.

Having recently completed a major rebrand and entered a new phase of growth, we are expanding our leadership team, investing in product and technology, and building the operational foundation required to scale responsibly. This is an opportunity to join early, make a meaningful impact, and help shape the future of the business.

The Opportunity

The Head of VIP & Loyalty will be responsible for developing and scaling The Boss's VIP, loyalty, and high-value player strategy.

Reporting directly to the General Manager, this role owns the retention, engagement, and long-term value of our most important players. You will lead VIP strategy, loyalty development, player segmentation, reinvestment frameworks, and personalized player experiences that strengthen relationships and maximize lifetime value.

This role requires a balance of hospitality, commercial acumen, analytics, and player-first thinking.

Success is measured not simply by player activity, but by retention, profitability, player satisfaction, and long-term loyalty.

Key ResponsibilitiesVIP Strategy & Player Value

• Own the VIP strategy and player lifecycle for high-value players.
• Develop segmentation frameworks that identify emerging and high-potential VIPs.
• Create personalized experiences that strengthen engagement, retention, and loyalty.
• Monitor player value, profitability, and long-term retention.

Loyalty & Retention Programs

• Partner with Product and CRM teams to evolve loyalty, rewards, and engagement programs.
• Develop benefits, experiences, and promotional frameworks that drive long-term player value.
• Identify opportunities to improve retention, purchasing behavior, and loyalty participation.
• Ensure loyalty investments generate measurable business impact.

VIP Operations & Reinvestment

• Establish reinvestment frameworks and player treatment guidelines.
• Evaluate offer effectiveness, promotional efficiency, and player profitability.
• Balance player experience with responsible commercial decision-making.
• Develop processes that support a scalable VIP operation.

Player Experience & Relationship Management

• Champion exceptional service for VIP and high-value players.
• Establish standards for communication, responsiveness, and personalized engagement.
• Monitor player feedback and identify opportunities to improve satisfaction and loyalty.
• Partner with Customer Support, Payments, Risk, and Product teams to remove friction from key player journeys.

Leadership

• Lead and develop the VIP team.
• Establish goals, performance standards, and operating processes.
• Partner closely with CRM, Product, Analytics, and Casino Operations teams.
• Serve as a key member of the leadership team and advocate for the voice of the player.

Success in the First 12 Months

• Improve VIP retention and long-term player value.
• Establish a scalable VIP and loyalty framework.
• Increase identification and development of emerging VIP players.
• Improve player satisfaction and engagement among high-value segments.
• Create measurable improvements in reinvestment efficiency and profitability.
• Become a key member of the leadership team and trusted advisor to the General Manager.

QualificationsRequired

• 5+ years of experience in VIP, loyalty, CRM, customer lifecycle, or player development roles.
• Strong understanding of player retention, engagement, and relationship management.
• Experience managing high-value customer segments.
• Strong analytical and commercial decision-making skills.
• Excellent communication and leadership capabilities.

Preferred

• Experience within Sweepstakes Casino, Online Casino, iGaming, Sports Betting, or Social Casino.
• Experience managing VIP hosts or player development teams.
• Experience with loyalty programs, CRM strategy, and player segmentation.
• Familiarity with player value models, reinvestment frameworks, and retention analytics.
• Experience operating in a high-growth environment.

Candidate Profile

You are a relationship builder, strategist, and player advocate. You understand how to balance hospitality and commercial performance, creating experiences that players value while supporting long-term business objectives.

Most importantly, you believe that loyalty is earned through exceptional experiences, thoughtful engagement, and a deep understanding of what players value most.