Head of VIP & Loyalty

Arena Entertainment•Miami Beach, FL

13d

About The Position

Arena is a digital entertainment company building platforms people genuinely love and we build them differently. Since 2021, our portfolio has grown to include MetaWin, WOW Vegas, BetZoo Media, Hit.com, and Rolla, with further brands in development. Our teams operate across London, Malta, Gibraltar, and Miami. AI isn't something we bolt on it's the foundation we build from. We operate with an AI-first mindset across every function, using intelligent automation and modern technology to make faster, smarter decisions at every level of the business. We're not constrained by legacy systems. We're blue-sky thinkers, and our VIP operation is central to how we grow. This is a rare opportunity to own and shape the VIP and loyalty function across a fast-growing portfolio of social sweepstake casino brands. You'll inherit a small, established team and scale it building the people, processes, and programmes needed to deliver a world-class high-value player experience across WOW Vegas, Rolla, and beyond. This isn't a maintenance role. We're looking for a leader who brings genuine ambition, commercial sharpness, and a passion for building exceptional player relationships, someone who can operate strategically while staying close enough to the detail to drive real outcomes.

Requirements

Proven track record in a senior VIP management role within social sweepstake, iGaming, or a high-value consumer entertainment environment.
Demonstrated success across both VIP acquisition and retention, you're comfortable owning the full player lifecycle, not just one side of it.
Experience leading and developing a team, including hiring, performance management, and building a high-performance culture.
Strong commercial acumen, able to own a P&L, manage budgets, and make confident, data-driven decisions.
Proficiency in CRM platforms and player data tools, with an eye for process improvements that enhance personalisation and operational efficiency.
Exceptional interpersonal and communication skills, able to build genuine, lasting relationships with demanding high-value players while operating effectively across internal teams.
Highly organised and self-directed, able to balance strategic thinking with hands-on delivery in a fast-moving, multi-brand environment.

Nice To Haves

Experience within social sweepstake platforms or familiarity with the US sweepstake casino landscape.
An existing network of high-value players or VIP contacts in relevant markets.
Experience designing or rebuilding a loyalty programme from the ground up.
Familiarity with CRM automation tools or analytics platforms for player communication and retention.
Multi-brand or multi-market VIP management experience.

Responsibilities

Personally acquire and onboard new high-value players, cultivating lasting relationships that drive long-term revenue and advocacy across our brand portfolio.
Develop targeted outreach and referral strategies to grow the VIP player base at scale.
Serve as the senior point of contact for our highest-tier players, delivering a premium, personalised experience at every touchpoint.
Define the right mix of bonuses, gifts, and exclusive VIP experiences to attract and retain high-value players competitively.
Own the loyalty programme architecture across the portfolio, defining tier structures, reward mechanics, and engagement pathways that drive sustained player activity and spend.
Build and optimise the VIP CRM and player contact strategy, using data-driven segmentation to deliver personalised, timely, and relevant communication.
Monitor player engagement and health indicators, proactively intervening to retain at-risk VIPs before they disengage.
Design and execute player propositions that reward positive, profitable behaviour and deepen long-term brand loyalty.
Lead, develop, and inspire an existing VIP team, setting clear performance standards, targets, and a high-accountability culture from day one.
Define the team structure needed to support growth, hiring and onboarding VIP Managers and Account Managers as the function scales.
Mentor and upskill team members, fostering a player-obsessed culture where every interaction is an opportunity to build loyalty.
Own the full VIP P&L and marketing budget across the portfolio, with accountability for revenue contribution, retention rates, and return on VIP spend.
Track and report on core VIP KPIs, including active player count, revenue share, LTV, churn rate, and reactivation performance.
Provide clear, insight-led reporting to the COO with strategic recommendations that inform broader business decisions.
Work cross-functionally with Product, Marketing, CRM, and Tech teams to ensure our platforms and tooling support a best-in-class VIP experience.