Head of Product (United States)

Location: Remote (United States 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 Product will own the product strategy and player experience for The Boss.

Reporting directly to the General Manager, this is a hands-on leadership role with end-to-end responsibility for Product and Product Design. You will set the direction, determine where we invest and lead the team responsible for turning player and business opportunities into measurable results.

You will own the evolution of the customer journey across web and mobile, from registration and first purchase through game discovery, promotions, loyalty/VIP, repeat play and redemption - while also improving the internal products and tools that enable the business to scale.

This role requires deep experience in casino gaming, strong commercial judgment, a passion for understanding players and the ability to translate customer insight, behavioral data and business opportunities into differentiated products.

Key Responsibilities

Own Product Strategy & Roadmap

• Set and communicate a clear product vision and strategy for The Boss, working closely with the General Manager and leadership team.
• Own the product roadmap, prioritizing the opportunities with the greatest customer and commercial impact.
• Lead the full product lifecycle from identifying and validating opportunities through design, development, launch, adoption and ongoing optimization.
• Evaluate new ideas and the opportunities behind them, turning the strongest into clearly defined and measurable initiatives.
• Translate emerging player behaviors, competitive dynamics, industry trends and technology shifts into opportunities that strengthen the product.
• Identify opportunities to simplify the experience, improve performance and remove unnecessary complexity.
• Treat product investment as commercial investment, establishing a clear hypothesis, expected outcome and measure of success for major initiatives.

Own the Casino Player Experience

• Own the end-to-end digital player experience across registration, onboarding, purchase and wallet experiences, lobby and game discovery, promotions, rewards and loyalty, VIP experiences, redemption and mobile.
• Develop a deep understanding of casino player behavior and identify opportunities to make The Boss easier, more engaging and more differentiated.
• Partner closely with Casino Operations, Marketing, CRM, VIP, Customer Support and Risk to create a cohesive player experience.

Own Customer Insight & Voice of Customer

• Establish and own a structured Voice of Customer program that brings player insight directly into product strategy and prioritization.
• Build a deep understanding of players through direct interviews, surveys, customer service and VIP feedback, reviews, behavioral data and transactional data.
• Create a regular feedback loop across Product, Customer Support, VIP, Marketing and Casino Operations so recurring customer pain points and opportunities are visible and addressed.
• Use customer feedback and data to identify friction, unmet needs and opportunities across the player lifecycle.

Product Design, Testing & Optimization

• Own and lead Product Design, including UX/UI design and external design resources.
• Set a high standard for usability, consistency and quality across web and mobile experiences.
• Use prototypes and customer testing to validate concepts before significant development investment.
• Use controlled experiments and A/B testing where appropriate to test assumptions and optimize the player experience.
• Establish clear success measures before development and use post-launch results to determine whether to improve, expand or stop an initiative.

Drive Commercial & Customer Outcomes

• Connect product decisions directly to measurable outcomes across acquisition, activation, purchaser conversion, retention, gameplay, customer value, net revenue and operational efficiency.
• Use product analytics, customer insight and commercial data to prioritize opportunities and evaluate performance.
• Partner with Analytics to understand player cohorts, funnels and behaviors and translate insights into product opportunities.
• Work with Engineering to balance speed of delivery with experience quality, platform performance, reliability and long-term scalability.

Leadership

• Build, lead and develop the Product & Design organization, creating clear ownership and accountability.
• Partner closely with Engineering, Design and Data to understand problems, assess options and deliver high-quality products.
• Manage product relationships with key technology partners and vendors, holding them accountable for performance and delivery.
• Create strong partnerships across Marketing, Casino Operations, VIP, Customer Operations, Risk and Finance.
• Use AI and emerging tools where they can materially improve product discovery, customer insight, analysis, prototyping or team efficiency.
• Serve as a key member of the leadership team and strategic partner to the General Manager.

Success in the First 12 Months

• Establish a clear product strategy and prioritized roadmap focused on the biggest player and commercial opportunities.
• Build a repeatable Voice of Customer program and demonstrate that player feedback is materially influencing product priorities.
• Deliver meaningful improvements across the core casino journey, including onboarding, purchasing, lobby/game discovery, promotions, loyalty/VIP and redemption.
• Launch and optimize The Boss mobile app experience across iOS and Android.
• Introduce consistent success measures, instrumentation and post-launch reviews for major product initiatives.
• Establish a strong experimentation discipline, including customer testing and A/B testing where appropriate.

Qualifications

Required

• 7+ years of product management experience, including experience leading product teams and owning product strategy.
• Meaningful product leadership experience within Sweepstakes Casino, Online Casino, Social Casino or real-money iGaming .
• Deep understanding of the digital casino player journey and core product mechanics, including game discovery, promotions, wallets/purchasing, loyalty and retention.
• Experience owning consumer-facing digital products with accountability for measurable commercial and customer outcomes.
• Experience owning a product strategy and roadmap tied to KPIs such as conversion, retention, customer/player value, gameplay, GGR/net revenue or similar measures.
• Strong experience using customer research, analytics and commercial data to inform product decisions.
• A track record of leading digital products from discovery and design through launch, measurement and ongoing optimization.
• Experience partnering closely with Product Design/UX and establishing a strong consumer experience across digital products.
• Experience managing agencies, technology vendors or strategic partners.
• Strong communication, commercial judgment and people leadership skills.
• Ability to operate effectively in a fast-moving environment with imperfect information and competing priorities.

Preferred

• Direct experience within the U.S. sweepstakes casino market.
• Experience with product analytics, experimentation and data visualization tools.
• Experience designing and evaluating controlled experiments, including A/B tests.
• Experience launching or managing consumer mobile applications across iOS and Android.
• Experience leading globally distributed teams across different cultures and time zones.
• Experience working in high-growth or venture-backed businesses.

Candidate Profile

You are a hands-on casino product leader who enjoys building, improving and scaling consumer products.

You deeply understand digital casino players and the experiences that drive them to register, purchase, play, engage and return. You are equally comfortable speaking directly with customers, reviewing a Figma prototype, digging into a conversion funnel, challenging a roadmap and discussing commercial trade-offs with senior leadership.

You thrive in a fast-moving environment, bring clarity when priorities compete and give people the context and trust to take ownership. You are comfortable making decisions with incomplete information, testing assumptions and turning customer and business problems into products that deliver measurable results.

You believe great product management starts with understanding the customer but does not end there. You combine customer insight, product judgment, data and commercial thinking to determine what should be built — and you measure whether it actual]]> <