Director, OSB Regulatory Compliance

At DraftKings, AI is becoming an integral part of both our present and future, powering how work gets done today, guiding smarter decisions, and sparking bold ideas. It’s transforming how we enhance customer experiences, streamline operations, and unlock new possibilities. Our teams are energized by innovation and readily embrace emerging technology. We’re not waiting for the future to arrive. We’re shaping it, one bold step at a time. To those who see AI as a driver of progress, come build the future together.

The Crown Is Yours

The Director of Online Sportsbook Regulatory Compliance, is responsible for leading and managing the company’s online sportsbook (OSB) regulatory engagement program across all operating jurisdictions. The ideal candidate will bring deep expertise in regulatory frameworks, a proven track record of building and maintaining rigorous and scalable processes, and the leadership skills to inspire and manage a high-performing team. A key focus of this role is to proactively build and maintain strong relationships with regulatory bodies while enabling the business to innovate responsibly.

What you’ll do as a Director of OSB Regulatory Compliance

• Proactively build strong relationships with regulators across all sportsbook jurisdictions
• Deliver a coordinated regulatory strategy in partnership with other regulator-facing teams
• Serve as the primary escalation point for complex and high-stakes regulatory matters
• Represent the company in discussions with regulatory bodies and industry organizations to advocate for fair and forward-thinking policies.
• Provide sound advice to internal business partners on compliance with gaming regulatory requirements
• Collaborate with internal stakeholders to develop the regulatory approval strategy for new products and features.
• Collaborate with Government Affairs to assess new markets and changing regulations
• Design, implement and document scalable processes to ensure compliance with regulatory obligations, timeliness, and efficiency
• Develop recurring compliance dashboards and executive-level reports to senior leadership.
• Maintain the internal control documents. Optimize the process for making updates across all jurisdictions.

What you’ll Bring

• Bachelor’s degree
• 10+ years experience working in highly regulated industries with a strong focus on process and team building.
• Demonstrated success managing regulatory relationships and guiding organizations through complex regulatory landscapes.
• Strong understanding of regulatory frameworks
• Proven ability to lead cross-functional initiatives and influence at all levels.
• Exceptional communication, negotiation, and problem-solving skills.
• Commitment to high ethical standards and meticulous attention to detail.
• Knowledge of sports betting product mechanics is a plus.
• Demonstrated comfort using or learning AI tools to enhance work efficiency, decision-making, or creativity
• Openness to adapting workflows and responsibilities in response to evolving AI technologies, with an awareness of ethical and responsible use

Join Our Team

We’re a publicly traded (NASDAQ: DKNG) technology company headquartered in Boston. As a regulated gaming company, you may be required to obtain a gaming license issued by the appropriate state agency as a condition of employment. Don’t worry, we’ll guide you through the process if this is relevant to your role.

If this job posting does not include compensation information, this is due to a technical error that our team is working to resolve! We will repost this position with compensation information as soon as it is resolved. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.