The Crown Is Yours
As a Director, Leadership Effectiveness, you'll shape how leadership evolves at DraftKings by building the experiences, capabilities, and tools that help our leaders thrive in a fast-moving, high-stakes environment. You'll define our strategy for leadership effectiveness, reimagining how leaders grow through AI-enabled learning, meaningful leadership experiences, and impactful coaching. Working across the business, you'll turn bold ideas into scalable experiences and AI-enabled solutions that help leaders make better decisions, build stronger teams, and drive better business outcomes.
What You'll Do
- Own DraftKings' strategy for leadership effectiveness, shaping how leaders grow through innovative leadership experiences, AI-enabled coaching and tools, and operating rhythms that enable high-performing teams.
- Design and scale leadership solutions, including milestone experiences, coaching, simulations, AI-enabled learning, and manager enablement for performance development that build leadership effectiveness across the leadership lifecycle.
- Design AI-enabled leadership copilots and personalized manager support experiences that help leaders make better decisions, build stronger teams, and grow in the flow of work.
- Build and evolve our leadership ecosystem by leveraging AI, enterprise coaching, external partners, and emerging technologies to support leadership effectiveness at scale.
- Partner with senior leaders across the business to align leadership development with company priorities, business strategy, and the evolving needs of our leaders.
- Translate DraftKings' leadership expectations and culture into practical leadership behaviors and scalable experiences.
- Partner across HR and the business to deliver measurable improvements in manager effectiveness, leadership capability, organizational health, and execution.
What You'll Bring
- At least 10 years of experience in leadership effectiveness, talent development, or organizational development, with experience in a high-growth technology or fast-paced environment.
- Proven success designing and evolving enterprise leadership development experiences that build leadership effectiveness from new managers through senior leadership.
- A clear point of view on leadership effectiveness and the future of leadership development, with the ability to translate emerging trends, AI, and new ways of working into practical, scalable experiences.
- Exceptional strategic thinking and execution skills, with the ability to connect strategy to business outcomes, influence stakeholders, and deliver high-impact experiences.
- Expertise in leadership development, including designing engaging learning experiences that help leaders grow in the flow of work; facilitation skills are a plus.
#LI-TA1
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.
The US base salary range for this full-time position is 172,000.00 USD - 215,000.00 USD, plus bonus, equity, and benefits as applicable. Our ranges are determined by role, level, and location. The compensation information displayed on each job posting reflects the range for new hire pay rates for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific pay range and how that was determined during the hiring process. 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.
Skills Required
- Minimum 10 years experience in leadership effectiveness, talent development, or organizational development
- Experience in a high-growth technology or fast-paced environment
- Proven success designing and scaling enterprise leadership development programs across manager through senior leadership levels
- Ability to translate AI, emerging trends, and new ways of working into practical, scalable leadership experiences
- Exceptional strategic thinking, execution skills, and ability to influence stakeholders and connect development to business outcomes
- Expertise in designing engaging learning experiences and manager enablement for performance development
- Facilitation skills
- May be required to obtain a state gaming license as a condition of employment
DraftKings Compensation & Benefits Highlights
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Parental & Family Support — Family support is positioned as comprehensive, with 14 weeks of 100% paid parental leave globally plus adoption, surrogacy, fertility benefits, backup care, and lactation resources. Company materials highlight these as core programs, with U.S. enhancements such as Care.com support.
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Healthcare Strength — Healthcare coverage is described as robust, including medical, dental, and vision options alongside mental‑health support via Lyra therapy, Calm access, and wellbeing initiatives. Benefits begin on day one, with HSA/FSA options and fitness reimbursement adding depth.
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Leave & Time Off Breadth — Time off is framed as flexible, with U.S. employees told they have flexible or unlimited PTO and supportive leave policies. Feedback suggests PTO is a meaningful part of the package, though norms can vary by team.
DraftKings Insights
What We Do
It's simple, at DraftKings, we believe life is more fun when you're in on the action. For that reason, we’re committed to responsibly creating the world’s favorite games and betting experiences. We’re developing the most innovative and entertaining real money products and offers; to forever transform how people experience sports; to be a fully vertically integrated sports betting operator. It's our ultimate goal to build the best, most trusted, and most customer-centric destination for our players. We’re defining what it means to build and deliver the most extraordinary sports and entertainment experiences. Our global team is trailblazing new markets, developing cutting-edge products, and shaping the future of responsible gaming.
Why Work With Us
Here, “impossible” isn’t part of our vocabulary. You’ll face some of the toughest but most rewarding challenges of your career. They’re worth it. Channeling your inner grit will accelerate your growth, help us win as a team, and create unforgettable moments for our customers. Ready to own what’s next?
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Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our flexible hybrid policy empowers team members to work where they’re most productive—whether at home or in our collaborative offices. We trust our teams to choose what works best for them to thrive and innovate.

















