Director, Leadership Effectiveness

DraftKings Inc.; Boston (MA); On-site; USD 172,000 - 215,000; Full time

Job summary

DraftKings Inc. in Boston, MA is seeking a Director of Leadership Effectiveness to shape how leaders grow using AI-enabled learning and coaching.

You will design scalable experiences, partner with executives, and translate leadership expectations into practical behaviors. The role requires 10+ years in leadership development within fast-paced tech, proven ability to scale programs, and a strategic mindset that ties development to business outcomes.

Qualifications

• 10+ years in leadership effectiveness or organizational development in a fast-paced tech environment.
• Experience designing enterprise leadership programs that scale from new managers to senior leaders.
• Ability to translate trends and AI into practical leadership experiences.

Responsibilities

• Own strategy for leadership effectiveness and AI-enabled coaching tools.
• Design scalable leadership experiences and manager enablement across lifecycle.
• Create AI copilots and personalized support to improve decision-making and team growth.
• Evolve leadership ecosystem with partners and emerging tech at scale.
• Align development with company priorities and executive expectations.
• Turn leadership culture into practical behaviors and scalable experiences.
• Collaborate with HR and business leaders to improve organizational health and execution.

Skills

Leadership development

Organizational development

Talent development

Strategic thinking

Facilitation

Job description

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

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.

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.