Senior Manager, Leadership Effectiveness

DraftKings; Boston (MA); On-site; USD 142,000 - 177,000; Full time

Job summary

DraftKings seeks a Senior Manager, Leadership Effectiveness, to shape how leaders develop in an AI-enabled business. You’ll identify capabilities, build practical experiences, and integrate tools to strengthen leadership impact across teams.

You’ll lead initiatives like milestone programs, simulations, coaching, and manager development experiences, partnering with HR and cross-functional teams, using data to improve outcomes.

Qualifications

• 7+ years in leadership development, talent development, or organizational development.
• Experience designing, delivering, and evolving leadership programs that drive measurable behavior change.
• Strong understanding of adult learning principles and learning experience design.

Responsibilities

• Shape leadership development by identifying needed capabilities for an AI-enabled environment.
• Lead design and evolution of core leadership initiatives (milestones, simulations, coaching).
• Create engaging learning experiences driving lasting behavior change with real-world challenges.

Skills

Leadership development

Stakeholder influence

Adult learning

Coaching

AI-enabled learning

Data-driven

Strategic thinking

Tools

AI-enabled learning tools

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 Senior Manager, Leadership Effectiveness, you’ll shape how we develop leaders to thrive in a fast-moving, AI-enabled business. You’ll identify the leadership capabilities that matter most for the future and build practical experiences, tools, and resources that help leaders strengthen their impact. Working across teams, you’ll bring together coaching, peer learning, real-world application, and AI-enabled solutions to make leadership development part of everyday work. Your work will help leaders navigate change, build stronger teams, and drive business performance.

What You’ll Do

• Shape our approach to leadership development by identifying the capabilities leaders need to succeed in an AI-enabled environment and translating them into practical, impactful learning experiences.
• Lead the design and evolution of core leadership development initiatives, including milestone programs, simulations, coaching, and manager development experiences.
• Build engaging learning experiences that drive lasting behavior change through real-world challenges, hands-on practice, peer learning, feedback, and ongoing reinforcement.
• Explore and integrate AI-enabled tools, coaching, and learning solutions to deliver more personalized, accessible, and scalable leadership development experiences.
• Partner with senior leaders, Human Resources Business Partners, and cross-functional teams to identify leadership challenges and develop solutions that strengthen team effectiveness and business performance.
• Evaluate the impact of leadership development initiatives using data, feedback, and business insights to continuously improve experiences and outcomes.
• Help shape the future of our leadership development offerings by connecting emerging learning practices, business priorities, and evolving leadership expectations.

What You’ll Bring

• At least 7 years of experience in leadership development, talent development, organizational development, or a related field, preferably within a high-growth technology company or fast-paced business environment.
• Proven experience designing, delivering, and evolving leadership and manager development programs that strengthen leadership capabilities and drive measurable behavior change.
• Strong understanding of adult learning principles, learning experience design, and practical approaches to developing leadership capabilities through real-world application.
• Experience facilitating leadership development experiences, coaching leaders, and creating opportunities for meaningful peer learning and collaboration.
• Familiarity with AI-enabled learning, coaching, or performance support tools, with an interest in applying emerging technologies to enhance leadership effectiveness.
• Strong ability to influence senior stakeholders, build cross-functional partnerships, and translate complex business challenges into actionable development solutions.
• A data-driven mindset with experience evaluating learning effectiveness, gathering feedback, and using insights to improve leadership development initiatives.
• A strategic, hands-on approach to problem-solving, with the ability to navigate ambiguity, manage competing priorities, and turn ideas into impactful experiences.

#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 141,700.00 USD - 177,100.00 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.