Senior Technical Product Manager, Talent & Rewards

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 Technical Product Manager, Talent & Rewards, you’ll own the strategy, roadmap, and evolution of the technology experiences that power how employees grow, develop, perform, and are rewarded across DraftKings. This role sits at the intersection of workforce technology, AI, product management, and employee experience, focused on transforming traditional talent and rewards processes into intelligent, AI-enabled, and embedded workforce experiences.

You’ll partner closely with Talent Management, Total Rewards, People Operations, IT, AI engineering teams, and business leaders to design scalable solutions that bring performance, development, feedback, growth, and rewards experiences directly into the flow of work. This is a highly impactful role for a technical product leader who is passionate about leveraging AI, automation, integrations, and modern enterprise technologies to deliver innovative workforce experiences at scale.

What you'll do as a Senior Technical Product Manager, Talent & Rewards

• Own the Talent & Rewards technology product portfolio, including performance management, career development, employee growth programs, ongoing feedback, compensation planning, rewards experiences, talent intelligence, and workforce insights

• Define and execute the product roadmap, prioritization strategy, and long-term vision for talent and rewards experiences across the organization

• Partner with Talent Management, Total Rewards, HRBPs, IT, AI engineering teams, and business leaders to translate strategic priorities into scalable technology solutions and product capabilities

• Lead the design and development of AI-powered workflows, intelligent automation, and embedded workforce experiences that simplify and enhance talent and rewards processes

• Collaborate with AI and technology teams to implement conversational employee experiences, AI-powered manager guidance, workflow orchestration, and intelligent talent workflows

• Identify opportunities to leverage AI and automation to improve employee engagement, manager effectiveness, operational efficiency, and workforce development outcomes

• Reimagine how employees and managers interact with talent and rewards programs by embedding experiences directly into collaboration and communication platforms

• Deliver capabilities such as AI-powered performance guidance, embedded feedback experiences, intelligent development nudges, conversational career development interactions, and AI-assisted manager support

• Extend workforce technology capabilities through integrations, AI orchestration, workflow automation, conversational interfaces, and modern experience layers

• Partner with enterprise platform owners to enhance and augment Workday capabilities while maintaining governance, security, compliance, and enterprise architecture standards

• Ensure workforce experiences remain aligned with enterprise data models, operational governance, and long-term platform strategies

• Define and track KPIs that measure adoption, engagement, manager effectiveness, AI utilization, workforce experience outcomes, operational efficiency, and employee satisfaction

• Leverage analytics, experimentation, and stakeholder feedback to continuously improve product strategy, user adoption, and workforce experience design

• Drive innovation by evaluating emerging technologies and identifying opportunities to modernize talent and rewards experiences through AI, automation, and embedded workforce technologies

• Promote scalable self-service, intelligent automation, and intuitive employee experiences that improve organizational effectiveness and employee growth

What you'll bring

• 7+ years of experience in Product Management, Enterprise Technology, HR Technology, Workforce Technology, Digital Workplace Technology, AI Platforms, or related technology domains

• Experience owning and evolving enterprise platforms that support workforce experiences, employee engagement, operational workflows, automation, or self-service capabilities

• Strong background in product strategy, enterprise systems, workflow orchestration, integrations, platform governance, and technical product management

• Demonstrated hands-on experience leveraging modern AI platforms such as Gemini, ChatGPT, Claude, or similar large language model technologies

• Strong understanding of enterprise systems architecture, APIs, integrations, workflow orchestration, and interconnected technology ecosystems

• Experience designing AI-enabled workflows, intelligent automation solutions, conversational interfaces, and embedded employee experiences

• Familiarity with AI orchestration concepts including knowledge grounding, AI-assisted support models, workflow automation, conversational interfaces, enterprise AI governance, and intelligent search and retrieval systems

• Experience working with enterprise workforce technologies such as Workday, collaboration platforms, workflow automation tools, AI ecosystems, knowledge platforms, and workforce experience technologies

• Strong understanding of Workday Talent, Performance, Compensation, or related workforce management capabilities

• Ability to operate as a hands-on technical product leader, balancing strategy, experimentation, and execution

• Experience prototyping workflows, testing AI use cases, and supporting lightweight automation solutions using low-code/no-code technologies and modern automation platforms

• Familiarity with AI tooling, prompt engineering, workflow builders, integrations, APIs, and automation frameworks

• Strong systems-thinking and problem-solving skills, with the ability to connect platforms, workflows, data, integrations, and user experiences across complex ecosystems

• Experience partnering with engineers, integration developers, enterprise architects, AI teams, and operational leaders to design scalable solutions

• Strong analytical skills with experience leveraging operational metrics, adoption data, and workforce insights to guide product decisions and roadmap priorities

• Excellent communication and stakeholder management skills, with the ability to simplify complex technology concepts for technical and non-technical audiences

• Curiosity, adaptability, and a passion for emerging AI technologies, intelligent automation, and workforce experience innovation

• Ability to thrive in a fast-paced environment while balancing innovation, governance, operational excellence, and business priorities

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.