Senior Technical Product Manager, Talent & Rewards

DraftKings•Boston, MA

18h

About The Position

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.

Requirements

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

Responsibilities

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