Senior Manager, HR Technology

At Underdog, we make sports more fun.

Our thesis is simple: build the best products and we’ll build the biggest company in the space, because there’s so much more to be built for sports fans. We’re just over five years in, and we’re one of the fastest-growing sports companies ever, most recently valued at $1.3B. And it’s still the early days.

We’ve built and scaled multiple games and products across fantasy sports, sports betting, and prediction markets, all united in one seamless, simple, easy to use, intuitive and fun app. 

Underdog isn’t for everyone. One of our core values is give a sh*t. The people who win here are the ones who care, push, and perform. If that’s you, come join us.

Winning as an Underdog is more fun.

About the role and why it’s unique:

We’re looking for a strategic, hands-on Senior Manager to lead and evolve our HR technology ecosystem. This role will scale and optimize Workday processes while building and managing other HR tools that power our people operations—from onboarding and performance management to people analytics. You’ll own our HR tech roadmap, connect systems and workflows, and help us design efficient, thoughtful infrastructure as we grow.

• Workday Process Design & Ownership
• Lead configuration, optimization, and governance of core Workday processes (HCM, onboarding, offboarding, contractors, reporting).
• Drive configuration improvements, automation opportunities, and end-user experience enhancements (e.g., notifications, security access roles, historical data migration and data sanctity).
• Manage integrations across platforms (e.g., Greenhouse, ChartHop) ensuring data integrity and seamless workflows.
• HR Systems Strategy & Roadmap
• Own the HR technology roadmap in partnership with the Senior Director and cross-functional leaders.
• Evaluate, implement, and scale new HR tools to meet organizational needs.
• Ensure all systems and tools work cohesively, aligned with both compliance requirements and user experience.
• Project Management & Execution
• Lead end-to-end HR tech projects—from discovery to deployment—including but not limited to Workday enhancements and AI pilots supporting People team effectiveness.
• Manage vendor relationships, contracts, and service levels.
• Develop supporting documentation, training materials, and change management strategies for system rollouts.
• Cross-Functional Collaboration
• Partner with HR, IT, Legal, Compliance, Finance to align processes, systems, and data flows.
• Surface insights and drive process improvements that balance compliance, efficiency, and employee experience.

Who you are:

• 10+ years of experience in HR technology or HR operations.
• Expert-level, hands-on experience with the Workday ecosystem.
• Strong systems thinking: ability to see interdependencies, simplify complexity, and future-proof design.
• Experience managing system roadmaps and working with cross-functional teams 
• Fast learner who can adapt to shifting priorities and emerging tools.
• Strong project management and execution skills in a fast-paced environment.
• Excellent stakeholder management and influencing skills, with the ability to drive change and build consensus.
• Comfortable toggling between strategy and execution; no task is too big or small.

Our target starting base salary range for this position is between $147,000 and $175,000, plus target equity. The starting base salary will depend on a number of factors including the candidate’s skills and experience, among other things.

What we can offer you:

• Unlimited PTO (we're extremely flexible with the exception of the first few weeks before & into the NFL season)
• 16 weeks of fully paid parental leave
• Home office stipend
• A connected virtual first culture with a highly engaged distributed workforce
• 5% 401k match, FSA, company paid health, dental, vision plan options for employees and dependents

#LI-REMOTE

This position may require sports betting licensure based on certain state regulations.

Underdog is an equal opportunity employer and doesn't discriminate on the basis of creed, race, sexual orientation, gender, age, disability status, or any other defining characteristic.