The fastest-growing sports gaming company – ever.
We build innovative games, products, and experiences for American sports fans.
We’re here to shake up the fastest growing industry with bold ideas, custom-built tech, and the drive to win.
Founded in 2020, our team has built four of today’s most widely played fantasy games and launched the Underdog Sportsbook – built entirely in-house with our own technology. That means we control our product, move fast, and create experiences you won’t find anywhere else.
In just over two years, we’ve reached over a $1.2 billion valuation, with investors like BlackRock, Spark Capital, SV Angel, Mark Cuban, Kevin Durant, and Adam Schefter. And we’re just getting started.
At Underdog, we believe that sports are for everyone. Join us.
About the role and why it’s unique:
- Manage the end-to-end execution of L&D initiatives (e.g., New Manager Onboarding, Group Coaching, Interviewer Certification, etc.)
- Lead project planning, logistics, communications, and stakeholder engagement for learning programs
- Build engaging learning content, including training decks, job aids, and asynchronous materials
- Design and facilitate or co-facilitate live learning experiences (virtual and in-person)
- Track and analyze learning impact; use data to improve programs and inform decision-making
- Collaborate with key partners (e.g., HRBPs, People Ops, Talent Acquisition, Employee Experience) to deliver integrated development offerings
- Coach individuals and teams on topics such as development planning, feedback, and growth
- Contribute to ongoing improvement of the L&D roadmap and team strategy
Who you are:
- 4–6 years of experience in Learning & Development, Talent Development, or related areas
- Proven success in managing learning programs end-to-end: planning, building, facilitating, measuring
- Strong project management skills: organized, proactive, and detail-oriented
- Confident facilitator with experience designing and delivering engaging learning experiences
- Adept at building scalable resources for async learning (slides, videos, documentation, etc.)
- Collaborative and communicative—able to build trust across cross-functional teams
- Comfortable using learning metrics, survey data, and feedback to inform improvements
- Deeply learner-centric and inclusive in your approach
Even better if you have:
- Experience scaling L&D in a high-growth or startup environment
- Familiarity with tools like Notion, Articulate, LMS platforms, Zoom, Slack
- Coaching certification or small group coaching experience
- Familiarity with modern manager development frameworks and performance philosophies
Our target starting base salary range for this position is between $100,000 and $125,000, 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
- A $500 home office allowance
- 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
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.
Top Skills
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
