Lead high-impact strategic initiatives across Underdog’s core business lines – including prediction markets and fantasy sports – translating ambiguous problems into clear recommendations for senior leadership
Build and maintain financial models supporting high-stakes strategic and commercial decisions, including complex multi-party transactions and partnership structures
Conduct rigorous analysis of market trends, competitor positioning, and customer behavior to surface actionable insights and inform long-range planning
Own the development of strategic roadmaps, defining short
and long-term objectives and metrics to track progress against them
Serve as a connective tissue between business units, synthesizing cross-functional inputs and ensuring alignment across product, finance, marketing, and operations
Prepare board-level and executive-facing materials that distill complex analysis and trends into clear narratives
Identify and evaluate new business opportunities, partnerships, and adjacencies that align with Underdog’s growth strategy

3-6 years of experience in strategy consulting, investment banking, or corporate strategy, with demonstrated ability to work independently on high-stakes projects with executive stakeholders.
Exceptional financial modeling skills; comfortable building models from scratch and pressure-testing assumptions across internal and external data sets
Strong analytical and structured thinking, with a track record of turning data into decisions
Polished communicator who can influence at all levels – from analyst to C-suite – in both written and verbal formats
Excel at operating in fast-moving, ambiguous environments where priorities shift and resourcefulness matters
Genuine passion for sports and the evolving consumer and prediction market landscape

Unlimited PTO for full-time employees (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

Senior Associate, Strategy – Business Operations

Key skills