Senior Associate, Strategy & Business Operations

Underdog

19h•$128,000 - $150,000•Remote

About The Position

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 sht. 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: 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.

Requirements

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

Nice To Haves

Experience working on complex, multi-stakeholder deals and/or partnerships
Background in prediction markets, capital markets, fantasy sports, sports betting, or adjacent consumer tech
Experience operating in or analyzing rapidly evolving regulatory or consumer landscapes

Responsibilities

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