Underdog

SeniorAssociate,Strategy&BusinessOperations

$128–150k Chicago, Illinois, United States; Tel Aviv, Israel; United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Senior Associate, Strategy & Business Operations at Underdog. Skills: Strategy, Business Operations, Financial Modeling. Lead strategic initiatives. Translate ambiguous problems”

Industry & Context.

Problems you'll solve

Structured thinking; Data-driven decisions

What They're Looking For.

Must Have

3-6 years strategy consulting, 3-6 years investment banking, 3-6 years corporate strategy, Demonstrated ability to work independently, High-stakes projects with executive stakeholders, Exceptional financial modeling, Build models from scratch, Pressure-test assumptions, Analytical and structured thinking, Track record of turning data into decisions, Polished communicator, Influence at all levels, Operate in fast-moving environments, Resourcefulness matters, Genuine passion for sports, Genuine passion for prediction market landscape, Sports betting licensure

Nice to Have

Experience on complex deals, Experience on multi-stakeholder deals, Experience on partnerships, Background in prediction markets, Background in capital markets, Background in fantasy sports, Background in sports betting, Background in adjacent consumer tech, Experience analyzing regulatory landscapes, Experience analyzing consumer landscapes

What You'll Do.

Lead strategic initiatives

Translate ambiguous problems

Build financial models

Maintain financial models

Conduct market trend analysis

Conduct competitor positioning analysis

Conduct customer behavior analysis

Surface actionable insights

Inform long-range planning

Own roadmap development

Define short-term objectives

Define long-term objectives

Track progress against metrics

Synthesize cross-functional inputs

Ensure alignment across product

Ensure alignment across finance

Ensure alignment across marketing

Ensure alignment across operations

Prepare board-level materials

Prepare executive-facing materials

Distill complex analysis

Identify new business opportunities

Evaluate new business opportunities

Identify partnerships

Evaluate partnerships

How You'll Work.

Team & Collaboration

Connective tissue between business units; Cross-functional alignment

Communication Scope

Executive-facing materials; Board-level materials; Written communication; Verbal communication

Process & Methodology

Roadmap planning

Full Job Description

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: 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 Who you are: 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 stakehol

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