Underdog
What's It Like to Work at Underdog in New York?
This page summarizes recurring themes identified from responses generated by popular LLMs to common candidate questions about Underdog and has not been reviewed or approved by Underdog.
What's it like to work at Underdog?
Strengths in benefits and product innovation coexist with volatility from strategic shifts, workload spikes, and recent headcount reductions. Together, these dynamics suggest the Brooklyn office offers high-impact work with strong support, but employees should be comfortable with change and periodic intensity.
Key Insight for Candidates
Defining pattern: Even for Brooklyn-based staff, Underdog runs remote-first with high-urgency, peak-season sprints and occasional in-person touchpoints. This matters because PTO and workloads tighten around sports windows, and company-wide pivots can rapidly reshape priorities—regardless of proximity to HQ.Evidence in Action
- Remote-First Meetups Rhythm — The "remote-first" setup and periodic in-person events "Training Camp" and "Camp Underdog" define how teams connect. Brooklyn employees collaborate primarily online, then reinforce relationships and alignment during these company meetups without imposing a fixed in-office cadence.
- Urgency And Ownership Values — The "Act with Urgency" and "Give a Sh*t" values codify speed and ownership expectations. In Brooklyn, employees ship quickly, take end-to-end responsibility, and adapt to shifts without waiting on heavy process.
Positive Themes About Underdog
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Benefits & Perks: As the headquarters location, Brooklyn teams benefit from a remote-first setup with flexible PTO, fully paid parental leave, comprehensive healthcare, a 401(k) match, learning stipends, and home-office support. Feedback suggests these tangible perks help sustain a fast-paced environment.
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Innovation & Products: Work in Brooklyn spans novel problems at the intersection of fantasy sports, prediction markets, and regulation, creating chances to ship quickly on differentiated consumer experiences. Feedback suggests this scope attracts builders who value ownership and rapid iteration.
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Market Position & Stability: The Brooklyn HQ operates within a company that reached unicorn status and expanded into federally regulated exchange infrastructure, signaling momentum and investor confidence. This backdrop provides resources for product bets and selective hiring.
Considerations About Underdog
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Job Insecurity: Brooklyn teams recently felt the impact of company-wide layoffs tied to the pivot toward prediction markets, with reductions across multiple functions. This has introduced uncertainty around roles and near-term org structure.
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Change Fatigue: Strategy has shifted quickly—from fantasy and a state-launched sportsbook to a national prediction‑markets focus—requiring Brooklyn teams to adapt to evolving priorities and KPIs. Such rapid turns can tax planning cycles and focus.
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Workload & Burnout: Seasonal spikes around major sports windows can drive nights and weekends work for Brooklyn-aligned functions closest to live operations. This intensity can strain balance during peak periods despite flexible policies.
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