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Underdog

Legal Operations Associate

Sorry, this job was removed at 08:08 p.m. (CST) on Friday, Jan 09, 2026
Easy Apply
Remote
Hiring Remotely in United States
Easy Apply
Remote
Hiring Remotely in United States

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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
  • Own and manage the end-to-end legal billing, accruals, and spend tracking process including full ownership and administration of the Legal billing software/platform while partnering with Finance to ensure accuracy and timely reporting.
  • Oversee contract lifecycle workflows to ensure timely execution, proper storage, and audit readiness.
  • Support litigation and regulatory matters, including document management and collection, vendor coordination, and tracking of key deadlines.
  • Manage the Legal team’s schedules and calendars, coordinate meetings and deadlines, and own meeting logistics — including drafting agendas, taking notes, and tracking action items to completion.
    Develop trackers and dashboards to improve visibility into legal spend, contract status, and team metrics.
  • Maintain company org charts, governance calendars, and entity management documentation.
  • Partner with stakeholders across the business to improve contract review and approval processes.
    Identify opportunities to streamline operations and implement best practices for Legal’s tools and systems.
Who you are

You’re a detail-oriented, process-driven problem solver who thrives on bringing organization to fast-moving environments. You’re comfortable working cross-functionally and love making complex workflows simple and scalable.

  • 4+ years of experience in legal operations, legal project management, or a similar role.
  • Vigorous attention to detail, organization, and follow-through.
  • Experience managing legal billing platforms, budgets, invoices, and contracts in Legal, Finance, or Compliance settings.
  • Robust technical proficiency and comfort working with business and productivity tools (e.g., Microsoft Office and Google Workspace).
  • Familiarity with legal operations tools or the ability to quickly master new systems.
  • Excellent written and verbal communication skills with a collaborative mindset.
  • Comfortable managing multiple priorities in a dynamic, fast-paced environment.
  • Bachelor’s degree required; advanced degree or paralegal certification a plus.

Our target starting base salary range for this position is between $100,000 and $130,000, 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
  • 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

#LI-REMOTE

We're a remote-first company and value in-person connection. That said, we expect everyone to gather 2-3 times per year for team and company offsites, trainings, and more.

This position may require sports betting licensure based on certain state regulations.

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.

California Applicants: Review our CPRA Privacy Notice here. 

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With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

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