Chief of Staff

Why this role is unique:

Underdog is at a pivotal moment in its growth, having nearly tripled in size over the last 18 months. As we gear up to launch our most ambitious product yet, this role puts you at the heart of our journey to become the largest sports gaming company in the U.S.

You’ll work directly with our Chief Product Officer, serving as their right-hand partner and trusted advisor. With oversight of engineering, product, design, and data—spanning 200+ team members—the scope is vast, and so is your impact. You'll gain full visibility into high-stakes decision-making and play a central role in advancing mission-critical initiatives. This is an unparalleled opportunity to fast-track your path to becoming a CTO, CPO, or CEO.

This is not a backseat, assistant-esque role. You’ll lead cross-functional, high-impact projects, tackle our toughest challenges, and contribute directly to growing Underdog from a 9-figure company to a 10-figure industry-leader within three years. From driving strategic alignment across teams to incubating new products, your influence will be felt company-wide.

What you’ll do:

• Partner with the CPO and their team to bring data-driven analysis and structured thinking to mission-critical initiatives. You’ll get your hands dirty operationally, digging into some of our toughest problems. 
• Act as a force multiplier for the CPO by managing priorities, ensuring follow-through on key decisions, and driving operational efficiency across teams.
• Lead strategic projects such as incubating new products, optimizing team workflows, and developing organizational roadmaps.
• Facilitate collaboration between engineering, product, and design teams to enhance product velocity and unlock business impact.
• Represent the CPO in meetings, ensuring clarity, documentation, and execution of action items.

Who you are:

• Product Focused Background: 7+ years of engineering, product, or operations experience within a startup, ideally with founder experience or ambition to run an org or found a company. 
• Highly Analytical: Exceptional ability to draw insights and drive business decisions from diverse datasets (quantitative and qualitative; financial, operational, and competitive). Structured thinker with impeccable business judgment. 
• Polished Communicator: Whether it’s a proposal, deck or memo, you convey ideas succinctly and powerfully. 
• Action-Oriented: You thrive under pressure, have a bias for action, and excel at finding creative solutions to complex and messy problems.
• Sports Enthusiast: You have a genuine passion for sports, fantasy sports, or sports betting.

Our target starting base salary range for this position is between $190,000 and $290,000, 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
• A $500 home office allowance
• 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

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