Chief of Staff

Summary

Join Underdog, the fastest-growing sports gaming company, as a highly impactful strategic partner to the Chief Product Officer. This pivotal role involves leading cross-functional projects, driving operational efficiency, and contributing directly to the company's growth. You will work with a team of 200+ across engineering, product, design, and data, influencing high-stakes decisions and shaping mission-critical initiatives. This unique opportunity offers a fast-track path to a leadership position (CTO, CPO, or CEO) and significant influence within a rapidly expanding company. The role demands a strong engineering background, exceptional analytical skills, polished communication, and a passion for sports. Underdog offers a competitive salary, equity, and a comprehensive benefits package.

Requirements

• 7+ years of engineering experience, ideally with founder experience or ambition to run an org or found a company
• 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
• Ability to convey ideas succinctly and powerfully in proposals, decks, or memos
• Ability to thrive under pressure, have a bias for action, and excel at finding creative solutions to complex and messy problems
• Genuine passion for sports, fantasy sports, or sports betting

Responsibilities

• Partner with the CPO and their team to bring data-driven analysis and structured thinking to mission-critical initiatives
• 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

Benefits

• 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