Job Description:
• Drive end-to-end planning, execution, and delivery across Underdog's 200+ person EPD organization, connecting strategy to outcomes and improving how the entire org operates
• Own and optimize the operating cadence including town halls, leadership reviews, planning cycles, and monthly updates to ensure consistent organizational rhythm
• Manage cross-functional product delivery updates, including bi-weekly All Hands presentations and monthly company-wide product update decks
• Assess and improve productivity systems (Jira, GitHub, Notion) and SDLC workflows, identifying bottlenecks and implementing solutions that increase visibility into priorities, timelines, and risks
• Lead strategic initiatives that require cross-functional partnership on quick timelines, supporting emerging roadmap priorities with high complexity and high returns
• Build and maintain relationships with Directors+ across Engineering, Product, and Design to understand pain points and accelerate solutions
• Establish feedback loops (surveys, retros) to surface org health insights and drive continuous cultural improvements
Requirements:
• 7+ years of experience in Technical Program Management, Product Operations, or Engineering Operations roles at scale
• Proven track record of driving operational excellence across large, complex EPD organizations (150+ people), not just individual teams
• Expert in managing productivity systems and tooling at scale, with hands-on experience optimizing Jira, GitHub, Notion, or similar platforms
• Skilled at building and maintaining cross-functional relationships with senior leaders, earning trust and driving alignment without direct authority
• Strong communicator who can distill complex information into clear, actionable actions and updates for diverse audiences from ICs to executives
• Highly organized with exceptional program management skills—you bring structure to ambiguity and can juggle multiple high-priority initiatives simultaneously
• Action-oriented operator who cares deeply about velocity, quality, and impact—you give a sh*t and push to perform
Benefits:
• Unlimited PTO for full-time employees (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