Underdog Fantasy

Compensation

Full Description

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