Set the vision, strategy, and execution plan for all engineering domains (product engineering, data engineering, ML, security, infrastructure, IT), aligned with business goals
Build, mentor, and grow high-performing engineering leaders and teams (managers, tech leads, ICs) across ~150+ engineers
Drive performance management: ensure consistent feedback, coaching, goal setting, and development plans
Establish clear metrics and accountability for engineering health (e.g. uptime, latency, MTTR, deployment frequency, error budgets)
Oversee the technical architecture, platform roadmap, and infrastructure investments to scale the product and data stack
Maintain strong collaboration with Product and Design: co-own planning, prioritization, tradeoffs, and delivery
Own security, compliance, governance, and data privacy at the enterprise level
Elevate operational excellence by helping strengthen CI/CD, observability, incident response, and technical debt reduction to improve productivity and reliability
Modernize engineering practices by driving adoption of AI-assisted development, automation, and continuous improvement in delivery pipelines
Champion cultural and organizational shifts needed to scale engineering velocity and quality
Represent engineering externally in engagements with regulators, industry groups, and key strategic partners
Act as a culture carrier: embed Underdog values (ambition, urgency, ownership, teamwork) in how engineering operates
Requirements
15+ years of experience in leadership roles within high-impact engineering organizations, ideally in fast-paced, consumer or data-intensive environments
Proven track record scaling engineering teams through multiple phases of growth
Deep expertise in technical domains including data infrastructure tooling, cloud infrastructure (AWS, GCP), security, and large-scale distributed systems
Experience in both strategic and hands-on contexts: able to dive into architecture, code reviews, design when needed
A strong performance management mindset: coaching, career paths, accountability, metrics-driven
Exceptional at cross-functional partner relationships, especially with Product, Design, and business stakeholders
Excellent communication skills—able to distill complexity for executives, and inspire engineers
Bias for action, ownership, urgency, and continuous improvement
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
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard skills
data engineeringmachine learningsecurityinfrastructurecloud infrastructureAWSGCPCI/CDobservabilitylarge-scale distributed systems