urity, infrastructure, technical compliance, and IT. You'll be the technical and operational backbone - ensuring stability, velocity, and excellence - while partnering tightly with Product, Design, and the rest of the exec team to set and deliver on the roadmap.
About the role
- 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
- Manage budgets, resource allocations, vendor & tooling decisions
- 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
Who You Are
- 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
Even better if you have
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Experience in gaming, consumer platforms, or real-time systems
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Experience with regulated environments (e.g. compliance, audits)
The anticipated salary range for this role is between $300,000 and $400,000 per year plus pre-IPO equity. Actual compensation may vary depending on skills, experience, qualifications, geographic location, and internal equity considerations.
What we can offer you:
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Unlimited PTO (we're extremely flexible with the exception of the first few weeks before & into the NFL season)
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16 weeks of fully paid parental leave
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Home office stipend
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A connected virtual first culture with a highly engaged distributed workforce
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5% 401k match, FSA, company paid health, dental, vision plan options for employees and dependents
#LI-REMOTE
This position may require sports betting licensure based on certain state regulations.
Underdog is an equal opportunity employer and doesn't discriminate on the basis of creed, race, sexual orientation, gender, age, disability status, or any other defining characteristic.