Director, IT

We’re Underdog.

The fastest-growing sports gaming company, ever. We’re here to make sports more fun. We pair intuitive user experiences with innovative game designs to build the best experience for sports fans in America.

Since 2020, we’ve launched four of today’s most widely played fantasy games, and built the Underdog Sportsbook entirely in-house with our own tech. We move fast, act with urgency, and create experiences you won’t find anywhere else.

With a $1.2 billion valuation and backing from investors like BlackRock, Spark Capital, SV Angel, Mark Cuban, Kevin Durant, Adam Schefter, and more, we’re just getting started.

At Underdog, we play and win as a team. We take chances and are unafraid to attack hard problems. We face challenges with ambition and optimism. We play for the love of the game.

We’re Underdog. And winning as an Underdog is just more fun.

Join us.

We’re seeking a Director of IT Operations & Enterprise Systems to lead our internal technology function. In this role, you’ll set the vision, build the roadmap, and lead the execution for IT infrastructure, enterprise applications, and internal systems — ensuring performance, scalability, and security as we grow. You’ll balance strategic leadership with hands-on problem-solving, building a high-performing team that keeps our systems running smoothly and our employees empowered.

About the role

• Oversee corporate network infrastructure, end-user computing, service desk, and endpoint security.
• Manage identity and access management platforms (Okta, AD) and endpoint management tools (Kandji, JumpCloud).
• Lead ERP, HRIS (Workday), CRM, and other core business applications.
• Ensure systems are well-integrated, reliable, and aligned with business needs.
• Partner with Finance, People, Security, and other teams to optimize workflows and reporting.
• Drive high availability, incident response, and disaster recovery readiness in the Enterprise environment.
• Partner with Security on compliance, risk management, and data privacy requirements.
• Manage technology vendor relationships, contracts, renewals, and SLAs.
• Evaluate new solutions and negotiate for cost efficiency and innovation.
• Implement IT governance, ITSM best practices, and scalable support workflows.
• Establish and monitor KPIs for service delivery and system performance.
• Hire, coach, and develop IT and enterprise applications staff.
• Foster a culture of agility, service excellence, and continuous improvement.

Who you are

• 10+ years of progressive IT operations and enterprise applications experience in high-growth environments.
• 6+ years leading teams, with a track record of scaling IT capabilities in complex, fast-paced B2C or tech settings.
• Deep expertise with ERP, HRIS (Workday), identity platforms (Okta, Azure AD), and endpoint management (Kandji, JumpCloud or similar).
• Strong understanding of SaaS heavy environments, integration architecture, and IT governance frameworks.
• Proven vendor management skills, including contract negotiation and performance management.
• Excellent leadership, communication, and stakeholder management abilities.

Our target starting base salary range for this position is between $185,000 and $210,000, plus target equity. The starting base salary will depend on a number of factors including the candidate’s skills and experience, among other things.

What we can offer you:

• 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

#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.