At Underdog, we make sports more fun.
Our thesis is simple: build the best products and we’ll build the biggest company in the space, because there’s so much more to be built for sports fans. We’re just over five years in, and we’re one of the fastest-growing sports companies ever, most recently valued at $1.3B. And it’s still the early days.
We’ve built and scaled multiple games and products across fantasy sports, sports betting, and prediction markets, all united in one seamless, simple, easy to use, intuitive and fun app.
Underdog isn’t for everyone. One of our core values is give a sh*t. The people who win here are the ones who care, push, and perform. If that’s you, come join us.
Winning as an Underdog is more fun.
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.
- 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
- 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
#LI-REMOTE
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.
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