Senior IT Systems Engineer

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.

As the Senior IT Systems Engineer, You aren’t just keeping the lights on; you are engineering the engine that powers our internal growth. In this role, you will move beyond standard ticket closing to architect automated identity solutions and SaaS integrations that support our scaling workforce. You’ll be the technical escalation point for the entire IT organization, turning complex manual problems into streamlined, automated workflows that allow us to scale securely.

About the role

• Automate provisioning and de-provisioning of applications using SAML and SCIM.

• Design and execute automated workflows for employee onboarding, off-boarding, and lifecycle management.

• Administer and optimize various SaaS tools, leveraging APIs to manage functionality and integration.

• Troubleshoot complex identity and access management (IAM) issues and handle technical escalations from junior IT staff.

• Collaborate with cross-functional teams to drive technical solutions for company initiatives.

• Document system administration operating procedures and advocate for knowledge sharing across IT.

• Provide training and mentorship to support staff to shift knowledge left.

• Stay current with industry best practices, trends, and security standards.

Who you are

• 7+ years of experience with end-user support and Systems Administration.

• Advanced administration experience with multi-domain Google Workspace instances in a global environment (1000+ users).

• Proven experience managing large-scale device fleets (Mac/Windows) via MDM tools like Jamf, Kandji, or JumpCloud, including policy creation and compliance reporting.

• Deep expertise in Identity/SSO/SAML systems (Okta preferred) in a large-scale environment.

• Experience automating user lifecycle management

• Advanced administration skills within Slack Enterprise Grid.

• Ability to work independently across functions and communicate effectively with all levels of management.

• Strong analytical skills with the ability to adapt to a dynamic project environment.

Even better if you have

• Advanced understanding of Workday, Google Workspace, Okta, and MDM management Tools (Kanji, Jumpcloud).

• Extensive knowledge in Okta technologies (Okta Workflows, Governance, Access Requests, Identity Threat Protection).

• Proficiency in scripting (BASH, Python).

• Relevant certifications (Okta and Google Workspace).

Our target starting base salary range for this position is between $135,000 and $147,500, 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

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.

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