IT Services Lead

We're defining what it means to build and deliver the most extraordinary sports and entertainment experiences. Our global team is trailblazing new markets, developing cutting-edge products, and shaping the future of responsible gaming.
Here, "impossible" isn't part of our vocabulary. You'll face some of the toughest but most rewarding challenges of your career. They're worth it. Channeling your inner grit will accelerate your growth, help us win as a team, and create unforgettable moments for our customers.
The Crown Is Yours
We're looking for a Lead IT Services Technician to join our high-performing team and elevate the way we deliver support across DraftKings. In this role, you'll lead by example-bringing hands-on expertise, proactive problem-solving, and mentorship to every aspect of IT service delivery. From resolving complex technical issues to implementing scalable improvements, you'll help shape the tools, processes, and experiences that keep our teams running smoothly.
What you'll do

• Act as go-to escalation point for advanced issues across hardware, operating systems (macOS and Windows), and enterprise SaaS platforms.
• Build and maintain automation tools using PowerShell, Python, or Bash to improve IT operations and streamline service delivery.
• Manage and support core productivity tools, including Microsoft 365, Google Workspace, Slack, Zoom, and other enterprise SaaS platforms.
• Lead root cause analysis for recurring issues, implement long-term fixes, and help prevent future incidents.
• Mentor junior technicians and provide technical leadership that helps grow capabilities across the team.
• Collaborate closely with teams like Infrastructure, Security, and DevOps to resolve cross-functional challenges and implement new technologies.
• Drive service improvements, evaluate tools and processes, and lead incident management efforts for high-impact technical issues.

What you'll bring

• 5+ years of experience in IT support or services, including 1-2 years in a senior or lead capacity.
  Proven experience scripting and automating workflows with PowerShell, Python, or Bash.
• Strong understanding of SaaS productivity platforms (O365, Google Workspace, Slack) and modern endpoint ecosystems.
• Deep troubleshooting skills with macOS, Windows, and hardware platforms.
• Passion for learning and staying current with emerging technologies.
• Ability to work independently, solve complex problems, and drive projects to completion.
• Familiarity with identity and access management (Okta, Azure AD) and endpoint management tools.
• Excellent communication, customer service, and interpersonal skills.
• Demonstrated leadership experience, especially in coaching or mentoring peers.

Join Our Team
We're a publicly traded (NASDAQ: DKNG) technology company headquartered in Boston. As a regulated gaming company, you may be required to obtain a gaming license issued by the appropriate state agency as a condition of employment. Don't worry, we'll guide you through the process if this is relevant to your role.
The US hourly rate for this full-time position is 34.62 USD - 43.27 USD, plus bonus, equity, and benefits as applicable. Our ranges are determined by role, level, and location. The compensation information displayed on each job posting reflects the range for new hire pay rates for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific pay range and how that was determined during the hiring process. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.