Senior Engineer, IT Operations

Purpose of the role

This person will be Checkout.com's only IT Operations engineer in the Americas. They'll own workplace technology across five growing offices (New York, Atlanta, San Francisco, Mexico City and Brazil) and support remote employees. They solve what can be solved locally. When something needs a central Technology team, mostly based in the UK and five hours ahead, they escalate with evidence. They turn recurring problems into documented fixes that scale. They give the CEO and the newest joiner the same standard of service, and they keep users informed until each issue is closed.

Key responsibilities

• Be the senior IT point of contact for Americas offices and remote employees, including executives in the New York Office.
• Own complex issues through to resolution, or hand them to the owning team with a clear escalation. That covers end-user devices, endpoints, identity, meeting-room AV, office technology and basic-to-intermediate networking.
• Run Americas onboarding and offboarding, including the onboarding sessions and hardware logistics.
• Support office openings, moves and events across the region, traveling as needed (up to 25%).
• Manage vendor relationships, local inventory and procurement, and follow through on each.
• Log all work in Jira Service Management queues so it's auditable and colleagues can step in during absences.
• Spot recurring issues and fix them at scale through automation, scripting, AI tools, documentation or process change, then measure the impact.
• Build working relationships with office leaders, HR, Workplace Experience, Facilities, Engineering, Operations and the service desk teams.
• Take an active part in the wider, mostly UK-based IT team: present in meetings, contributing, not working in isolation.
• Mentor colleagues and share knowledge. As the Americas team grows, help bring new hires up to speed.

Essential requirements These are the four CV-screen filters Tom picked, in the order he named them:

• Regional autonomy: has been the sole or primary IT presence for an office or region, working independently while the central teams sat in other time zones. Knows when to fix locally and when to escalate.
• Operational improvement: has spotted recurring problems, fixed them at scale and stopped them coming back, and can state the measured impact.
• Technical depth and breadth: across macOS and Windows devices, identity, collaboration tools, meeting-room AV and networking fundamentals.
• Independent service ownership: has owned a service, project or operational area end to end, and stayed accountable through diagnosis, recovery, root cause and prevention.

Also essential:

• Experience with each category of the core tooling: device management, identity, collaboration suite and IT ticketing. The exact products aren't required. A candidate with neither the tool nor the domain is not a fit.
• Gives executives and junior employees the same standard of service.
• Communicates openly. Can talk users through fixes remotely and sends updates without being chased.
• Drives their own learning rather than waiting to be trained.
• Able to travel up to 25%.

Desirable

• Checkout's stack: Google Workspace, Slack, Okta, Jamf (macOS), Intune (Windows), Jira Service Management, Google Meet (Zoom experience is fine), and Poly room/Logitech hardware.
• In-house corporate IT background, preferred over managed service provider (outsourced IT) experience.
• Practical AI use, such as building workflows in Claude, and helping others adopt it.
• Scripting in any language.
• Technical lead or mentoring experience, and real interest in moving into first-line supervision.

Not required

• Deep network architecture expertise.
• Formal people management.
• Experience with every Checkout tool.
• A specific scripting language. This is not a DevOps role.

Salary Range: $112,800 - $141,000

Additional Information

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.