Senior Engineer, IT Operations
Checkout.com · New York City · $112,800–$141,000 (stated in the posting)
Company Description
We’re Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day.
We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers.
Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale.
If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact.
With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.
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
Bring all of you to work
We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.
Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands.
We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.
It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.
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.
Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.
For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram
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