Senior IT Engineer

Senior IT Engineer

Cherry is a fast-growing FinTech offering the simplest, fastest, and most inclusive BNPL solution for medical practices—including dental, medical aesthetics, and veterinary etc. We help practices treat more patients by making care financially accessible. Cherry is led by Stanford entrepreneurs with a previous successful exit and backed by top investors, including Kleiner Perkins and DCM.

About the Role

Cherry is looking for a Senior IT Engineer to own and evolve the internal systems, tools, and infrastructure that keep every team at Cherry moving fast and securely. You'll be the technical backbone of our internal IT function — designing how we provision and secure devices and accounts, automating the manual work of onboarding and offboarding, and building the identity, endpoint foundations a fintech company needs to earn customer trust.

What You'll Do

• Own Cherry's internal IT stack end-to-end: identity and SSO (Okta), Google Workspace, device management (MDM), and the core SaaS tools every team relies on.
• Design and automate employee onboarding and offboarding. Provisioning, deprovisioning, and access changes across all internal systems.
• Own endpoint management and the device lifecycle end-to-end. Procurement, provisioning/imaging, inventory tracking, repair/replacement, and secure retirement for a fully remote workforce.
• Be the first responder for all IT issues across the company — triaging, troubleshooting, and resolving day-to-day hardware, software, account, and access problems as they come in.
• Partner with Security to support SOC 2 and other audit requirements, including access reviews and least-privilege enforcement.
• Reduce manual IT work through automation and scripting.
• Serve as the escalation point for complex IT issues and act as a hands-on resource for the whole company.
• Own our ITSM practice: manage the ticketing system, define workflows for incidents/requests/changes, and track SLAs to keep support fast and predictable as the team grows.
• Document systems, runbooks, and processes so IT knowledge scales with the team.

What We're Looking For

• 5+ years of experience in IT engineering, systems administration, or a similar internal-IT role, ideally at a startup or in a regulated industry.
• Hands-on experience administering Okta (or similar IdP), Google Workspace, Microsoft 365, and MDM tools.
• Experience with ITSM platforms and designing incident, request, and change management workflows.
• Comfort writing scripts or light automation to eliminate repetitive work.
• Working knowledge of networking fundamentals, endpoint management/device lifecycle tools, and access control best practices.
• Experience supporting SOC 2, PCI-DSS, or similar compliance audits from the IT side.
• Strong communication skills and the judgment to operate independently as a senior or sole IT resource.
• A security-first mindset balanced with genuine empathy for end users.

Nice-to-Haves

• Experience in fintech, healthcare, or another regulated environment.
• Familiarity with Zero Trust networking tools.
• Basic working knowledge of AWS or GCP for internal tooling and infrastructure.
• Experience standing up IT processes from scratch at an early-stage company.

Benefits (for U.S.-based full-time employees)

• Competitive Base + Bonus
• Generous equity grant
• Medical, vision, and dental benefits
• Fully remote company
• Flexible PTO

Cherry provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law.