IT Systems Engineer

Founded in 2015, Sure is the first AI-native insurance platform. With AI built into every layer, from underwriting guardrails to claims automation, Sure's enterprise infrastructure powers the world's most recognized brands and carriers.

Our APIs and AI agents streamline the entire insurance lifecycle, making quoting, binding, policy servicing, and claims faster and smarter. The result: faster time to market, better customer experiences, and intelligent insurance at scale. Sure is building the technology rails transforming how insurance is distributed, underwritten, and experienced.

Why join our team?

🌐 Remote-first culture. We work from home and embrace digital collaboration

💥 Impactful work. We're transforming a trillion-dollar industry that touches everyone's lives

🏆 Award-winning growth. Named among Deloitte Technology Fast 500, Inc. 5000, Forbes Fintech 50, and CNBC World's Top Insurtech Companies

🤝 Culture is everything. Join an incredible team of smart, passionate, collaborative and driven individuals

Own the service desk. Triage and resolve IT requests from a fully remote team through Slack and our ticketing system.

Provision, change, and remove user access across Google Workspace, Slack, AWS, and the rest of our SaaS stack. Keep onboarding and offboarding clean and fast.

Manage our Mac fleet through MDM. Handle procurement, shipping, repair, recovery, and inventory for company equipment.

Administer company tooling so the rest of the team doesn't have to.

Support our security program. Triage alerts and findings from tools like Wiz, Datadog, and our endpoint protection, and route them to the right engineer with clear context.

Collect and organize evidence for SOC 2 and PCI audits, and help fill out customer security questionnaires.

Write down what you learn. Build runbooks and documentation so fixes happen once, not every time.

Recommend and implement improvements to IT policies, processes, and tools. Use AI and scripting to automate repeat work.

5+ years of experience in IT systems administration or IT support across more than one company or environment.

Hands-on experience administering Google Workspace and a SaaS-heavy stack, including identity and access management.

Experience managing macOS devices with an MDM (Iru, Jamf, or similar).

Working knowledge of AWS, including IAM basics.

Comfort with shell scripting or Python to automate routine tasks.

Exposure to security tooling (CSPM, EDR, SIEM, or vulnerability scanners) and a strong interest in growing on the security side.

A service-first attitude. You are patient, clear, and friendly with non-technical teammates.

The courage to jump into unfamiliar systems, ask how urgent a request is, and prioritize without waiting for permission.

Clear written communication. You document your work so others can follow it.

Nice to have: experience supporting a SOC 2 or PCI audit, experience with Wiz or Datadog, or experience working alongside software engineers in a SaaS company.

Unlimited PTO, and we mean it

Mental health support: meditation app access and a weekly wellness hour

Remote work stipend for your setup

Comprehensive medical, dental, and vision options

Equity and 401(k)

Generous parental leave

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

For more information, visit https://www.sureapp.com/. Follow @SureHQ on Twitter, Facebook and Instagram.