Sr. IT Systems Administrator

Insurance touches people during some of the most challenging moments in their lives. Hi Marley is on a mission to transform how the P&C industry communicates, making those moments faster, easier, and more empathetic for carriers and the customers they serve. We build AI-powered software that keeps everyone in the claims conversation informed and connected. If you believe insurance can combine operational excellence and automation with a human touch, we’d love to meet you.

We are looking for a Sr. IT Systems Administrator to own Hi Marley's identity, endpoint, and IT service management strategy: architecting our Microsoft Entra and device trust posture, running our macOS fleet, and building the Jira Service Management workflows that make the rest of the company self-sufficient. You will own these systems end to end, from design through rollout and support, rather than operate as a ticket-queue administrator.

Teamwork and shared enthusiasm are a core part of our culture, which is why this role involves joining us in the Boston office for 3 days each week. What You'll Do:

Jira Administration & IT Service Management:
Own Jira administration across the business: build and maintain workflows, project configurations, issue/ticket types, and schemes for the teams that run on Jira. Maintain the Jira Service Management (JSM) portal, request types, and approval workflows that route and resolve IT requests. Set the tiering, SLAs, and escalation paths and help keep the IT queue under control.

Identity, Access & Device Trust:
Own Microsoft Entra end to end: group-based access control, Conditional Access and device trust policies tied to endpoint compliance, SCIM provisioning, and the automated onboarding/offboarding workflows integrated with our HRIS.Endpoint & Device Management:
Serve as the senior owner and escalation point for our macOS fleet: MDM baselines and zero-touch deployment in Jamf, fleet-wide security hardening, device lifecycle operations, and hands-on troubleshooting when issues exceed first-line support.

SaaS Administration & Governance:
Administer and govern core platforms (Microsoft 365/Entra, Slack, Confluence), setting the roles, permissions, and configuration standards the rest of IT builds on.

Automation, Integrations & Internal Tooling:
Own Hi Marley's automation stack:
Zapier and other low/no-code tools that eliminate manual IT and People Ops work, cut provisioning time, and reduce manual toil across the business.

Email & Internet Security Support:
Own SPF/DKIM/DMARC configuration, Exchange Online security policy, and secure routing and deliverability for the company's email infrastructure.

Responsibilities may evolve over time, and additional tasks may be assigned as new systems, workflows, and technologies are introduced.

What We're Looking For:

5-7+ years of hands-on experience in IT systems administration, identity and endpoint architecture, or a comparable senior IT admin role.

Experience owning Jira administration: workflows, project configurations, issue types, and schemes, plus building request types and approval workflows in Jira Service Management (JSM) or similar ITSM tooling.

Proven ownership of Jamf for macOS MDM, zero-touch deployment, and fleet-wide security hardening.

Deep, hands-on experience with Microsoft Entra:
Conditional Access, device trust and compliance-driven access policies, SCIM, and SAML.Knowledge of email security and authentication standards (SPF, DKIM, DMARC, MTA-STS, BIMI).Proven ownership of Zapier or similar low/no-code automation tools: building and maintaining multi-step automations end to end. No coding required.

Strong communication and cross-functional collaboration skills, with a service-oriented mindset.

Nice-To-Haves:

Experience administering…