Sr. IT Systems Administrator

Hi Marley • Boston, MA

1d • Hybrid

About The Position

Hi Marley is transforming how the P&C industry communicates, making challenging moments faster, easier, and more empathetic for carriers and their customers. We build AI-powered software that keeps everyone in the claims conversation informed and connected. 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. This role involves owning systems end to end, from design through rollout and support, rather than operating 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.

Requirements

• 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 Zoom and supporting conference room or meeting room AV hardware.
• Basic scripting or API experience (Python, PowerShell) for advanced automation use cases.
• Experience supporting AI copilots or LLM-powered internal tools (e.g., ChatGPT, Cursor).
• Exposure to AWS, Twilio, or modern SaaS infrastructure used for internal systems.
• Background in SOC2/ISO-aligned environments, familiarity with audit evidence and access reviews.
• Experience with SaaS license optimization and cost management across a distributed environment.

Responsibilities

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

Benefits

• Equity grants for all employees
• A 4% matching 401(k) program
• Medical, dental, vision, disability, and life insurance coverage for employees working 30+ hours per week
• Monthly wellness stipend
• Paid parental leave
• A flexible vacation policy

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed