Sr. IT Systems Engineer

Insurance plays an important role in people's lives, providing protection and peace of mind through life's adventures and unexpected turns. In the moments that matter, people want to know their insurer is there for them. At Hi Marley, we help insurers deliver on that promise through communication that brings greater clarity and connection to the policyholder experience.


We are looking for a Sr. IT Systems Engineer 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 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.

Compensation, Benefits & Perks:
At Hi Marley, we are committed to fair and transparent pay practices. The annual base salary for this role is expected to fall within the range of [$94,500-$148,500], depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity.


In addition to base pay, we support your wellbeing and growth with:

• Equity grants for all employees
• 401(k) with a 4% employer match
• Medical, dental, vision, disability, and life insurance for employees working 30+ hours per week
• Monthly wellness and annual professional development stipends
• Paid parental leave
• Flexible Time Off to recharge, plus enjoy Wind-down Week, our annual year-end company shutdown

Who We Are:


Three core values guide how we work:

• Max Courage: Dream big, try new ideas, and take measured risks to maximize impact.
• Be Humble: Lead with appreciation, compassion, and openness to learn from anyone, anywhere.
• Ubuntu: Align behind a shared purpose to achieve our fullest potential together.

Life at Hi Marley combines meaningful work with clear expectations. We communicate openly and with care, stay curious, take ownership, and value every perspective. Our flexible, hybrid environment is built on trust, accountability, and mutual support-both at work and when life needs our attention.


Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves.