Sr. IT Systems Administrator

Hi Marley; Boston (MA); Hybrid; USD 95,000 - 176,000; Full time

Benefits offered by this job

Equity grants

401(k) matching

Medical/Dental/Vision insurance

Wellness stipend

Parental leave

Flexible vacation policy

Job summary

Hi Marley is seeking a Sr. IT Systems Administrator to own identity, endpoint, and IT service management.

You will architect Microsoft Entra and device trust posture, manage the macOS fleet with Jamf, and build Jira Service Management workflows to enable self-sufficiency across the company. The role requires 5-7+ years in IT and a strong track record with Jira, Entra, and macOS management, while collaborating across teams in a hybrid Boston office.

Qualifications

• 5-7+ years in IT systems administration or senior IT roles.
• Experience owning Jira administration and ITSM workflows.
• Proficient in Entra, device trust, and macOS management (Jamf).

Responsibilities

• Own Jira administration, workflows, and JSM portal configurations.
• Manage Microsoft Entra identity, access, and device trust policies.
• Lead macOS MDM, Jamf deployment, and endpoint security hardening.
• Oversee core SaaS platforms and automation tools.

Skills

Jira Administration

IT Service Management

Jamf for macOS

Microsoft Entra

Endpoint Security

Email Security Standards

Automation with Zapier

Communication & Collaboration

Tools

Jamf

Microsoft 365

Confluence

Slack

Exchange Online

Job description

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 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–$175,500], depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity. It’s most common for new hires to start near the midpoint of the range, allowing room for growth as employees develop in their role.

In addition to base pay, we offer a comprehensive total rewards package that supports both your wellbeing and professional growth, including:

• 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 - we all work hard and take time when we need it

Who We Are:

At Hi Marley, our culture is built on three core values that every employee embodies:

• Max Courage – We encourage our team, our customers, and their customers to dream big, try new ideas, and maximize impact by measuring risk.
• Be Humble – We lead with appreciation and promote a culture of humility, compassion, and openness to learn from anyone, anywhere.
• Ubuntu (“I am because we are”) – We believe true success is much bigger than any single individual or company. By aligning our individual aims behind a shared purpose, we can achieve our fullest potential — together.

Life at Hi Marley:

Life at Hi Marley is shaped by collaboration, learning, and genuine connection. We’re proud to foster an environment where people can do their best work, feel supported, and grow alongside a team that celebrates both individuality and shared purpose.

• A fun, lively startup culture that embraces creativity and innovation
• Core values-based leadership that guides our decision-making and daily interactions
• A culture of engagement, diversity, inclusion, and belonging — everyone’s voice matters
• Flexible, hybrid work environment that values balance and trust
• Ample opportunities to learn, take on new challenges, and make an impact in a fast-growing organization
• Meaningful work that directly supports our mission to help people and organizations communicate with empathy and clarity

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.

Hi Marley participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. For more information, please review the documents under "E-Verify Poster" here: https://e-verify.uscis.gov/web/OnlineResources.aspx