InsurTech, AI/ML, SaaS, Conversational AI

Sr. IT Systems Engineer

Boston, MAHybridFull TimeSenior$94,500–$148,500 /yrPosted 1 month agoVisa sponsorship available

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Required skills

Microsoft Entra
device trust
macOS
Jira Service Management
Jamf
MDM
zero-touch deployment
security hardening
Conditional Access
SCIM

Nice to have

Zoom
conference room AV
scripting
API
Python
PowerShell

Role summary

Hi Marley is seeking a Sr. IT Systems Administrator to lead their identity, endpoint, and IT service management strategy. This role involves architecting Microsoft Entra and device trust, managing the macOS fleet using Jamf, and building Jira Service Management workflows. The administrator will own these systems end-to-end, from design to support, focusing on automation and governance of core platforms like Microsoft 365 and Slack. The position requires 5-7+ years of experience in IT systems administration and specific expertise in Microsoft Entra, Jira Service Management, and Jamf. This is a hybrid role based in Boston, requiring 3 days per week in the office.

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.

About the Role

You'll own the systems everyone at Hi Marley signs into, works on, and asks for help through: identity, our Mac fleet, and the IT service desk. This isn't a ticket-queue job. You'll design these systems, roll them out, and support them end to end, building the access policies, device baselines, and service workflows that make the rest of the company self-sufficient. If you'd rather automate a request away than answer it twice, you'll love this role.

We spend Mondays, Tuesdays, and Thursdays together in our Boston office to connect, collaborate, and learn from one another. Recurring meetings generally fall between 9:30am and 4:30pm, allowing flexibility around the start and end of your day. Wednesdays and Fridays are remote.

What You'll Do

Own identity in Microsoft Entra end to end, from Conditional Access and device trust to automated onboarding and offboarding

Run our macOS fleet in Jamf, with zero-touch deployment, security hardening, and hands-on help when issues go past first-line support

Own Jira across the business and build the Jira Service Management portal, approvals, and SLAs that keep IT requests moving

Automate manual IT and People Ops work with Zapier, and own the security of our company email

About You

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

Deep, hands-on Microsoft Entra experience (Conditional Access, SCIM, SAML) and proven ownership of Jamf for macOS

Experience owning Jira and Jira Service Management administration, and building multi-step automations in Zapier or similar, no coding required

Working knowledge of email security standards like SPF, DKIM, and DMARC, and able to work from our Boston office 3 days a week

Nice to Have

Basic Python or PowerShell scripting for more advanced automation

Experience in SOC 2 or ISO-aligned environments, including audit evidence and access reviews

Zoom administration and conference room AV support

Don't check every box? If this role excites you, we'd still love to hear from you.

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.

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