As we continue to grow, we're looking for a Sr. IT Systems Engineer to own the internal technology stack that powers how Hi Marley operates. Hi Marley is building an AI-native operating model: personal agents, team agents, MCP connectors, and AI deeply integrated into how we build, sell, and serve enterprise insurance carriers. Underneath all of it sits the identity, endpoint, and SaaS ecosystem that every team depends on every day. That layer needs a senior engineer who can make it operationally excellent, automated, secure, and well documented.

This is a hands-on, systems-minded role. Working within the architecture and frameworks set by our senior technology and security leadership, you'll do the engineering that makes them real: automating identity and access lifecycle, hardening the SaaS applications our teams rely on, managing our device fleet, and building the AI-enabled workflows that eliminate manual toil. You'll script the repetitive work so it runs itself, and build the controls that keep us compliant and audit-ready as we scale.

You'll thrive here if you think in systems and integrations rather than one-off fixes, you reach for automation before repetition, and you care as much about the reliability and security of what you build as the speed of shipping it. Teamwork and shared enthusiasm are a core part of our culture, which is why this role involves joining us in the Boston office 2-3 days each week.

What You'll Do:

• Identity, Access & Lifecycle Automation: Implement conditional access control in our IdP, SCIM provisioning, and automated onboarding/offboarding workflows integrated with our HRIS and internal ticketing system.
• IT Service Management & Request Portal Modernization: Build and maintain a modern Jira Service Management (JSM) request portal with structured forms, approvals, and embedded knowledge articles to reduce email-based IT intake.
• Endpoint & Device Management: Develop and maintain macOS MDM compliance baselines, enforce security controls, support zero-touch deployment, and manage device lifecycle operations.
• AI-Native Productivity & Internal Tooling: Enable employees get the most out of Hi Marley's internal AI tools. Provision and manage access to Claude, ChatGPT, and Cursor; support colleagues who are building and running personal and team agents, automations, and internal tools; and troubleshoot AI-related issues as they come up. Coach safe, policy-aligned use of AI tools and MCP connectors, following the governance framework set by Security.
• Automation, Integrations & Internal Tooling: Automate high-volume IT and People Ops workflows using scripts, APIs, and low-code tools; improve self-service and reduce manual provisioning.
• SaaS Administration & Governance: Administer core platforms (Microsoft 365/Entra, Slack, Jira/Confluence, Zoom, Salesforce) and implement lightweight governance for roles, permissions, and configuration consistency.
• Email & Internet Security Support: Maintain SPF/DKIM/DMARC configurations, tune Exchange Online and email security policies, and support secure routing and deliverability improvements.
• 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+ years of hands-on experience in IT systems engineering and SaaS operations.
• Strong experience with identity, SSO, and provisioning workflows (Microsoft Entra, SCIM, SAML).
• Experience supporting end users of LLM-powered tools and agents (e.g., Claude, ChatGPT, Cursor): provisioning access, helping people build and fix simple agents or automations, and guiding safe use within established policy.
• Knowledge of email security and authentication standards (SPF, DKIM, DMARC).
• Proficiency using Jamf for MDM/endpoint management.
• Ability to automate workflows using Python, APIs, or low/no-code automation tools (e.g. Zapier).
• Practical experience administering Microsoft 365, Slack, and Jira/Confluence in a production environment.
• Strong communication and cross-functional collaboration skills, with a service-oriented mindset.

Nice-to-haves:

• 7+ years of hands-on experience in IT systems engineering and SaaS operations.
• 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 [$89,000-$164,000], 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