Systems Administrator

We are looking for a productivity-focused technology professional to improve the IT experience of non-engineers at Smartleaf. This position requires a flexible (50%-75%) in-office presence at our Boston headquarters.

About Us

Smartleaf is an investment portfolio rebalancing service handling over $100 billion in assets. We're approaching 50 people, who are primarily skilled software and system engineers. Until now, our SaaS operations team has handled internal IT as a secondary responsibility. That sufficed when we were nearly all engineers, but we've added non-technical staff and we need someone to handle IT and productivity as their main job.

You can shape how this function works and have a meaningful impact on the day-to-day experience of everyone at Smartleaf.

What You'll Be Doing

Most of your time will be spent building and improving systems rather than responding to tickets. We expect roughly 75% systems work and 25% support, with bouts of near-full-time support from time to time.

You'll administer our productivity stack: Google Workspace, Zoom, and other SaaS tools and own relevant vendor relationships from evaluation through renewal. You'll improve our onboarding and offboarding processes, manage device provisioning and MDM, and identify manual work worth automating. You'll also handle desktop support for macOS and Linux environments and access management. We will also ask you to help out with the Operations team’s work from time to time.

Requirements

5+ years of experience in IT operations, sysadmin, or a similar role, ideally in a startup or growth-stage company

Familiarity with scripting (Bash, Python, Ruby or similar) for automation

Happiness in a non-MS environment: you’ll be managing and troubleshooting MacOS and Debian Linux systems. We use LDAP but not Kerberos or AD.

Experience with MDM tooling for device management and lifecycle

Strong documentation habits

Able to work independently, prioritize, and communicate clearly with both technical and non-technical colleagues

Ability to lift 50 pounds on occasion

Nice to Have

Experience with SSO/identity providers (Okta, Google SSO, etc.)

Prior experience standing up an IT function at a small company

Exposure to SOC 2 or similar compliance frameworks

Hands-on Google Workspace administration experience — user management, groups, Drive policies, domain configuration

You'll Be a Great Fit If You

Want to own a function

Enjoy a mix of building systems and solving immediate problems

Notice process friction and fix it

Prefer to automate manual processes to reduce your workload

Growth

The Operations team will work closely with you

Smartleaf does not subscribe to “Up or Out” - you can expand your responsibilities and grow your skills without being required to move up a chain

If future growth requires additional people, you will have the opportunity to manage them or stay an individual contributor

Visa Sponsorships

Smartleaf is unable to provide visa sponsorship now or in the future. This includes, but is not limited to, H-1B, F-1 (including OPT/CPT), J-1, or any other employment-based immigration or work authorization sponsorship. Candidates must have current and ongoing authorization to work in the United States without sponsorship.

Tools & Stack

We prefer on-prem services where practical

Google Workspace, Zoom, and related SaaS productivity tools

macOS and Debian Linux

What Success Looks Like in Six Months

Month 1–2: Full audit of our current tools, vendors, and access controls; document and prioritize gaps; handle over half of desktop support issues

Month 3–4: Onboarding/offboarding workflows documented and critiqued; MDM coverage complete; vendor contracts reviewed; handle 75%+ of desktop support

Month 5–6: Self-service IT resources live; at least two meaningful manual processes automated; first onboarding peak handled with no significant issues

Compensation

$100,000 – $150,000, depending on relevant experience