Senior Systems Engineer

Engg; Chicago, New York, San Francisco (IL, NY, CA); On-site; USD 152,000 - 210,000; Full time

Job summary

Engg in Chicago seeks a Senior Systems Engineer to own the macOS platform, drive endpoint management, and align device trust standards across IT. You will partner with Security to enforce Zero Trust and manage Jamf Pro, AutoPkg, and Okta integrations.

You will define technical standards, mentor teammates, and lead cross-functional programs affecting IT Support, Security, and People teams. This role includes after-hours on-call rotation and a focus on scalable tooling, scripting, and enterprise

Qualifications

• 8+ years of hands-on macOS management at scale with enterprise MDM (e.g., Jamf Pro, Kandji, Mosyle) and/or open‑source tooling (e.g., Munki, Puppet, Chef).
• Production experience building AutoPkg recipes, overrides, trust controls, and automated promotion into an enterprise MDM environment is required.
• In-depth understanding of Apple’s MDM protocol and Configuration Profile specifications, including the shift to Declarative Device Management.
• In-depth understanding of installers and packages, LaunchDaemons and LaunchAgents, the preferences subsystem, system extensions, macOS built‑in security tooling (Endpoint Security Framework, SIP, XProtect, Gatekeeper, openBSM), and unified logs.
• Proficiency in at least one general‑purpose or scripting language (e.g., Python, Swift, Bash, Go) for API interaction and automation.
• Solid understanding of Zero Trust / BeyondCorp concepts and how endpoint posture feeds identity‑based access decisions.
• Track record of decisions spanning multiple systems, balancing scalability, compliance, cost, and long‑term maintainability.
• Comfort defining a problem before solving it, and aligning stakeholders around a technical direction.

Responsibilities

• Own the macOS platform and Jamf Pro environment, including profiles, groups, policies, MDM commands, and change standards.
• Own AutoPkg-based software pipeline, packaging, deployment, patch management, and disk encryption across the global macOS fleet.
• Build automations and shared tooling that accelerate work beyond your own – scripts, patterns, and integrations other IT engineers can adopt.
• Own zero-touch provisioning and device enrollment (Automated Device Enrollment, Setup Assistant, bootstrap workflows).
• Use scripting and APIs to create custom integrations and reduce manual IT operations.
• Partner with Security to enforce a Zero Trust / BeyondCorp model and device posture in authentication decisions.
• Establish the endpoint standards the IT organization follows and lead cross-functional delivery across teams.
• Mentor peers and support enablement to reduce ticket loads and improve resilience.

Skills

MDM management

Cross-functional collaboration

Scripting (Python)

Problem solving

Documentation

Tools

Jamf Pro

AutoPkg

Okta

osQuery

CrowdStrike

Kandji

Munki

Job description

About the role

We are seeking an experienced Senior Systems Engineer to own our macOS platform and drive endpoint management and device trust standards across Chime’s IT ecosystem. As a Senior Systems Engineer, you will drive multi-system initiatives across our IT domains – endpoint management, identity, and security tooling – with a primary focus on macOS and Jamf Pro. You’ll establish the technical standards other engineers work to, and partner cross-functionally on programs that affect IT Support, Security, and every Chimer with a laptop. This is a role for someone who thrives in ambiguity: you’ll often define the problem before solving it, and align stakeholders around a technical direction rather than waiting for a specification. We believe a secure access platform can be built entirely in the cloud, leveraging tools such as Jamf, AutoPkg, Okta, osQuery, and CrowdStrike. Pairing closely with our Security team, this role makes sure our fleet stays in sync with all policies and posture checks before devices are allowed access to corporate data. This role participates in an after‑hours/on‑call rotation for critical endpoint and device‑management issues. Rotation frequency, response expectations, and escalation procedures will be communicated during the interview process. This position will report to the IT Engineering Manager.

Salary and Benefits

The base salary offered for this role and level of experience will begin at $152,000.00 and up to $210,000.00 . Full-time employees are also eligible for a bonus, competitive equity package, and benefits. The actual base salary offered may be higher, depending on your location, skills, qualifications, and experience.

Responsibilities

• macOS Platform and Endpoint Management Platform Ownership: Own the technical direction, operation, and continuous improvement of our Jamf Pro environment, including configuration profiles, smart groups, policies, MDM commands, and change standards.
• Software Delivery: Own our AutoPkg‑based software pipeline: recipes, overrides, trust verification, and automated import into Jamf, alongside packaging, deployment, patch management, and disk encryption across the global macOS fleet.
• Automation & Reusable Tooling: Build automations and shared tooling that accelerate work beyond your own – scripts, patterns, and integrations other IT engineers can adopt rather than rebuild.
• Provisioning: Own zero‑touch provisioning and device enrollment (Automated Device Enrollment, Setup Assistant, bootstrap workflows) so new Chimers are productive on day one.
• Scripting & API Integration: Use scripting and general‑purpose languages (Python, Swift, Bash, Go) and vendor APIs to create custom integrations and eliminate manual IT operations.

Security, Governance, and Compliance

• Security Posture: Partner with Security to identify and mitigate risks to the fleet, enforcing a Zero Trust / BeyondCorp model through device trust, adaptive authentication, and least‑privilege access.
• Device Trust: Connect device management to our identity provider (Okta) so device posture is a factor in authentication and application access.
• Compliance: Implement compliance processes and tooling to report configuration status, and assess and implement benchmark standards (e.g., CIS) against a documented, risk‑based rationale.
• Reporting: Develop metrics and reporting reflecting the inventory, health, and compliance state of all devices.
• Troubleshooting: Serve as the Tier3 escalation point for complex endpoint issues.

Standards, Collaboration, and Mentorship

• Technical Standards: Establish and document the endpoint standards the broader IT organization works to, and raise the bar on testing, monitoring, and maintainability through example and influence.
• Cross‑Functional Delivery: Lead initiatives spanning IT Support, Security, and People teams – reconciling competing priorities and keeping stakeholders aligned from planning through rollout.
• Mentorship: Mentor peers, engineers, and technicians through technical guidance, documentation, enablement, and example.
• Support Enablement: Work with IT Support to identify pain points and implement systemic fixes that reduce ticket load rather than absorbing it.

Requirements

• 8+ years of hands‑on experience managing macOS at scale with enterprise MDM (e.g., Jamf Pro, Kandji, Mosyle) and/or open‑source tooling (e.g., Munki, Puppet, Chef).
• Production experience building and operating AutoPkg recipes, overrides, trust controls, and automated promotion into an enterprise MDM environment is required.
• In‑depth understanding of Apple’s MDM protocol and Configuration Profile specifications, including the shift to Declarative Device Management.
• In‑depth understanding of installers and packages, LaunchDaemons and LaunchAgents, the preferences subsystem, system extensions, macOS built‑in security tooling (Endpoint Security Framework, SIP, XProtect, Gatekeeper, openBSM), and unified logs.
• Proficiency in at least one general‑purpose or scripting language (e.g., Python, Swift, Bash, Go) for API interaction and automation.
• Solid understanding of Zero Trust / BeyondCorp concepts and how endpoint posture feeds identity‑based access decisions.
• Track record of decisions spanning multiple systems, balancing scalability, compliance, cost, and long‑term maintainability.
• Comfort defining a problem before solving it, and aligning stakeholders around a technical direction.
• Excellent written and verbal communication for technical and non‑technical audiences, including the structured documentation that scales understanding across a distributed team.
• Nice‑to‑have Jamf Certified Admin (300/400) or equivalent demonstrated mastery of those knowledge domains.
• Familiarity with Windows endpoint management (Intune/Endpoint Manager, PowerShell, MSI packaging, WMI, registry) – Windows is a smaller part o