Desktop System Software Engineer II

AlphaSense•Chicago, IL

13h•$80,000 - $110,000

About The Position

AlphaSense is seeking a Desktop System Software Engineer II to join the Corporate Technology team. This role focuses on enterprise endpoint engineering and desktop application diagnostics, managing the health, behavior, and configuration of macOS and Windows endpoints at a systems level. The position acts as a technical liaison between Corporate IT and the AlphaSense product engineering organization, with a specific emphasis on the performance of AlphaSense's desktop applications on managed devices. The role involves working with technologies such as Kandji/Iru, Microsoft Intune, CrowdStrike, and Cloudflare, and requires the ability to reproduce, isolate, and help resolve issues within AlphaSense's own desktop applications.

Requirements

3–5 years of experience in a systems engineering, endpoint engineering, or desktop platform role (not generalist IT support)
Deep hands-on experience with macOS (preferably) and/or Windows at a configuration and troubleshooting level beyond standard user support
Demonstrated experience with one or more enterprise MDM platforms: Kandji/Iru, Jamf Pro, or Microsoft Intune
Proficiency in at least one scripting language: Bash, Python, or PowerShell
Hands-on experience diagnosing desktop application issues — including crash log analysis, OS permission models, app sandboxing, auto-update mechanisms, and the interaction between security tooling and application runtime behavior
Familiarity with enterprise security tools (EDR, Zero Trust/CASB, identity platforms) and how they can affect desktop application behavior
Ability to write clear, detailed bug reports and escalation summaries that product engineering teams can act on without requiring additional back-and-forth
Strong written communication skills — able to produce runbooks, diagnostic guides, and engineering documentation

Nice To Haves

Experience with Kandji/Iru specifically, including Blueprint architecture, Liftoff enrollment, and custom enforcement scripts
Familiarity with Electron-based desktop applications and their specific packaging, update, and permission behaviors on macOS and Windows
Experience with CrowdStrike Falcon, including understanding how sensor policies and network containment affect application-layer behavior
Experience with Cloudflare Zero Trust / WARP in a managed enterprise environment and its impact on desktop app traffic
Exposure to Okta device trust or certificate-based authentication flows as they relate to desktop application SSO
Background working in a SaaS product company where IT and Engineering teams collaborate closely on end-user issues
Experience using Qualys VMDR or similar vulnerability management tooling
Familiarity with Jira Service Management for ticket and change management workflows

Responsibilities

Collaborate and contribute on the strategy and execution of macOS and Windows endpoint configuration, policy enforcement, and lifecycle management via Kandji/Iru and/or Microsoft Intune
Build, maintain, and iterate on device enrollment workflows, configuration profiles, compliance policies, and custom scripts
Design and enforce software deployment, patch management, and application allowlisting/blocklisting strategies
Collaborate with Security on EDR (CrowdStrike Falcon), Zero Trust (Cloudflare WARP/Gateway), and identity (Okta) integrations at the endpoint layer
Maintain scripting libraries (Bash, Python, PowerShell) to automate endpoint management tasks and reduce manual intervention
Serve as a primary technical escalation point for issues users experience within AlphaSense's desktop applications on managed endpoints
Reproduce client-side issues across macOS and Windows versions, app build versions, and endpoint configurations to isolate root causes
Investigate and diagnose desktop application behavior including crash analysis, rendering issues, performance degradation, update/upgrade failures, and OS-level permission or sandboxing conflicts
Partner with product engineering teams to log detailed bug reports, provide environmental context, and validate fixes as they are released
Capture crash logs, console output, network traces, and system-level diagnostics to accelerate resolution of complex application-layer problems
Maintain a diagnostic runbook library covering common desktop application issues on Kandji/Iru- and Intune-managed devices
Test new desktop application releases against the managed device baseline before broad rollout, flagging regressions early
Monitor endpoint fleet health, identify systemic issues, and drive proactive remediation before issues impact users
Contribute to internal tooling and automation to improve IT operations and reduce ticket volume
Document configurations, processes, and runbooks in the team's knowledge base
Participate in incident response for endpoint-related security events alongside the Security team