Senior Software Engineer - Endpoint

About the role

TokenShift is PointFive's newest product – a lightweight CLI proxy that sits between AI coding agents and the developer shell, routing requests to the optimal model and compressing output to reduce token spend. As a Senior Software Engineer (Endpoint) you will own the infrastructure that makes TokenShift work at scale, from per‑agent harnesses to compression strategies and installation mechanics.

Key responsibilities

• Design and maintain installation and enrollment mechanics, including CLI flows, MDM scripts, and platform‑specific packaging (Windows MSI/EXE, macOS PKG, Linux DEB/RPM) for fleet‑scale deployment.
• Instrument and monitor endpoint behavior through a telemetry pipeline to improve coverage and detect regressions.
• Build and sustain a lab environment for automated R&D of new capabilities and platforms by AI agents.
• Develop and maintain agent harnesses that integrate with Claude Code, Cursor, Copilot CLI, Codex, and future agents.
• Create and extend compression rules for various command types (git, build tools, infra CLIs, search) while ensuring reversible, loss‑less operation.
• Guarantee correctness and resilience of the proxy layer – silent failures, non‑blocking hooks, and transparent error handling.
• Collaborate with the research team to turn new agent architectures into production‑grade harnesses.

Required profile

• Solid understanding of Windows and Unix fundamentals (process model, shell execution, I/O streams, permissions, IPC).
• Deep familiarity with MDM deployment patterns (Jamf, Intune, JumpCloud, Ansible).
• Strong proficiency in Go, the primary language of the TokenShift CLI.
• Experience building or maintaining production‑grade CLI tools.
• Attention to edge cases and correctness, anticipating failures before they occur.
• Ability to work across macOS and Linux platforms and understand system‑level differences.

Required skills

• Go
• TypeScript
• Windows
• Unix
• macOS
• Linux
• MDM tools (Jamf, Intune, JumpCloud, Ansible)
• CLI development
• AI coding agents (Cursor, Claude Code, Copilot CLI, Codex)
• Semantic compression / output parsing
• Cloudflare
• Snowflake