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PointFive is an AI Efficiency OS that helps engineering and FinOps teams manage AI spend and cloud costs. The company recently closed a $60M Series B led by Accel and was founded by the team behind IntSights (acquired by Rapid7).
TokenShift is PointFive's newest product—a lightweight CLI proxy that sits between AI coding agents and the shell or server. It routes to different models for optimal model-to-effort fit, compresses command output to reduce token spend, and provides fleet-wide visibility. As Senior Software Engineer (Endpoint), you will own the foundational infrastructure layer that makes TokenShift work on developer machines at scale.
Key responsibilities:
- Own installation and enrollment mechanics: CLI flows, MDM scripts, and platform-specific packaging (Windows msi/exe, macOS pkg, Linux deb/rpm) to deploy TokenShift to developer machines at fleet scale.
- Instrument and monitor endpoint behavior through the telemetry pipeline to improve coverage and catch regressions.
- Build and maintain a robust lab enabling automatic R&D of new capabilities and platforms by AI agents.
- Build and maintain agent harnesses—per-agent adapters that hook into Claude Code, Cursor, Copilot CLI, Codex, and future agents to route network and shell commands through the TokenShift proxy.
- Develop and extend compression rules and strategies for new command types (git, build tools, infra CLIs, search, etc.), ensuring token reduction never sacrifices semantic accuracy.
- Maintain correctness and resilience of the proxy layer: compression must be reversible on demand, hooks must never block developer commands, and failures must be silent and transparent.
- Collaborate with the research team to translate newly supported agent architectures into production-grade harnesses.
The role offers early-stage leverage where your work directly shapes the product, culture, and go-to-market strategy. You'll build infrastructure that runs on every developer's machine, making AI agent sessions cheaper and more visible.
REQUIREMENTS:
Must-have:
- Solid understanding of Windows and Unix fundamentals: process model, shell execution, stdin/stdout/stderr, file permissions, and IPC.
- Deep familiarity with MDM deployment patterns (Jamf, Intune, JumpCloud, Ansible).
- Strong proficiency in Go—the TokenShift CLI is written in Go and is where core work happens.
- Experience building or maintaining CLI tools in production environments.
- Attention to correctness and edge cases; ability to think through failure scenarios proactively.
- Ability to work across platforms (macOS and Linux) and understand their differences at the system level.
Nice-to-have:
- TypeScript experience.
- Hands-on experience with AI coding agents (Cursor, Claude Code, Copilot CLI, Codex) as a user or developer.
- Experience with semantic compression, summarization, or output parsing.
