About

Agents everywhere. Production nowhere.

Sidekick Machines is a Canadian company that builds and operates digital workers. Here's why it exists.

Enterprises invested heavily in agents. Budgets approved, platforms licensed, pilots launched — and 95% of generative-AI pilots delivered zero measurable P&L impact (MIT NANDA, 2025). Gartner expects over 40% of agentic-AI projects to face cancellation by end of 2027. Sidekick Machines started with that gap — and a specific diagnosis of why it exists.

Our diagnosis: intelligence was never missing — workforce infrastructure was. A pilot proves a model can do work. Production demands what a real hire gets on day one: an identity someone governs, boundaries someone writes, supervision someone staffs, accountability someone signs. Enterprises buy agents as tools, so every one of those duties lands back on their busiest teams — and nobody owns results. Pilots stall right there, year after year.

So we built a company that supplies all of it. Workforce infrastructure — identity, bounded autonomy, telemetry, evaluations, guardrails — productized once and reused across every digital worker we field. One senior team spanning software, data, infrastructure, identity, security, and operations. A commercial model with two fixed fees and outcomes we contractually guarantee. We're Canadian, and we build for sovereignty in a practical sense: workers run where your data lives, under your controls, with every work product landing in your systems. It's why we can put our name on a guarantee — someone signs for results. Sidekick Machines signs.

Principles

How we run engagements

  • We charge for outcomes

    Engagements are scoped to a digital worker doing real work in production — never to seats, usage, or hours.

  • Success criteria come first

    Every build starts with measurable criteria, agreed in writing before engineering begins.

  • We build in your environment

    Your cloud, your identity stack, your controls. Sensitive data stays inside your perimeter.

  • We operate what we build

    Monitoring, evals, incidents, and upgrades stay with us after launch, under a flat annual fee.

  • Your work stays yours

    Data and every work product live in your systems — an exit never strands your history.

Our team

Senior, small, and forward-deployed

Sidekick Machines is a senior team spanning every discipline production workers demand — software engineering, data, infrastructure, identity, security, and operations. We work forward-deployed: inside your environment, alongside your people.

Start with one job description.

Send us a job you'd staff tomorrow if you could. We'll come back with how we'd build that worker — scope, timeline, and both fees.