This episode contains some screen sharing so it’s best watched on YouTube
What happens when one product leader decides to stop copy-pasting between chat windows and instead build an operating layer that puts coding agents in the hands of an entire company?
In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Kyler Ross, Head of Product at Cloaked, to walk through the internal “harness” he started building last Thanksgiving: an agent-friendly system of context files and scripts that lets agents read from and write to the team’s real tools. Kyler explains how it gets installed on every company machine, why he treats each new agent session like onboarding an employee, and how a self-improving loop of skills and automated reviews keeps it getting better.
They explore his day-to-day setup for running many agents at once, why worktrees and Claude Code hooks exist to make failure nearly impossible, a one-on-one prep skill that pulls context from every corner of the company, and the layered guardrails, including a nightly “librarian” agent, that keep confidential information from leaking.
If you’re a product or engineering leader trying to make your team more AI-native, someone wiring agents into real workflows, or anyone wrestling with how to run agents safely at scale, this episode is for you.
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In this episode, we covered the following topics:
* (01:15) The Thanksgiving origin: copy-pasting between chat windows and losing prompts pushed Kyler to build a harness
* (02:32) What the harness is: an agent-friendly directory of context plus scripts that give the agent hands to read and write
* (06:18) How Cloaked deploys it: installed by default on every company machine, with nearly everyone using it
* (07:07) Why he owns ~80% of the code, treating it as a nights-and-weekends hobby separate from his day job
* (08:52) The self-improving loop: anyone can trigger a skill to fix a bad session and submit a PR
* (12:23) Using the harness as a testing ground for a more AI-native way to ship code
* (15:17) Why Slack agents, not Claude Code for everyone, democratize access for non-technical roles
* (16:21) Branding it “PMAI” and the Start Cloaked app that onboards employees
* (30:04) His iTerm2 setup and a keyboard shortcut that launches Claude Code in the right place
* (35:48) Maximizing concurrent agents, and the “infinite canvas” he wishes existed
* (39:14) Why running many agents at once becomes a key skill differentiator, and its fatigue tax
* (44:33) Worktrees and Claude Code hooks as deterministic guardrails that make failure nearly impossible
* (50:44) A one-on-one prep skill that pulls Slack, Granola notes, tickets, and docs into one place
* (54:53) Layered confidentiality guardrails and the nightly “librarian” agent, plus the 50,000-line PR story
* (1:01:20) Gratitude Corner: Kyler thanks Mike Carafa and Aashima Ratti
* And more!
Links:
* Cloaked: https://www.cloaked.com/
* Cloaked Job Board: https://jobs.ashbyhq.com/cloaked
* Sr. Product Manager opening: https://jobs.ashbyhq.com/cloaked/f1b12f94-a114-4d4b-a78e-5a6a2b6ee1fe
* Mike Carafa: https://www.linkedin.com/in/michaelcarafa/
* Aashima Ratti: https://www.linkedin.com/in/akratti/
* Kyler Ross: https://www.linkedin.com/in/kyler-ross-63552595/
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
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