CTO Apprentice
Sholder
Remote · location unlistedContractPosted 3w agoStill listed 3 days ago
See where you stand before you apply. No sign-up to start.
You apply on the posting's application page, with no Olive account needed.
Watch jobs like this. New remote roles like this one, by email.
Don't just apply. Show up ready.
Olive works from this exact posting.
At a glance
Olive focuses on jobs in the United States, including remote roles you can work from there.
Job overview
Sholder is seeking a remote CTO Apprentice to learn how its technology systems, compliance, and release processes work alongside the CTO and its AI development system, Jarvis. The engagement begins with shadowing and learning, then transfers ownership of SOC 2 compliance, with development and release responsibilities growing over time. It is a paid contract role for about 10 hours per week.
Skills & qualifications
Skills
Full job description
Contract · Remote · About 10 hours a week CTO Apprentice Learn to run a modern, AI-built technology organization from the inside — starting with keeping us SOC 2 compliant, every single week.
The short version Sholder's engineering is driven largely by Jarvis, our AI development system, working alongside our CTO. We're looking for someone to join that partnership: to learn how our systems, compliance and release process fit together, then own a growing share of them. You'll start by tagging along to see everything up close, take ownership of our SOC 2 compliance, and grow from there into development and releases.
About Sholder Sholder is building the infrastructure for human support — a platform that connects people with their own network of trusted advisors, coaches, and peers, powered by an AI layer that makes every relationship more intentional and every session more effective. We're a small, focused team. Our product is live. Our users are real. And our development model is unusual: the majority of our engineering is driven by an AI system named Jarvis, working within a codebase and product framework built to move fast without losing quality.
How this engagement works This is a paid contract role, remote, at about 10 hours a week. You'll work directly with our CTO and with Jarvis. The first weeks are tag-along: sitting in, asking questions, learning how the pieces connect. From there, SOC 2 becomes yours, and development and release responsibilities grow as you're ready for them.
What you'll do First — learn the system
- Shadow the CTO across compliance, development and releases to see how the work actually flows
- Learn how Jarvis and our AI development teams build, review and ship
Then — own SOC 2 compliance
- Keep our compliance at 100% every week, ready by Monday at 11:00 AM Mountain
- Report our compliance percentage at our weekly leadership meeting, and what you did to get it there
- Chase down gaps as they appear — evidence, access reviews, policies, failing checks — before an audit ever finds them
Over time — grow into development and releases
- Help guide work through our pipeline, review what gets built, and steward releases from testing to production
What success looks like Every Monday by 11:00 AM Mountain, SOC 2 compliance is at 100%, and you can say exactly how it got there.
Who you are
- You see systems, not just tasks. You notice how one change ripples through everything else, and you love making the whole thing work.
- You think like an engineer: you'd rather understand why something broke than make the symptom go away.
- You're a relentless problem-solver. A stubborn gap is a puzzle you want to crack, not a ticket you want to pass on.
- You bring your own drive. Nobody needs to chase you, because you're already ahead of the next thing.
- You're genuinely coachable. You ask, you listen, you adjust, and you grow fast because you want to.
To apply Send a brief note to [email protected] with two things:
- A system you understood deeply enough to improve — and what you changed.
- Why learning to run technology alongside an AI development system excites you.
Apply nowWe read everything.
Prepare for this role
You've read the whole posting — now see how you match it.