Head of Systems & AI — Source Club

Build the AI-native operating system that lets a 7-person dental GPO run like a 30-person company. $120K–$180K base, fully remote

Salaried | Fully Remote (US-based) | Head of Systems & AI

The Role

You'll own the operating system that runs Source Club — the tech stack, the automations, the data, and the AI workflows that let this small team punch like a much bigger one. You'll partner with Arthur, our in-house tech IC, who builds the deep technical work — you scope, sequence, and translate; Arthur ships the hard parts. You sit on the leadership team with the CEO, VP of Growth, and Head of Customer Success, and you own the build side of how Source Club operates. You touch the keyboard every day. This is a builder seat. The "Head of" is real — leadership-team peer, direction-setter, owner — but you also ship.

About Source Club

Source Club is a dental Group Purchasing Organization reinventing how dental practices buy supplies. We charge a flat monthly subscription, take zero vendor kickbacks, and pass the savings straight to our members. The average practice saves $10,000–$30,000 a year on the exact same products they were already buying — they just stop overpaying. We were founded by the former VP of Supply Chain at a 200+ office DSO and today serve 400+ practices.

We're a 7-person team. Lean by design. We use leverage — systems, automation, and AI — to do the work of a much bigger company.

Benefits

• $120,000–$180,000 base salary, depending on experience
• Fully remote (US-based)
• Generous PTO
• We keep it simple and pay you well rather than burying the value in perks

Responsibilities

• Architect and ship the flagship business automations — the savings analysis pipeline (our top priority), bookkeeping automation, onboarding automation, lifecycle/missed-savings comms
• Connect and clean the tech stack — HubSpot, Stripe, ZenOne, QuickBooks, Notion, GA/Meta — so the whole company runs off one trustworthy data layer
• Manage Arthur day-to-day — sequence his work, write clean specs, sit in on the cross-departmental calls where systems decisions get made
• Run the AI enablement program for the company — interview every teammate, find the highest-leverage automation opportunities, then go build them
• Drive cross-functional projects from decision to done — own the top 3–5 initiatives in flight at any time
• Stand up company dashboards in Notion that roll up project, task, and KPI reporting automatically

Results We Expect — first 90 days

• The savings analysis pipeline is live and shaving 5+ hours/month off the leadership team
• HubSpot ↔ Stripe billing reporting is live; no more cross-referencing spreadsheets
• One company dashboard in Notion that everyone opens daily to see what's moving
• Every teammate has at least one AI workflow they use in their daily work
• The project queue is moving 2–3x faster than today

Requirements

Required

• You've built production AI/automation systems hands-on — Claude Code, Codex, OpenAI/Anthropic APIs, custom data pipelines. Not "directed engineers who did" — you, on the keyboard.
• Strong systems-architecture judgment — you've integrated CRM, billing, and ops tooling at a real company and know which connections survive contact with reality
• Deep fluency in HubSpot (or peer CRM), Notion, Zapier/Make, and SQL or a scripting language
• Builder by default — you ship to real users, you don't just diagram
• Strategic communicator — you can sit with a non-technical teammate, draw out the real automation opportunity, and write a spec someone else could ship from

Bonus points

• Background as a forward-deployed engineer, technical founder, or RevOps/Systems lead at a sub-30-person company
• You've run an EOS or weekly leadership cadence — own a scorecard, run a quarterly planning rhythm
• Healthcare, dental, or B2B subscription industry context

Other Perks

• Tiny team, real leverage — you're not the 47th systems person at a 500-person org. You're the leverage layer for the entire company.
• Direct line to the CEO and VP of Growth. No four-layer org chart between you and the call.
• Real autonomy on the stack. You'll make the architecture decisions; we want a thinker, not an executor.

What We Love in a Candidate

• You've built and shipped — production stuff, not deck stuff
• You ask "what's the simplest thing that works" before "what's the cleverest architecture"
• You're curious about the business itself, not just the tech under it
• You pick up new tools fast — you've used at least three of: Claude Code, Cursor, Codex, Replit, Bolt, V0, Lovable
• You write specs other people can actually ship from

Equal Opportunity

Source Club is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by law.

How to Apply

Apply through the Source Club careers page: https://www.sourceclub.io/careers/. In your application, please include one specific example of a production AI/automation system you've built end-to-end — what it replaced, what you owned, and the measurable result.

What's next: quick application review → a short paid case study (the actual savings-analysis pipeline problem we're solving) → final interviews with Brad (CEO) and Jake (VP of Growth). The whole process runs in about two weeks.

Application Questions

1. What has you looking for a new position?
2. Walk us through the most complex AI/automation system you've built end to end — what you owned, what you decided, what shipped, and the result.
3. Who are your last 3 bosses (name + employer)? How would each rate your performance 1–10, and why?
4. What's the proudest build of your career? Why that one?
5. How do you decide build vs. buy vs. integrate when designing a new system?
6. What recent books, courses, or trainings have sharpened your AI / modern-stack skills? What did you take away?