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Open · Remote

Cutover Lead

Remote (US) · occasional client visit · Remote

Cutover-only, not customer-success. Days 0-30 of every new operator. Once the operator is live + clean past Day 30, support hands off to the in-platform AI assistant. No long-tail CSM exists. Your work compounds because every cutover teaches an exception pattern that gets baked into the migration tooling.

Compensation

Base $110-140k DOE + bounty per clean cutover ($2,500 per customer that hits Day-30 with zero open critical-tickets) + equity track. Aligned with cutover quality, not throughput.

Why this role exists

By cutover #15, the AI handles 80% of what cutover #1 needed because you’ve documented the exception patterns. By customer #50, the role may not need to exist anymore (or shrinks to part-time). That’s a feature, not a bug — you’re building yourself out of a job, and the equity track recognizes that compounding contribution.

What you’d do

  • Days 0-7: scope the operator’s existing POS state (Dutchie / Treez / Flowhub / Cova / BLAZE), extract the data Sureel needs to migrate, audit the prospect’s hardware
  • Days 8-21: dry-run the migration on a sandbox; coordinate hardware compatibility (printers, drawers, scanners); train staff via the in-app walkthroughs (you’re not the trainer — you supervise)
  • Days 22-28: parallel-run weekend (CannAgent shadow-running alongside the legacy POS so the operator can compare receipts in real-time)
  • Day 28: cutover. Operator goes live on CannAgent. You’re on-call.
  • Days 29-30: watch the audit log + first weekend of real transactions. Surface anything weird before the operator notices. Day 30: clean hand-off to in-platform support.
  • Per cutover, document 1+ exception pattern that should be baked into the migration tooling so the AI handles it next time

What we’re looking for

  • 5+ years in retail-systems implementation or technical project management. Cannabis experience preferred but not required — operator-savvy + project-discipline matter more
  • Comfortable in the database-export + data-migration weeds. You’ve personally moved data between two POS systems and lived
  • Hardware troubleshooting muscle — printers / cash drawers / barcode scanners shouldn’t intimidate you
  • Direct-style communication. You can tell an operator their old POS data is corrupted without panicking them
  • Preference for compounding work — your goal is to make the next cutover easier than the one you just finished

What we’re NOT looking for

  • Customer-success folks looking for a long-tail relationship role. This is cutover-only.
  • Implementation consultants used to billable-hour engagements. The bounty model rewards quality, not duration
  • Anyone uncomfortable handing off to an AI on Day 30. The hand-off IS the model

First 90 days

  1. Day 1-14: shadow the operator team on the operator-founder’s production deployments (Wenatchee + Seattle). Learn the cutover playbook end-to-end.
  2. Day 15-45: own first cutover from week 0 → Day 30. Document every exception pattern hit.
  3. Day 46-90: second cutover concurrent with maintaining first. Push 5+ exception-pattern bake-ins back into the migration tooling so cutover #3 is genuinely easier than #2.
  4. By day 90: 2 customers live, 0 critical post-cutover tickets, ≥5 documented patterns reducing AI-Sales-Engineer ticket volume.

Apply directly.

No portal, no recruiting funnel. One email.

careers@cannagent.ai →