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vertical-onboarding

Onboarding-and-switching playbook for SMB Product-Builder products. Defines the first-run experience that turns a prospect leaving an incumbent (ServiceTitan/Toast/Mindbody/Shopify/QuickBooks) into an activated user — import-first onboarding, the activation milestone, sample-data fallback, and the time-to-first-value target. Applied by migration-import-engineer and architect/pm so onboarding is designed as a funnel, not an afterthought. Our whole wedge is "low switching cost"; this skill makes that real on day one.

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avelikiy/great_cto
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SKILL.md (original)

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Vertical onboarding — switch them in, to first value, fast

The incumbent's moat is switching cost. Our wedge is dissolving it. Onboarding is where that promise is kept or broken. Design onboarding as a funnel with one activation milestone, import-first.

1. Import-first, not blank-slate

The default first-run path is "bring your data from {incumbent}", powered by migration-import-engineer's import contract — not an empty dashboard the user must fill by hand. A new user should see their own customers/jobs/menu/listings within minutes.

  • Offer the import on screen one, with the named incumbent ("Import from ServiceTitan").
  • Run it as a dry-run preview the user approves (the import contract's operator step).
  • Provide a sample-data fallback ("Explore with example data") for users who can't export yet — never a dead empty state.

2. One activation milestone (define it per product)

Pick the single action that means "this user got value" — the north-star of onboarding. Everything in first-run drives toward it. Examples:

productactivation milestone
quoting (home services)sent first priced quote
online-ordering (restaurants)published menu + took first test order
class-booking (fitness)imported members + first class booked
inventory (retail)synced catalog + first reorder rule set
transaction-coordination (real estate)first transaction checklist created
sponsorship-crm (creator)first sponsor + deal stage

Measure time-to-first-value (TTFV); target minutes, not days. State the target in the architecture doc.

3. The onboarding funnel (spec these steps)

1. Identify incumbent → 2. Import (dry-run → approve) → 3. Verify own data
→ 4. Complete the one setup the product needs → 5. Activation milestone → 6. Invite team

Each step: a clear single CTA, skippable where safe, resumable, and with progress shown. Defer everything not on the path to the activation milestone.

4. Reduce setup to the minimum

  • Pre-fill from imported data wherever possible (branding from the website, hours from the listing, tax rate from the address).
  • Sensible defaults over required choices; advanced config lives in settings, not onboarding.
  • One required integration max before activation (e.g. Stripe for quoting) — sequence the rest after first value.

5. Trust + reversibility

  • Show what was imported and let the user undo a batch (ties to the import contract's rollback) — trust comes from "you can't break anything."
  • Don't ask for payment details before the activation milestone unless the product is charge-to-use.

Output

When applied, contribute an Onboarding section to the architecture or design doc:

## Onboarding
- incumbent(s): <names> → import via docs/data-import/IMPORT-{slug}.md
- activation milestone: <the one action>
- TTFV target: <minutes>
- funnel: identify → import(dry-run→approve) → verify → setup → activate → invite
- empty-state fallback: sample data
- required-before-activation: <≤1 integration>

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