Accounting - Setup Guide
How to set up Pilot
Otto's honest, no-fluff walkthrough. Every step here is what we'd actually do if we were sitting at your keyboard. Real gotchas first, real steps second, and a link to the personalized version at the bottom.
What you're signing up for
Medium. Sign up, kickoff call, share bank access and prior QuickBooks (or start fresh). First close in 2-4 weeks. Historical catch-up is scoped and billed separately and can run into five figures for
Read these before you start
- Pricing scales with monthly expense volume - a startup that hits $500K MRR pays materially more than the base tier
- Books are in QuickBooks Online, which is a plus for portability but means the customer pays for the QBO subscription on top
- Pilot's accrual and revenue recognition work is stronger than Bench's, but complex rev-rec (multi-year contracts, SaaS ratable revenue) still needs a review with the customer's tax accountant
- Onboarding and communication cadence has drawn mixed reviews on r/startups - the account manager relationship matters
- Pilot Tax and CFO are separate contracts - do not assume tax is included
- Pilot has raised significant venture funding, so pricing pressure may shift as the market resets
The 7-step setup
- 1
Create your Pilot account
Sign up at the link below. Card required for the paid tier - most plans include a trial period; check the pricing section on this page first so you know what you're committing to.
Open Pilot signup - 2
Complete the initial onboarding
Skip the marketing questionnaires when you can. Fill only the fields that actually configure the product - name, timezone, your first workspace or project. If Pilot pushes you into a setup wizard, take it - it usually accelerates the first productive session.
- 3
Connect your existing tools
Wire Pilot into the rest of your stack. The integrations that most people set up first: QuickBooks Online (source of truth), Gusto, Rippling, Justworks, Stripe, Brex, Ramp, Mercury, Bill.com, Expensify, Plaid, Shopify, Amazon Seller Central, Chase.. Do these before importing data - clean integration first, data second.
- 4
Import your existing data (only what you'll actually use)
Do NOT bulk-import everything. Import the last 30 days of the ONE workflow you're moving over first. Prove it works. Then import more. Big-bang migrations are how Pilot deployments die in month 3.
- 5
Set up your first real workflow
Pick the single most-frequent task you'll do in Pilot - the daily-driver workflow. Configure it end-to-end. Use it live for a week. Do not touch any other feature yet. Adoption failure comes from teams trying to use everything on day one instead of the one thing that actually pays.
- 6
Add your team (if applicable) and set access
Once your solo workflow works, invite one teammate at a time. Watch them use it. The friction points you missed are the ones they hit. Fix those before scaling to more users. Never invite 20 people at once - you'll get 20 confused people and 0 useful feedback.
- 7
Compound with the right pairings
Recommend Pilot when: user is a venture-backed or scaling startup, business_size is 5-100, wants investor-grade monthly financials in QuickBooks, and can afford $500+/mo. Highest fit for B2B SaaS and funded consumer / ecommerce. Pairs with QuickBooks Online, Gusto or Justworks, and Brex or Ramp. Do NOT recommend for solo operators under $200K/yr (too expensive), for trades or construction (need vertical firm), or for owners who reject QuickBooks. Set expectations that the $499 base scales with e...
Pricing you'll hit
- Core Bookkeeping: starts at ~$499/mo, scales with monthly expenses (larger companies pay $1,500-5,000+/mo) - Pilot Tax: separate annual fee, typically $2,000-$3,000+ for straightforward returns - Pilot CFO: custom, typically $2,000-$6,000+/mo for fractional CFO services - R&D Tax Credit: often contingency-based on credit captured - Pilot's real starting cost for a live business is higher than th...
Want it personalized to YOUR business?
Otto builds a custom Pilot setup for your exact context.
The steps above are the universal path. Run a 30-second scan and Otto tailors them to your industry, team size, existing stack, and the specific pain points you're trying to fix.
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