1. Pick one buyer and one painful job
Do not sell to "small businesses." Pick one buyer, like a solo bookkeeper with 20 to 40 clients, or the ops manager at a 10-person ecommerce brand who does the books on Fridays. Then pick one job your tool does better than a human, such as categorizing bank transactions or reconciling Stripe payouts in QuickBooks Online or Xero. Write it as one sentence: "I cut Stripe and Shopify reconciliation from 6 hours to 1 for bookkeepers on QBO."
2. Find them where they complain
Bookkeepers talk shop in r/Bookkeeping, r/QuickBooks, and r/Accounting, and in Facebook groups like "QuickBooks Online Users" and Xero user groups. Search Reddit for "reconciliation takes forever", "miscategorized transactions" or "month end close" and sort by new. On LinkedIn, search the titles "Bookkeeper", "Fractional CFO" and "Fractional Controller" and filter for people who post. Make a list of 30 names before you write a single message.
3. Reply with help, not a pitch
When someone posts about a reconciliation mess, answer the actual question in the thread first. Then DM them: "Saw your post about Stripe payouts not matching in QBO. I'm building a tool that does exactly that matching. Could I run your last month through it for free and show you the result? No call needed, I'll just send a screenshot." A free result on their own data is worth more than any demo.
4. Show the result on their data
Ask for a read-only export, like a bank CSV or a Stripe payout report, never login credentials at this stage. Run it, then send back a short summary: how many transactions were matched, which ones were flagged, and roughly how long it would have taken them by hand. Let them check it against their own work. Trust in bookkeeping comes from accuracy they can verify, not from your claims.
5. Ask for money in the same message
Once they see the result, ask right away. Say: "Want me to do this for all your clients for the next 30 days? It's $300 for the pilot, covering up to 10 client files. If it doesn't save you at least 5 hours, I'll refund it." A fixed price, a fixed scope and a clear success test make it easy to say yes. For in-house buyers at a small company, $150 to $250 for one entity is a fair starting point.
6. Make paying take 2 minutes
Send a Stripe Payment Link or invoice in the same thread, not a contract. Add a one-paragraph scope: what you will process, the dates, what counts as success, and that data is deleted on request. Bookkeepers are cautious about client data, so say plainly where it is stored and who can see it. If they ask for a call, take it, but bring the payment link.
7. Run the pilot like a service
For 30 days, check every output yourself before they see it, and fix errors fast. Send a weekly note: "This week: 412 transactions categorized, 9 flagged for your review, 2 errors I caught and fixed." Track hours saved in their words. At day 25, ask: "Want to keep going at $X per month?" Price per client file so the price grows as they grow.
8. Repeat daily until you have three
Send 10 helpful replies or DMs a day from your list and keep a simple sheet: contacted, result sent, asked, paid. Most will ignore you, so volume and follow-up matter more than clever wording. Hulby, an AI cofounder, does this prospecting and follow-up daily for a founder.
People asking this right now
Real, public posts from the last few weeks. Each one is somebody you could help today.
Mistakes to skip
- Offering a free pilot with no end date, which teaches them your work is worth nothing.
- Asking for QuickBooks or bank logins before you have earned any trust.
- Pitching "AI" instead of the specific hours saved on a specific task.
- Waiting for the product to be finished before asking anyone to pay.
Want this done for your AI bookkeeping tool, every day?
Hulby finds the people asking for what you built, writes every reply and email, and keeps you on it until they pay. Free to start.
Find my first customersQuestions
How much should a first pilot cost?
Enough that they feel it. $150 to $500 for 30 days with a clear scope works for most bookkeepers and small finance teams.
Should I offer a refund?
Yes, tied to a measurable outcome like hours saved. It lowers the risk for them and forces you to define success.
What if they say they need to think about it?
Ask what would need to be true for a yes, then offer a smaller scope, like one client file for $100.
Who buys faster, bookkeepers or business owners?
Solo bookkeepers usually decide faster because the time saved is their own money and they need no one's approval.