Ashley Ford didn’t set out to rebuild Pretty Penny’s billing stack. She set out to buy a firm. Her Seattle-based accounting practice had spent four years finding its rhythm — 120 monthly bookkeeping clients humming along inside Anchor, a team she trusted, a calendar she could predict. When the acquisition closed last summer, it brought in 250 more clients, a different tax platform, and a pile of contracts that had never met her payment processor.
The deal itself was the easy part. What nobody modeled in the LOI was the software sprawl that came attached. The acquired firm ran contracts in one tool, collected payments in another, and prepared taxes in TaxDome. None of it talked to anything Ashley’s team already used.
01 · The ChallengeTwo firms, three systems, one tax season.
“We were managing 120 monthly bookkeeping clients in one system,” Ashley remembers, “and preparing to set up 250 tax clients in another. It was creating unnecessary complexity at the exact moment we couldn’t afford any.”
The timing was the cruel part. If the acquisition had closed in July, Pretty Penny would have had the summer to consolidate. It closed in September.
“Our tax platform wasn’t giving us the ability to move the billing from the firm I purchased over to my firm. So we had to turn off all the auto billing.”— Ashley Ford, Owner & CEO
Turning off auto-billing wasn’t the plan. It was triage. Every day the acquired clients stayed on manual invoicing meant another day the team was rebuilding a workflow by hand.
The problem wasn’t volume. It was the lack of a single system.
- Recurring clients lived in Anchor, where billing ran itself — but that was only half the book.
- The acquired firm’s contracts were in one tool, payments in another, and tax prep in TaxDome.
- Tax season agreements needed to go out at scale — 250 of them — with consistent terms and pricing.
02 · The SolutionOne month. A few hours of client time. A consolidated firm.
The rollout was compressed on purpose. Ashley’s team didn’t have six months; they had tax season. Week one, Anchor absorbed the acquired firm’s client records and consolidated them into Pretty Penny’s existing workspace. By week two, the team was building the tax-season agreements in bulk — 250 of them, templated once, sent in a single batch.
“Anchor makes it really easy for the client.”— Jessica Critchfield, Onboarding Specialist
Week three was the pricing change. Pretty Penny had wanted to ship an annual 5% increase for two years. Inside Anchor, it was a policy, not a project. The increase was applied across the book, the clients were notified, and it shipped in an afternoon.
Tax-season readiness · Pretty Penny
03 · The Results$50K in new revenue. Zero manual follow-up.
The numbers showed up first on the revenue side. The 5% annual price increase, applied across a $1M+ book, generated more than $50,000 in new annual recurring revenue — without a client conversation, a renegotiation, or a single bespoke agreement.
“With Anchor, I’m not even concerned about it because of how user friendly it is.”— Jessica Critchfield
By the time tax season ramped in earnest, the firm’s agreements supported amendments, mid-engagement add-ons, and automatic fee collection without anyone on the team touching a spreadsheet.
“I know it sounds small,” she says. “Honestly, it was the biggest operational change we’ve ever made.”
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