How Pretty Penny added more than $50,000 in annual revenue without taking on a single new client

Pretty Penny is a growing accounting firm led by Ashley Ford, who built the practice over eight years. The firm serves a recurring base of bookkeeping and CAS clients on monthly billing alongside a substantial tax client base billed on seasonal engagements. Ashley is well known in accounting circles for sharing what works openly with peers, and the firm reflects that same commitment to doing things the right way. As Pretty Penny grew and merged with another established practice, the complexity of its billing operation grew with it.

“This is the first system where I feel like it feels easy on both sides. It feels really intuitive and it moves really smoothly.” Ashley Ford, Owner & CEO, Pretty Penny

01 · The ChallengeSix plus systems, one spreadsheet nightmare.

Over eight years Ashley and her team cycled through a long list of billing tools, including Dubsado, QuickBooks, TaxDome, PandaDoc, Practice Ignition, and PDF-based DocuSign workflows. Each one solved part of the problem. None solved all of it.

The recurring pattern was the same across every platform: glitches during client payment setup, unreliable autopay, and constant manual oversight. One team member maintained a dedicated spreadsheet to track every client's billing status, every failed payment, and every follow-up required. With hundreds of clients, keeping that spreadsheet current was a real time commitment each month.

"Before Anchor, if we wanted to keep giving our team raises, my team was just going to have to somehow find time to take on more clients. That was the only way we were bringing in more revenue. Now we're able to continue to grow without just trying to max out my team."
Ashley Ford, Owner & CEO, Pretty Penny

The tax billing workflow compounded the problem. The firm's practice was to complete every return before requesting payment. After the client reviewed and signed, the team sent an invoice, waited for payment, then e-filed. During busy season that sequence became a bottleneck. The team chased clients through email, phone, and direct messages on social media simply to unlock filing before deadlines.

Pricing was a third pressure point. Ashley had long encouraged other firm owners to raise rates consistently. For Pretty Penny itself, implementing those increases had always felt complicated. Without a smooth mechanism to roll out changes and get client acceptance, the conversation was easier to delay. The result was years of inconsistent pricing that made team raises or business investment contingent on simply taking on more clients.

02 · The SolutionWhy Anchor

Ashley first heard about Anchor through an accounting Facebook group and later saw the product at an industry event. Because Anchor is free to start, she piloted it on a single new client, a QuickBooks cleanup engagement, without touching anything in her existing workflow.

"There was someone on my team who literally tracked every single client's billing, when it went through, when it didn't, every failed payment. We have hundreds of clients. We don't have to do that anymore."
Ashley Ford, Owner & CEO, Pretty Penny

The result was immediate. The proposal went out cleanly, the client paid quickly, the deposit landed with lower processing fees than she had been paying, and the experience on both sides felt straightforward. Within about a month, Pretty Penny had migrated roughly half of its clients.

What made Anchor different from every platform before was that it was the first system where both sides of the transaction felt easy, for the firm and for its clients. Ashley also cited specific features built around accounting firm workflows: automated annual price increases, auto-acceptance of agreement amendments, clean autopay setup, and client-managed payment details. As new features rolled out her team treated each one as a reason to go further into the platform.

03 · The Results$50K in new revenue. Zero manual follow-up.

Pretty Penny migrated to Anchor in two deliberate phases. The first covered all recurring bookkeeping and CAS clients, those on monthly billing with predictable schedules. That process went smoothly enough that the team committed to a second phase before tax season: moving all tax clients onto Anchor as well.

Internal buy-in required real attention. Two team members had invested significant time building out billing workflows in TaxDome and felt some hesitation about starting over. Ashley led with visible enthusiasm, arranged demos with the Anchor team for her staff, and reinforced that the change would solve problems her team dealt with every day. Anchor's support responsiveness throughout the process built confidence. Once the team got into the rhythm, hesitation gave way to active engagement as new features rolled out.

On the client side, adoption was quiet. The main task was confirming that clients had noticed the setup email. There were no complaints about the platform itself. The process was simple enough that clients completed it without friction.

The price increase was the most consequential change. For the first time in the firm's history, Pretty Penny implemented a consistent, automated annual increase across its recurring client base. Using Anchor's built-in price increase feature, the firm rolled out a 5% increase with no client pushback. Based on the firm's own estimate, that single increase added more than $50,000 in annual revenue. Instead of growing revenue by adding clients and stretching the team further, the firm could give team raises and reinvest in the business without asking anyone to carry more.

On the operations side, the manual billing tracking spreadsheet is gone. The team member who had logged every client's payment status, every failed charge, and every required follow-up each month no longer does that work. Anchor's automated payment flow and notifications handle what the spreadsheet was built to catch.

The tax billing workflow was rebuilt from the ground up. Tax clients now sign their engagement agreement through Anchor, connect a payment method, and pay a 25% deposit before any return work begins. When the return is complete and reviewed, the team charges the remaining balance and e-files at the same time. The back-and-forth that had stretched some engagements into months of waiting is gone. Filings move faster, the team spends less time chasing, and clients experience a cleaner, more professional process.