01 · The Challenge
The firm's nonprofit focus introduced a billing complexity most firms do not face. Nonprofits have higher leadership turnover than other client types. When an executive director steps down or a billing contact changes, every billing record tied to that person has to be updated. In the old setup, that meant submitting a support ticket for each change.
Out-of-scope charges followed a similarly drawn-out path. Chris would email the client to explain the charge, wait for written approval, update the sales receipt in QuickBooks, adjust the billing in Pluto, and confirm everything was reconciled. A process that should take minutes regularly consumes a day or two.
"When I was in charge of all these manual processes, trying to remember who I needed to change a sales receipt for, who I needed to change it back for after that sales receipt was sent out, just all of the pieces working in conjunction, it was really hard for me to remember. I had to keep an extensive spreadsheet with all the notes for every day of the week."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
Managing all of this became significantly harder in October 2023, when Chris had an MS attack that affected his speech and memory. Keeping track of which clients needed amended sales receipts, which contacts needed updating, and which billing changes needed to carry forward across multiple tools created a real cognitive burden. Chris maintained a detailed daily spreadsheet just to track who was on or off billing each week.
In a typical month, Chris estimates he spent around 25 hours on billing-related work: creating and adjusting sales receipts, sending approval emails, reconciling across systems, and managing follow-up.
02 · The SolutionWhy Anchor
The firm's principal discovered Anchor at a conference approximately a year and a half ago and asked Chris to evaluate it alongside other options. Chris reviewed roughly half a dozen tools. Most covered parts of the workflow but left at least one manual step in place. Anchor was the only option that handled everything in one system without requiring additional tools to fill gaps.
The sandbox environment was an important part of the evaluation. Chris could test proposal creation, billing setup, and payment flows in a live environment without affecting real clients. That allowed him to validate how the platform worked before committing to the migration.
"Some of them were kind of comparable, but they didn't have this piece here or there was still a manual process there. With Anchor, I literally can just do it all. I don't have to worry about extra systems."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
Implementation
The migration moved the firm off Better Proposals, Pluto, QuickBooks invoicing, Zapier, and Notion. The most significant structural change was how client payment information is handled. With Anchor, clients cannot complete signing a proposal until they have entered their payment details. That removed what had previously been a separate, often slow step where Chris had to chase banking information after the proposal was already signed.
Clients entering their own payment information also resolved a discomfort Chris had with the old setup: he no longer needed to collect or hold sensitive banking details directly. When a client's banking information changes, they can log in and update it themselves.
"They can't sign the proposal until they enter their banking information. That takes all the weight off my shoulders. It puts it all on them. And if people want their bookkeeping done, they're going to get the information entered."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
03 · The ResultsEliminated Time-Consuming Tasks
The impact showed up across every part of the billing workflow. Key outcomes, based on Chris's own estimates:
* Monthly billing time dropped from approximately 25 hours to approximately 4 to 5 hours, a reduction of roughly 80%
* New client onboarding dropped from about one week to a few hours, specifically the time needed for a test deposit to clear
* Out-of-scope charges went from a 1-2 day email-and-approval process to approximately 5 minutes in Anchor
* Billing contact changes are now handled directly in Anchor, eliminating the support tickets that had consumed 2-3 requests per week during periods of high nonprofit turnover
The daily tracking spreadsheet is gone. Chris no longer needs to log who is on or off billing each day, which clients need amended invoices, or which contacts need updating. Those tasks either no longer exist or are handled in seconds.
"This past week, I had six consultations. The most I've ever had before that was three. And looking at the timing, the early part of the month, I would have mostly blocked off to take care of billing stuff."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
The time freed from billing directly changed what the early part of each month looks like. Chris had previously blocked out the first days of every month for billing tasks. That time is now available for business development. In one recent week, he completed six consultations. His previous record was three.
What Chris Said
Chris describes himself as a skeptic about change. He came into the Anchor evaluation cautiously.
"I am a skeptical person. Change is hard for me. I was skeptical coming into this relationship. But having the support we did early really put my mind at ease. I would recommend Anchor as a great company. If you want to reduce time spent on stuff that should not be a time suck, go with Anchor, honestly."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
"The ability and willingness to look at different options when things might be able to smooth out some, that's just another plus for Anchor."
Chris Jackson, Sales Manager, Nonprofit Bookkeeping
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