Before Anchor, running Upkeeping's client billing meant working across two disconnected tools and hoping nothing slipped. Erin built proposals and engagement letters in Dubsado, then switched over to QuickBooks Online to manually set up a recurring invoice for each client. The tools did not share anything, so every new client meant rebuilding the same terms twice, by hand, in two places.
The setup felt dated and fragile. Erin describes the Dubsado interface as archaic and hard to navigate, and the manual steps left room for mistakes she could not fully guard against. Her biggest worry was not speed. It was accuracy. She was, in her words, terrified of forgetting to update the terms for a client's proposal or engagement letter, and that fear followed her every time she logged in.
The proposals themselves were slow to produce. Each one took more than 30 minutes, in large part because by the time Erin sat down to write, she was trying to reconstruct what had actually been discussed and agreed to on the discovery call. The delay got bad enough that she sometimes did not send proposals at all.
Collection was its own gap. Erin ran on net-15 terms with no payment method captured up front, so once an invoice went out she was relying on clients to follow through, and following up on the ones who did not pay added more time to the month. All told, she estimates the full cycle of proposals, billing, and collections consumed as much as 10 hours a month.
On top of the time, Erin was absorbing her clients' credit card processing fees herself, at 2.9% plus 30 cents per transaction, across the whole client base.
“Every time I had to log in, I had this underlying fear that I was going to make a mistake with every proposal I sent.”
Erin Pohan, Founder, Upkeeping
Why Anchor
Erin first came across Anchor at Intuit Connect in Las Vegas in 2024, before she was a customer. What sold her was not a formal demo but a conversation with the people behind the product, which told her as much about how the company worked as any feature list would have.
What made her actually switch was the fit with the problem she had. Her old setup was two tools stitched together by hand, which was exactly where the errors and the rebuilt terms came from. Anchor collapsed that into one system: the proposal, the signed agreement, the payment method, and the recurring billing all live in the same place and flow from the same agreement, so there is nothing to re-enter in a second tool and nothing to forget to update.
Two things stood out in her evaluation. First, Anchor captures the client's payment method at the moment they sign, so the money side is settled before any work starts and there is no chasing after the fact. That directly answered the net-15 gap she had been living with. Second, Anchor gives the firm the option to pass credit card processing fees to clients rather than absorbing them, which at Upkeeping's revenue level was immediate money back in the business.
For a solo founder who had been terrified of getting a client's terms wrong, the deciding factor was simpler than any single feature. One agreement drives everything downstream, so what she agrees to is what gets billed, without a manual hand-off in between where a mistake could creep in.
Implementation
Erin did not just drop Anchor in beside her old process. She built it into an onboarding flow that now runs largely on its own.
It starts when a prospect books a discovery call through the Upkeeping website and fills out an intake form. The details are captured in a lead tracker, and after the call Erin uses an AI note-taker and a short prompt to turn the conversation into a bulleted scope list. That list drops straight into an Anchor proposal template she has already built, so the proposal that used to require reconstructing the whole conversation from memory now assembles in minutes. She adds a custom note to each one, which is where most of her remaining proposal time actually goes.
From there the lead tracker updates itself at each stage, proposal sent, won, or lost. When a client accepts, they move into an automated onboarding sequence that gathers system access, sets expectations, and captures their payment details through Anchor before any work begins. Once that is done, billing runs on the first of every month with no manual step from Erin.
The agreement stays live after signing, too. When one recurring client asked for a grant reporting add-on, Erin created it in Anchor, the client got an email to approve the change, and the new amount was folded into their automatic monthly charge, no new engagement letter, no separate invoice.
“The add-ons have been amazing. They're so easy. You just create it in Anchor and then they get an email, they accept the change to the agreement, and it's just added on to their automatic bill.”
Erin Pohan, Founder, Upkeeping
The clearest change is one Erin names first: no more errors. The setup she was afraid of, rebuilding terms by hand in two tools, is gone, and with it the fear that followed her into every login. One agreement now drives the proposal, the billing, and any changes, so there is nothing to forget to update.
The time change is just as concrete. Proposals that took more than 30 minutes each now take 3 to 5. Across the roughly 40 proposals Erin sends in a year, that is about 18 hours returned on proposal work alone. Looked at across the whole cycle of proposals, billing, and collections, the load has dropped from as much as 10 hours a month to under one. That is as much as 108 hours a year, close to three full working weeks, given back to the business. At the $125 an hour Erin uses for her own admin-level time, that time is worth as much as $13,500 a year.
The money side is just as direct. Because clients now choose between paying by ACH at no cost or by card with the processing fee passed through, Upkeeping has stopped absorbing those fees. At roughly $300,000 in annual revenue, Erin estimates that is about $8,700 a year kept in the business rather than paid out on her clients' behalf. Dropping the old Dubsado subscription removed another $420 a year.
Payment now arrives without anyone chasing it. Because every client's method is captured at signing and billing runs automatically on the first of the month, the net-15 waiting and the follow-up emails are simply gone.
With the time she has reclaimed, Erin has turned to creating content for the wider accounting community, a project she treats as a genuine passion alongside her client work.
“There's no work to be done on billing. It's automatic every month on the first. So, it's really, really awesome and easy.”
Erin Pohan, Founder, Upkeeping
For Erin Pohan, the move to Anchor was less about shaving minutes than about no longer running her billing on a setup she did not trust. The two-tool workflow that made her double-enter terms and dread a mistake is gone, replaced by a single agreement that drives the proposal, the payment, and every change after it. What she agrees to with a client is now what gets billed, automatically, without a manual step in between where something could go wrong.
The proof shows up in both time and money. Proposals that ate more than half an hour now take a few minutes, the full billing cycle has dropped from as much as 10 hours a month to under one, and an estimated $8,700 a year in card fees stays in the business instead of leaving it. For a solo founder, that combination has turned billing from a source of background worry into something she no longer has to think about, and freed her to spend the reclaimed time on work she actually wants to do.
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