How Upkeeping Cut Proposal Time by 90% and Reclaimed Hours Every Month with Anchor

01 · The Challenge

Before Anchor, Upkeeping's billing workflow was a chain of disconnected manual steps. Erin was using Dubsado to create proposals and engagement letters, then switching to QuickBooks Online to set up recurring invoices manually. Dubsado carried a monthly subscription fee of $35 and, despite the automated invoicing she had configured in QuickBooks, payments were not guaranteed. Erin was operating on net-15 terms and relying on clients to follow through without any pre-authorized payment method in place.

“Whether it's a money or time issue, Anchor can solve both.”
Erin Pohan, Founder, Upkeeping

The result was a routine she came to dread. Proposals alone took more than 30 minutes each to build, in part because Erin struggled to reconstruct the details of discovery conversations by the time she sat down to write. The Dubsado interface felt difficult to navigate, and every time she logged in she was worried about making an error. Following up on outstanding invoices added further strain. All told, she estimates the full billing and collections process consumed between 5 and 10 hours each month.

On top of the time cost, Erin was absorbing credit card processing fees herself, at 2.9% plus 30 cents per transaction, across her entire client base. With Upkeeping approaching $300,000 in annual revenue, that came to roughly $8,700 per year flowing out of the business to cover clients' preferred payment methods.

“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

02 · The SolutionWhy Anchor

Erin first encountered Anchor at Intuit Connect in Las Vegas in 2024. The introduction came not through a traditional demo but through a conversation with the Anchor team, which left a strong impression. What she learned in that conversation aligned directly with the operational problems she was trying to solve: a single platform that could handle proposals, signed agreements, payment collection, and automated billing without requiring her to work across multiple disconnected tools.

Two factors stood out in her evaluation. First, Anchor captures a client's payment method at the point of agreement signing, which eliminates the need to chase payment after the fact. Second, the platform gives firm owners the option to pass credit card processing fees to clients rather than absorbing them. For a firm at Upkeeping's revenue level, both represented meaningful and immediate financial impact.

Implementation

Erin integrated Anchor into a broader automated onboarding process she had built for Upkeeping. When a prospective client books a discovery call through the firm's website, they complete an intake form. The information from that call is captured in a lead tracking system, and within minutes Erin uses an AI note-taker and a simple prompt to generate a bulleted scope list she can paste directly into an Anchor proposal template.

The proposal is sent, and the lead tracker updates automatically at each stage: proposal sent, proposal won, or proposal lost. When a client accepts, they are added to an automated onboarding email sequence that collects system access, sets expectations, and captures their payment details through Anchor before any work begins. From that point forward, billing runs on the first of every month with no manual intervention required.

Erin has also used Anchor's agreement amendment feature to handle scope additions mid-engagement. When one recurring client requested a grant reporting add-on, she created the add-on in Anchor, the client received an email to accept the change, and the updated amount was added to their automatic monthly charge.

“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

03 · The ResultsDirect Savings

The shift in Erin's time commitment to billing has been substantial. Proposals that previously took more than 30 minutes each now take 3 to 5 minutes. Discovery calls are supported by a note-taker and an AI prompt, and the resulting scope list drops directly into an existing Anchor template. For a firm fielding 5 to 10 discovery calls per month, the total proposal time has dropped from several hours to under an hour.

“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

The broader billing and collections workload has followed the same trajectory. Erin estimates she was spending between 5 and 10 hours per month on billing admin, invoicing, and collections follow-up before Anchor. That total is now under one hour per month, based on her own assessment. Because every client's payment method is captured at signing and billing runs automatically on the first of each month, there is no follow-up work to do.

The financial impact has been equally direct. By giving clients the choice to pay via ACH at no cost or via credit card with the processing fee passed through, Upkeeping has stopped absorbing those fees. At approximately $300,000 in annual revenue, that represents an estimated $8,700 per year returned to the business, based on the firm's own calculation.

With the time she has reclaimed, Erin now focuses on content creation for the broader accounting community, a project she describes as a genuine passion alongside her client work. Results vary by firm size, client mix, and prior billing setup.