Before Anchor, billing at Hathaway Companies was not one process. It was three, each cobbled together from a different set of tools. Two of the companies ran on QuickBooks. The AI business ran on Stripe. Contracts went out through DocuSign and PandaDoc. And to track who had actually paid, the team kept it all in Airtable, by hand.
Every step required someone to touch the data. When a client changed a virtual assistant from part-time to full-time, Allie's team calculated the proration themselves, sent a fresh contract through PandaDoc or DocuSign, updated the amount in Airtable, generated the invoice, then went back into QuickBooks to confirm the payment landed.
Collections were worse. The team sent an invoice, then waited. When payment did not come, the chase began. That job fell to Sloan Bennett, the firm's Client Success Manager, who spent her time emailing, cold-calling, and cold-texting clients for money they already owed. The late fees the firm collected never came close to covering the effort.
Underneath the wasted hours sat a quieter cost. Every Stripe transaction and every QuickBooks payment carried a processing fee, and across three companies those fees added up to thousands of dollars a month that never showed up as a line anyone was watching.
“Contracts and payment in 17 different places. It was just a disaster and a nightmare for us.”
Allie Rice, COO, Hathaway Companies
Why Anchor
Hathaway did not come to Anchor through a sales pitch. The referral came from one of Anchor's existing customers, a firm Allie already trusted.
What made the answers land was that Anchor did not solve one piece of the problem. It replaced the whole arrangement. Instead of QuickBooks for two companies, Stripe for a third, DocuSign for signatures, and Airtable to track it all, the proposal, the signed agreement, the payment method, the billing schedule, and the reconciliation would live in one system, for all three businesses. The signed agreement itself would drive the billing, so a change made once would flow through without anyone rebuilding it by hand across separate tools.
That mattered most on the two things that had cost the firm the most: fees and follow-up. Payment collection moving to Anchor meant the firm was no longer absorbing thousands of dollars a month in Stripe and QuickBooks processing charges. And because the agreement authorized payment up front, the firm could charge clients on schedule instead of invoicing and waiting.
For a firm running three businesses, the appeal was simple. One place to see everything, one system to run it, and far less money leaking out the sides.
Implementation
Hathaway went live on Anchor on February 1, 2026. The firm's main concern was not the software, it was the clients. Many were used to being invoiced after the work was done, and moving them onto authorized, scheduled payments was a change in how they paid, not just where.
Sloan led the transition. The firm emailed clients ahead of the switch, walked them through what would change, and timed the rollout so there was runway before the February 1 go-live.
The billing model itself did not have to change to fit Anchor. Hathaway already billed the first of the month up front, so that part carried over cleanly. The friction that did surface was ordinary. Not all of the firm's clients check their email, so a few were caught off guard despite the notice. Allie framed it as normal for any business owner, not a problem with the move.
One thing got easier almost immediately: scope changes. When a client adds a service now, the firm builds the approval into what it sends, with an automatic approval deadline. As Allie described the flow, it is part of what the client already signed, and if they do not act, it approves on its own after a set number of days. The manual proration math and the fresh contract for every change were gone.
“We communicated up front. We had a walkthrough of how to do it. We sent reminders, and then we went live.”
Allie Rice, COO, Hathaway Companies
The biggest change did not show up in hours. It showed up in margin. Across three companies, Hathaway had been paying thousands of dollars a month in processing fees. In January, the firm spent about $3,000 on QuickBooks fees alone. After moving payments to Anchor, that figure dropped to about $300 in a comparable month once the firm's onboarding credit ran out. That is a reduction of roughly 90%, about $2,700 back in the firm's pocket every month, or close to $32,400 over a year.
Cutting DocuSign added about $1,000 a year on top. Together, the fee reduction and the dropped subscription put over $33,000 a year in direct savings back into the business, money that had been leaking out across separate tools without anyone tracking it as a single number.
The time savings were real too, just secondary to the money. Allie estimated the team got back 10 to 15 hours a month on the billing and invoicing side, split between her and Sloan. Over a year that is roughly 120 to 180 hours, worth about $6,000 to $9,000 at the $50 an hour Allie assigned to that time. She was candid that this was billing-side only. Chasing signatures on the sales side still happens; what disappeared was the manual invoicing, the proration math, and the payment follow-up.
That follow-up had been Sloan's job. With auto-charging in place, her role changed. Instead of cold-calling and cold-texting clients for overdue payments, she moved to client support and escalation.
The work that got automated was not just hours on a spreadsheet. It was the least pleasant work in the business.
“I feel like I have more pleasant client interactions. My role is now more support and escalation on issues with the virtual assistants, things that are less related to payments and billing, which I prefer.”
Sloan Bennett, Hathaway Companies
Hathaway Companies did not set out to overhaul its finances. It set out to stop running three businesses on a tangle of tools. What it got was a margin story. Processing fees fell about 90%, from roughly $3,000 a month to about $300, and a $1,000-a-year DocuSign subscription disappeared, putting over $33,000 a year back into the business. The team recovered 10 to 15 hours a month on billing, and the work that vanished, the cold-calling and cold-texting for overdue payments, was the work no one wanted to do.
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For a firm running multiple entities, the lesson is that fragmentation has a price, and most of it hides in fees and follow-up nobody is tracking. Pulling billing, payments, and agreements into one system made that cost visible, then removed most of it.
