How Hathaway Companies Consolidated Three Billing Stacks and Reclaimed Up to 15 Hours a Month

01 · The Challenge

Before Anchor, Hathaway Companies was managing billing across a patchwork of disconnected tools. One entity ran on QuickBooks, another on Stripe, and the team relied on PandaDoc and DocuSign for contract execution. Invoices were created and sent manually. Payment tracking lived in Airtable spreadsheets. When a client wanted to change their service level, such as moving from part-time to full-time, the process meant sending a new contract through a separate tool, manually recalculating the prorated amount, updating the tracking spreadsheet, sending the revised invoice, and then following up in QuickBooks to confirm payment.

Late payments were common. Sloan handled collections directly, which meant emailing clients, cold calling, and cold texting when emails went unanswered. The firm collected some late fee income from overdue invoices, but, as Allie put it, the amount of late fee income did not equal the amount of effort required to chase it down.

Contracts and payments were scattered across too many systems. It was, in Allie's words, a disaster and a nightmare.

“Contracts and payment in 17 different places. It was just a disaster and a nightmare for us.”
Allie Rice, COO, Hathaway Companies

02 · The SolutionWhy Anchor

The introduction came through a referral from an existing Anchor customer the team trusted. Allie came to the initial call with Nathan Ellwood at Anchor ready to ask detailed questions, got the answers she needed, and the decision was straightforward from there. The referral source's credibility, combined with Anchor's clear fit for the multi-entity billing challenge Freedom.ai faced, made the evaluation process short.

The pricing model also mattered. Anchor is free to use, with fees tied to payment processing rather than a monthly subscription. For a firm that had been absorbing QuickBooks transaction fees and DocuSign annual costs across multiple entities, that structure was immediately attractive.

Implementation

Hathaway Companies went live on Anchor on February 1, timed deliberately to give the team and clients enough runway to prepare for the transition. Sloan led the change management effort, sending client communications in advance, providing walkthroughs of the new payment setup process, and sending reminders before the go-live date.

A small number of clients were caught off guard because they had not checked their email, which Allie attributed to the nature of working with busy business owners rather than any failure in the communication plan. Overall, the migration was orderly. Clients completed their payment setup without significant friction.

“We communicated out front. We had a walkthrough of how to do it. We sent reminders, and then we went live.”
Allie Rice, COO, Hathaway Companies

03 · The ResultsDirect Saving

The most immediate operational change was in billing time. The team estimates they recovered between 10 and 15 hours per month that had previously gone to manual invoicing, spreadsheet updates, reconciliation, and payment follow-up.

On the cost side, the savings were concrete. In the months before switching, Hathaway Companies was spending approximately $3,000 per month on QuickBooks transaction fees alone. After moving to Anchor, that figure dropped to around $300 in a comparable month, a reduction of approximately $2,700. The team had also been spending over $1,000 per year on DocuSign, a cost that was eliminated when proposal and agreement execution moved into Anchor.

Scope changes, which had previously required a separate contract tool, manual proration math, and multiple manual updates, now run through Anchor's amendment workflow. The team sets automatic approval deadlines on scope changes, reducing the back-and-forth that had previously added to Sloan's workload.

Sloan's role itself shifted. Time that had gone to chasing payment now goes to client support and escalation, work she finds more valuable and that directly serves Hathaway Companies and its clients.

“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, Freedom.ai

Managing three entities also became simpler. Rather than toggling between QuickBooks, Stripe, and a separate contract tool depending on which entity was involved, the team now works from a single platform.