The Background
Payroll is not a forgiving industry. For the HR professionals, business owners, and payroll managers who depend on getting it right every cycle, a delayed answer or a missed update lands directly on their employees' paychecks.
Checkwriters was founded on the belief that payroll and HR software could feel personal. Headquartered in Northampton, Massachusetts, the company built its reputation as the relationship-first alternative to large national competitors, companies that route clients through call centers and automated systems where no one knows your name or your account. At Checkwriters, real people pick up the phone. The same team that onboards a client stays with them through every payroll run. That continuity is what clients come for, and what keeps them.
That promise made Checkwriters credible in a market dominated by giants. It also made growth complicated. As the company expanded and its client base climbed over 4,000, the question became whether they could deliver that same quality of experience at scale, without the model straining under its own weight.
The Challenge
When the System Becomes the Bottleneck
For Checkwriters' clients, the stakes of a slow answer are immediate. A payroll manager trying to reconcile attendance data before a run cannot wait two days for a response. A business owner preparing for year-end compliance cannot afford to be stuck in a queue. These are clients who chose Checkwriters specifically because they believed someone would be there when it mattered.
Inside the company, the tools were working against that promise. For years, Checkwriters had run its sales organization on Salesforce. Dakota Hebert, now Executive Vice President, had watched the platform's limitations compound over time. Sales reps could not contact Salesforce support on their own. Every ticket had to go through Dakota. Every system change, every configuration update, every time someone needed help, it routed back to him.
"It was almost impossible for our admins to get a Salesforce support specialist on the phone. You had to log a ticket for everything and wait days or weeks to hear back." Dakota Hebert, EVP, Checkwriters
Dakota spent hours each week troubleshooting a platform his reps could not fully access. The system had been designed to lock down access, and for Checkwriters, that design was expensive, in time, in momentum, and in the kind of attention Dakota should have been spending elsewhere. A platform that concentrated every decision and request in one person was a ceiling, and the team was pressing against it.
One-to-One Does Not Scale to 4,000
The same pressure was building on the client-facing side. As the client base grew, so did the volume of support inquiries coming into the customer success team. The model had always been personal: one team member, one client, one conversation at a time. It was the model that built Checkwriters' reputation, and it was starting to bend.
Sam Hathaway had lived that model from the inside. She started at Checkwriters as a customer support rep, and eventually became Technical Solutions Manager, the connective tissue between product, development, and the client experience. She knew exactly what clients needed, and she knew the team was being asked to deliver it to more people than the old approach could sustain. At Checkwriters, the customer success team operates as a hybrid function, handling both reactive support and proactive client retention. As the client base grew, both sides of that responsibility grew with it.
In a model built around individual conversations, patterns disappear. Every interaction stayed in its own thread. There was no way to look across hundreds of client questions and understand what people were consistently struggling with. The team answered what was in front of them. The bigger picture stayed out of reach.
The Solution
A System Built for People Who Do the Work
When Checkwriters replaced Salesforce with HubSpot, the most immediate change was access. Sales reps could contact support directly. Dakota stepped out of the middle. Marketing, sales, and client success moved onto the same system of record, and the information silos that had kept departments operating in parallel finally gave way.
Campaigns that used to take four weeks are going out in three days. The events and conferences pipeline, where sales and marketing had previously coordinated by email with no shared record, moved into HubSpot. Every event became a tracked deal. Everyone had visibility. When a prospect became a client, an onboarding deal was generated automatically, no handoff email required.
The meeting scheduler gave the sales team a link in every email signature, making it easy for prospects to reschedule rather than cancel. Cancelled calls dropped by 25%.
Building Checkster: When AI Becomes a Colleague
For Checkwriters' clients, speed and accuracy at the moment of need had always been the promise. As the client base grew, Sam knew the team needed a way to deliver on that promise without routing every question through a person. She led the build of Checkster, Checkwriters' branded Customer Agent, trained on the company's knowledge base and product documentation.
The rollout was intentional but open-ended. Sam's team knew what they wanted Checkster to do. They were less certain what their clients would actually use it for. That uncertainty turned out to be exactly the point.
"We launched the customer agent without really knowing what to expect. But people took to it fairly quickly. And what surprised us was what it showed us about what our clients were actually looking for." Sam Hathaway, Technical Solutions Manager, Checkwriters
Checkster gave clients immediate answers without waiting on a team member. Lower-tier support inquiries, the routine how-to questions, started to tick down in the customer support queue. The team gained back time that had been spent on repetitive work. Sam estimated the savings at somewhere between one and three hours per person per week across the customer success team, roughly the equivalent of one additional full-time employee per week.
What Checkster Taught Them About Their Clients
The insight was transformative. Every question Checkster could not answer identified a gap. The knowledge base and tech writing team, which meets weekly, started reviewing those gaps systematically, using them to prioritize what got written, updated, and published. For the first time, the team had a real-time window into what clients needed that no one had thought to document yet.
One pattern stood out immediately. A high volume of attendance-related questions was surfacing, far more than the team expected, and the volume pointed to something deeper than a missing article. The attendance platform needed to be rebuilt. That revamp is now underway, driven by what clients were actually asking, captured and surfaced by Checkster.
Sam also noticed a generational shift happening in payroll. A newer cohort of clients wanted answers immediately, through the interface, without picking up a phone. Checkster met them there, and the weekly review of its gaps became a window into where the industry was heading.
Breeze Assistant extended that same readiness to client-facing staff. Before meeting a client at an event or stepping into an account review, staff now have full relationship context before any client interaction, without the manual legwork. Dakota described using Breeze Assistant before visiting a major client, catching an outstanding issue in the summary, and resolving it before the meeting. The relationship stayed intact because someone showed up prepared.
Help Desk gave the broader operation its structure. Sam implemented Help Desk to replace a one-to-one support model that had no infrastructure behind it. As ticket volume grew with the client base, Help Desk gave the team shared visibility into every open issue, consistent routing, and a clear record of each client relationship. When Checkster routes a question it cannot resolve to a team member, that handoff lands in Help Desk with full context already attached. The team arrives to every conversation prepared.
The Transformation
The Promise, Kept at Scale
Checkwriters' clients still get through to a real person when it matters. Checkster handles the volume. The team handles the complexity. And the patterns Checkster surfaces are actively shaping what Checkwriters builds next.
Revenue has grown 20% since replacing Salesforce. Cancelled prospect calls dropped 25%. Marketing campaigns that took four weeks now take three days. The customer success team has grown roughly four times to keep pace with a client base that has expanded to 4,000 and continues to climb. The infrastructure absorbed that growth because it was built to.
Dakota no longer spends his week mediating between his team and their tools. Sales reps manage their own workflows. Marketing and onboarding operate from shared pipelines. The system runs with the team.
Sam's team listens to clients at scale now, in a way that was never possible when every interaction lived in a single email thread. The knowledge base is a living document. The weekly review of Checkster's gaps is a ritual. Product decisions are made with real client signal behind them.
"Checkster became our tool, our friend, our coworker. It is helping us deliver on what we’ve always cared about most: listening to our clients and giving them the best payroll experience." Sam Hathaway, Technical Solutions Manager, Checkwriters
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