If you’ve ever finished a month-end close and thought “I know I’m undercharging for this,” you’re not imagining it. You probably are.
But it’s not because you’re bad at business. It’s because pricing bookkeeping services is hard. Accounting programs teach you to be an excellent technician. They don’t teach you how to build a pricing structure that holds up when a client asks for more than reconciliation and reporting.
That’s exactly what SmartPath founder Will Hamilton covered in a recent training session hosted through CPA Academy. In 60 minutes, he walked through a framework that most bookkeepers have never seen laid out this clearly.
Here’s a recap of what he covered, and why it matters if you’re serious about building a practice that doesn’t burn you out.
The Real Problem Isn’t Your Rates. It’s Your Structure.
Most bookkeepers don’t have a charging problem. They have a structure problem.
Will made this distinction clearly in the training, and it’s worth sitting with. When firms undercharge, it’s rarely because they lack confidence or don’t know their worth. It’s because they’re pricing out of a system that was never designed to capture the full value of what modern bookkeeping actually looks like.
Think about what happens when a client adds two new entities, three new bank accounts, and starts asking for cash flow projections but still expects the same monthly fee. Or when you’re doing work that functionally looks like CFO-level advisory but you’re charging for basic reconciliation because that’s what you quoted 18 months ago.
The session opened with a simple question Will poses to firms he works with: when is the last time you updated your pricing structure? Not just your rates, but the actual architecture of how you package and present your services?
For most bookkeepers, the honest answer is never.
Rule #1: Do Smarter Discovery Before You Ever Quote a Price
The first pricing rule Will covers is what he calls smarter discovery. It’s the foundation everything else is built on.
The core idea is this: if you don’t know what a client actually needs and why they need it, you’re not pricing. You’re guessing. And when you guess, you almost always undercharge.
Most bookkeeping intake processes ask the same surface-level questions. How many bank accounts do you have? How many transactions per month? What accounting software are you using? These are operational questions, not discovery questions. They tell you how to set up the engagement. They don’t tell you why this client needs a bookkeeper, what they’re trying to accomplish in the next 12 months, or how much that outcome is actually worth to them.
Will’s approach is to anchor every discovery conversation to a bigger business goal. Before you talk about scope or price, ask the client: what’s one or two things you really want to make progress on in your business over the next 12 months?
The answers change everything.
In the training, Will walks through a real example: an HVAC company doing $750,000 a year with an admin who’s struggling through the books. On the surface, they need bookkeeping. But deeper discovery reveals they need cash flow forecasting to bid on a large corporate job and still make payroll, clean financials to apply for a business line of credit, and payroll integration to support an S-Corp conversion their tax professional is recommending.
Three goals. Three reasons why accurate, up-to-date books aren’t a nice-to-have. They’re directly tied to things this business owner is trying to accomplish. That changes the entire pricing conversation, because now you’re not selling reconciliation. You’re solving specific problems that have real financial stakes for the client.
Will’s point is a good one: the car salesperson who asks what vehicle you actually need earns more trust than the one who’s just trying to close a deal. Discovery is how you get out of the selling seat and into the advisor seat. Once you’re in the advisor seat, pricing conversations get a lot easier.
Rule #2: Build Three Clear Value Tiers (And Make the Differences Obvious)
Once you know what a client needs, the next question is: which level of your service is the right fit for them?
If your answer is that you price everything custom, that’s exactly the problem Will addresses in the second rule.
He breaks bookkeeping value into three distinct levels that most firms have never formalized:
Level one is historical value. This is reconciliation, transaction categorization, basic financial statements. It’s compliance work, and it’s genuinely valuable. It’s also the level where AI and automation are getting very, very good. Which doesn’t mean it goes away, but it does mean it’s the lowest-margin tier going forward.
Level two is strategic reporting and analysis. Did anything change, and if so, why? This is where you’re doing monthly or quarterly reviews, custom reporting by department or location, cash flow analysis, budget versus actuals tracking. You’re not just telling the client what happened. You’re helping them understand what it means.
Level three is recommendations and insights. What should we do about it? This is CFO and client advisory services territory. Rolling 12-month forecasts, scenario planning, proactive recommendations, strategic planning sessions. You’re helping a client make better long-term decisions about their business, not just keeping their books current.
Most bookkeepers price all three of these levels the same way. That’s the seats on the plane problem Will describes: you only have so much capacity. If you fill every seat with $300 a month clients, you’ve made it structurally impossible to ever do $1,500 a month work, even if you want to and even if you’re good at it.
Two pricing psychology principles Will covers here are worth knowing. The first is the psychology of choice: giving a client one price forces them to decide yes or no. Giving them two or three options shifts their brain from “is this for me?” to “which one is right for me?” That’s a fundamentally different and more favorable buying decision. The second is what he calls the wine list effect: a higher-priced option on your menu doesn’t just represent revenue. It anchors the lower-priced options and makes clients feel better about choosing the middle tier. Without a high-end option, everyone migrates to the bottom.
Rule #3: Help Clients See the Value Before They Have to Decide
The third rule is where most bookkeepers lose the deal without realizing it.
Even if your discovery is solid and your tiers are clear, clients won’t commit if they can’t quickly see and understand what they’re getting. In a world where clients are overwhelmed, distracted, and shopping around more than ever, the window for getting buy-in is shorter than it’s ever been.
Will’s observation from working with over 1,800 firms: most bookkeepers send either a basic email with a price, a plain PDF proposal with no visual structure, or a contract full of legal language. None of those help a client feel confident about what they’re buying.
What clients are actually buying, as Will puts it, is not bookkeeping. They’re buying peace of mind, time back in their business, confidence in their numbers, and the ability to make better decisions. If your proposal is a list of services and a monthly fee, you’re not showing them any of that. You’re just showing them a cost.
The shift Will recommends is moving toward a visual presentation of your tiers that makes the difference between each level immediately obvious. Not just a checklist of deliverables, but a clear picture of what the client gets and what it means for their specific situation. The 90-day onboarding roadmap, the concrete examples of what a cash flow forecast actually looks like, the specific outcomes clients can expect: that’s what creates faster buy-in.
He also covers the practical mechanics of making it easy to say yes: electronic signature, automatic payment setup, immediate next steps. The faster a client can move from yes to started, the less time they have to second-guess.
Why This Framework Works Right Now
One thing that stands out in this session is how clearly Will frames the urgency around this.
The bookkeeping and accounting industry is changing faster than most firms’ pricing structures are keeping up with. AI is getting genuinely good at historical compliance work. Outsourcing options are expanding. Clients have more choices than they’ve ever had. In that environment, competing on price is a race to the bottom. The only way to avoid it is to compete on value.
The firms that are going to win over the next decade aren’t necessarily the ones with the most clients or the lowest fees. They’re the ones that have a clear, structured answer to the question: what level of value are we offering, at what price, and how do we show clients why it’s worth it?
That’s what these three rules are designed to build.
Watch the Full Session
This recap covers the framework, but Will goes much deeper in the actual session. That includes the specific questions to ask in discovery, exactly what to include at each tier, real examples from firms he’s worked with, and how SmartPath’s tools (including the Magic Client Pricing Link, the Three-Tiered Roadmap, and the Customized Client Guide) help bookkeepers implement this without starting from scratch.
If you’ve been meaning to fix your pricing and haven’t found a practical place to start, this is it.
[Watch The 3 New Pricing Rules for Bookkeepers, free, on demand, no re-registration required]