Small firms are often pegged as tech laggards, but many are adopting at higher rates than their corporate counterparts—they’re just being more thoughtful about it.
Tyler Otto is about to do something that, at face value, sounds a bit backwards for someone who sits on the partner advisory councils of half the software vendors he works with. He is revising his firm’s website messaging to talk less about technology.
“You go to every website now and it’s like, ‘Let AI transform this’ and ‘AI here,’” says Otto, who runs Specialized Accounting, a hospitality-focused firm he scaled from a $20,000-a-year book of business into a 16-person operation in roughly five years. “I’m about to rebrand my website as only talking to people.”
It’s not that he’s afraid of software. Otto leverages technology about as aggressively as anyone in his field. But he has noticed something that the firms racing to bolt the word “AI” onto everything seem to have missed.
In other words, he knows his audience—and they are always in the back of his mind when he’s deciding where (and where not) to insert technology into his firm’s operations. It’s a philosophy shared by most of the firms featured in the Proudly Small issue of Two Cents Magazine—one that cuts against the lazy assumption that the little guys are still running on shoeboxes and spreadsheets while the big firms surge ahead.
In reality, small firms are often running even tighter systems than their corporate counterparts. And they got there not by chasing every shiny new product release, but by being ultra-choosy about which tools they plug into their processes—and which jobs stay human. Because, as Otto warns, “The moment our firm and what we do becomes a commodity and there’s no human relationship behind it, it’s easy for them to replace us.”
The laggard myth, busted
The expectation is that a two-person shop muddles along on whatever it can afford, and the firm with a hundred employees has the most sophisticated stack on the block. But the more you dig into the reality behind the numbers, the more the picture flips.
Alisa McCabe built First Steps Financial as a remote, all-women firm years before the available technology could fully support her vision. “I wanted to create a company that supported women who wanted to have a work-life balance,” she says. So, she started paving a path toward that goal—figuring the tools would eventually evolve into what she needed them to be.
Documentation and delegation
For growing firms, the impetus for tech implementation is often the need to delegate. As a firm owner or leader, you can’t move work off of your plate until the process for completing it to your standards exists somewhere outside your own head. (And for anyone in an operations or admin seat, this type of documentation is especially mission-critical.)
Tamra Helton learned the documentation lesson the hard way. She ran Tied Out Books out of her head for way too long, and as the firm grew, she realized she had unintentionally become the single point of failure for everything. So, she spent months rebuilding all of her workflows, SOPs, and video walkthroughs inside her practice management software—really taking the time to make sure she was using the technology to its full potential. That way, her team could operate without her hovering over every task.
Anne-Marie Kaden, who built Tiny Paws Bookkeeping into a 100-client firm serving the pet-care industry, also recommends building with the assumption of growth (even if you have no plans to hire anyone in the near future).
Kaden has invested a lot of time over the last year documenting and centralizing workflows. She’s also fine-tuned the new hire training process to help ensure every team member is equipped to deliver the exceptional level of service the firm is known for. Today, new employees spend roughly six months working alongside Kaden or her manager—slowly progressing from observing client meetings to leading them.
Where visibility meets flexibility
Regardless of how or where you document your workflows, the ultimate goal is creating shared visibility in a clear, accessible way. That’s what enables firm leaders to comfortably remove themselves from the minutiae of each task while still trusting that the work will get done.
At Capovario, Dave Kersting runs a firm with no set hours. Nobody clocks in or out, and he always encourages his team members to put their lives first—and their jobs second. The main reason he’s able to do that without the entire operation collapsing into chaos is that everything—client history, notes, the next action on every account—lives where the whole team can see it.
“My entire team has access to my entire caseload,” Kersting says. So, if one person is offline at their kid’s event in the middle of the afternoon, another can step in, answer the client, and move the task forward—and nothing slips.
It’s the same concept that keeps things running smoothly across Hutcherson’s remote team. Without their shared system, freedom and flexibility would be nearly impossible. In that sense, technology is what turns “work whenever you want” from a nice slogan into something a firm can operationalize.
Purpose-driven implementation
If there’s a single trait that separates these firms from the tech-averse stereotype, it’s how they’ve integrated their carefully selected tech stack into all facets of their operational flow. In some cases, that even extends to their criteria for ideal-fit clients. Katie Helle, who founded Scaled Accounting Solutions and went full-time with it in late 2024, made tech-forwardness an actual condition of working with a client.
Helle knows that her entire operational model—which includes an offshore team, an automated onboarding process, and a client base she can serve well without drowning—depends on both sides moving in harmony. And that can only happen when they have the same attitude toward tech.
McCabe is equally bullish on technology. “We are very tech focused,” she says. “We want everything, all the systems to link together so that there’s less chance of mistakes, so that you get your information faster and better.”
The line between technology and the human touch
That brings us back to Otto—and to the most telling thing about this group of firm leaders: if they are intentional about where they will leverage technology as part of their operations, they are perhaps even more intentional about what they won’t automate.
For Otto, that line is the relationship. He uses the best tools he can find, but he refuses to let the work become some faceless commodity, because a commodity is something you can always get cheaper somewhere else. His firm’s website rebrand isn’t a rejection of technology, but rather a bet that in a market shouting about automation from all directions, sounding human is a major advantage.
Kaden describes the human layer in a deeper, more nuanced way. A surprising amount of bookkeeping, she has found, is emotional work—clients arrive scared of what their numbers will say. “We always try to approach those conversations with a level of compassion,” she says. It’s similar to the way you might approach a frightened animal: slowly, gently, and empathetically. A tool can’t do that (nor should it try).
Even the most AI-forward firm owners are overwhelmingly cautious about the boundaries they draw. McCabe is open about using AI tools where they fit, but she is resolute in her belief that AI is not the end all, be all.
That’s really the bottom line across the board—not anti-technology, not technology-for-its-own-sake, but a steady insistence on knowing which jobs can be outsourced to machines and which must remain with people.
PRO TIP: What to Automate, and What to Keep Human
Automate the repeatable with technology.
- Client intake and onboarding. This is the near-unanimous “automate this first” among most firm owners and leaders. Katie Helle, for example, pipes website leads straight into her practice management software, and she built in three screening questions to flag bad-fit clients before an intro call ever happens.
- Workflow documentation. Tamra Helton layers Loom-style walkthroughs into every workflow in her practice management software so any team member can follow the steps without her. (It might also be helpful for firm owners or leaders to record themselves talking through workflows, and then turn the recordings into documented processes and templates.)
- Task and deadline tracking. For Laraine Hutcherson’s 15-person remote team, a centralized system isn’t optional. It’s the only way to know what’s due for which client at any given moment.Internally, for efficiency: You grouped similar clients and let your team specialize internally, even with no outward niche (e.g., Cathryn Vidal from Crema Bookkeeping and Sarah Queale from Synergy Tax & Business Solutions)Around a specific type of person: You focus on who you serve, not what they do (e.g., Lynn James-Young from Bring It Bookkeeping and Angela Jenkins from Mindfull Money Matters)Around values: You built your client list around shared values (e.g., Melissa Miller Furgeson from Bookkeeping for Good)
Keep the irreplaceable with humans.
- The hard conversations. Anne-Marie Kaden treats a client scared of their own numbers the same way you’d treat a frightened animal: with patience and empathy. No tool can replace that.
- The relationship. Tyler Otto’s rule: the moment the work becomes a faceless commodity, you’re replaceable. Human connection is a moat.
- The client judgment call. The ultimate decision on whether a client belongs on the books is one Katie Helle and Alisa McCabe make personally—not one they offload to an algorithm.
The story beyond the stack
Even if this is a story about technology, software is not the main character. Yes, most successful firms are running on well-defined systems. Yes, many of those systems depend on software. And yes, small firms often outperform the behemoths on system efficiency and effectiveness.
But by and large, small firms aren’t out to win a technology arms race. Their leaders know innovation for the sake of innovation is a fool’s errand. Instead, they are building with a goal of protecting what makes them special—and what they care most about.
Helton is trying to create a firm that can run without her—not so she can generate more revenue, but so she can stand on the sideline for every single one of her daughter’s soccer games. “My end goal is to spend as much time with my daughter and my husband as possible,” she says. “And I can’t do that if I’m sitting here.”
Kersting sums it all up in six simple words: “I want life, and then work.” For him, the tech stack is merely the scaffolding holding that vision up.
That’s the subtle sophistication of the proudly small firm. They might not have the longest list of tools, but they often do have the clearest sense of what each one is for—and the discipline to keep the human parts unequivocally human.
Get a clear picture of how bookkeeping firms are managing their tech—and where inefficiencies are holding them back.
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