How Filevine, MyCase and Smokeball Won Small Law Firms

About this episode

A small law firm can go live on new software on Friday and be back on spreadsheets by Monday. That Monday is why selling software to small firms is so hard, and why Filevine, MyCase and Smokeball are worth studying: each one won this buyer with a different move.

In Episode 4 of WhoBringsTheBusiness, Sagar Pratap Singh breaks down how three practice management companies won small and mid-sized law firms, what each move tells you about how small firms buy, and what a firm owner (or anyone selling to small businesses) can borrow from them.

Key takeaways

• Small firms buy confidence, not features. The managing partner decides between client calls and the office manager carries the risk, so the real question is “will this break my Monday?”
• Depth before breadth. Filevine started inside litigation and personal injury, the practice its founder had lived, and only then expanded to larger firms, insurance defence, corporate legal teams and government.
• Sell the relationship, then go where money already moves. MyCase was built around a client portal and later joined AffiniPay, the parent of LawPay, which many firms already used to take payments.
• Sell what the buyer loses without you. Smokeball leads with lost time, not features, through automatic time capture.
• Three questions before you switch platforms: who in your office owns the switch, which two numbers you will measure in the first 90 days, and how you would get your data out if you ever left.

Chapters

• 0:00 Cold open: the Monday problem
• 0:44 Why these three companies
• 1:35 Who actually buys software in a small firm
• 3:02 Playbook 1: Filevine goes deep before going wide
• 5:35 Playbook 2: MyCase sells the client relationship
• 8:38 Playbook 3: Smokeball sells lawyers their time back
• 11:40 What all three have in common
• 12:30 Three questions before you switch platforms
• 13:25 The Transferable Bit
• 14:12 Where the small firm software market is heading
• 15:25 Wrap-up and next episode

Mentioned in this episode: The First Five Minutes, a free session for law firm leaders on how firms win or lose clients at the first call, on Friday 18 December 2026 at 10:30 AM Eastern.

Company details in this episode come from public announcements, press coverage and founder interviews, including LawNext, Startup Daily, Clio’s 2025 Legal Trends Report for Solo and Small Firms, and the companies’ own announcements. This episode is not sponsored by any company mentioned.

Transcript

Cold open: the Monday problem

Picture a Monday morning in a six-lawyer firm. The new case management system went live on Friday. By ten o’clock one paralegal is back on her spreadsheet. A partner can’t find a client’s file.

And the office manager is quietly asking whether they can switch back. That Monday is the reason selling software to a small law firm is so hard. And it’s the reason three companies are worth studying today. You are listening to Who Brings The Business with your host Sagar Pratap, powered by Dizital Connect.

Welcome back

Welcome back. Last week we looked at the demand letter, and how EvenUp, Supio and Eve turned it into a product. Today is about the system the whole firm runs on. Practice management. Case management. The place where matters, documents, deadlines, time and billing all live.

Three companies have won small and mid-size firms here, each with a different move: Filevine, MyCase, and Smokeball. As always, most numbers you’ll hear are the companies’ own announcements, or press reports. I’ll name the source each time, and the full list is in the show notes.

Who actually buys software in a small firm

Let me start with the buyer, because I spent years selling to this buyer. For more than twelve years I worked on the support side of US law firms, selling outsourced legal support to firm owners. Here’s what I learned about how they decide. In a small firm, nobody’s job is to buy software.

The managing partner decides, usually between client calls. The office manager carries the risk. And if the switch goes badly, the firm loses billable time it can never get back. So the small firm doesn’t ask, “Is this the best product?”

It asks, “Will this break my Monday?” The good news for vendors? Most of this market has already moved to the cloud. Clio’s 2025 Legal Trends report for solo and small firms found that 79 percent of solo firms and 81 percent of small firms use cloud-based practice management software. Larger firms? 47 percent.

That changes the sale. The question isn’t whether a firm will use a system. It’s which one it trusts enough to move its whole practice into. And whether it’ll ever move again. All three companies we’re about to look at worked that out, in three different ways.

Playbook 1: Filevine goes deep before going wide

Filevine was founded in 2014, in Utah. Its co-founder and CEO, Ryan Anderson, was a founding partner at a personal injury, mass torts and employment class-action firm, before he built software. According to LawNext, the company started in the basement of his law firm. Anderson has said he was “constantly bombarded with urgent tasks and problems” as a lawyer.

And instead of putting up with it, he built a system to fix it, with engineers who wanted clean, cloud-based design. The growth since then is large. A 108 million dollar Series D in April 2022. Then in September 2025, 400 million dollars, raised across two rounds.

LawNext reported nearly six thousand customers, and about a hundred thousand legal professionals on the platform. So what was the move? Filevine didn’t try to serve every lawyer at once. It started where its founder had lived: litigation and personal injury.

A practice where one case runs for months, touches dozens of documents and deadlines, and involves a whole team. It built for that workflow first. In depth. It also followed the case back to the front door. By 2022 it had bought Lead Docket, a lead tracking and intake tool, so a firm’s intake could sit in the same system as its cases.

And from that litigation base, according to LawNext, it has since expanded into larger firms, insurance defence, corporate legal teams, and government. For your firm, the lesson is depth before breadth. Most small firms try to market to everyone with a legal problem. The firms that grow fastest usually pick one practice area and one type of client, and become impossible to ignore there.

Ask yourself: which cases would you happily take a hundred more of? That’s where your marketing should start.

Playbook 2: MyCase sells the client relationship

MyCase was founded by Matt Spiegel, who was a criminal defence attorney in San Diego. You may remember his name from Episode 2, because he later founded Lawmatics. MyCase’s own January 2011 announcement says Spiegel started the company after struggling to find technology that let him talk to clients efficiently. That announcement was for MyCase 2.0.

And it describes a product built around a secure, cloud-based client portal. A place where clients could check the status of their case, view and upload documents, and ask questions. With practice management, time and billing alongside. In the same announcement, Spiegel said: “MyCase is low-cost and fundamentally changes the relationship between client and attorney.”

He also said that practice management software had been adopted by less than 40 percent of the market at the time. That’s the first move. Most legal software was sold to the lawyer as a back-office tool. MyCase sold it as a better client relationship, which is something every small-firm owner already worries about.

The second move came later. In September 2020, the private equity firm Apax bought MyCase for 193 million dollars. Then in June 2022, AffiniPay, the parent company of LawPay, acquired MyCase. LawPay is a payment tool built for law firms, and many US firms already use it to take card payments from clients.

According to LawNext, the combined company served about 65 thousand law firms, and almost half of them didn’t yet have practice management software. Think about what that means. The company that already handled how a firm gets paid now owned a system to run the whole firm. AffiniPay’s CEO at the time, Dru Armstrong, said they wanted “to put the lawyer first.”

For your firm, two lessons. First: sell the relationship, not the service. Clients rarely judge you on your legal skill, because they can’t. They judge you on whether they knew what was happening with their case.

Second: look at where money already moves in your client’s life. The professionals who touch your clients’ money, accountants and financial advisers, are often your best referral partners.

Playbook 3: Smokeball sells lawyers their time back

Smokeball’s co-founder and CEO is Hunter Steele. He grew up watching his father run a five-person law firm in a country town in New South Wales, Australia. In Smokeball’s own interview with him, Steele says he watched his father work long hours and carry clients’ stress home, and saw how software helped. In law school he noticed something else.

Students were taught to practise law, but not how to run a business. His conclusion is worth quoting. Small law firms, he said, “weren’t just law firms. They were actually small businesses.” Here’s an unusual detail.

Although the company’s roots are in Sydney, Smokeball’s own history says it launched in Chicago in 2013, and only expanded to Australia in 2016. Steele has said there were about ten thousand small firms in Australia, and about two hundred and fifty thousand in the United States. So the company went where the buyers were. Now, the move I want you to notice is how Smokeball talks to that buyer.

It doesn’t lead with features. It leads with lost time. One of its signature features, AutoTime, launched in 2017. LawNext described it like this: it tracks a user’s activity in Smokeball, works out which matter that activity belongs to, and creates the time entry.

So the lawyer isn’t rebuilding the day from memory at six o’clock. In 2021, Smokeball announced its first capital round: 30 million, after years of bootstrapping, from private investors and employee shareholders. And Steele told Startup Daily that Smokeball clients bill over four hours a day, against an industry average of two. That’s the company’s own claim, so treat it as a claim.

But look at the pitch. It’s not, “buy our software.” It’s, “get paid for the work you already did.” Steele has another line I like.

“The goal, then, is to never allow lawyers to drop the ball.” For your firm: clients, like lawyers, buy what they lose without you. A personal injury client isn’t buying a lawsuit. They’re buying back the months they’d spend fighting an insurer alone.

So say what the client gets back, in time, money, or peace of mind, in the first sentence of your website and your intake call.

What all three have in common

Three companies. Three moves. Filevine built inside one practice, and went deep before going wide. MyCase started with the client relationship, then joined the company that handles the firm’s money. Smokeball sold lawyers their own time back.

But all three understood the same buyer. The small firm doesn’t buy software. It buys the confidence that Monday won’t break. Each of them lowered that risk in a way the buyer already understood:

A founder who’d lived the problem, a vendor the firm already paid through, or a promise measured in hours.

Three questions before you switch platforms

If you run a firm and you’re thinking about changing platforms, here are three questions to ask before you sign anything. One. Who in my office owns the switch? Not the vendor. A named person at your firm, with time set aside for it. Without that person, the Monday problem wins.

Two. What will I measure in the first ninety days? Pick two numbers before you start. For example, how quickly new enquiries get a reply, and how much time gets billed each week. If those numbers don’t improve, you’ll know.

Three. How do I get my data out? Ask every vendor how you’d export your matters, documents and billing history if you ever left. A vendor that answers that clearly is one you can trust to stay with.

The Transferable Bit

Not a lawyer? This still applies to you. If you sell to small businesses, your buyer looks exactly like a small law firm. No IT team. No time. And a fear of breaking what already works. So borrow the three moves.

Go deep in one segment before you go wide. Show up where your buyer already spends money and time. And describe your product in what the customer gets back, not in what it does.

Where the small firm software market is heading

Before we wrap up, a quick look at the field, because it’s crowded. Clio is one of the biggest names in cloud practice management, and we covered how it won firms in Episode One. Filevine leans into litigation and personal injury. MyCase sits alongside LawPay, under AffiniPay.

Smokeball focuses on small firms, with automatic time capture. And all of them are adding AI to the platform the firm already uses: Filevine in litigation workflows, MyCase through AffiniPay’s AI tools since 2024, and Smokeball through Archie, the AI tool it introduced in 2024. My advice?

Whichever one you look at, ask for a reference call with a firm your size, in your practice area, that switched in the last year. And ask them about their first Monday.

Wrap-up and next episode

That’s it for today. Small firms don’t buy the best software. They buy the change they trust most. Next week: Inside the Rooms Where Legal Buys. What the big legal tech conferences show about meeting buyers in person. And on Wednesday, the 18th of November, at 10:30 AM Eastern, I’m hosting The First Five Minutes.

A free session for law firm leaders on how firms win or lose clients at the first call. The link is in the show notes. If you want one short note like this every week, subscribe to my newsletter, Your Honor, We Need Clients. Comment or reply HONOR, and I’ll send you the link.

I’m Sagar Pratap, and this has been Who Brings The Business.