Issue #32 | October 30th, 2026

Happy Friday!

I’m in Utah today at Zion National Park. It’s raining. Yesterday we hiked up to Angels Landing!

Today I wanted to write about how I think about the mid-market and how those clients differ from the SMBs we all typically work with. At Celerity, this is our ideal client these days so I’ve gained quite a bit of exposure to this.

This is based on my presentation at Intuit Connect from Monday.

So I thought the mid-market would mean more accounting work. More transactions, bigger fees, and more complicated financial problems to solve.

What I didn’t anticipate, though, was how much time we’d spend ensuring our client’s business actually worked.

We found we weren’t just doing accounting anymore, we were fixing the processes surrounding the accounting as well.

One time, a client moved from shipping their own products to drop shipping pretty abruptly. What this means is, they went from holding inventory and shipping it themselves to having vendors ship straight to customers.

This means more bills. Within a few months we went from entering maybe 100 bills a month to 500+ bills a week!

It was burning out the team member stuck figuring out how to get those entered & the risk of errors kept climbing too.

While she entered bills all day, I did some research and was able to find an AP solution that fully automated the entry of about 90-95% of those bills. Only exceptions had to be reviewed.

This saved the engagement for us, and luckily the client was willing to pay for the solution. In the mid-market, it’s about the systems and working smarter, not harder. This situation repeats anytime we get a new client or a client makes a major business shift like this.

In the mid-market, changes can be engagement altering. In this scenario, the volume made mistakes more frequent, it risked burning out my team, and it reduced profitability within weeks.

The books depend on everything around them.

What does that mean?

Purchasing creates an order, operations receives the goods. Someone enters and someone approves the bill. Accounting needs all of this to be accurate and work in order to do our job.

Taking responsibility for the accounting is like taking responsibility for their entire flow. We become the team that ensures it stays running smoothly.

As we moved up to the mid-market, our role changed from accountant to systems builder + accountant.

Our clients trust us. Accountants are smart, we see the details, the weeds. And we’re problem solvers so this is a natural evolution of our role. Oh, and we need it done right at the end of the day.

So why do I love it? The problems keep changing, we get to work with dynamic and intelligent leadership, and we become a part of their team.

Yeah, the larger fee is great too, but, the challenges that arise keep us useful and the team improves with every problem solved.

Working with a founder that built a business from zero to $50 million, means probably working with someone with crazy ideas and a big personality. For me, this is fun.

I want to empower people who are changing the world and making an impact.

Moving into the mid-market requires more than just accepting a larger engagement. You need to understand the operation, price the actual work, and establish where your responsibility begins and ends.

Do you just do their books? Or do you do AP, AR, the books, and ensure that SO/PO’s stay cleaned up, and handle collections too? Ensure you keep this defined well because you can fall into scope creep easily when you’re filling a bigger role with clients.

We’re the closest thing to an in-house employee, and honestly, that’s typically who we find we’re replacing with newer clients a lot of the time.

You’ll want to get access to their books, pull the G/L and audit data, and review the whole engagement before you price it out. My firm does a mix of value pricing + estimating # of hours.

The stakes are so much higher with clients like these. If you mis-price an engagement, your loss potential could be so much higher until fixed. Also, their standards are higher and continue to grow with AI and evolving tech. You’ll have to grow to keep up.

If you’re nervous about trying out clients at this size, here’s what I would say.

Try it.

You don’t have to jump from tiny clients to $100 million sized clients. You can take baby steps. Try 5 million, then maybe a $10-15 million ranged client. See how it makes you feel. You’ll learn pretty quickly what needs to change in your firm to work with these clients.

If you have questions, reply to this newsletter. I’m always happy to talk mid-market and bigger clients.

Question of the week

Join me at WorkflowCon, November 9–10

I'm speaking at WorkflowCon 2026, a free two-day virtual conference for small and growing accounting and bookkeeping firms. My session, Would You Fire This Client?, is on November 9th. There are five tracks and a theme I believe in: Focus is the New Flex.

Click here to register

Have a fantastic weekend!

- Tailor