How to Fire Someone

If you’re a finance leader in the SF area, I’d love to buy you a Miller Lite or three on Thursday February 12th. I’m hosting it at an undisclosed Bay Area location, guarded by a squad of ferocious miniature Bernedoodles.

Seriously though, let’s all have a fun night of “networking” (ugh I hate that word).

RSVP below to meet fellow nerds.

This week we have the following CFOs answering your reader questions:

They are two gentlemen I’ve looked up to for a long time, and I couldn’t be more pumped to get their input on the following topics:

Let’s get into it!

John from Calendly:

This is actually a great first assignment for your new controller. I’d ask them to own the transition end-to-end and come back with a clear project plan. In parallel, lean on the fractional firm — they should be very used to this. The big things to confirm are:

If things are in decent shape, a clean transition usually takes 30–60 days. The goal isn’t perfection on day one — it’s continuity, audit readiness, and no loss of institutional knowledge.

Steve from Bloomerang:

Non CPA here.

Congrats on hiring a Controller. The hard part is already done. Seriously. Picking the right full-time human is way tougher than sunsetting the fractional firm that’s been maintaining your books for the last few years. Now it's just project management.

Your goal should be to wrap the transition in 30 days. No reason it should take longer, unless they’re holding your chart of accounts hostage. Start by asking for a clear list of what they currently own. Close process, reconciliations, payroll, rev rec, state tax filings. If they can’t give you a checklist, even more reason to move on.

Have your Controller shadow a full close cycle from start to finish. They should walk out with the keys in hand and confidence to drive. Ask the fractional team what’s “weird.” Journal entries, manual workarounds, audit adjustments. That’s the stuff that will bite you in three months. Also how quickly your Controller wants to take everything is a great first test.

John from Calendly:

You’re ultimately going to be working with a person, not a logo — so partner quality matters a lot. But it’s not a 50/50 tradeoff.

I’d work backwards from talent and distribution. In competitive markets, especially in software, your ability to attract great people is one of the few durable advantages you can create. Like it or not, employees and customers often outsource their own judgment to your investors. A strong firm brand still carries real signaling power.

My bias: don’t ignore brand lightly. If you love the partner at a newer firm, make sure you’re clear-eyed about what you’re giving up — network, recruiting pull, credibility in future rounds. The right answer isn’t universal, but the costs are real.

Steve from Bloomerang:

Trust your gut. You don’t work with a logo, you work with a person. A big name on the cap table might not return your calls when you miss plan. A great partner at a lesser-known fund will roll up their sleeves and help you figure it out.

Sure, a name-brand firm can help with recruiting, signaling, and future fundraising, but only if the partner doing your deal has juice and shows up when it counts. A logo can’t jump on a Sunday call. A great partner can. And will.

I’m a Midwest guy. We tend to pick people we trust over people who own Patagonia vests with their fund’s logo on them (kidding I love a good vest). So my rule of thumb? It’s 80% person, 20% firm. Go with the investor who’s going to get in the trenches with you, not just pose for the Series A press photo. This is a marriage. Pick the person who’s going to show up when it’s hard, not just when it’s headline-worthy.