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As a CFO, I've always hated how much of my day is choosing between control and speed.

You either get real-time visibility or you get your team moving fast — never both.

My Brex card is different. Brex gives me the controls I need without slowing down important expenses, like Wally’s dog treats or Producer Ben’s cool gizmo sound things. With Brex, receipts are automated, expenses hit in real time, and categorization doesn't require three people and a spreadsheet. I can see exactly where money's going while we focus on growing the Mostly Metrics world empire (also, Sales Guy Matthew, just because you CAN expense and eat $32 of Chipotle doesn’t mean you HAVE TO).

Finance doesn’t have to slow companies down - it can and should push them forward.

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Job Stuff

Gee wiz. I run a recruiting company now. Life comes at ya fast.

Mostly Talent is currently filling positions for a Director of Strategic Finance, Controller, FP&A Manager, and VP of IR across Series B through Pre-IPO companies. These searches move fast.

Should you fire some of your customers?

I have an exercise for you. It goes like this:

  • Segment your customers by how much they spend per year (ARR band).

    • Then calculate the percent of total ARR that band represents

  • Next, look at total percent of Customer Support + Success hours spent on that band

    • CS people F’in love to log their hours. The data should exist.

    • Note: This isn’t a customer level profitability assessment (if you want that, you can learn about that analysis here)

    • We are staying at a slightly higher altitude… Just get the rough % of total CS time serving that band

  • Finally, look at the relative NPS of each segment

    • Stack rank the happiest and most likely to retain customer bands

So to summarize - we’re coming up with a view that pulls in customer spend, CS hours, and customer NPS.

The results are probably not what you thought. For many companies, their lowest value customers take up the most CS resources, and are also the least likely to promote them.

As my dad would say, “That and a dollar will get ya a cup of coffee!”

(He came up with the saying pre inflation, obviously).

So yea, not exactly a winning formula!

It creates a P&L blackhole that can go undetected for years, one that you continue to fund even though it creates a non linear pull on the rest of the org’s bandwidth.

  • Finance spends time resolving billing issues with smaller, unhappy customers

  • Product and Engineering spend time building small feature adds to help support their lack of real ERPs / CRMs

  • Human resources spends time filling more CS roles when they should be filling more quota carrying sales rep roles

  • CFOs are losing their minds because total renewal rates are dropping while gross margin points are being nibbled away

“Tony? From Albuquerque Gum who’s always complaining about our Quickbooks integration?”

I was talking to Cassie Young on the Run the Numbers podcast, a serial Chief Revenue / Customer officer at growth stage startups. She brought me back to a time when she was running CS at Sailthru. They ran the analysis I described above, and what they discovered broke their mental models:

  • The sub $100K contract value segment was 13% of the total ARR of the biz

    • But it was consuming 40% of the CSM’s teams time

    • And if you went to the $500K segment it was literally the inverse

  • The sub $100K contract value segment had the WORST NPS of all their segments

    • Not only were they they least margin accretive, they were the least likey to stick around after pouring all those resources into their development

They came to the conclusion that if these smaller, needier customers were going to stick around, they needed to pay for the resources they were consuming. They presented them with three options:

  1. Buy a service package for $12K per year (or $1K per month) to maintain access to a CSM

  2. Stay at the same price, but you don’t get to call a CS person anymore; you just get basic support. “I’m sorry, but we can’t support you in a high intervention way going forward.”

  3. You can tell us to kick rocks, and we’ll let you go month to month. That way you can self select to leave whenever you want

Some customers left. But remember, they weren’t great customers anyway.

Shockingly, most stayed. And they also took the first option, ponying up an incremental $1K per month, which brought the profitability profile of the segment back in line.

It’s scary to communicate this negative message to anyone who’s giving you money (even if they are giving you seventy five cents for the dollar of resources you are giving them). Regardless of the unit economics, it’s awkward turtle.

But the reality is, they probably don’t want to be a ‘bad customer’. Your customer probably sells something too (hint: all customers also sell something, which is how they have money to be your customer). So they are empathetic to the dynamic.

(Plus, keep in mind, they are using your CS team all the time. So it’s not like they think everything is “going as planned”.)

Not to mention, you risk being in a situation where your roadmap starts to get dictated by the loudest, yet usually not the largest, customers.

Before you hit send…

OK, so you’ve done the analysis above and come to the conclusion that you need to cut the crops.

Before you let that email rip, two things to keep in mind:

First, the tone, and the quality of the off ramp, really matters.

Blasting out an email saying we will not serve you anymore, you stink, we’re turning the lights off in a week, is not a great look. The blast radius will reverberate back to the customers who you DO want to retain. And they will think “do I really want my eggs in this basket if it could happen to me?” Bad news travels fast, and between segments.

In the Sailthru example, they gave customers three options, none of which said “Vacate the premises in 30 days.” The “firing” was really customers firing themselves… they were self selecting out based on the optoin set. It put the onus on them. And, hey, if they chose the door, Sailthru was nice enough to move them to a month to month plan (if they were on annual) when they really didn’t have to do that.

Finally, keep in mind that it’s OK, even perfectly normal, for your ICP to shift over time. It’s a sign of maturity that your product is deep enough and serves valuable enough use cases to earn a corresponding increase to revenue.

I hate to say it, but the harsh reality is that not all the customers who got you here will get you there.

It doesn’t mean you are disrespectful or ungrateful. It simply means you shift your resource allocation over time to be more in the way of the money. And honestly that’s probably what they are doing with their respective company’s as well.

Just make sure to do it with data and respect.

Run the Numbers Podcast

Tune in on: Apple | Spotify | YouTube

Cassie Young brings hard earned lessons from a career spanning CRO roles, customer success leadership, turnarounds, and now investing as a General Partner at Primary Venture Partners.

We talk about:

  • building and rebuilding go to market teams,

  • why sometimes you should fire customers on purpose, and

  • how churn is a lagging indicator that hides deeper retention issues.

Quote I’ve Been Pondering

“A job is really a short-term solution to a long-term problem.”

Rich Dad, Poor Dad by Robert Kiyosaki

Hoping we aren’t in a bubble,

CJ

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