Ecom CFO Notebook - people problems and you

Welcome to this issue of Ecom CFO Notebook – a weekly letter for 7–9 figure ecommerce founders and CFOs, sharing my perspective and stories for profitable growth.

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Sam here.

Before we start, a very small favor to help guide this content:

Last week, I talked about defining Core Focus — a big gap I’m seeing with clients as they navigate today’s environment.

Now that your strategy is at least 1% better, the next logical step is the who.

Who’s going to execute the strategy?

How org charts are changing right now

Just in the last few weeks, I’m observing bigger changes with client’s teams:

• $50M+ client laid off their CFO and 6 other employees

• $30M+ client delaying in house accounting hire

• Clients are sticking with contractors and agencies longer

• The best internal people getting poached

More and more founders are asking themselves: 

“Do I need to make hard decisions about my team?”

Things have changed.

The org chart hasn’t.

That’s where the pain creeps in.

You can feel it when ownership gets vague, meetings get slower, and work quietly lands back on your plate.

Sometimes the answer is obvious.
Other times… not so much.

This isn’t just about cost cutting.

Most of our clients aren’t going to cut their way to growth. And worse, when a senior person leaves, it’s usually the founder who picks up the work.

But regardless of who picks up the slack, we still need to ask ourselves uncomfortable questions: 

• [PERSON] got us here, but will they get us there?

• If I could hire them again today, would I?

• Are they still the right fit for where we’re headed?

Most problems are people problems.

And most of the time, the people problem is you. 

• You hired them (a long time ago when the business was less complicated)

• You trained them (well, you kind of trained them and then assumed they’d figure it out)

• You defined performance expectations (well, at least you give them a bonus that’s “bigger than last year”)

Sometimes it feels like I’m writing to myself…

Why founders stay stuck

One founder told me they’ve been wrestling with their org chart for months.

They weren’t overstaffed. They were just stuck because expectations weren’t clear, senior hires weren’t “delivering”, and the founder was backfilling work they thought they’d delegated.

Another client kept a C+ Director of Ops on the team for four years out of loyalty and fear… not because she was driving results, but because letting her go felt emotionally exhausting.

That’s what most founders don’t factor in: the switching costs feel higher than they actually are.

Sure, a few things will fall back on your plate. But not all of them matter.

Some are low-leverage distractions you shouldn’t be doing anyway.

Others only matter if they stall for weeks, not hours.

That founder tells me, “I’d rather keep my C+ Director of Ops than deal with supplier emails and customer refunds.”

But the real question is:

What’s the cost of a delayed refund reply… versus the cost of months of misalignment?

Only you know the answer.

Three paths forward - some hope

When the structure’s not working, I usually see founders do one of three things:

Option 1: Replace the person. Just do it.

Usually the most uncomfortable, disruptive path.
And for a while, it makes your life harder.

But if someone’s consistently underperforming (and coaching hasn’t helped) this is the move.

Every week you delay is another week of missed KPIs, vague ownership, and growing resentment. From you and from the A-players who do notice what’s going on.

I struggle with this too, but I try to remember: misalignment compounds. Rip the Band-Aid.

They’ll be ok. You’ll write a nice letter of recommendation and help them find a new home.

Option 2: Hire above them.

This one’s underused because it’s the most expensive in the short term, but extremely powerful.

A client of ours recently hired a COO to manage a team of long-tenured B-level players. The goal was not to fire everyone. Instead, they were brought in to bring structure, systems, and accountability the founder wasn’t equipped to provide.

And it worked.

The COO set expectations, tightened up roles, quietly transitioned out underperformers, and coached up the ones worth keeping.

The founder stepped back.
The team leveled up.
The business started moving again.

This only works if you’re willing to let go of control.

One of my favorite lines from Dan Martell’s Buy Back Your Time is “80% done by someone else is 100% awesome.”

But only if they can actually deliver that 80%.

Option 3: Supplement them

This is the middle path and it works when the issue isn’t effort, but support.

If someone has potential, and the real issue is lack of structure or coaching (not a lack of effort), then you don’t have to fire them or hire over them.

Supplement them.

Here’s how:

1. Reset expectations with a Responsibilities Map

Most founders have never actually defined what someone’s responsibilities are.

That’s the power of the Responsibilities Map. It’s a written list of what they own and how they’re doing, so you can coach from clarity, not gut feel.

It works across finance, marketing, ops, and HR 

I made a quick video walkthrough

And here is a template that shows how we map roles and assess fit across the team.

2. Bring in a coach or advisor

If the problem is you don’t have time to manage or mentor this person, outsource some of that leadership.

If you truly believe they’re capable, but the problem is you — because you’re not managing them — then give them a coach.

You can find advisors on Intro.co, Upwork, or from your own network.

We’ve done this ourselves and seen dozens of clients do the same.
Have a coach step in, guide the person, hold them accountable, and help them level up.

This isn’t free.

But it’s a fraction of what you’d spend hiring a new exec and it could save someone who’s close to thriving, but unsupported.

What to do about it

There’s no exact script and you don’t need to redo the whole org chart.

But start with one role that’s felt off and walk through this:

• Get honest about performance. Are they adding leverage or creating drag? Don’t let loyalty cloud what you already know.

• Set clear expectations. Use the Responsibilities Map to define what they own and how success is measured.

• Decide what they really need. Is it structure, support… or an exit? And if it’s not working then rip the Band-Aid.

Next week...

I’m continuing down this inherently non-financial path and getting into the two of my favorite EOS tools: Rocks and the Issues List.

• How do you set priorities that actually get done and not just talked about?

• How do you surface real problems without letting them swirl in Slack for weeks?

I’ll show you how the best 7–9 figure teams use these tools to stay focused, fix what’s broken, and actually move the business forward.

See you next week,

— Sam

1. Find me on LinkedIn

2. EcomCFO provides CFO and accounting support for 7-9 figure ecommerce brands - book a brainstorming session with me here