Why I fired four senior marketers in a row

When I was building RORA I was surrounded by ops and accounting experts. That was amazing. But if you ask an accountant to help you with marketing often they … don’t like it. 

No problem, I thought as I started work on my marketing job spec. 

Four unsuccessful hires later I realised there was a problem. 

Every single time I was desperate when I hired them. And every single time, when it ended, the main thing I felt was relief.

At the time I assumed the problem was me. A bad boss who couldn't hold on to people.

Turns out I was about half right.

Let's dive in.

It should have been the easiest hire on the list

Back then I was running Quantico, the business I later renamed RORA.

We had a genuinely punchy challenger message. Accounting was broken. It was old fashioned, retrospective, backward looking, and it was letting down both the accountants doing it and the startups paying for it. We had something better: FinOps, forward looking, technology led, young, ambitious, actually useful to a founder trying to make a decision this week rather than explain a decision from last year.

I knew exactly what we stood for. I knew who I was talking to. We had a handful of channels that we already knew worked, and a plan for each of them.

So hiring someone to help felt like the simplest thing on my to do list. I wasn't asking anyone to invent a category or find a market. I was handing over a message I'd already tested to an audience I already understood.

I got it wrong four times.

The same six months, four times over

Looking back, every one of those hires followed the same shape.

Month one is great. There's relief in it. Someone else is finally going to carry this thing.

Month two, they come back with a plan. The plan is a brand refresh. Or a website rebuild. Or a positioning workshop. Never the thing itself.

By month three or four I'm frustrated. Very little has shipped. I start quietly doing bits myself again in the evenings, which is exactly the situation I hired someone to end.

By month six it's over, and I'm back where I started, only poorer and more tired.

Then I'd do it again. Because I was desperate, and because each time I told myself the last one simply wasn't the right person. The next one would be.

Four times. It took me far too long to work out that I didn’t make four mistakes. I just made the same mistake four times. 

Founders shouldn't hire like normal people

The first thing I got wrong was treating this like a normal hire.

Founders are, by definition, unusual people. If you were normal, with normal preferences and a normal appetite for risk, you would have a job. You'd have a manager, a salary, a holiday allowance and someone else's problems to go home from. You chose this instead, which means you're a bit weird. 

Sorry if I’m the first one telling you this. 

My weirdness was in every meeting I ever ran.

Founders are driven in a way that isn't always healthy. They're impatient. They usually have a very precise picture in their heads of how the thing should work, often can't articulate it properly, and know instantly when what's in front of them isn't it.

Working for a founder is a different job to working for a manager. It's a different job even when that founder has been a manager, because managing a team inside somebody else's business is not the same thing as building your own. I'd managed plenty of people before I started up. It didn't make me a normal boss.

Not everybody can work like that, and that isn't a criticism of them. Plenty of excellent people need a clear brief, a stable set of priorities and a boss who doesn't change his mind on a Sunday night. Those people will do great work somewhere else.

But I was hiring as though none of this mattered. I hired against a job spec: years of experience, sector background, channels run, tools known, all the normal stuff. I tested carefully whether people could do marketing. I barely tested whether they could work with me.

Everybody wants to be a strategist. Nobody wants to be an operator.

The second thing took me longer to work out, and it cost me a lot more.

Every marketer I hired wanted to work on brand, website and vision. Not one of them wanted to do the job I actually needed doing.

I understand why. Strategy is the glamorous end. It's the bit that gets presented to the board, talked about at conferences and printed on the next CV. Operations is treated as the basic stuff underneath it. The execution layer. Something you delegate once you've had the clever thoughts.

I think that's backwards, and it was very obviously backwards in my business.

These were capable people. They just didn't understand accounting. They didn't know what it feels like to be sat in a client's meeting room at nine o'clock at night, working through a file that nobody will ever read, wondering what exactly you trained for. I'd sat in that room. That was what we were selling against, and not one of them had ever felt it.

Most of them had come from B2C. Ecommerce, consumer apps, products. And a lot of the received wisdom in that world, the stories marketing tells itself about funnels and campaigns and creative, simply didn't apply to what I was doing.

So when they went to work on the message, they made it worse. Broader and blander. More like everybody else in the market, every time.

I didn't need somebody to tell me what to say. I knew what to say better than any of them could have, because I'd lived it. I needed somebody to keep saying it, in the same few places, long after I'd got bored of hearing it.

What actually fixed it

Two changes fixed it, and neither of them was hiring a better marketer.

Cultural fit mattered more than competence fit.

Once I accepted that, hiring got easier, because I stopped reading CVs the way I'd been reading them. I started testing for the things that actually predicted whether it would work. Can this person take a strong opinion from me without either folding or squaring up? Are they comfortable owning something unglamorous for a long time? Do they get their energy from finishing things rather than starting them? Can they cope with me changing my mind, and tell me when I shouldn't?

The skills the marketing industry rewards turned out mostly not to be the skills I needed. So I stopped selecting for them.

I needed marketing ops, not marketing strategy.

What I actually wanted was somebody to take a small number of channels we already knew worked and run them efficiently, rigorously and sustainably. Every week, not in bursts. Measured properly. Nothing dropping off when things got busy, which they always did.

That was the job. It was never a strategy job. I'd been writing a strategy job spec for a delivery problem, then getting annoyed when strategists turned up and behaved like strategists.

Turns out it wasn't just me

For years I filed all of this under things I got wrong. Idiot tax, paid four times.

Then I started working with other founders through Redway Ops, and I kept hearing my own story back with the names changed.

Four marketers becomes three CFOs, or a run of very impressive senior hires who each lasted a couple of quarters. The shape is identical every time. Founder with a clear vision hires senior, hires for strategy, gets a plan instead of any actual work, gets frustrated, ends it, then starts again six weeks later.

It's one of the most common patterns I see, and one of the most expensive. Recruitment fees, half a year of salary, half a year of the work not getting done, and a chunk of the founder's confidence gone with each round.

So if you're somewhere in that cycle now, ask yourself three questions before you write the next job ad:

• Do you need somebody to decide what to do, or somebody to do it? Most founders I meet already know what to do.

• Is the thing you're hiring for genuinely undecided, or is it decided and just not happening?

• Have you tested whether this person can work with you specifically, or only whether they're good at the function?

I'm not going to pretend I've solved hiring. I still find it hard and I still get it wrong.

But I've stopped believing that four failures in a row made me a bad hirer. I was a fairly normal founder, making a fairly normal founder mistake, with a job spec that described the wrong job entirely.

I wish somebody had made me rewrite that job spec after the first one. It would have saved me three more.

If this sounds familiar, or you're staring at a hire that isn't working, drop me a message. It's most of what I do these days.