Hey there,
I want to tell you a story I don't share often.
A few years ago, I was Head of Sales at a fast-growing company.
Not my business. I was an employee.
Revenue was going up.
Deals were closing, and I was building from the ground up a stellar sales team.
I started hiring 1 person, then another, then another.
They knew the product.
They knew the customers.
We were cruising well.
Then, we get our Series A. Lots of money for the time, what do we do?
“We need to scale the sales team. NOW.”
You probably know that moment. (It was right in post-COVID) 👀
So we moved fast.
In six months, we hired 7 new salespeople.
From 3 to 10. It felt exciting. I remember bragging to my friends about it.
The team looked bigger on paper.
And I'll be honest, I felt proud.
Fast forward, 8 months in, and everything fell apart.
The original top performers quit. One after the other.
The new hires weren't ramping up.
The pipeline looked full, but quickly we were running out of deals and leads.
A few months later, we had to downsize the team.
Back to where we started.
So what went wrong?
With 3 people, things worked because everything was close.
They learned directly from me, and I was very much involved in closing deals.
Culture worked because the team was small.
With 10 people?
I couldn't train everyone.
Despite rushing to build onboarding documents and processes, we hired a batch of 3-4 AEs and SDRs.
This leads to problem number 2...
What should have happened?
Hire 2 people. Ramp them.
Write down what works and document everything in a sales playbook.
Then hire two more and see if the process holds.
What actually happened?
We hired in batches of 3 and 4...to go faster...
Each group started before the previous one was productive.
I was always onboarding.
Plus, everyone felt like being in an average team since nobody was hitting goal...while ramping.
Even if we called ourselves "SaaS."
I know you may feel like “another head of sales who didn't hit and starts blaming the product”...😅
But that’s what happened. We had a big switch in the organisation, from marketplace to SaaS. Offering, pricing, website, branding...
Although we called ourselves “SaaS,” we weren’t a SaaS.
The market told us. Clearly.
People wanted the old model (marketplace), but we kept packaging and selling it like a SaaS.
It was post-COVID. This is what the board was pushing for.
The market was right...
With 3 people, I spent over two hours a week with each of them.
Coaching. Deal reviews. Real feedback.
With 10? Thirty minutes per person, at best.
I had no budget for mid-layer managers; I had to manage all of them. (another problem...)
I stopped coaching and started reacting. I started firefighting.
People felt left alone, even if they didn’t say it.
Despite my efforts, some of the top performers started leaving.
The product issues delivered a hard truth about our team: we build with no foundations.
Also, imagine for one second being in a team where 3 people hit their goals, and 7 don't.
Not the best inspiring environment to spend 8 hours per day.
Of course, Microsoft, Slack, and LinkedIn offered better jobs to my AEs, and they started leaving.
The bond we created, the culture we had at the beginning, which I tried to hold as much as I could - faded in less than 2 years.
What we built in 1,5 years...gone in 6 months.
That experience changed how I think about building sales teams.
Growth without structure is like being in a dishwasher all day long.
But most importantly, you have to have a product that delivers regardless of how good your sales team is.
"Now, when founders tell me 'we need to hire 3-5 people,' I ask:
If the answer is no, we don't hire. We build the system first.
That's what the Inscaler transition is for. Message me for more info to start working with me.
Thanks for reading this far. See you all next week.
