The business was an online learning platform, which was made up of a female team: the CEO, myself, and a head of Ops. The idea was to support young professionals to overcome the firsts they’d experience in the workplace. The model was SaaS with a built-in subscription tool, serving both B2B and B2B2C audiences.

I joined as employee number one at a time when we had two customers. Over the course of a few years, we grew from selling to a few higher education teams to working with brands including LinkedIn Learning, Nationwide, Tech Nation and more. The company was acquired last year.

That all sounds very positive, but we all know the reality of building and growing a startup isn’t smooth sailing. There are days when you question why you’re doing it, or you tell yourself “growth mindset” whilst clenching your teeth.

A personal gripe I have with much of what is shared about growing startups is that people rarely talk about their mistakes. You only hear of the success stories and not the gritty details about how they actually got there.

It was during our acquisition that I started to write about the mistakes I made while working in-house. I managed to turn it into a consultancy, working with tech founders to help them reduce risk and increase their run rate.

Here are some of the biggest mistakes that I still think about:

Mistake 1: Thinking the job on the advert was the one I’d be actually doing.

A few months into the job, something felt off. I'd turned up to work with my tools, processes, and models, but when I’d run campaigns or look at the free trial to paid conversion rates, nothing was landing. And when people asked me what we did, I’d often leave them looking confused.

I went in thinking as the head of marketing I’d be talking to customers, spending my marketing budget on partnerships, and running a team. The reality was very different.

The two mistakes I’d made here:

• I didn’t really understand the stage the startup was actually at
• Just because I’d marketed to an audience before, didn’t mean I knew how to market this tech product to them

Assuming that we were near to product-market fit was a big oversight on my part. I’d come from an established business, as the marketing director, and thought that this startup had sorted its retention challenges and had left the customer discovery stage.

How wrong I was. I wasn’t doing what I was supposed to be doing, what was pitched to me at the interview stage. It wasn’t their fault, but very quickly I realised that my role was about to change.

When you join a startup, it’s okay to question what the run rate is, what the retention rate is, and how growth is going. These will largely reflect the stage of the business and what kind of job you’re about to take on.

Mistake 2: Just because someone tells you they love your product - doesn’t mean they’re going to activate their trial.

We’d talk to people who’d tell us they loved the idea. They’d laugh, they’d be polite, they’d listen to our sales pitch. At the end of the conversation, we’d offer to set them up with a free pass to our platform to get a feel for the content.

A few days would pass and… nothing. We’d email them, say hello on LinkedIn… but there was more ghosting. But they told us they liked our product. What was going on?

It turns out we made a few mistakes:

• We were talking to our fans… but they had no urgency to solve the problem nor the cash to sign off and buy from us.
• Our questioning technique was so biased. It was after we came across the Mom Test that we realised our approach was all wrong. We were creating and building for people who didn't really need us.

How we fixed this: we drew up a list of ideal customers and ranked them by priority - targeting those who had an urgent problem to solve and who were using the competitor we knew we had the “best” chance of winning a sale over.

We also stopped talking about features and instead, spoke of what our customers could do as a result of our tech. Any mention of a feature on the website was swiftly moved to the pricing page.

Mistake 3: Thinking you’re creating a new category.

At the time we were operating in the emerging online learning space. We’d tell people what we did but the message didn’t really land. We’d tell ourselves that’s because we were creating something new - we just needed to find the early adopters and we’d be on our way (!)

As we began to ramp up our growth strategy we realised that we had a new competitor: LinkedIn Learning. How does a three-person team compete with LinkedIn Learning?

We told ourselves that we were creating a new category. That’s how we were going to take on this giant in online learning.

It’s only when you read that back that you realise how daft that approach was. The market you enter will largely determine your marketing, sales, growth and positioning.

For us, we weren’t creating anything new. But what we were doing was niching down or, as it’s referred to, re-segmenting the market. We were building upon what was already available by improving and addressing the gaps.

It took us a while to figure that one out, but once we realised what market strategy we were pursuing, working out what our positioning was against these big names became very easy. 

These are just a few of the mistakes we made. Others included trying to use the metrics of Spotify, considering freemium, thinking a self-serve model was best before we had validated a new segment, and leaving a lot of our technical decisions to those farthest away from the customer.

See, I told you there were many mistakes. Today, as part of my consultancy I work with tech startups, helping them to navigate customer acquisition and avoid some of the mistakes we made along the way.