What makes a successful pilot? 5 things I learned about intrapreneurship from launching Women in Software

Intrapreneurship: the act of behaving like an entrepreneur while working within a large organisation

Adele Barlow
5 min readFeb 11, 2020
The WIS 2020 launch

One of my first jobs out of university was co-founding a startup called yMedia. This was over 12 years ago and looking back, it was a lot of fun but also the hardest I’ve ever worked in my life.

Still, I got to create something which I believed was making a positive difference. And that was a great feeling, a founder’s high. While I worked for Escape the City, I stumbled on that feeling again, when I helped to launch the Escape School. After that I went on to work for a startup within Virgin and then at Lexoo.

It took me years of working on other’s startups to learn that you could get the high without being the founder. As startups tend to be over-stretched and under-resourced, this makes them ideal environments for entrepreneurial people. Entrepreneurship is a muscle that you can stretch within someone else’s startup, as long as it’s aligned with the overall business goals.

Makers is a coding bootcamp that I’ve been working with since mid-2017. At the end of 2018 we decided to run something that would celebrate some of the amazing rising stars in tech who were women.Yet when we launched Women in Software, I was pretty skeptical about how it was going to turn out.

For starters, I don’t really buy into the ‘empowering women’ schtick. We are not little girls who need gold stars and stares because ‘wow we’re women AND we can do great work (?!)’—instead, I believe in elevating women. In this case, shining a spotlight on the rising stars within tech.

I remember when the conversation and decision happened to run with this idea and I was excited to lead the 2019 pilot.

At the WIS 2019 reception

I was lucky that Alex Bailey, who runs Makers’ marketing, was a true partner in developing the concept. She could have easily killed the project or decided it wasn’t a priority, but she chose to believe in it and together we drove it forwards with Makers, Computer Weekly and Level39.

So much so that we ran a successful launch of Women in Software 2020 last week, an event designed and led by Haylee Potts (who also designed and led the evening reception last year).

The WIS 2020 launch

Post-launch, I started thinking about what any intrapreneurial pilot needs in its infancy. So many businesses lament that they want more creativity (which is the seed of entrepreneurialism). But you can’t get creativity without mutual trust within the team. When there isn’t psychological safety and there isn’t trust — how can you be bothered to be creative?

The best projects I’ve worked on have started with making a random observation then feeling safe and supported enough to build on it and follow the rabbit hole, to see where things end up. This was no different — but what makes any pilot successful?

1. People at senior levels want to see it happen

For something to go far and to last, at the very least you need the person leading your team to believe in it. Alex gave a bright green light and got excited, and involved. We got buy-in from senior levels, which was crucial.

2. Partners want to see it succeed

Another vital aspect was aligning with external communities (this year, we’ve also had Google for Startups show their support — plus The Woolf Partnership is sponsoring an instant cash prize of £3,000 for the 2020 Woman in Software). This ignites the initiative with more gravitas.

The WIS 2019 evening reception

3. There is one clear leader for each different area

If people don’t know what they’re responsible for, things get messy: egos get scarred, people feel invisible, then deflated, then demotivated. It’s hard to define roles when it’s a pilot — fitting this new yet temporary set of deadlines into someone’s existing obligations can be tricky. Sometimes people want to be involved but realistically don’t have capacity.

4. One person takes overall ownership

It’s so easy when things fail for people to point to someone else and say ‘oh I thought you were handling that?’. Ultimately the buck has to stop with someone: ONE person has to take overall responsibility and to fill in inevitable gaps between teams, misunderstandings, and miscommunication. I enjoyed being the human FAQ.

5. There’s a strong and undeniable why

Often projects fall down when someone just wants to do their own little part that’s easy for them but shrink away from the less attractive tasks. Last year I found myself doing a ton of frankly very dull admin and part of me thought — should I really be doing this? Is this the best use of my time?

I mean, with any pilot, resources are tight as it’s a gamble how it’s all going to turn out. What really helped was having a strong sense of mission. It is frustrating hearing about problems non-white non-males are having in tech.

Experiencing and witnessing invisible sexism, misogyny, the gender pay gap, a lack of role models, etc…it’s tiring. That’s why it can be uplifting to celebrate the counter-narrative: while change might be slower and more gradual than we’d like, at least it is happening.

Know an amazing woman in tech? She could win £3,000. Women in Software 2020 nominations are open until March 6th here.