Leading a start-up, winning and walking away

Leading a start-up, winning and walking away


Back in June 2014, I was looking for a new challenge, somewhere with space to create and lead and landed a role with a prelaunch social purpose tech startup.

There were just 3 other (pretty demotivated) staff. The product had been in development for over 2 years. Millions had already been spent (truly). Everyone seemed disenchanted. But I could see a way through and defined a new shared purpose and a vision. We rebranded and repositioned in the market.

It didn’t take long to realise the issue wasn’t  a marketing problem but a product problem: no one wanted to use the platform,  there was no product/market fit.

We had no MVP. We had no core product that delivered value. Worst of all no one seemed to have any clear sense of the problem we were trying to solve.

I started to turn things around by bringing a user focus to the product. Developing user persona’s and scoping needs from their perspective. Defining the problem. I kept reading, digesting multiple books on product development, user journey mapping, lean UX, and product management. We needed to pivot, fast.

We managed to secure a further 3 million in ongoing investment and mapped a path to success. I built the team up to 20 with 12 developers. I joined all the standups, sprint planning meetings, and retros sharing my insights from a customer perspective. At first I was only a participant – but over not much time I was leading them. I found my intuitive assumptions were often right. But still we continued to workshop and test with small mixed teams.

At first I got a lot of push back from the developers and producer. My input was disregarded. What could I know about tech?  But I continued, leading with my user focused perspective. I didn’t need to know a heap about tech – because the real issue was understanding the problem from user perspective and ensuring the product delivered some value to the user’s world – otherwise why would they use it? We certainly would never be able to reach the level of virality required for sustained growth.

So we embraced customer development principles and I secured a partnership with a major university to collaborate with us piloting and testing the platform to ensure that it could at least meet their needs – they were keen – even delighted. The team also found this validating – somehow the platform had been in development for nearly 3 years and no one had ever even talked to a would be end user!

This was tough work – but the team started to really reach it’s stride. I couldn’t have been prouder of them. We took the prints of the walls in our boardroom and started mapping the user journey, rows of post-its, debating, questioning and testing each assumption. Sometimes just a few of us, sometimes all. This built awesome consensus and camraderie. It took a huge amount of energy to get it to here but it was worth it.

We secured international endorsement, and major support and interest from several large mutinationals. We were starting to see major wins in subscribers. Growth was happening. The Red Cross wanted to partner.

But the Founder was uncomfortable. He wanted it to be about his choices  – and I disagreed believing we needed to meet customer demand if we were to scale.

And then one day after a lengthy discussion on future strategy the Founder said to me: “Rebecca, you know what, you are brilliant. I know if I got out of your way, you would smash this out of the park. But I am not going to let you.” True story. I started looking for my next opportunity the next day.

Walking away was hard. I was hurt. I had put a lot into that business – it had been a rollercoaster ride – and I had learnt more and found it to be more rewarding than any job I had ever done before.

And I had discovered a true passion for tech and digital product development it is all the things I love: collaborative, challenging, creative work.



Change when it’s non adaptive

I joined my current workplace 9 months ago, it’s a purpose driven NGO. I was lured by the digital transformation/ organisational redesign and rebrand work underway. I love this stuff. But as an entrepreneurial creative with a strong appetite for change, I was surprised by what I found once firmly planted in my new role. Change is really hard for most people. While I understand this is the case, and there are plenty of books written about it, I don’t entirely get it. I seem to have a brain wired for continuous development/change: at work constant iteration suits me. Perhaps because of my artistic leanings; perhaps because I spent my teen and early adult years strengthening these neural connections; perhaps because of life in general, early challenges and the need to adapt. For one reason or another it seems my work journey has been a series of experiments, some more successful than others but I like it this way.Change within the work environment seems to be non threatening for me as I am poised, ready to make a move to a new challenge, take a step – try something new.

But then I guess the experience of change is whole lot different if you see you have something to lose. Power, an office, a title, maybe just respect.

I read somewhere that it is the multiple experiences of loss/failure or setback that actually prepare you well for adaptive leadership. I’ve had my fair share. But it is also a lot about remaining hopeful for the future and seeing the possibility – and keeping the vision at the heart of my work. Creative training prepares you well for this. Artists have been making art and objects of beauty out of not much at all for pretty much always.

So I have discovered that these are great skills for the workplace – but I realise now – that to some – my approach is simply bewildering. I am the alien in the room. In tech start up land (where I have migrated from) my approach works: it’s lean/agile/collaborative/fluid (I’ll write more on this) – in fact it is exactly what is required.  But in a 60yo NGO my style needed to shift (and I think it has – not to say I can’t bounce back).

So I have now spent a fair while thinking work in my NGO doesn’t need to be like this. It doesn’t need to be about bureaucracy and politics. Days don’t need to be wasted in multiple meetings. Creative should not be sucked out of new projects when it is this very energy that allows new initiatives to transform and get off the ground. Moving to implementation planning when we haven’t even established what the problem is we are trying to solve is sheer madness – or so it feels to me. And if a 2 hour meeting is scheduled it better be a workshop or I won’t be there.

I have been actively looking for answers, for ways through. I don’t want to throw in the towel just yet! I was chatting with some of the folks at Thoughtworks as many of the challenges I am hitting up against are of the oldshool IT/digital rapid iteration variety and have valued the conversations’s with Gary O’ Brian and Danelle Jones, they see the struggles I am talking about everywhere they go – and some of their thinking is in this keynote on Lean Enterprise.  And it may be serendipitous but I had also been reading Frederic Laloux’s Reinventing Organizations. He totally get’s it too, early in this book he poses:

How can we have meetings that are productive and uplifting, where we speak from our hearts and not from our egos? How can we make purpose central to everything we do, and avoid the cynicism that lofty-sounding mission statements often inspire? 

Laloux works through these challenges by investigating pioneering organisations that have managed to shift in this direction – that is if they weren’t built this way to start with. He connects organisational development to human evolution.

If we want to recruit and hang on to super smart and talented operators (and I definitely do). We need to do something about this now.

Note: I have started blogging again today after 3 years on a promise. I won’t claim that it is good but I do need to get my thoughts down. Shout out to Christian  for keeping me honest.