Improbable Defence

#IBelong: Libby Penn, Chief Operations Officer

Libby Penn, Chief Operations Officer, Improbable Defence

Q: What’s your role at IO?

A: My role focuses on providing the organisation with the people, processes and frameworks we need to deliver against our strategy. From setting OKRs to ensuring our IT can scale, from workforce planning through to reputation management, from budgeting through to reviewing our rituals and routines that bring our culture to life.

I’m a goal oriented person and focus on assessing the landscape, analysing risks and opportunities, to identify the right path to deliver against our objectives. It often requires me to synthesise a lot of information from diverse sources, so developing an ability to process things quickly has become my super power.

Q: How did you get here?

A: Serendipity! My career has come about through building connections with people with shared values and missions. Improbable was no different.

I’d spent some time working in augmented reality and had become increasingly concerned around some moves China was making on facial recognition. As I thought about my next move, I knew I wanted to work in a company that was using tech to help preserve our democratic values, rather than as a weapon against these. Via a serendipitous series of events, I connected with Improbable and the rest is history.

Q: What is the most important piece of career advice you have been given?

A: Always speak truth to power.

Q: What’s been the toughest moment of your career?

A: I look back at my career and think I’m the culmination of all the mistakes, the obstacles and challenges I’ve faced. The worst moment was not being able to make payroll (not at Improbable, I hasten to add!) and relying on the trust and good will of the team to stand by us.That moment taught me a lot – as the most challenging points in our lives often do. It showed me the importance of honesty and humility in leadership, and the depth of people’s commitment when united by a common goal.

Q: How do you unplug from work?

A: Five months ago, I would have said spending time in the mountains hiking or snowboarding, but now it’s spending time with my five month old baby. I hope, as she gets older, the answer will be spending time with her hiking and snowboarding in the mountains.

Q: If you could have dinner with three inspirational leaders, dead or alive, who would they be and why?

A: I have a theme in the leaders I’d like to invite for dinner: they’re all women who have challenged the status quo. Each of them have spoken their truth and challenged the establishment in their own ways.

  1. Dame Stephanie “Steve” Shirley. Her book Let it go is an inspiring reminder of what can be achieved when you challenge the status quo. She comes across as a formidable but humble woman, and her career journey has always been an inspiration for me.
  2. Billie Jean King. I’ve always been inspired by her ferocious spirit, humour and commitment to equality, plus I’m a tennis fan, so would love to get some tips!
  3. Ruth Ginsberg. The “notorious RBG” whose resilience, integrity and passion I think has inspired many across the world. Her quote “I would like to be remembered as someone who used whatever talent she had to do her work to the very best of her ability” has been something of a guiding mantra for me. For me this is about grit – passion plus resilience (see another great woman Angela Duckworth’s TED talk on the subject) – where you find the intersection of doing something that you love but have to strive hard and overcome obstacles to achieve. If it was easy, it wouldn’t be so fun!


Q: How do you balance work and life responsibilities?

A: I think COVID really challenged all of us as the physical boundaries between work and personal life became blurred. There were some benefits to that – the ability to keep on top of chores in breaks throughout the day and saving on commute time – but equally the pressure of working out of bedrooms with colleagues you’ve never met in person and with inadequate infrastructure (don’t get me started on Virgin Media…) has also been incredibly trying for many of us.

As we now look to the new normal which, for me, now includes a baby and a dog that I didn’t have pre-pandemic, I think it’s going to require a conscious effort to be fully present in whatever space I’m in. I know I’ll need to be more organised than ever, accept that I can’t do everything and learn to ask for help more than perhaps I’m naturally inclined to. I think it’s going to be a real learning curve for me over the next couple of years as I find that balance between motherhood and career.

Q: What book or podcast would you recommend to anyone thinking about a career in tech?

A. The Phoenix Project: A Novel About IT, DevOps, and Helping Your Business Win. It’s a book I find myself coming back to again and again, even though my role is non-technical. The lessons in there about project planning, prioritisation, leadership, as well as the insights into Dev Ops and Agile delivery are really useful. I often find myself thinking on Brent, the person who has been around for a while and who fixes things in a crisis. On the surface Brent seems like a valuable asset, but the book shows you how that kind of behaviour can be detrimental, Brent is a bottleneck not an enabler. I think on Brent often.

Q. What does a supportive work environment look like to you?

A. A place that understands that life goes on outside of work, that respects those commitments and allows flexibility to keep the balance between work and personal life. We strive for a high trust model at Improbable, whereby we trust our team to know what’s best and balance work and their personal lives accordingly. For me, that’s now about making space for childcare, so I can make nursery drop off and pick up, and can take the time I need to ensure I get to spend time with my daughter in the day, catching up in the evening if needed.

Q: Have you faced any barriers in your career (due to being a woman)? If so, how did you overcome them?

A: There have been many micro moments where I’ve been dismissed, mis-labeled (who’d’ve thought the COO could be a woman!), spoken over, or criticised in a way I believe a man would not have been. Those micro moments are incredibly wearing and demotivating but I’m fortunate none of them have been insurmountable. I’m sure it’s not the same for everyone. I’ve always endeavoured to challenge those situations with candour, humour and good grace, and not take it personally, although sometimes that’s been easier said than done.

Q: What advice would you give to women trying to break into engineering and technology fields?

A: Don’t be afraid to ask for help and advice. People love talking about themselves and sharing their journey and lessons learned.

Q: What woman inspires you and why?

A: Jacinda Ardern – she’s shown the world what political leaders could be like. She’s shown that leaders can be decisive and impactful whilst being empathetic and authentic at the same time.

Join Improbable Defence and you’ll be helping users plan and train to meet the world’s most complex security threats. If your ambitions are high, we’ll give you the tools, support and culture to take them even higher. Check out our open roles to find your perfect fit.