From Zero to CTO – Aubrey Stearn

Aubrey Stearn

Name: Aubrey Stearn

Current position: Interim CTO at Oakam

Short Bio:

Bubbly, former cage fighting transgender technologist that lives with her two cats and girlfriend.  Aubrey’s held roles in both IT Operations and Engineering for most of her career.  Hobbies include, videography, learning new things, video games, Peloton and teaching her girlfriend how to code using ReactJS and NodeJS. 

Tell us about your life before leadership – what kind of roles and projects did you work on?

Let’s go way back! Started off with BASIC on the C64, I was probably around 6 or 7, I hated manic miner and hated that my dad could finish it, one day I drew a picture of it using the ACSII symbols on the keyboard and asked him how to make it move; he told me I should have asked before I drew it, and thus I was gifted that massive BASIC ring-binder book.

At school I hit a limitation of not being able to create subroutines in excel, my teacher had the good grace to explain to me what I was actually trying to do and what I needed, a pirate copy of visual basic later and mastered the art of making the office assistant fly around the screen and say things using the voice synthesizer.

Fast-forwarding slightly I’ve always sat somewhere between development and operations, a lot of my early contracts started with deploying TFS and ended up with me developing code.

One of my favourite projects was a gig with a famous pizza company, I think everyone involved in that project upped their game, from code to DevOps, culture to what a high performing team meant and trade-offs involved.

How did your first leadership position come about, and was it intentional on your part?

My first big CTO role was at Nationwide, building the digital cloud platform, definitely intentional, CTO has always been my dream job, I wanted to do this role more than anything, I’ve met some total dud CTOs and some absolutely game-changing folks that alter the way you think.  Just those moments where you say ‘When it’s my turn, I won’t do it like that’ or the inverse.  I’d been very active in the DevOps community and because my skill set was everything from cloud infrastructure to development, it was a great fit, I was also fortunate enough to find someone who believed in me.

I landed at Nationwide with an incredible team. I’d never run a team that size before, I think they took a huge risk with me and ended up building something special that I won’t ever stop being proud of.  

I actually remember sitting on my friend’s sofa the day I broke down in tears at work and had to have the whole conversation about transitioning, there was this thing I knew about myself that had to change and it would potentially wipe out my career trajectory/opportunities and I made peace that night with probably never being able to get that CTO role; I remember realising what a deeply sad moment that was for me personally.

How did you manage the transition? What came easily / what was difficult?

Honestly, I think by the time you step up to the plate to bat you’ve been armed with so many positive and negative experiences that will shape your style of leadership, put simply I wasn’t lost for direction or where to start.

I think having worked in both startup and regulated financial services, I’ve learned to take stock, figure out where the organisation thinks it needs me vs where it really does need me.  Being a capable developer is a great tool but it’s not a solo sport, good for good it can inspire and show the art of the possible, in challenging environments it can be my own worst enemy.  

I guess what I mean by that is you’re not going to move faster than your own ship, so feeling like you can do something faster than someone else will only lead to high-stress levels and frustration.  Moving the ship ultimately comes down to your direction as captain and the willingness of your team, so you need to pop a different kind of engineering hat on and debug your vessel.

I have definitely made mistakes and I think more than anything I’ve become aware of how strong external pressures can be, how quickly they can influence your behaviour and decision-making ability.  I think recently I’ve also figured out my walking away point, the point where you believe no more good can be done, it’s a good line to understand because crossing it means you’ve probably stopped believing in what you set out to do.

What was your biggest failure in that first leadership role?

Politics.  There are people far better at playing the long game than me, I’m not quite at the point in my career where I want to be a big politician, which is why I’m very comfortable working in the interim space.  If you hire me, you probably need to fight some fires, fix something broken and turn something around from wartime to peacetime ready for a safe pair of hands.  Poker face is a difficult move to pull off when you have a habit of welling up because you believe deeply in something, so for now, heavy politics just isn’t my game and I enjoy doing change & transformation far more, although we can’t escape that politics is a part of that.

What made you keep doing it?

“The only way to get smarter is by playing a smarter opponent” – Fundamentals of Chess, simply put I want to keep getting better, I’ve changed and evolved so much in just 4 years, both personally and as a technologist and as a leader.  I keep doing this because I love the job, I love the people, I love technology and if I quit when I failed or felt despair, I wouldn’t be the woman I am today.

Tell us a fun fact that nobody knows about you

I’ve bought almost every resident evil game and never finished a single one because I’m a massive chicken when it comes to horror games, the only one I completed was RE3 and that was on the PC, with the sound off for the whole game and a trainer on so I couldn’t die, I was still scared!

What are the three key skills you think every leader needs?

Your ability to traverse the business and technology problems is key here, speaking the language of the business will give you the credibility you need to invoke change.  Communication ranks high, being able to decompose vast or complex concepts and present them at the right level for your audience is also important.  Finally empathy, people have lives, you have the ability to impact them, it’s something to think about every day, ask yourself how you would feel about that interaction if you were on the other side.

I have a line in my notes that I wrote before I started my first role, “Remember you have the outright ability to Titanic this company”, a stark reminder of the “Great power” line from spiderman.

What have you learned about acquiring and retaining talent?

Do it right and these folks will find you later and join you on many other adventures, this is a team sport though so sometimes it’s not just us it’s the company, the culture it embodies, sometimes you don’t always have the reach to make the change to keep good folks with you.  Having a crew of people that will follow you into the unknown can have a dramatic ability to help accelerate and de-risk delivery.

How do you motivate your team and manage their stress levels?

Right now during apocalypse season we have quiz day on Fridays, we’ve kept the retro cadence the same, every 2 weeks, I try and 1:1 with folks and make sure they know I’m accessible.  We’re in the middle of a re-platforming exercise so it’s a very exciting time, a lot of interlocks with people to make the right choice so folks are talking all the time.  In some ways I’m very lucky we have this particular distraction and the work is interesting.  When it comes to stress, I always encourage my folks to take a moment if they need one, health is really important to me.

How do you manage your own stress levels and productivity?

Being productive I’ve never really struggled with, I always have a list of things that I need to do, I’ve got a lot better at collecting todo lists or hobbies to learn when I have downtime.  Stress is another question, I think the honest answer is Dan, my girlfriend, she’s like a hawk, my levels of stress start with eczema on the wrist, progress to tummy and legs, she clocks that sort of thing really quickly, she will make me take breaks and time off work, in a lot of ways she’s the other part of a high performing team, she provides my checks and balance.  I think with interim work you give up a part of your soul for your craft and quite often you need that 3rd party to keep you grounded.

How do you stay in sync with other parts of the business?

Exco is a good interlock opportunity, I try to 1:1 with all my other CxO counterparts during the week outside of exco, just to give each other digest and make sure all is well, it can be challenging to find the time, especially during this challenging time so having folks on WhatsApp outside of work can be helpful to make communication more fluid and less formal.

Where do you see yourself in 5 years’ time?

In 5 years, I’d like to be running something really special, with the most awesome and brightest people you’ve ever met.  Bright & hungry people are always looking for a challenge, more than anything I’d like to create a kind of consultancy that puts a massive focus on giving back to the community, independent development and software creation, and using that experience to enrich our customer’s organisation rather than bouncing from one to the other.  I want folks to hire us because we built something beautiful or awesome or profitable as an independent, rather than because your competitor hired us last year.

What product do you wish you’d invented?

SoapShoes! Sonic actually wore them in the Dreamcast game Sonic Adventure, and I bet no one remembers these but they were shoes with grind pads in the arch, and you could jump on railings the way skateboarders did and grind down in your shoes.  I think a lot of folks really hurt themselves using them, but they looked really cool though. The geeky answer is I wish I could have been a part of the General Magic team; if you haven’t watched that documentary, it’s one you should keep on standby if you need to be inspired.

Thanks very much, Aubrey!