Take the Leap with Bex Eastwood

Sophia Witherington
October 1, 2020
Bex Eastwood

The Startmate Fellowship works to create pathways for talented women to find their sweet spot in a rocketship startup.

For Fellows, the program fast tracks your knowledge, network and presence in the startup world. The Fellowship connects you to a powerful network, works with you to translate your skills and experience into startups, and helps you land your dream job.

By showcasing women who had taken leaps and risks in their career — from corporate to startup, or from one career into something seemingly unrelated — we hope to have inspired our broader community to join our Fellowship program.

Let’s hear directly from women in the ecosystem who took the leap, before anything like The Fellowship existed...

Bex’s squiggly line career started from the moment she graduated law. She landed a place on Telecom NZ’s grad program where she rotated through roles in procurement and IT service delivery, before dipping her toe into the legal world with a project that saw Telecom and Chorus demerge. Eventually she moved to a top tier corporate law firm where she created a name for herself as one of NZ’s go-to startup advisors.

She escaped the world of billable hours to be closer to the tech coalface by joining one of her clients — a risk and cyber analytics scaleup — working alongside the CEO and CFO in a ‘special projects’ (a.k.a. operations mishmash) role. She now applies this unique mix of experience and skills to help CEOs and their teams drive growth.

What was attractive about climbing the corporate ladder? What do you miss?

Being a lawyer came with certainty and prestige. Within the firm your role is clear, there’s a hierarchy and you know the steps you have to take to progress. Externally, almost every person in the western world has an idea of what a lawyer’s job entails.

Plus, it brings with it an assumption that you’re hard working and intelligent. It’s a very obvious ‘career’.

Stepping away from that was hard at the start. But now my work isn’t bound to the confines of legal advice and I’m not constrained by the rigid ways that law firms operate. No two days are ever the same, and I love that.

At what point did you decide to leave corporate land?

After a super busy and stressful period of work I ended up in hospital with bad chest pains. My body was telling me: enough is enough.

However I’d made up my mind long before that point that I didn’t see a future for myself within a traditional law firm. There was too much that I wanted to change, and I didn’t think I’d ever get the power to make all that change happen.

At the time I was also studying for the GMAT, thinking that an Stanford/Harvard/LBS MBA could be my ultimate answer to switching careers. Again, there was an element of certainty and prestige bias in this thought track — people who get MBAs are smart, hard working and have strong career prospects.

The physical breaking point forced me to stop and take notice of the opportunities around me.

In particular, the CFO at one of my clients was dropping several not-so-subtle hints that he wanted me to join his team. So after a relaxing holiday (remember those?!), I put the MBA to the side (zero regrets), joined the scaleup and I haven’t looked back.

How have your career goals evolved throughout your career?

My career goals used to be very linear and short-term focused. But I’ve come to realise that we need to do much more than master one role or industry in order to prepare us for the evolving world that lies ahead.

So now I’m all about embracing the squiggly line.

I remain focussed on a mission and seek to build cross-discipline skill sets, rather than chase job titles.

How did you build a network out of corporate and land a startup job?

My work as a lawyer meant that I had already strong connections into startup land in NZ, so I used these connections to build relationships with people. I went out of my way to help people in the startup world by connecting them to other people or providing advice wherever I could.

When I moved from NZ to Melbourne a few years ago I had to rebuild my network all over again. At first I tried to immerse myself by going to lots of different startup events. There were many to choose from, so I became quite skilled at picking the good from bad.

On that note, I’d highly recommend all Startmate events! I also based myself out of One Roof (a coworking space for businesses founded by women) one day per week and met some great people as a result.

Ultimately, though, I found that one-on-one chats were a more productive use of time. I used my network back in NZ to introduce me to people here, and that led to more meaningful conversations and resulted in a job.

Generally speaking, the startup world is full of people who like to help other people. The best thing you can do is approach every conversation with an open and curious mind, ask lots of informed questions, be helpful where you can and don’t be afraid to ask for help.

If you’re a good human you’ll eventually meet someone who will steer you in the right direction.

Who have been your mentors?

Controversially, there aren’t one or two people in particular that stand out to me. I realise that is probably contrary to every personal development rulebook. Instead, I have a network of people I call on for help and guidance.

I’ve also had some amazing managers, but I would class them as sponsors rather than mentors. These people were willing to give me a chance in a role I knew very little about, raise up my confidence and promote me to others (often when I was full of self-doubt).

I think they each saw that I was curious, pragmatic and had a capacity to quickly digest information and synthesise it to make good, clear decisions. Good sponsors are critical if you’re looking to switch roles or industries.

What is your advice to people wanting to make a change

Change can be complex. It feels daunting if the path isn’t clear. But unless you take a leap out into the unknown you’ll never learn how to navigate through uncertainty.  You’ll never reap the reward that results. The older you get, the harder that step will feel, so there’s no time like the present!

Remember that you are more than the roles you’ve done and the industries you’ve worked in. There will be a place somewhere within the startup world that is a perfect fit for you — a place that will challenge you, grow you and see you thrive.

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