From Unhappy Entrepreneur to Elated Corporate Executive in One Fell Swoop

October 20, 2017 Financial Post

From Unhappy Entrepreneur to Elated Corporate Executive in One Fell Swoop: Or, how one burned-out startup pro used her Silicon Valley experience to pivot into a Canadian career opportunity

By: Alexandra Skey

A year ago, I was living in San Francisco as the CEO and co-founder of my company, Ella. Today I find myself in Victoria, B.C. as the head of customer experience for a company that was just acquired for US$1.75 billion.

I never climbed a corporate ladder, yet at 31 I found myself at the top of a global fintech company. Here’s what helped me get there, lessons I’ve learned along the way and advice to those who are also looking to accelerate their growth.

My unconventional climb started 10 years ago when I dropped out of Queen’s University to start my first business. While that one didn’t succeed (and I went back to finish my degree), I became hooked on entrepreneurship and building remarkable experiences. My approach in becoming a young executive was like learning anything else — I was curious, asked a lot of questions and knew I had a massive amount to learn. I expected to make mistakes, because learning is anything but a smooth growth curve.

Over the next decade, I dove head first into everything I could and started three more businesses. It was an intense journey. And at the end of last year, I was burned out. I wanted to come home to Victoria, be with my family, spend time outdoors and get back to myself. I’d been an entrepreneur for so long I needed a break. So with encouragement from my mentor, close friends and family, I left my startup and San Francisco.

Do not worry about your career path: focus on your people path

After taking five months to recharge, I wanted to get back to what I loved best, building teams and world-class experiences. That’s when I heard Bambora needed someone to re-imagine their customer experience team, and my background in entrepreneurship gave me a leg up and confidence to take on the monumental challenge.

The lessons I learned as a twenty-something entrepreneur have proven essential in my current role. One of the first things to learn as a young executive is how to work with multiple generations. Workplaces are changing at a rapid pace. Everything from how we work, to what we build, to how we delight customers is in constant acceleration. Teams have changed, leadership styles have changed, and understanding that I grew up in a different generation was key to understanding others.

Our experiences give us a lens on how teams get things done, so naturally people’s approaches and executions are quite different. Understanding this has allowed me to tap into the magic of multi-generational teams, where I’ve learned — through trial and error — how to communicate in a way that resonates with each person. As well, I now know how to incorporate advice from those older (and younger) than me, while still being able to provide guidance.

Another valuable lesson was around making assumptions. In San Francisco, my teams never minded me asking them to work late. In fact, working crazy hours showed your commitment to the vision. That isn’t so hard when you don’t have children. Now, a large portion of my Bambora team has families and can’t commit to the long days. While I initially found it frustrating, I quickly learned this isn’t an indicator of commitment — or success. They are better at managing their time, and focus on getting more of the right things done, because they need to do a brilliant job and still leave in time to pick up their kids.

So, what’s my advice to those who are looking to grow, climb, skip or jump over the corporate ladder? Learn where it is you need to grow. As a young executive, I needed help on the operations side of running my business. So I surrounded myself with people who’d done it before, and absorbed everything I could. I hustled to get into Techstars, one of the best accelerators in the world for technology companies. And I read everything I could get my hands on.

One more thing.

Don’t worry about your career path — focus on your people path. The best opportunities in my life happened because of the people I surrounded myself with. While my startup in San Francisco didn’t succeed the way I planned, my time there (on and off the clock) was invaluable. It gave me the opportunity to, for example, kitesurf with some of the top entrepreneurs and investors from around the world. This opened my mind and career to possibilities beyond belief. So, be picky about who you invest your time with, because they’re the people you’ll learn from, grow with and who will help you achieve goals beyond your wildest dreams.

Alexandra Skey is a technology executive. As a member of Techstars and the Young Entrepreneur Council, she’s founded four companies and is currently Head of Customer Experience for North America at Bambora. She is a delegate for the G20 Young Entrepreneurs’ Alliance, has been declared one of the Top 8 Female Founders To Watch by Women 2.0.

Read the full article at Financial Post here: http://business.financialpost.com/executive/a-young-executive-chronicles-her-unexpected-leap-up-the-corporate-ladder