Want to work at a startup? Here are four tips for shifting jobs mid-career

Changing jobs is hard — scary even — especially for those who’ve spent years building experience and financial security in traditional workplaces. But moving to a startup can, in fact, be a sure-fire way to bulletproof your career and find meaningful, socially-conscious work.

Startups value and nurture resilience far more than their corporate cousins, because risk (and the profit that follows it) is in their DNA. Startups encourage hires to learn on the fly, cultivate new skills and make bold business decisions. In other words, startup employees are expected to act like entrepreneurs, which in turn prepares them for the increasingly volatile job market.

“Tech’s disruption has completely changed employer demands,” says Yung Wu, CEO of MaRS. “Today, there are no more jobs for life, just a life of endless job opportunities.”

Don’t ignore the feeling of being stuck. Below, we’ve listed some tips from mid-career professionals who jettisoned the corporate hamster wheel for the tech world — and never looked back.

Don’t sell yourself short: startups want workers with unexpected skills

You don’t have to be a computer programmer to work at a startup. Take a look at the careers page at Ample Organics (a Toronto-based cannabis software company serving more than 70 percent of the Canadian market) and chances are you’ll notice its needs are diverse and ever-changing: scrum master; system administrator; HR professional. You don’t need to be a technology wiz to thrive at Ample Organics — you just have to be curious. “Every day, I’m learning about different facets of the business, from farming to prescriptions to software architecture,” says Paulina Lizewski, an international account manager. “It’s a great challenge, but I do it because I care about the company.” Prior to joining Ample Organics, Paulina had worked in sales, but shifting jobs allowed her to take on more responsibility and quickly climb the company’s leadership ranks. Today, Paulina’s the frontline contact for some of the company’s biggest global clients.
Takeaway: Startups care less about what you did and more about what you can do. So, go out there and do it.

Help recruiters help you

Everyone has the same dream: find a job that makes you happy. Which is why you need to do your research and determine how your abilities can elevate a would-be employer above its competitors. That’s what landed Nadia Kumentas her dream job. A former competitive swimmer and naturopathic doctor who places wellness at the core of her personal and professional identity, Nadia had wanted to work at meditation startup InteraXon for years. She did some sleuthing and identified the company’s skill gaps. “Recruiters love when you do the hard work for them,” Nadia says. “Most startups don’t have time to hire. I told InteraXon exactly how my experience could meet their wants and needs. I made the process easy for them.” Now, as vice president of marketing, Nadia is in charge of shaping and sharing InteraXon’s incredible story. She’s been a crucial author of the company’s brand, one that argues fostering mental health can be both compassionate and cool. Most importantly, Nadia’s found new fulfillment knowing her work is helping people live healthier lives.
Takeaway: Startups covet people who take the initiative. So, take the initiative.

Get to know your potential co-workers — you’ll be spending lots of time with them

Some of the best features of startup life are the tight-knit teams. It’s best, then, to make sure you fit in with your co-workers, especially since decisions must be made quickly and without friction. Fiona Gao loved everything about vision-restoring company eSight: its mission, tech and, of course, its people. “Before starting my new job, I talked to some of my potential teammates and had honest conversations,” says Fiona, now the company’s head of marketing on strategy. “It’s all worked out great. I learn from my team every single day.” Fiona has previously held senior marketing positions in the entertainment and automotive sectors. But her entrepreneurial nature and desire to make positive change drew her to the startup community: “I think the key to great marketing is sharing the emotional value of a product. And that’s quite seamless when you work with people in the business of touching lives.”
Takeaway: A startup is as good as the company it keeps. So, target one with company worth keeping.

Think of this next job as a launchpad for your career (don’t worry, it’s expected)

Startups don’t expect employees to wait years before moving into more senior positions since new roles — some even invented for you — always surface for those keen to take them on. “If you have a unique perspective, tech people will push you to step up and lead your peers,” says Jillian Gora, manager of operations at storytelling startup, Wattpad. “That’s how you move up.” A veteran of both creative and technical industries, Jillian has seen first-hand how startups can be a launchpad for your career. “By reinventing yourself, you can gain the hard and soft skills, as well as connections to secure leadership roles at other organizations.” Or you can stay at a startup for years and seemingly experience many different careers all under one roof.

Takeaway: Working at a startup means building bridges. So, it pays to be a leader who loves to learn and listen.

This story was originally published in January 2020 and was updated March 2022.

Visit the MaRS tech job board to stay informed on the latest career opportunities in Canadian tech.