Photography by Jenny Jay

With one of their mottos being: “Your bank will hate us as much as you love us”, Planswell, a rapidly growing tech start-up company from Toronto, means business. As a team of financial experts, engineers & designers, they believe financial planning should be available to everyone.

Head of People Operations at Planswell, Jenny He knows a thing or two about the importance community. She’s responsible for ensuring the success of the company’s leadership team, coaching middle managers and creating employee resource groups, as well as a whole host of other responsibilities.

However before starting her career in HR, she nearly had a very different future, before life handed her a lemon!

Keep reading to find out how rejection lead to opportunity, how her definition of success has changed over the years and her impact on Planswell as a start-up:

Tell us about a time that life handed you lemons. Did you make lemonade?

Before pursuing a career in HR, I was an aspiring Physiotherapist with a Health Sciences degree. Life threw me a lemon in the form of a rejection letter from U of T’s Physiotherapy program and I was devastated. But rejection is a good teacher and reflecting on the failure taught me a lot about myself. I bounced back by putting my all into chasing a new career that I have come to love more than I ever imagined, so I’m thankful to that lemon!

Describe your ideal work environment to get sh*t done.

When it comes to teamwork, I excel when out-of-the-box thinking and diverse opinions are encouraged. That’s why Planswell is such a great fit for me – people here not only allow, but push each other to speak their mind and be the most genuine versions of themselves. It makes for more inclusive collaboration.

When not at work, or when collaboration isn’t involved, I love taking a corner seat at a cozy coffee shop and doing work to an acoustic playlist.

How much of your success as an entrepreneur has come from taking risks versus playing it safe?

The biggest career risk is not taking any risks at all. Almost two years ago, I packed up my life in Toronto, left the corporate world, and joined a SaaS startup in Florida. It was far from safe, but in hindsight the best decision I could have made for my career at that point.

An important skill you can build is to develop a strong compass on which risks to take, and when to take them. Here’s a summary of what I’ve learned:

Start early. That first step is the most difficult. Risk aversion increases with age, and rightfully so.

Worthwhile risks aren’t all big. It’s not always finding a new career path; sometimes the right risk is asking your manager to give you challenges on the edge of your capability. In fact, always say yes to stretch opportunities.

When picking that next step, bet on your manager and the culture (as opposed to title and salary). This is especially true earlier on in your career. Choosing a strong mentor that believes in you will not only push you along faster, but will put on you on a completely different growth curve.

How do you measure success in your career?

Two years ago, a mentor asked me what career success meant to me, to which I replied “Head of People Operations at a growing tech company”. I still pull up that email from time to time to remind myself of how far I’ve come. Back then, success was a title and a vague idea of what that title meant. Now I’m proud to have a much richer definition of success – one grounded in the tangible impact I have every day on the company’s future success.

“Now I’m proud to have a much richer definition of success – one grounded in the tangible impact I have every day on the company’s future success.”

You're 30 minutes away from walking into an important meeting. What do you do to get yourself in the right headspace?

Take deep breaths, visualize the meeting going well, then put on a mood-lifting tune (e.g. “You Make My Dreams Come True” - Hall and Oats)!

What is something that you read, watch or listen to regularly?

Taking a look at my bookshelf, Netflix history and Spotify...

Read: Mastery (George Leonard), Hard Thing about Hard Things, The Little Prince and any Murakami novel

Watch: The Office (the only show I’ve rewatched)

Listen: NPR podcasts (especially “How I Built This” with Guy Raz), StartUp Podcast by Gimlet, Naval Ravikant’s Tim Ferris episode on happiness hacks. Also, Daniel Caesar and Sabrina Claudio are on repeat on my Spotify!

What impact are you making through your work?

In the early stages of a startup, success lives and dies with the leadership team.

At Planswell, my biggest impact is in pushing our leadership team to be the best version of themselves every day. One example is working with my CEO to establish clear communication channels as we scale and add layers in the organization. Another is coaching our new layer of middle managers as they take the leap from “how can I do better” to “how can my team do better”.

Finding time for yourself can be difficult. Do you have a self-care routine and what does that look like?

Self-care is all about doing more of what enriches your mind and fills your soul. For me this means laughter, deep conversations, belting out my favourite songs, reading fiction and practicing yoga.

Give us the play-by-play of your typical morning routine.

By 7:30 a.m., I’ve hit the snooze button about 10 times. I head for the streetcar around 8:00 a.m. and put on a podcast (tip: play at 1.5x speed). At 8:15 a.m., I make a stop at Fahrenheit Coffee for my favourite Diablo latte. When I arrive at the Planswell office, I start by checking my to-do list on Trello to plan out the day’s priorities.

What's next for you? Can you tell us a little bit about something exciting you're working on?

An exciting project of mine is bringing more employee resource groups (ERGs) to Planswell! One that is currently in place is “Plansgals” – a safe place for the ladies at the company to connect, receive/provide mentorship and share ideas. These groups are based on employee affinities and will help deepen the sense of community.