in good company // issue no. 15 // emily key

in good company // issue no. 15 // emily key

Who: Emily Key, Growth Focused Operations Leader, Shopify
What: Tribe leader, tech obsessed, connector at heart, mama, wife, trailblazer, go-getter
Where: Toronto, ON
Follow: @theemilykey

One of the questions I asked Emily in our interview was rather an embarrassing one: Where did we meet? Needless to say, I was relieved when she replied with ‘good question….I have no idea’.

(Insert the blonde jokes here).

Regardless of this mishap, I’m trying to prove a point: two women in business who likely met via networking or mutual colleagues, but admired each other so much, they stayed in touch. And by stay in touch, I mean followed each other’s career on social media as one does, but also having our paths continually cross. Call it an online love affair in the most digital way, we were bound to connect at some point in our lives.

This would be that time.

Emily Key is impressive to me, and her reply to that would probably go something like this:

“Seriously? Honey, I’m just trying to hold it together, brush my teeth on the regular, feed my kids and connect with my husband more than once a week. It’s called SURVIVING.”

Well where do I start? She’s brilliant and funny and has carved out a path - both in family and career - that is admirable. Married in her 20’s followed by the birth of her two little humans, she has managed to do more in 10 years than most people. And recently, her life has taken an even BIGGER detour - a good one - but challenging to say the least. Both her and her husband decided to follow EMILY’S career to Toronto (see where I’m going with this ladies and gents….woman’s liberation at its finest) as she takes on the new role as Growth Focused Operations Leader at Shopify.

She’s ballsy, determined, outspoken and encouraged by other women who carved a path before her.

Sounds inspiring to me.

I would like you to tell me what one word best describes you as a (FACT: she asked her hubby to answer these):

Business Lady: DRIVEN

You have quite the impressive career with a focus on operations, technology and software. How did you get involved in these areas?

Thank you! It feels like a windy path, and I’ve tried to keep that growth mindset as I learn new things every day. I was really introduced to software in 2008 when I first moved to Vancouver. There was this creative, futurist-type group I became a part of, and eventually a few of us started a company together. They had great ideas, and I loved translating those ideas into execution. We bootstrapped it and truly had no idea what we were doing. That said, we put in the time and did the work, figuring it out as we went. We grew it, sold it, and I joined another hyper-growth startup in Vancouver and continued to cut my teeth in that world, this time in a VC-backed environment.

Now, I’m with a public tech company, so it’s yet another world. It’s really neat to be rounding out this experience with companies in 3 entirely different stages of growth. It’s also crazy to think I’ve spent 10 years in growth company mode, 150%+ headcount and revenue growth. I can’t wait to see what’s next!

You recently moved your whole family to Toronto from Vancouver, taking on a operations role at Shopify. How did this opportunity come to be and what lead you to take this giant leap?

The opportunity to work for one of the most exciting companies in tech came via Twitter, of all places. Someone at Shopify followed me and knew of my experience, and reached out about a particular role. We danced the dance for a couple of months and, while it was quite different than what I’d done in the past, I knew it was another great challenge to take on, and an extension of my skill set. What can I say, I do enjoy biting off more than I can chew! While I had put myself out there as a candidate in Vancouver, I hunted for about a year with nothing that was quite the right fit for me. My children are young, so the impact is manageable, and my husband is in a leadership role with a company that has offices in both Toronto and Vancouver. He commutes, and we make it work.

Tell us about your new role at Shopify. What does your day to day involve?

The company has expanded rapidly, and there is an opportunity to bring a level of sophistication to how shit gets done without stifling the incredible creative efforts of that team. As an operator, I love to help people more efficiently and effectively accomplish their goals. So, in a nutshell, I do that!

Define the "operations" of a company for those who may not know what it is.

Ha! Operations is often a catch-all, so I have my own definition while others might describe it as something quite different. Some people think it means the “admin” portion of a company. Some think it’s just process-improvement or project management. I see my role as an operator as one of understanding the entire machine - P&L, strategy, human capital, product, technology - and sorting out how they can more effectively operate together to achieve their goals. I’m often wary of titles, as operations is not for the faint of heart and can often be unglamorous.

What impact do you hope to make at Shopify?

Oh wow, that’s such a wonderful question and I feel sheepish answering because I’m not quite sure yet. I love helping both people and companies grow. Growing and coaching a high-performance team that really understand the ins and outs of the company will be a fun opportunity, and to bring some organized chaos into the mix.

You have 2 children that are still young and a husband you love dearly. How do you balance your work life and personal life? How DO you do it all, if in fact that does exist?

I want to say “this is how” and give you the guide book, tell you “you can do it!” but the truth is that I don’t balance it, I don’t do it all, and I don’t actually believe it exists. I’m quite fatigued by the projection from people or companies that this ideal life is possible...maybe it is, but I just feel like I’m average at just about everything right now. Maybe it’s a phase, or maybe it’s life. We’re just doing our best and hope to learn from the daily struggles whenever we can!

We are incredibly lucky to be at a point in our lives and careers where we can call in the reinforcements when needed: grocery delivery instead of going to the store, babysitters so we can attend work events, and going for a bike ride with the kids to get some form of exercise. It’s bleak sometimes, but we get to live this life once and are really trying to enjoy the little things. We’ve had to learn to be okay letting things go.

Emily Family smaller.jpg

What has been the best and worst decision you've ever made?

Best: having children.
Worst: having children.

What do you think is the most significant barrier to female leadership?

Our ability to have children.

Look, there are a million things working against women, especially women of colour, and we need to buckle down, continue to do our best, and also do more to help change this. It’s a lot to shoulder, and sometimes I want to just say ‘fuck it’ and go hide somewhere, but the reality is I view my role here in my short time on earth as having to make it better for the next generation. So, we have to work. We have to hire women. We have to coach and mentor women. We need to promote women, and build systems and policies and teams around them to help them succeed. We must invest in women. Keep. Going.

What women inspire you and why?

  1. Kara Swisher, for relentlessly reporting on the good, bad, and ugly in tech, and doing so with humour and journalistic integrity.

  2. Constance Wu, for bravely calling out Hollywood racism, and not ever backing down.

  3. Angela Ardenhts, for making an incredible leap from Burberry to Apple.

  4. Jenna Lyons, for her epic contributions to J. Crew, and for courageously leaving.

  5. Arlan Hamilton, for building the new standard of VC firms in the Valley, and for her incredible story.

I'm obsessed with podcasts. Do you have any faves you can share with us?

Yes! I’m relatively new to them, and I don’t know how I was so late to the game, but here are some of my faves:

  1. Kara Swisher’s Recode Decode is a must if you’re remotely interested in technology.

  2. Sophia Amoruso’s Girlboss Radio is really high quality and has wonderful entrepreneurs and business people...who happen to be all women.

  3. Pandora Sykes and Dolly Alderton’s The High Low is a brilliant pop culture podcast that is a treat to listen to.

  4. Takara Small’s I’ll Go First by The Globe and Mail is a nice Canadian addition with entrepreneurial guests.

You know technology well. Where do you see technology going/advancing to in 5 years?

There is so much innovation happening around the world that it’s hard to keep up. The list below isn’t an exhaustive list at all, but some of my favourite things to keep learning about are:

AI: it is undoubtedly going to change the world, as we’ve seen some fantastic application. I think it will be even more exciting once we figure out how to remove human biases from affecting it.

VR and AR: these are incredibly exciting spaces to watch as they will change how we buy, sell, play, and communicate.

Robotics: this area has been growing steadily now for several years, and the advances and applications are so exciting.

Cars: It feels like we are on the edge of a massive shift with electric vehicles. I love the big moves around cargo trucks in this space.

Clothing: With new, more durable and multi-purpose fabrics, a whole other world of fashion becomes possible. I’m also really excited about sustainability in this space.

What are your favourite types of technology you own and why?

I love our Little Bits Kit. It is a fun little activity for our kids to learn about the basic fundamentals of software development without any added screen time.

For me, the iPhone is a pretty powerful piece of machinery. I didn’t get a cellphone until I was 18, and I’m still in awe of the access I have in the palm of my hand.

Also: Netflix get it’s own shoutout.

What does mentorship mean to you?

Mentorship is hugely valuable. To me, it means spending time helping someone achieve a goal by sharing your expertise and insights along the way. I love mentoring, and I love being mentored. It’s hugely helpful! Mentors come in all shapes and sizes, and don’t just have to be work-related. In fact, having a varied group of people offering different perspectives allows you to formulate your own.


You hold an important leadership role. What do you think makes you a great leader?

Thank you! I have an evolving idea of what management and leadership means to me, and I don’t know if I’m a great leader yet. I think it’s possible and that I have it in me to get there, and that my curiosity and care for others might be key to that. I’ll keep you posted.

My favourite leaders are those that give a damn about the world, and genuinely care for the people who are helping them change it. I love helping people discover how awesome they are, that it was in them the whole time, and that they have all the potential in the world. It’s really fulfilling to empower people to truly own their greatness.

You've worked with some phenomenal start ups in your career. What's the most thrilling part of this and what's your least favourite thing about working for start ups?

For me, the most thrilling part is the people! Most startups are filled with really ambitious and creative people who care a lot about their work. I find that really fulfilling and energizing to be around. I also enjoyed the need to wear multiple hats, as that helped me figure out my strengths and what I actually enjoy doing.

My least favourite thing about working for startups is probably the insanity around fundraising and burning through other people’s cash. Some people find that really exciting, but I find that it makes me queasy. Pre-kids? Probably would have answered that differently. I still enjoy risk, but I also enjoy being able to pay for those insanely expensive daycare costs.

I wrote a blog about egos + business and how they don't mix (or to put it mildly, why egos are unnecessary in business). What's your opinion on this?

Egos can really hurt us, or hurt a business. But they can also guide us to doing things we also never thought we would. So, I have a mixed opinion!

I think I’m pretty bought into Adam Grant’s idea of the Humble Narcissist. That it can, in fact, take a bit of narcissism to have the gaul to build a successful business, but that there are leaders out there who have done that AND are also willing to acknowledge their weaknesses and learn from their mistakes. He’s done quite a bit of research on it and I’ve enjoyed digesting his findings.


What are the top 3 business books you would recommend for women?

  1. Mindset by Dr Carol Dweck

  2. Strengths-Based Leadership by Tom Rath and Barrie Conchie

  3. How Fucked Up Is Your Management by John and Melissa Nightingale


For women specifically (but maybe also men?): How Remarkable Women Lead by Joanna Barsh and Susie Cranston.

I’ve written another feature on companies & organizations that support women returning to the workforce after they've been absent for a while. How important do you think this movement is & what was your experience returning to work after having children?

I loved that piece! Thank you for writing it. While there is some awareness around the challenges of returning to work, it’s typically only amongst those who are experiencing it!

Frankly speaking, I wish we didn’t need a movement and that it was just a given that we should have work environments and government policies that supported this. I wish it was normal, natural, and not a big deal. I hated thinking about it, planning it, and experiencing it. And I was in the position to make it whatever I wanted. I constantly felt like a burden (and was told I was!), inconveniencing everyone from the tax man to my employer.

Fuck that.

So, you’re right - a movement it is! I love the new norms taking shape in the Nordic countries, where paternity leave is a use-it-or-lose-it deal, and where 81% of dad’s take it. Hell yes! That’s progress. Canada is reasonable, but the actual impact at work is dreadful* and we need help there.

My advice for anyone about to deal with that is to find another parent in your workplace who has done this, buy them coffee, and make sure you understand what worked for them and what didn’t. Poll more parents if they are available. Otherwise, send me a note and let’s chat so we can make sure you have as good of an experience as allows!

*I’m sure there are some people who had great experiences and I hope they are out there sharing what made it successful with the rest of the world.

I'm a big believer in 'ah-ha' moments, that timing is everything and things happen for a reason. What has been your biggest ah-ha moment in life?

It’s pretty cool how all of the broken roads lead to where you are right now. It sounds cheesy, but it clicked for me when I realized I didn’t have to do this all alone, that there were kind people in the world that I could trust and rely on, and who truly supported and believed in me. I second guessed that for a really long time, and it wasn’t until I just got over myself and let people in that I really learned to enjoy life. I don’t know if it was a moment, but more of a mid-twenties thing.

Now, in my 30s, it’s even more pronounced. Like the ‘ah-ha’ is blurred thought that becomes more and more clear over time. It makes sense in my head, but zero sense when I write it!

What are three qualities you look for in the tribe of women you surround yourself with and what’s the one thing women can do better at to support each other?

This is a timely question. I’ve had to really reassess who I’m surrounding myself with, and also really examine what I bring to friendships.

Personally, I really enjoy women who a) don’t take themselves too seriously and are generally humorous, b) have something they care about or are passionate about, and c) are curious and/or non-judgmental.

One thing women can do better to support each other is to fucking check in. It doesn’t take much. Just ask. How are you? What can I do? It’s lonely enough out there, the least we can do is be there for each other! Show up. Bring food or wine. Listen. I freaking love my friends because they do it, they’re happy to do it, and they know I’m happy doing it for them.

What’s a typical day like for you?

Long. Isn’t it like that for everyone?

I’m up at 5:30am to walk the dog and try to get some sort of workout in. Then, I get myself ready and I take my sweet time because it’s probably the only time I’ll be alone throughout the day. I like using delectable skin products, styling my outfit, and sipping my coffee while it’s still hot. If Greg doesn’t have his nose in a book, we usually have a chat about our day and remind each other of the bigger picture. We enjoy cheerleading each other.

Then, it really begins. The kids are up! It’s non-stop from the moment they wake until the moment I drop them at daycare. I head to work and do my work thing, and I have recently learned to pace myself instead of burning out. Mini meditations and walks have been crucial to my survival lately!

Afterwork, I’m either at a work-related event, sipping wine with fantastic women who inspire me, or I curl up with Greg, takeout in hand, and chat. Sometimes, when we’re quite sick of each other or the world, we just read.

Rinse. Repeat.

On that note, you recently experienced a concussion that rocked your world during your transition into a new role and city. Tell me about the recovery and what you’ve learned through physical therapy, meditation and healing.

Getting a concussion was a huge learning experience for me. It happened mid-August, and I’m still recovering and suffering from post-concussion syndrome. I do rehab several times per week, and that consists of a melange of specialists who focus on both cognitive and physical recovery. I get frustrated at the slowness of it all...two steps forward, a dozen steps back. Sometimes I feel like I’ll never get better, but I actively tell that thought to fuck right off! Pair all of this with the newness of moving across the country and a team of people who don’t really know me or how I work yet. You can imagine the amount of emotion that gets wrapped up in it for me.

Invisible injuries are awful. I heard myself telling people “oh, I’m fine” and I sounded ridiculous. I wasn’t fine. I’m not fine. But I looked fine and could work really hard to fake that I was fine. There were times I wished that I’d instead broken an arm or leg. Anything but something that people couldn’t see. I couldn’t bathe my children without getting a piercing headache. It’s hard for me to have a meaningful conversation with my husband. I can’t really exercise aggressively; I can’t watch TV, and need to have quiet time along in a dark room every 30 minutes or so. I feel like I’ve lost 2 months of my life so far, and I really hope rehab and an unrelenting focus on recovery means I don’t lose much more.

What's the one word of advice you would give your younger self?

Stop trying to please everyone else. It literally doesn’t matter. It’s you. All you. Just do you. The world will shift for you.

What inspires and motivates you to get out of bed in the morning?

I love the morning. Another day, another opportunity to fuck it all up again! Just kidding. Sort of.

Knowing my time here on earth is short is a pretty great reality check. I want to make the most of it, and I want to help make it enjoyable for everyone. Knowing there is so much to be done in the world to help others is what gets me out of bed.

When have you been the most satisfied in your life?

That is a great question! I love thinking about it, and it’s not an easy answer because I tend to be a restless person who wants to go go go and is never ‘done’. I think I think of ‘satisfied’ with ‘complete’. So, never? That can’t be right. The image that comes to mind is one of me sitting and watching my kids play, maybe paired with a vague notion that the house is somewhat tidy, the To Do list isn’t overwhelming, Greg is beside me and the dog is resting at my feet. There may or may not be red wine in my glass. There aren’t many of those moments, but those are the ones that feel like satisfaction to me.

motherhood and anxiety

motherhood and anxiety

zucchini almond butter blondies

zucchini almond butter blondies