Jennifer currently works as the Growth Manager for Sales Channels at Shopify. I worked with her at Wave Accounting, where her insatiable thirst for learning and, in turn, sharing her knowledge within and outside the company was evident and admirable. She’s had quite the journey into tech, and continues to push boundaries and encourage others to do the same. I had the pleasure of chatting with her to learn more about her intriguing career path, her experiences and learnings throughout this journey, and what the feminism and diversity movements means to her.

 ♦ On Life  ♦ On Career  ♦ On Women

On Life

Tell me a bit about yourself and your journey so far.

My name is Jennifer Daly and I work as a Growth Manager for Sales Channels at Shopify. I’m a bit of an odd ball – most people would describe me that way, which is cool [laughs]. I’m not married and have no kids, but I do have an incredible Mini Golden-doodle that I love a ton. I have this insatiable appetite for what’s next, so right now I’m very focused on my career and learning. I’m very invested in my work, which is probably one of the reasons I’ve only worked for two other companies in my life; I worked at Rogers for 5 years, which is a long time for someone in their early 20s, and then at Wave for nearly 4 years.

I’d definitely describe myself as someone who wears their heart on their sleeve, which means I sometimes have a love-hate relationship with people and projects I’m working on. While some people hide or suppress their feelings, it’s my process to let it out. I think I’m so transparent because I’m so committed to what I do that I can’t let it poison me when something isn’t right. I’m getting better at how I approach that, the older I get.

Looking back at your life so far, are there any pivotal moments that helped shape your life or who you are today?

Growing up, we had a weird dichotomy in our household; it’s funny that my parents ended up together because they had totally different lives. My mom came from an average middle class family and was raised almost as an only child because of the age difference between her and her two younger brothers. In contrast, my dad’s childhood was very different because as the oldest of 9 brothers and sisters, it’s fair to say he never really had anything that was his; he didn’t go to university, he didn’t have access to those opportunities. He worked at Ford Motor Company for over 30 years, and this career defined much of who he was. A lot of my personality – which people can sometimes describe as prickly – is something I learned from my dad. My dad is, at times, a challenging person to be around; and growing up with someone like that, I had a mix of really great and a lot of not-so-great experiences. But now, as an adult, I know that experience contributed to who I am today, and why I have pretty thick skin for things.

Working at Rogers though, I had the opportunity to work with a lot of executives who had, let’s say, more refined communication skills than my father did. So I learned various cues from them that I’ve applied over the last couple of years, and that helps when my prickliness comes through [laughs].

What are your values or principles – the things that are important in, say, your work or life?

People probably think I’m a real asshole – and, fair enough, I come across that way sometimes. But as rough as I can be, those who know me well know that it’s important for me to help people. I think I go out of my way to help people mainly because I grew up with a dad who never had a lot of attention as the eldest of 9 kids. And even though I’m prickly, I’ve had extraordinary people take me under their wing, and be patient with me, so I feel like I need to do that too.

For instance, my neighbor has had to deal with a lot of terminal illness in his household. So when his wife had to visit their youngest daughter in BC, and he fell ill, I ended up taking care of him – making sure he went to hospital, meeting with his doctors, putting in place services he needed, and so on. Long story short, not many people would take time out of their day to care for someone next door to them. So I always prioritize my ability to help people over other things because at the end of the day, that’s the shit that matters – that’s what makes the world a better place.

What is a saying that you live by, or that influences your daily life?

Don’t be an asshole [laughs]! That’s my motto! And it works both personally and professionally. If you don’t understand why someone’s doing whatever it is they’re doing, don’t crowd them or try to change them; instead, try to understand their perspective. Being able to see things from different perspectives will make you a richer person.

What is the one thing that holds you back, or the one thing you wish you could stop doing?

From a professional perspective, I would like to be less disruptive. In the startup space, we see being disruptive as being a good thing – Shopify definitely has an environment where it’s encouraged. But, we’re reminded to have strong opinions weakly held; it’s a mantra that reminds us that it’s super important to be passionate, but at the same time you need to be flexible and open-minded because it’s a two-way street – no matter what position you’re in.

I have an incredible boss who has taught me that sometimes, even if you’re right, or your thing is going to move the needle 80%, it’s important to know what the casualty involved is. Are you gonna distract other groups? Maybe you’re moving the needle 80% on that item, but this results in other things, which you don’t have visibility to, being negatively impacted. So you should always go into working with cross-functional teams knowing that they have lot’s of different responsibilities, and that they’re not only doing your thing. That’s the one thing I’ve learned from my boss – even if he puts pressure on me to accomplish something, he does it in a way that’s minimally disruptive.

From a personal perspective, I wish I could stop shopping [laughs]! That’s the one pillar of my life – the one thing that I don’t have together.


On Career

You’ve had an unconventional journey into tech, having worked at Rogers, before you moved on to Wave. What did you learn from your roles outside of tech?

My first real job was working at Rogers as an administrative assistant. I worked for a female Vice President who was a very strong, independent woman. She dressed impeccably, was very refined, and had this stoic presence about her. I’d never had a professional, career driven, female role model in my life, and so I needed to find someone to emulate. The job was a maternity-leave contract.

When that contract ended, I briefly transitioned into a position as a coordinator for an internal project management group. Soon after, I was approached by the HR team about being an executive assistant for another female Vice President in the company. Working for her was one of my favorite jobs! She had worked at the company since she was an analyst and climbed up the ranks to Vice President; she may have been only 115 pounds and the only female on that floor, but she was the person people feared the most [laughs]! She knew the business inside-out and would often go down to the trenches, right to an analyst’s desk, to ask questions. If she wanted an answer to something, she’d just call people up! That’s where I learned how important it is to learn about every aspect of the business, and that the people who are in the weeds everyday likely know that stuff better than anybody on your senior team – so why not just ask them! It’s also very empowering for them to know that senior people are using the work they’re doing, so it’s good from a culture perspective. So being an executive assistant was the trade, but the learning experience was incredible!

After working for her for 2 years, I was salivating for business work; so I started working for the sales and marketing division of our retail channels under a completely different female at the Manager level. She was someone who’d had a super hard personal life, but was astonishingly very easy going. From her, I learned how to deal with the worst kind of stress. And in that job I learned how hard it can be being someone with no authority and trying to get things done; it was really eye-opening because as an executive assistant, I got a lot of what I wanted done because of who I worked for. That’s when I started learning everything from analytics, oracle databases, reporting, and so on because I could not handle waiting for other people to give me what I needed – doing it myself was the only way I was gonna get things done faster.

Can you describe what your role entails?

I specifically lead product adoption of Facebook Shop, Pinterest, Amazon, Twitter, and Kit – which is an artificial intelligence bot developed by awesome team based out of San Francisco. Shopify acquired Kit in April this year to help entrepreneurs with email marketing, and Facebook and Instagram ads.

Can you tell me about a failure you’ve gone through in your career, and what you learned from it?

I fail a lot [laughs]! I’m really lucky to have joined Shopify because it’s a really unique environment where we actually celebrate failure; the faster you break, the faster you can repair yourself. We’re moving quickly as a company and there’s a lot of things we’re trying to do, which means people are gonna break! So I’m really lucky that it’s the type of environment that loves people who love making mistakes, because I’m the type of person who makes a lot of mistakes! I would probably say, overall, if you’re not falling on your face, it means you’re not trying hard enough; people who don’t make mistakes are people who are not taking enough risks.

Some big failures for me are… I’m not always great with people; I’m prickly sometimes, and making people uncomfortable is what I do really well. By making people uncomfortable, I’m pushing them to do better, to break faster, so we can move forward. But I’m trying not to be as disruptive and instead use that energy to understand all the stakeholders at the table, and what I need to do to have them understand what I’m advocating. I’ve learned that transparency and understanding their pressures and goals helps us have meaningful conversations.

I’d also say, another area I’ve made some mistakes is that I’m so loyal to things to the point where it’s a disservice. There’s a few times in my career where I think I probably stuck with things a little too long; either they outgrew me, or I outgrew them – it just wasn’t working and I should have recognized that sooner.

In one of your medium posts, you mention that Tobi (Shopify CEO) spoke about actively recruiting people of all different walks of life. What is the importance of this deliberate effort to build a diverse workforce?

We had an AMA where Tobi said that if he hired people with similar characteristics such as race, education, upbringing, and so on, chances are that they would have likely experienced life very similarly. They might be super awesome, and very qualified to do the job, but they may lack the life experience we need in the team. For Shopify to be unique in the marketplace and to solve big problems – unique problems – we need to have people at the table with different perspectives; you can’t do that if everyone is likely to have similar life experience.

So he believes in hiring people from all backgrounds and people who’ve dealt with diversity issues, such as discrimination, in their lives; those are the people who thrive because they’ve managed to break through barriers. People with that experience and those perspectives, play a huge role in helping solve problems in a unique way. That’s why during interviews at Shopify, the focus isn’t so much on professional experience; instead we ask about your life story.



On Women

In one of your medium posts, you speak about being a closet feminist. Can you speak on the importance of the feminism movement to you?

Growing up I was always a little bit closer to my dad than my mom, mainly because it was really easy for me to win over my mom’s affection whereas I had to work a little harder for it with my dad. As a result, I learned things like how to install my own ceiling fan. As an adult I buy my own cars, and I know more about what’s under the hood of my car than the people selling me the car. And maybe because of that I really see a lot of these biases against women. Things like when I got pulled over for a speeding ticket and the officer made a comment that my daddy must have bought my BMW; or knowing that throughout my life, a man doing the same work as me was getting paid more. Or even seeing the second Vice President I worked for be the only female on the executive floor, working alongside all men, and knowing that she was working just as hard but not getting the same treatment; she had just as large an organization as the men on her floor and huge budgets to manage, but she was a Vice President while everyone else on the floor was a Senior Vice President. That fact really stood out to me.

I believe that professionally, some men are given a right of passage because of norms people accept. For example, if a woman is lacking a few years of experience, compared to a man, because maybe she took time off to have a baby, she’s at a disadvantage. Never mind that she has many great skills. She may not be learning these skills as the director of something, but instead as a mom on no sleep. Everything’s not so cut-and-dry, and we need to look at the different experience and life skills everyone brings to the table, not just men.

I also like Sheryl Sandberg’s book, Lean In, because it highlights that being bossy does not equate to being bitchy. When I’m having a bad day, I’m a bitch; when a man’s having a bad day, he’s not being an asshole – he’s just having a bad day! There’s a double standard there, and I still see it all the time. It doesn’t exist as much at Shopify but, with that said, most of our executive leadership team are men – we have one woman – and I know they’re actively trying to solve that problem. It’s not easy, but it has to be a conscious effort.

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

Surprisingly, many of the hardest people I’ve had to work with are other women. A lot of powerful women assimilate to men because it’s what’s given them success in the past – being one of the guys. And the biggest thing that those women do to be one of the guys is that they’re sometimes hard on other women. Don’t be one of the guys, and don’t be hard on other women. Like you, they’re having to work twice as hard to get where they need to be. So cut them some slack!

Do you have any book, blog, video, etc. recommendations that have inspired you as a woman in tech?

I think it’s important to get learning in various formats; I talk to people, I like to read very factual or very opinionated pieces, and I listen to a lot of podcasts. My favorite podcast is Freakonomics – they bring in experts who take a topic and look at it 360 degrees, and I’ve taken a lot of those learnings back to projects.

My favorite book, The Design of Everyday Things, takes you through why things are the way they are; it’s really genius how some things came to be.

Another thing I like to do is study really great companies and their founders, such as Slack, Apple, Airbnb, and Uber; or Steve Jobs and Elon Musk – both difficult people who’ve created things nobody else has. At Shopify, when we launch products, we don’t launch the best of things, just like Apple didn’t wait to launch the iPhone in it’s perfect form – if they did, somebody else would have created the iPhone. So studying other companies, their trajectories, and the people who make their products is really helpful. And so is reaching out to those people! Just make sure you are specific and demonstrate that replying to you will provide them value; use their product, look at what it’s doing, and ask specific questions – it’s easy to grab people’s attention as long as you’re being interesting and demonstrating value.


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