Anna Robinson – Product Manager


Anna Robinson is a Senior Technical Product Manager. She was interviewed as part of the 12 month Achievers Women’s Network (AWN) series. The series highlights women leaders at different stages of their career throughout the organization.

Aptly self-described as a ‘jack of all trades’, Anna walks me through her 10+ year journey at her current company, Achievers, and her return from maternity leave. Our conversation covers her diverse hobbies, interests and accomplishments. From photography, to ballroom dancing competitions, to small business ideas, it’s refreshing to speak to an accomplished woman in tech that prides herself on being so well-rounded. It’s obvious she has a strong work ethic but humble attitude which she credits to her parents and her early childhood experiences. 

As we sit sipping our morning coffee, Anna picks at her coffee-cup sleeve nervously until it’s a pile of pieces on the table. I struggle to hear her over a people chatting at the next table because she’s incredibly soft spoken even though her words are strong, fierce and candid. I realize quickly that ‘pegging’ Anna as any one type of person is futile and instead smile when this poised woman swears in one sentence, while discussing the importance of meditation in the next as she tells her story.

Her Back Story

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I was always trying to be someone I wasn’t and it was only later in life that I started to really understand myself and to feel comfortable with who I was.

Tell me about your family’s transition from Latvia to Canada and how that experience impacted you.

I was born in Latvia and came to Canada when I was 9 with my parents. It was a scary time. The Soviet Union had just fallen apart. My parents were Russian but lived in Latvia. There was a lot of Nationalism and Russians were being pushed out. People were working two or three jobs to make ends meet. My parents were applying everywhere including Canada just to get out of there.

My mom was a doctor in her country. When she came to Canada her degree did not transfer over. She started working any job because we only came here with $10,000. She was washing dishes, babysitting, cooking homemade food to sell — anything! You just get down to survival mode and that really taught me hard work. And when push comes to shove there’s no job low enough, you’ll do what you have to. My parents didn’t have the luxury of thoughts like “I need to find my calling in this job” or “this company doesn’t have a good work-life balance”. Because of their experience I learned hard work and humbleness, and prioritized different values, which is why, in some ways I don’t really relate to people my age.

Why Did You Pursue a Degree in Software Engineering?

My dad was the computer engineer in the family. He really tried to push all of his kids into it and I was the one that fell for it I guess [laughs]. I was really hooked onto solving problems and then building them out and watching something come to life. Visual Basic was my first programming language that I started working with. I spent hours just building games and playing around. It got me hooked on technology.

I think for me I was in such a little bubble. It was either going my mom’s route into medicine or the technology route with my dad. I didn’t want to touch people [bursts out laughing] so technology just looked more appealing to me. My dad put me into this Saturday workshop when I was 16 where you played around with photoshop, programming and that kind of stuff. I was the only girl so I got extra attention because the teacher was very excited to see a girl interested in it. As a kid I was into blocks and cars and more mechanical things. The courses I was always good at were the math and science courses.

From 13 onward I was very much exposed to technology. My dad has had a few family friends that would say why are you pushing her so hard, let her go into something else. She’s going to have such a hard time. My dad would just say, she’s going to be fine.

Tell me about your journey with your husband and his impact on you.

My husband and I were high-school sweethearts and we ended up going to the same university. He was in science and I was in technology so we got to grow up together. After university he wanted to pursue medical school in Ireland. It was four years of him in med school in Ireland and a long distance relationship that was obviously super, super tough. We had Skype-dates, but with internet lags and time differences it got frustrating at times. However, we had a strong foundation of trust. We knew we could click “pause” on our relationship, in a way, and be confident in knowing that when you click “play” you’re back to where you are. I took that as an opportunity to focus on my career, that’s where my movement to Product Management happened. It allowed us to be our own people for a bit because we were so young when we met. It was a positive in a way because we could focus on our own thing.  We finally bought a house and have our daughter together and finally settled down after all of that.

My biggest weakness is confidence, I’m always thinking “I don’t know if I can do that”. He’s the one that’s always pushing me, he’s my cheerleader and pushes me out of my comfort zone. He gives me those pep talks on a daily basis. His own journey is very inspiring to me since he has worked so hard to be where he is now.

Her Career Path

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Taking a problem apart piece by piece and solving it. It’s very rewarding and keeps me excited about my job.

Tell me about your current role and your responsibilities.

I’m responsible for a piece of a product. I’m responsible for its success, metrics and strategy and where we’re going next with it. You’re never a one person team. You’re partnered with the Developers to build what you’re thinking. You have Executives you have to sell your strategy to. You have Sales and Client Success teams that give you insight into our customers’ needs. Then you work with Marketing to bring your product to the market. You get to work with all the teams in the organization. You’re responsible for figuring out what’s coming next, for building it and then project managing it into life.

What do you find most rewarding about your role?

What’s most rewarding is seeing your idea come to life and seeing people use it. When I talk to our clients on the phone, I’ll listen to their pain points and how miserable a certain task is and I think to myself “okay, I know exactly how to solve that problem”. Sometimes you can implement and release the solution in a matter of weeks and you hear the client say “oh my god, this is amazing!” Sometimes they get so excited about an extra button you put in because it saves them hours of time. Those are the small wins. Then there’s the big projects, where you put in months and months of design. Taking a problem apart piece by piece and solving it. It’s very rewarding and keeps me excited about my job.

What do you find most challenging about your role?

It’s challenging to manage the influence. There are multiple departments and multiple clients with their own wishlists. Some have a larger voice than they should at times, and you have to learn to say no. I like to please people, so it’s hard for me to say to no sometimes and to manage all these inputs and come up with the best decision. You just have to make a decision and hope that you’re right but sometimes you’re not. It can be stressful because it’s your responsibility at the end of the day and it’s your product. You take it as a learning process. It’s rare you’ll make a very big mistake, you’re usually just a little bit off so you correct and move on. There’s no time to beat yourself up over it.

What are your long-term goals and plans?

Something that has always had in the back of my head is to run my own business. I have a lot of hobbies on the side and I’m pretty crafty. Photography is big passion of mine and eventually, I might pursue something in that field. Being a Product Manager, you’re the owner of a micro-company in some ways so it’s given me great experience in understanding how a product is born, how it matures and how it is marketed. My biggest, biggest dream is to run a bed & breakfast. Maybe it’s the Lorelei Gilmore fan in me [laughs].

I’m a jack of all trades kind of person. I’m not an extreme person in anyway, I’m very balanced and I think that reflects in my interests. I’m not going to spend all day reading blogs and going to technology conferences. I like my job but I try to do a million different things at once. I’m always looking and searching in hopes that I find that one thing that sticks but I don’t think I’ll ever be an extreme 100% live, breathe and die by one thing type of person. In a way though it makes me better at my job because I bring a different perspective to it.

What advice do you have for women pursuing your career path?

Don’t be intimidated by your gender. You’re going to walk into a room where you’re most likely going to be the only girl or one of two. Don’t let that intimidate you because you can bring a lot to the table.      

For me personally, in addition to being a woman, I’m also soft-spoken, so it’s a double whammy and I find it hard to command a room at times and get people to actually listen to you. Instead of this “go-away-little-girl” attitude I experience sometimes. I think in general, it takes a lot of time and effort for a woman to prove herself. I’ve seen boisterous men come into the room and by default, they have that respect. People assume that he must know what he’s talking about, but he may not know at all. Whereas for a woman, I find that it takes a few meetings and multiple times of repeating yourself to finally gain that respect. There are times when I’ll say something and someone else will reword what I said just louder and people will listen and agree. It’s frustrating but you have to keep pushing yourself and keep speaking out. Don’t be intimidated by the loud personalities in the room… which will most likely be men [laughs].   

Be confident in what you know and what you have to say and eventually you’ll gain that respect and you will be successful.

Her Lived Experience

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You’re going to walk into a room where you’re going to be the only girl. Don’t let that intimidate you because you can bring a lot to the table.

How do you navigate those moments of self-doubt or lack of confidence?

I’m working on my confidence, to say, “Listen! What I’m saying needs to be heard and is important”! I’ve pushed myself to join Toast Masters, I spent a year in that. Having to speak in front of a room on the spot was my biggest nightmare. I ended up doing pretty well and took on a VP of Public Relations role to help out with the day-to-day running of the club and recruiting new members. I try to push myself to do those kinds of things that scare me.

For me, confidence, comes with knowledge on the topic and preparation. I always try to be super prepared and that’s what helps me. I can’t just walk into a meeting and expect that I’m going to wing it. I’m not a ‘wing it’ kind of person. So I spend the extra hour preparing and it goes a long way in making me confident about what I have to say. It’s important to know your weaknesses and work with them.  

Only one day back from Mat Leave, what’s your plan for prioritizing your mental health and self-care?

My daughter is with people she knows and she loves. It’s me that has to adjust! Pre-maternity leave, that was super easy. My routine would’ve been get up earlier, go for a jog, listen to a nice podcast, stretch and meditate. I’m a huge introvert so on days when it’s back-to-back meetings my head starts exploding and I’ll get migraines. I’ll go for a walk, leave the office to ‘de-pressure’ myself. A 10 minute walk does amazing things. 

While I was on mat leave, you’re always just running around and you don’t have much time to yourself. My husband was always working crazy hours so walking is something we integrated into our life. It was a time to get away from electronics. We’d take the dog for a walk and we’d catch up, talk about politics, or the future or our next house. Future planning and dreaming [smiles].

Post-maternity leave, it’s going to be a lot harder to find that time but I need to come to terms with not feeling guilty about taking time for myself. If I need an hour to get in a car to go drive and take some pictures, I need to be able to say to myself that’s okay. If I’m not 100% then I cannot be 100% for my daughter. My husband is super supportive of that as well.

What life lessons do you plan on instilling in your daughter?

It’s funny, I’m thinking about that right now because we’re doing a time capsule for her birthday. I have a list that I put together for her. First, to just be herself and not be afraid of being different. I was always trying to be someone I wasn’t and it was only later in life that I started to really understand myself and to feel comfortable with who I was. I want her to pursue whatever she’s happy doing. She doesn’t need to follow the typical career path if she wants to be an artist or musician instead. As long as she has a passion for it and pursues it 100%.

Second, is that life is not going to give you anything. You have to fight for what you deserve. I always thought “oh I’m pretty good at that, eventually someone will recognize that and give me a promotion”. It takes self-promotion, which I’m not good at. You can’t just sit back and expect the world to notice that you’re awesome. Make plans for yourself and be the creator of your own path.

The third thing I would tell her is to not be afraid of challenging others if you don’t agree or if you don’t feel like it’s the right thing to do. Just because they are older or more experienced, doesn’t automatically mean they are right.

What biases do you think still exist in your field and how can men be part of the solution?

[long silence] It’s about having an open mind. There is definitely still bias based on gender.

I think that women have to work hard just to get up to a ground level and to start getting respect. Sometimes it feels like when you make one mistake, as a woman, it re-affirms the bias in people’s minds. It’s like “well, that’s what I thought, she doesn’t know what she’s talking about”. Where as a guy, is safe to make several mistakes over and over and over again before he loses that respect. It makes it harder for women to take more risks because they feel like they’re going to fail and mess it up for all the other women. That bias still needs to change.

Men in the field can help by respecting  their colleagues and just being a fucking good person [laughs]. Treating people the same way whether they’re a woman or a man and appreciate the fact that everyone can bring something to the table. Just because an idea is different than your way of thinking doesn’t mean it’s the wrong way to do something.

Any suggestions for blogs or general inspiration for women in tech. 

Some of the women that I follow on Twitter and Facebook are Sheryl Sandberg, Malala Yousafzai and Mayim Bialik. They are all strong and intelligent feminists, who are making some huge impacts in this world for women. I also love following Elizabeth Gilbert (author of Eat, Pray, Love). She is an incredibly grounded and positive person and her latest book is about embracing your inner creativity. I like following a mix of people who you relate to and who you may not to gain different perspectives.

The Achievers Women’s Network would like to acknowledge & thank the “In Her Own Way” blog for inspiring the 12-month series.

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