Kylie Woods started Chic Geek in 2012 as a side hustle. More than a decade later, it’s her full-time gig. Headquartered in Calgary, the company is making an impact on mid-career women working in the technology sector by helping them build their networks and giving them access to mentors. Woods spoke to Ten Thousand Coffees about the challenges of being a female business leader in a male-dominated industry, how her cultural background impacted the success of Chic Geek, and the role mentorship has played in her career.

10KC: Tell me about your career journey and what led you to starting Chic Geek.

Woods: I have a background in communications and public relations. When I graduated, I kind of stumbled into tech and start-ups. I said to myself, ‘Wow, this is an industry and a sector that's going to keep me engaged throughout my whole career.’ I was working in venture capital and at product management companies — and decided that I wanted to learn how to code. 

I had this misconception that to be in tech, you had to be a software developer. That’s what spurred me to learn how to code and ultimately start Chic Geek. 

It all started when I attended a Ruby on Rails meetup. I walked into the room, and it was an intimate group. I felt like everybody was looking at me. It was like, ‘Oh, they know that I don't belong here.’ I just froze. In that moment, it could have gone two ways for me. I could have let it sit and said to myself, ‘Okay, this isn't for me.’ Or if I'm feeling this way, there could be other people feeling the same thing, and I never want someone else to feel like how I’m feeling at this moment. How can I inspire change so this doesn't continue to happen? That was the route I went, and it spurred Chic Geek to life. 

I built Chic Geek to create gender diversity in technology because of that personal experience, and it snowballed. Now, we're a much larger community and team working to make an impact by engaging more women in tech. It's an exciting place to be. I see software and technology as an opportunity creator, and a way to make change in the world that's meaningful and large-scale. I love my work because my heart is in it every day.

10KC: What are some of Chic Geek’s success stories?

Woods: We build programs and services that are targeted to mid-career women in technology. We see this as a vulnerable drop off point. Research has shown women are leaving tech at twice the rate as their male counterparts. Often, they're not coming back, so we're losing that talent altogether. It creates this broken cycle where we don't have enough women in leadership and role model positions to inspire other women. 

We’ve also done research that showed women weren't connecting and building their networks — this means that women are missing out on critical access to new job opportunities and advancement opportunities.

To alleviate this, we created a service called Career Pathing, where we introduce women in tech to others in the field, to help them navigate their career journey. It’s a great way for them to build their strategic networks and to gain the career visibility that will help them understand their next steps, areas for growth, skill development, and how to build a support network. Focusing on role models and mentorship is important for women in tech.  

Since launching our career pathing beta six months ago, we had over 300 people sign up. That speaks to the interest and demand of women in tech wanting to invest in their careers. 59% of women who participated in our program responded that through connection and conversations they've been able to achieve greater career visibility and feel like they can advance their career. 

10KC: It’s Asian History Month and we want to highlight successful Asian leaders to elevate their voices and showcase their stories of success. What type of personal or professional challenges do you think you’ve encountered as a woman of colour? How have these experiences influenced who and where you are today?

Woods: My mum was born here. She's second-generation Chinese. My dad is first generation. He emigrated to Canada from Malaysia. They worked in government jobs their whole careers, with the same organizations for 35-40 years. This entrepreneurial journey and trying to build things my own way is very different from the experience that I saw growing up. I've been lucky that Chic Geek has been able to adapt and accommodate to what I need and how I want to design my work life. It's not something I grew up with. Chic Geek often looks at things from a gender lens. When we talk about things like intersectionally, culture comes into play as well. I think it’s great to have this space to talk about what our cultural influences are and how it has created opportunities or challenges for us in our careers.

Growing up in a Chinese family, the way we look at money and finances, at least for our family, was very much about the importance of saving. You do not spend. It's a very different experience being an entrepreneur or a business owner because sometimes you need to spend money to make money. For me, as I look to grow Chic Geek, what I am great at is building things on a shoestring budget, doing a lot with very little and making sure we're saving and spending our money in ways that's very conscientious. 

I grew up in Saskatoon and I remember being in elementary school. I wished more than anything for two things. I wished that I was a boy, because I thought being a girl was way too hard. And I wished that I had blonde hair and blue eyes and that I would fit in with everybody else. Even sharing that makes me sad. It seemed like I would be more accepted, that I wouldn’t be fighting for space. I don't know how much that has played into my career, but I do think moments of feeling like you wished you were something else and having to fight against that instead of embracing who you are can be an advantage. Those struggles can hold people back. I think that can be a shared experience for many who are a visible minority.

10KC: What type of additional support do you believe women from minority backgrounds need to succeed in tech companies? How is Chic Geek enabling this?

Woods: I think representation is key. Making sure that you have role models, from all sorts of backgrounds. Sometimes that rapport is built much quicker when you're like, ‘Oh, that person's going to get it, they know what it’s like to grow up in a Chinese family.’ It’s something to bond over. There is something to be said about the value of representation, especially in leadership roles.

We’ve also found through our own data that the number one reason women are leaving tech is because they can’t see a path to advancement. Our research also found that women’s career outlooks are much more positive working at companies that have diversity, equity and inclusion (DEI) initiatives compared to companies that don’t. There is this positive ripple effect around DEI that expands beyond just a company — it affects the larger community.

10KC: What role has mentorship played in your career?

Woods: It has been a core pillar in my career. I always say: Chic Geek is built off coffee and conversation. It’s because of all the amazing mentors that we’ve had along the way, folks who were willing to give me an hour of time and say, ‘Hey, here's what I know, here's where I see some gaps, here's my insight and experience to share with you.’ Mentorship for me has been unconventional. It's been this ongoing investment. It comes out in podcasts and books, having peer groups, folks that are running other non-profits. I think about mentorship as less of a long-term, ongoing thing with one person, and more of a constant in the way we operate. Mentorship is something I carve out a lot of time for as well. We need people giving back at all stages, not just when they've reached the height of their careers. We need them earlier than that, to remind people that you can do it, and if I'm doing it, you can do it. I have those conversations with mentees, at least a couple times a month, if not every week.

The mentorship conversations that leave me buzzing are the ones where I'm on the mentee side and I leave the conversation thinking, ‘Wow, the person on the other side of the table has really opened up and pointed me in the right direction, whether it’s funding or making an introduction for me.’  When I’m able to summarize a conversation in terms of, ‘Here’s what I’m learning, here’s what I’m going to do about it, here’s when I’ll circle back and check in with you and give you a progress report,” those are the most successful conversations as a mentee.’

Mentorship programs can transform people’s careers

‍Mentorship programs can connect women and underrepresented employees to mentors, managers and peers to help them succeed. Find out how Ten Thousand Coffees can help you create a mentorship program that elevates women and underrepresented groups.