Kylie Woods is paving career paths for women in technology

In honor of Women’s History Month, we’re celebrating the stories of the amazing women in small business that are conquering male-dominated industries and working to #breakthebias.

Name: Kylie Woods

Location: Calgary

Business: Chic Geek

What do you do? 

Chic Geek exists to build gender diversity in technology. Our mission is to engage, retain and support intermediate women in tech so they can thrive in their careers. 

We offer a program called Career Pathing, which connects mid-career women in technology with a new person every month. Through these conversations, women achieve greater career visibility, gather valuable insight, and build their strategic network. 

Why did you decide to start your own business? How did you get started?

I started Chic Geek because I’m passionate about seeing more women in technology. Our perspectives and experiences are integral to achieving dynamic and innovative results in the workplace (and the world)! 

Chic Geek started with $100, which was the cost for our domain name and hosting. We ran events and social media to test the concept and as we started gaining traction, we iterated and improved. We still take an experimental, iterative approach today, ten years later.

What is the biggest lesson you learned in the first year? 

Vision is critical. Know your WHY and talk about it all the time. I didn’t start Chic Geek with a focused WHY and we’ve had to refine it over the years. We started by serving women in technology AND entrepreneurship, at all stages of their careers, from elementary school to senior professionals. It took me a long time to learn that being more focused in our audience meant we can design better content and programs that meet their needs at a deeper level. Today, we focus on serving mid-career women in technology, a segment that other organizations don’t serve.

My biggest lesson learned is that you need to be fearlessly focused on your vision. It’s okay not to be everything to everyone.

What was the most surprising thing about becoming a business owner? 

The grind is real. Success as a business owner doesn’t happen overnight. Chic Geek has been operational for ten years and part of our success is that we have put the time in to build relationships, grow our community, and be a consistent presence in the ecosystem. 

What is an aspect of running a business that you needed to learn more about when you started? How did you learn about it?

Understanding financials, budgets, and forecasting was an aspect of business that I needed to learn more about. This wasn’t as important when Chic Geek started, because our operating budget was so small, but it’s become increasingly critical to the healthy and sustainable growth of the organization. I’ve continued to learn about this aspect of the business through hands-on practice and guidance from the board and our bookkeeping team. 

How does running your own business make you feel?

This question makes me laugh because I don’t think about it. I run Chic Geek because I think we have a unique perspective and value to add to the world. I’m in pursuit of solving a problem (that there aren’t enough women in technology) and that’s all that matters. The title of starting or running a business is a way to solve the problem, but it’s not the part I like to focus on. 

What are some of the challenges you’ve overcome or are working to overcome as a business owner? 

As a non-profit, Chic Geek is funded through grants, corporate partnerships and program revenue. We’re working towards a more equal distribution of revenue streams, but right now, are relying heavily on grants. This makes long-term organizational sustainability a challenge because we’re always pursuing short-term grant funding. 

What are your proudest moments? 

Some of my proudest moments come out of the most adversity. Launching Geeky Summit, the biggest conference for women in technology in Alberta; raising $300K in grant funding as we came out of Covid; coming back from maternity leave after having twin daughters, Lily and Mae, and pivoting the organization; and building a high-performing and inspiring team. 

What are the next big plans you have for your business?

We’re taking Chic Geek across Canada and making Career Pathing available to women all over the country. Career Pathing was designed to help women advance in their technology careers by providing strategic networking opportunities and conversations that would help them achieve greater career visibility. 

What are three things that you feel have contributed to your success as a business owner? 

Asking questions, always. I’m exceptionally curious about many things. I’m constantly reaching out to individuals in my network to ask for insight, guidance or help on different challenges I’m facing. Over the years, this approach has helped develop me as a leader and build strong champions for Chic Geek. 

Second, the wonderful humans who have been open to coffee, volunteering, or providing guidance in my Chic Geek journey. I’ve connected with hundreds of wonderful humans who are willing to share time with me over a coffee, video call or brainstorm session. Tapping into expertise outside of myself has helped the organization grow.

And third, an ability to put things into practice. This seems like a simple thing, but I’m often looking outward for inspiration and ways to apply new practices to Chic Geek. Whether it’s a book I’m reading, a podcast I’m listening to, or a conversation I’ve had, I always walk away with a valuable insight that I can apply to Chic Geek.

What challenges do you feel are unique to female small business owners?

One of the things I’ve struggled with as a women-identifying entrepreneur is the feeling of loneliness that comes from leading an organization. It’s been critical for me to create peer groups where I can share challenges, ask for support, or just vent. These relationships are invaluable and help get me through the hard times.

What advice would you give to other women starting their own business? 

Start. Now. Sometimes we hold onto our ideas longer than we should because putting them out in the world is a scary thing. Instead of launching a perfect business, just launch. It’s helpful to scale back what I’m working on. Find the minimum viable product that you can test and get feedback on. This saves you time, money, and other resources as you learn more quickly from mistakes. I’ve launched business concepts with emails, spreadsheets, surveys, and landing pages. 

When you’re having a tough day, who or what inspires you to keep going? 

Hard days are inevitable. When I have them, it’s important for me to create space to feel, so my emotions get heard. My husband, Sam, is a great support who will listen and validate how I’m feeling. When I can pinpoint how I’m feeling and why, it moves me through the feelings of acceptance so I can keep going. 

And sometimes, I just need to take a break. I’ll go thrifting, play badminton, take a walk, or do something else to get a break from the work. 

How can female business owners support one another and their community?

We need to tell more stories about ourselves so we can show other women what’s possible and challenge the assumptions we have about entrepreneurs. I’m a part-time founder & executive director of Chic Geek, which means I don’t put in a 40-hour work week. This was a conscious choice and how I want to design my work and life. 

For a long time, I felt guilty and ashamed for not working more. I questioned my validity as an entrepreneur because I didn’t fit the mold of hoodie-wearing, 80+ hour work week. It’s important for me to own this story and share it loudly so other women can know that being an entrepreneur looks like many things, including you! Yes, you! 

What’s your “power song” and why? 

“I Was Here” by Beyonce is my power song. It helps me see the big picture of my life and work through the difficult moments. 

To learn more about Chic Geek and support their business, visit their website or check them out on Instagram.