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  1. Blog
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4 Women Founders & Business Owners on Creating Their Unique Career Trajectories

“By focusing on what brings you joy and being open to the path your life takes you never know where you'll end up. Chances are it will be better than you could have imagined”

Entrepreneur mug that says "do it anyway"
Photo courtesy of CoWomen

This article is part of InHerSight's Career Trajectories series. Women's career paths vary significantly. Hear from women themselves about the pivotal career decisions that have shaped their growth and success.

This article is part of InHerSight's Partners in Diversity series. Discover companies partnering with InHerSight to better support women in the workplace.

When we think of founders and entrepreneurs, we often think of people with brick-and-mortar storefronts or fast-paced, open-office startups. But the reality is, business ownership varies, from full-time individual contributors managing their own clients to side-hustles that eventually become dream jobs to, say, a product manager joining forces with two colleagues to start a platform where women can anonymously rate their current and former employers. Striking out on your own can also mean forging a very unique career path.

For this installment of InHerSight’s Career Trajectories series, we asked women at our partner companies to share their stories of entrepreneurship—past, present, and future. Here are four women who’ve founded or run their own businesses sharing what they’ve learned about their careers in the process. 

Read more: Pivot! 7 Women on the Career Changes That Have Shaped Their Trajectories

4 women founders and business owners on creating their unique career trajectories

Angela Damiano

CFO/cofounder at Roundtrip

What do you do?

I’m the CFO, and my job is to make sure that everyone else can do their job without issue. I manage our books and financials, but also our regulatory, legal, and compliance foundation. I keep our team apprised of how we are performing versus our targets, and I arm our budget owners with the knowledge to make the best spending decisions possible. I make sure we are meeting all government mandates, fulfilling contractual requirements, and staying ahead of the changing health care compliance landscape.

How did you get where you are?

I was an analyst for an economic consulting firm, going deep into derivatives during the financial crisis. It was an intense period, which I loved, and I realized that I wanted to learn more about business operations. I went to business school with no idea what exactly I wanted to do, got my CFA charter, and ended up hopping around finance until my friend Mark came to me with his idea for Roundtrip.

What has most surprised you about your career?

I view myself as risk-averse and I crave stability, so no one was more surprised than me when I started a health tech company with a couple of friends. Looking back on my career, I’ve discovered that I get the most meaning from my work when I’m learning something new and solving real problems. My career is meaningful to me in ways I never expected, because I know it has driven positive change.

Jessica Goddard

UX Developer II at Alley and ran her own business for 10 years

What do you do?

As a UX Developer at Alley, I spend my days writing code to make user interfaces better on an enterprise level news site.

How did you get where you are?

As a self-taught developer, I ran my own business for over 10 years. This provided a lot of flexibility while my kids were young. Over time, I started to feel like I needed to be a part of a team to continue my professional growth. I worked for a couple of other companies before coming to Alley. Here I have finally found an environment with a culture and technical expertise in which I can thrive.

What has most surprised you about your career?

I have an architecture degree, so I never thought I'd end up here as a UX developer after years of running my own business. I always enjoyed being creative and analytical and never knew how much those intersected in my current profession.

Alice Burrows

Content Specialist at DoorDash and founder of Earth Glitter

What do you do?

As a content specialist in the customer experience team, I help to ensure that DoorDash's internal and external support resources are up-to-date and up-to-scratch! My responsibilities include but are not limited to: working cross-functionally to identify any gaps, plugging those gaps through the creation of knowledge-based articles and training modules, and brainstorming ways to improve support operations.

How did you get where you are?

I realized early on in my university degree that science and traditional methods of learning were not the paths for me—I was much more interested in business, tech, and earning money! I started working at Uber Eats while studying in 2016, and when I left in 2018, I had no plan to work in a lab or re-enter the food delivery space. After I took some time off in 2019 to launch my small business Earth Glitter, I felt a calling to return to tech. I joined DoorDash in February 2020, and once again found myself on a rocket ship headed to the moon! I'm not sure what the future holds for my career, but I'm excited to see where it takes me.

What has most surprised you about your career?

I never imagined that I would have worn so many different hats and built such a broad skill set in the last 5.5 years. I feel as though I could tackle any work handed to me and find a way to not only get it done, but do it well. 

Karolina Ciecholewska

Product Designer at Within (owner of Supernatural) and self-employed designer 

What do you do?

I design interfaces across web, app and VR headset, ensuring a beautiful and human-oriented experience. 

How did you get where you are?

I studied interior and special design, and after receiving my MA, I decided it's not the right field for me. I always loved design in all shapes and forms—made furniture, clothes, played with ceramics. I never thought that my happy spot would be in the digital world and now virtual reality. It's wonderful when you can see your creations used by others. 

What has most surprised you about your career?

That technology and digital is for me! I'm happy that I can make it look and feel more human and less scary. The changes in this field are constant and you always need to learn something new and adapt—that also is, surprisingly, very aligned to my personality.

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