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Ashlee Chapman comes from the world of law and management consulting, but she has recently shifted gears into the creative, innovative start-up space. These days, Ashlee is the Chief of Staff at the EdTech start-up Vygo. When she isn’t working on projects at Vygo, you can find her at Startmate where she coaches young people and helps turn their start-up dreams into a reality. 

Today, Ashlee shares more about her journey into the start-up space, and her advice for entrepreneurial women.


You started your unique career journey in the legal sector before eventually switching gears into EdTech. How did you find the transition, and in what ways have these pathways complemented each other?

When I switched from law to EdTech, particularly an EdTech startup, I found many differences. Still, I could leverage many skills developed through my legal studies and experience. The problem-solving skills that I refined at law school and in my legal experience helped me in my day to day strategic thinking and planning. Further, my background in law helps with my communication skills, as I do a lot of engagement with stakeholders internally. So I get a lot of leverage from the legal "toolkit". But there are also a lot of differences. Things move extremely fast in the startup space, and sometimes you have to be comfortable with imperfection, whereas in law, taking the time to be meticulous will always pay off. Also, the startup place gives a lot more space for creativity and innovation, which is something that attracts me.


What got you interested in EdTech and making life better for students through Vygo? Has this also inspired your coaching work with Startmate?

When I was thinking about my career, I thought deeply about what impact I would like to have and decided I wanted to work at a company where I truly believed in the mission. Vygo's mission is to champion all learners by providing them with the support they need when they need it. And it was Vygo's mission that interested me, combined with their growth to date, which made me think that by working in EdTech, I would be able to have a significant and scalable impact in the education space. Since being at Vygo, I have come to appreciate the importance of mentoring and coaching, and it inspired me to start coaching students in the Startmate fellowship.


What have been some of your highlights working at Vygo? Have you done anything that you are particularly proud of?

What I am proudest of in my work at Vygo is the culture and innovation initiatives that I have created and rolled out. One example was introducing virtual reality headsets for all employees as a way for remote staff to connect and interact in shared spaces. What started as a fun and playful experience has indeed reshaped how our team interacts with each other. Another achievement I am proud of is implementing diversity and inclusion policies and training throughout the company, which is very important to me as a woman in tech.


Who have been your mentors/role models throughout your career?

To date, the person who has had the most significant impact on my career was my Judge from my year as an associate. He taught me some of the most fundamental lessons in leadership through example. He taught me how important it is for managers and supervisors to be kind and empathetic.

And I also think that Jacinda Adern is incredible, and I look up to her as a role model.


What would be your advice to young women looking to follow in your footsteps?

I want to stress how much opportunity is available for young women starting their careers. It is very easy to think you only have one option or specific pathway. But what I have learned is that the possibilities are endless, and my understanding of my career is so much larger than what I initially believed it to be when I left law school. I would also say that learning and growth do not stop at university, and you should continue you be curious and explore the entire way through your career.


If you have any questions for Ashlee Chapman, please:

1. Leave a comment under our Woman of the Week FB post, or

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