Some of the common questions I receive from prospective candidates about the startup space are “how do I get involved If I’m not technical?” or “how do a I break into the space without related industry experience?”

If you’ve ever had those questions – Jennifer Couldrey will inspire you. She is a true success story of a courageous woman who broke into the space, and made things happen.

As Executive Director at The Upside Foundation, Jennifer has worked tirelessly to help startups and high growth companies give back to charities across the country. Her hard work and passion for giving back is contagious and since joining the organization, she has signed on over 250 companies including Wealthsimple, Hubba, Hopper, Wattpad, Borrowell, and many others.

What’s more – her passion for giving doesn’t stop at The Upside Foundation. She is also the Chair of the Board of Directors of Future Possibilities for Kids, and sits on the #Tech4SickKids and Western University Entrepreneurship Strategy councils. Last month in the face of COVID-19, Jennifer very quickly took action and helped to launch The HomeFront, a group of volunteers on a mission to support front line healthcare workers get the resources they need to fight COVID-19.  (Anyone looking to get involved and contribute meaningfully to this fight, check it out!)

I hope this interview inspires you as much as it did me!

Tell us, what is The Upside Foundation all about?  

The Upside Foundation is a charity that enables founders of early stage, high growth companies to give back to charities of their choice. They do this by pledging equity through stock options – and when a liquidity event happens, the money is donated.

It’s a really great way for companies who want to give back to do so in a way that costs no money or takes away from their time. So far, we’ve had great success with 7 liquidity events so far, which led to to over $1.2 Million in donations!

As Executive Director, what does your role involve?

I was hired on as employee #1 almost four years ago. I was brought on to build the organization from its roots of being entirely volunteer-led to a professional charity, responsible for everything from meeting with companies/founders, building awareness through attending community events and marketing, driving partnerships with accelerators, incubators, and investors, running programming for our members, fundraising, etc.

Since I started, a big focus of my role has been on creating a strong community for member companies. Entrepreneurship can often be lonely – and we feel it’s important to create a space where they can all connect, share learnings and obtain answers to common barriers. It’s involved hosting and organizing lots of events, which are typically small and intimate so entrepreneurs can really connect and lift each other up.

What attracted you to the tech space and working with growing startups?

I come from a corporate consulting background. Although I really enjoyed my time in that space, I wanted more purpose in my work. I ended up transitioning to a Corporate Social Responsibility role within the corporate space, which was a great change. During that time, I met people working in the startup space and became really intrigued by the work they were doing. I realized there was this world where entrepreneurial minded people were making an impact by building things that provided innovative solutions to different problems. It was intriguing, and I was determined to be part of it.

In a #MovetheDial interview, you talk about how you came to Upside Foundation with little experience in the space, and learned a lot of what you do on the job. You were clearly very successful in doing so – it’s truly inspiring.  What advice would you give to females looking to break into new role and/or industry?

Thank you! I think it starts with how you portray your skills and tailor your resume to the job description at hand. Look at all the skills they are looking for and do an inventory of your own experiences to try and leverage the skillsets you already have, though potentially in different contexts.

I think it’s also important to show a prospective employer your aptitude and ability to learn new things on the job. When I took on the role at Upside Foundation, I didn’t have any experience in sales or marketing – but I was confident that I could figure it out.

Most of my time at Upside has been spent doing things I’ve never done before. I believe that in today’s world, if you have the right attitude, grit and resilience, you can learn anything. Whether it was learning how to pitch, fundraise, write content, do social media, or work a room – I set goals, identified people I could learn from, invested time in reading or learning about skills, observed others and asked them about their approaches, tried, failed, and tried again. I’m convinced that if you are patient, humble, and willing to put in the effort – you can learn how to do whatever you want.

What would you say was a career defining moment for you?

In 2017, we set an audacious goal of hitting 150 members by July 1st in honour of Canada’s 150th year since confederation – and we did it!

At the time, we only had 75 members. We launched the campaign and within only 3 months we hit our goal. The community really got excited and supported us – it was a huge moment for the organization, and a moment we realized we could make a big impact.

What’s your advice for other women growing in the startup space?

I think it’s important for women to “find their tribe”. Put yourself out there and become part of as many groups as possible to align yourself with others in the industry, such as female tech meetups, events, online groups, etc.

With all the events you attend, what are some of the top networking resources you recommend to woman trying to “find their tribe?’

  • Dovetail – women community, women entrepreneurs
  • Catalyst Breakfast
  • #MoveTheDial events
  • Women in Tech monthly meetups

Of course, in the current climate of COVID-19 going to live events isn’t possible – but as an alternative, many of these groups have launched online virtual events which are great to join (and many at a discounted price) right now.

Her Take on Tech is a blog focused on championing and profiling females doing extraordinary work in Canada’s start-up and tech space. Is there someone you want to see featured? Send an email along with their name and a quick bio to Sarah at!

0 replies

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply

Your email address will not be published. Required fields are marked *