Jennifer Couldrey to depart executive director role at The Upside Foundation

Jennifer Couldrey
General manager Maria O’Reilly assumes interim ED position.

Jennifer Couldrey will be moving on from her role as the executive director of The Upside Foundation of Canada.

Couldrey made the announcement via LinkedIn. In the post, she noted that after reflecting on her life and career while on maternity leave, she decided that now is the time to move on from Upside.

“It feels like it’s the right time for me to move onto something new, and I think Upside could use a fresh perspective and renewed energy to fulfill our mission.”
– Jennifer Couldrey

Maria O’Reilly, general manager at Upside, is assuming the role of interim executive director. Couldrey told BetaKit that she will be officially leaving the organization after the end of her maternity leave on September 1.

Co-founded by Robert Antoniades (Information Venture Partners), Mark Skapinker (Brightspark Ventures), and consultant Janie Goldstein, Upside provides founders of early-stage Canadian companies to pledge equity to their charity of choice (BetaKit has been an Upside member since 2017, ed.).

Created as a way to encourage Canadian tech companies to give back, Upside was modelled after similar organizations, such as Israel’s Tmura and Silicon Valley’s Entrepreneurs Foundation.

Couldrey noted in her LinkedIn post that she was Upside’s first ever employee. When she joined, the organization had just recruited its first 50 companies.

Prior to joining Upside, Couldrey previously worked as the project manager on The Big Push Team for Alexio, a cybersecurity and compliance SaaS solution for healthcare practices. She was also the manager of community investment at SIMPACT Strategy Group, and a senior consultant at Deloitte Canada.

Under Couldrey’s leadership in the last six years, Upside recruited over 350 companies, established a partner program, hosted fifteen liquidity events, and raised almost $3 million for 28 charities.

RELATED: Upside Foundation reaches 300 members as Wattpad’s massive exit marks strong start for 2021

It was just last year that Upside reported more than $1 million donated to philanthropic efforts from 300 member organizations in the eight years since its founding.

During a tumultuous time for Canadian businesses and tech startups alike in 2020, Upside hosted a number of weekly events aimed to help companies survive during the pandemic. Upside also launched The Home Front, a volunteer organization dedicated to supporting frontline healthcare workers in the fight against COVID-19.

“I’m so proud of the impact we’ve had and how we’ve established Upside as an institution in Canada’s tech startup ecosystem,” said Couldrey. “Now that we are an established organization, it feels like it’s the right time for me to move onto something new, and I think Upside could use a fresh perspective and renewed energy to fulfill our mission.”

In terms of what’s next for Couldrey, she said that she is starting her own business as a professional entrepreneurial operating system (EOS) implementer.

Featured image courtesy Jennifer Couldrey.

Charlize Alcaraz

Charlize Alcaraz

Charlize Alcaraz is a journalism student at Ryerson University and a staff writer for BetaKit. Follow her on Twitter @charlizealcaraz

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