How Upside Foundation executive director Jen Couldrey automated business growth

With any venture, the leader will walk a lonely road (at least to start). When you can’t afford more people or it’s not the right call, let process be your ally, colleague, and efficiency booster

Like many entrepreneurs, Jen Couldrey does a little bit of everything at the Upside Foundation, the organization for which she is the Executive Director. In fact, with “about 12 jobs” under her retinue, there is a lot that the executive director wishes she could do for business growth, but can’t due to the pesky limitation of time.

It wasn’t until a moment of clarity in accepting that failure may happen did she get the freedom to prioritize. Speaking with PulseBlueprint, she shared how she automated business growth at the Upside Foundation. Automation helped her take on the tasks she couldn’t do–so she could focus on the tasks she had to.

Accepting no for an answer

Leading up to Canada’s 150th anniversary, the Upside Foundation, located in Toronto, had an ambitious goal to double their membership of companies that pledged 1% of their equity to charity. The organization had 75 members at the time and wanted to hit 150 in honour of Canada’s 150th year since confederation. It was audacious–when the goal was set, Canada 150 was only 3 months away.

“The community loved it and totally rallied around it,” said Couldrey. “We launched in April 2017 and I think hit 150 members by June 30th. That was a big pivot for Upside. We [realized] we could be a really big thing.”

The singular focus was energizing for Couldrey. Her board was behind her and she focused only on member growth. However, the infrastructure to support those members didn’t get as much initial focus – after all, Couldrey was the only employee – and that meant a huge basket of tasks to complete. The organization immediately shifted focus to all the necessary background tasks such as getting new customer relationship management (CRM) systems in place and figuring out their fundraising plans to continue to grow.

With the sheer volume of tasks all put to her, from operations to sales to day-to-day management, Couldrey wasn’t sure what to tackle. Every task felt like something she couldn’t fail on.

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