How Upside Foundation Executive Director Jen Couldrey Automated Business Growth

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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

Jen Couldrey speaking

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.

Jen at Elevate Tech Festival

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.

“It’s like trying to change the wheels on a bus while you’re driving it,” said Couldrey, speaking about the stresses of the many jobs she had.

Eventually, Couldrey came to a realization: when you’re juggling a ton of jobs, some might fail, or even have to fail, in order to offer the necessary time to focus on what’s important. In Upside’s case, that meant minimizing the focus on adding new members.

In order for efficient business growth, the organization needed funds to enable their strategic plan. That meant Couldrey’s job became fundraising, sometimes to the detriment of other tasks. She had to become ok with being bad a few jobs in order to be good at the one she needed to be, something fairly common in the startup world where fundraising becomes all-consuming for leaders.

Automating growth

As Couldrey focused on fundraising and business growth, the other areas of the business couldn’t simply fall off. Thankfully, some elements were made easier by technology like the CRM system to manage contacts. Others, however, needed a touch of process automation to scale Couldrey’s efforts and impact without (much) more work.

Self-education and strategic planning

In order to build wonderful processes that helped her and the organization scale, she had to educate herself on known process frameworks and thought leadership on the subject. It can feel like taking a step back when you aim to take a step forward, but a business leader’s job is to educate themselves.

To start, she bought a copy of what became her favourite book, Traction. The book and its “Entrepreneur Operating System” helped Couldrey understand her vision, her goals, and the tasks she needed to do in the short term that would build long-term growth.

In building the framework, Couldrey was able to identify which tasks were crucial to the short-and-long term success of the organization.

Testing sales messaging

With a new “operating system” in tow, the next step was to test out new sales messaging. The goal of the new message was to more clearly communicate the value that Upside brings to startups. Previously, said Couldrey, messaging had been more about what Upside does versus the value it provides.

“You can talk to 20 people and you will get 20 different approaches for the right way to position what you’re offering,” said Couldrey. “You have to take some input and pick what you think is best – then test that for a while. If it’s getting results, stick with it. If you’re not getting results, change it. My guiding principle is always to test something to see how it resonates.”

To start the tests, she made sure to chat with folks who she knew were likely not going to become clients. That way, if something flopped or failed to resonate, it wouldn’t severely damage a potential client relationship. It also gave her the chance to calm her nerves and get used to new messaging.

The next test was the messaging itself. So depending on the conversation and what type of person she felt she was chatting with, she’d try a slightly different way of describing the value the Upside Foundation offers.

Time prioritization

As a team of one, Couldrey felt the weight of “doing it all” and realized she needed to better prioritize her time. One of the Upside Foundation’s best sales channels is going to events, so Couldrey found herself at over 50 events in one year, talking to founders and funders.

But the problem was that not every event was worthwhile. One useless event cost anywhere from 3 hours to 2 days when you factor in commuting + event time.

To combat this, Couldrey set up the core principles of events she would attend. The principles are based on which types of events she had success finding new Upside members or meeting other business growth goals.

Prior to attending events, she sets a specific goal based on the type of event it is and how it may align with Upside’s goals. After attending events, she does the following analysis to see if they are worth attending:

  • Was it fun?
  • Was it interesting?
  • Did I cement important relationships?
  • Did I achieve the specific goal I had for the event?
  • Did I get visibility the organization?
  • Was this an event that should have been great, but wasn’t? If so, why?
  • Was it worth it, overall?

After doing this for as many events from the past as possible and adding new events every time, Couldrey was able to create her “Event Manifesto”. This document outlines the type of events – or specific recurring events – that make the best use of her time.

It’s a living document, but she outlined the kinds of events that are best-aligned with Upside’s goals. If an upcoming event doesn’t meet at least one or two of the criteria, she now passes on it.

“The goal is that I will go to way fewer events–and only the ones that have a high likelihood of being valuable,” she said.

Embracing the process

While it sounds great to say entrepreneurs should test things, the reality is that things don’t always go as planned. Thankfully, transparency helps a lot in these cases.

Couldrey recalled speaking with a potential member about one ‘test’ she was running that didn’t produce results. So, she changed her method. The problem was that the change happened before she had the chance to explain everything to this prospect.

“He said ‘I now see you’re doing something else – what happened?’” explained Couldrey. “I was just really honest with him. I explained we were having a lot of conversations and we shifted direction. This is where we’re at now. We’re happy to have you be a part of it if you’re still open to it.”

The prospect, happy with the honesty, continued the conversations with Upside about the new direction.

“I share a lot of my process,” she said. “I share what our goals are or self-interest is. I find people are pretty responsive to that and respect you for being open and honest. When they know where you’re coming from they’re more willing to work with you on it.”

No matter what, the process is bound to not be perfect. No business growth process ever is. Instead, Couldrey advises entrepreneurs – herself included – to embrace the reality and control what you can.

“It’s a messy process,” she said. “It’s iterative. It takes time and it’s not perfect. So you just have to start where you can, continuously look for feedback and opportunities to improve, and then be as transparent as you can.”

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Images courtesy Upside Foundation