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

“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.

“You can talk to 20 people and you will get 20 different approaches for the right way to position what you’re offering”

Jen Couldrey

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.”

“People … respect you for being open and honest”

Jen Couldrey

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.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.