What happens when a corporate exec bets on herself and has the right advisor

Looking back, Craven says she feels fortunate that she had been Jackson’s client for two years before she decided to launch her new business, which offers therapeutic services to restore pelvic floors. 

The two had connected in 2017 when Craven went through a divorce and needed financial advice through that major life transition, and then again when she blended families with her new husband. She liked that Jackson — effervescent and direct — was also a female leader in her field known for taking smart professional risks over the years. They “got” each other, she says. 

“UROSPOT was an idea I couldn’t shake and most people in my professional life were trying to talk me out of it,” Craven recalls. “But Jen was one of the people who didn’t. She didn’t judge. She listened and said, ‘Let’s plan and figure this out.’”

Jackson says she also knew she had found someone she would enjoy working with. Both women were attracted to “purpose-driven work,” she notes. 

“I’ve always believed in building a practice centered around strong, collaborative relationships with clients who share my values and vision,” she explains. What’s more, Jackson knew she could help smooth out some of life’s rough edges. 

“Most people in Erin's position haven't had time to tidy up their financial life because they've been so busy climbing the corporate ladder. They need someone to swoop in and organize their financial life for them.”

When working with clients, Jackson always ensures that their values, goals and aspirations are at the forefront. Her approach is to build a lifestyle-integrated plan that goes beyond retirement planning, she says. For Craven, it was about enabling her to “design her own life.”

Once Craven decided to become, in her words, a “corporate dropout,” the two quickly got to work. While her entrepreneurial ambitions were bold, she also needed a solid financial strategy. Jackson’s approach focused on simplicity: breaking down major financial moves into more manageable steps, consolidating assets and proactively adjusting plans as circumstances changed. Alongside Craven’s new husband, who eventually left his own corporate career for UROSPOT, they bounced ideas off each other. 

Step by step, Jackson helped to reframe the couple's financial life, working with them to create a crucial financial buffer when loans and private capital proved elusive.

UROSPOT quickly grew from a single private pelvic health and urology clinic in London to two locations with the addition of Toronto. Within a year, the company launched a franchising system in October 2020, hitting company targets despite a two-month pandemic shutdown. Today, UROSPOT spans 24 locations from Ottawa to Victoria, BC, including its newest clinic in Vancouver — a milestone Ms. Craven had long envisioned — and a clinic opening in the U.K. this fall.

Jackson’s ability to create a robust financial plan that integrated their lifestyle goals makes all the difference, says Ms. Craven. She's able to have a "top view" of their needs to ensure all the moving pieces fit together. Jackson frequently revisits the couple's plan and, with her clients’ blessing, makes changes so the couple can put their energy into what matters.

“They're not as focused on their wealth. Their energy is devoted to their family and UROSPOT,” she says. 

With the business now thriving, Craven’s leap from corporate executive to entrepreneur looks less like a gamble and more like a carefully calculated move. But Craven says she never felt she was navigating the pivot alone — even today amidst so much global economic uncertainty. 

“I felt we were very much in the right hands,” she says. “Jen has just always been there to answer questions and guide us to get the results we want.”

Jackson notes that in times of economic turbulence, a good advisor’s role is to help clients navigate uncertainty by providing clarity and perspective.

“I talk with clients candidly and transparently to keep them on track,” she says. “I have them focus on their financial plan. ‘Are you still on track for 2030? Let’s focus on the things we can control and not the things we cannot control.’”

She has this advice for women who are looking to find the right fit with a financial advisor: Trust is number one. 

“Women need to realize that it's going to be a multi-decade relationship. Are you comfortable putting your kids in front of this person someday?” Jackson says. “You want to work with somebody who’s willing to do a lot of work up front to establish that foundation of trust.”