Jacqueline Cook’s Journey to Building a Prairie Unicorn and Leadership Success

Vishal Teckchandani
February 9, 2022

On the day Vendasta’s Jacqueline Cook received a career-defining call that she had been selected as one of Canada’s top young leaders, she had a difficult choice to make.

Should she clink champagne glasses after work with her tight-knit executive team? Or should she go home to her husband and children? She chose family.

“I felt this award is really my family’s. When I got home, I ate cold chicken nuggets and french fries left on the stove. Everyone was ready to sleep, so I got to snuggle my little guys, give one a bottle, and tuck the other one into bed,” she says.

“And that's honestly the only way I would've celebrated: giving my boys and my husband a big squeeze, and thanking them for the time that it took to achieve this award. Well, maybe with  warm chicken nuggets.”

Cook’s inimitable trait of humility and the fact she could - and was celebrated by colleagues - for choosing family above all else underscores she’s at the forefront of a world where what defines leadership is rapidly changing. Enter an era where egalitarianism, empowerment, and sharing successes are the new normal.

In being named an honouree in Caldwell and PwC’s coveted 2021 Top 40 Under 40 list, Cook dispelled the myth that career and family are merely “competing priorities” and proven, especially to women, you can have it all.

“It’s surreal to know that everything that we've been working for at Vendasta has been recognized nationally. And I got to be the lucky recipient of that acknowledgment,” she says.

The early days: Change of strategy sees a new leader emerge

As Vendasta’s Chief Operating Officer. Cook is responsible for the development and execution of Vendasta’s revenue and go-to-market strategy. She plays an instrumental role in raising and allocating capital.

After having a stint at running her own business for several years, she joined Vendasta, headquartered in the Canadian prairie province of Saskatchewan, as a Partnership Development Specialist in early 2014 when the company had only around 50 employees, compared to nearly 600 today.

In the early years, Cook encouraged the business to shift away from expensive and slow-cycle sales methods designed to acquire enterprise customers towards a product, value, and education-led proposition aimed at the middle market, being digital agencies selling services to small and medium businesses (SMB).

This pivot saw Vendasta acquire more customers at a lower cost, while significantly widening its total addressable market. Within three years, mid-market customers outperformed their enterprise peers on all key metrics and now account for nearly 70 percent of revenue.

Impressed by her operational drive and strategic vision, Cook was elevated to Chief Strategy Officer in 2017 by Vendasta CEO Brendan King. A year later, she played a leading role in raising C$40 million for the company.

Following countless roadshow presentations to advisors and potential investors (who often needed to be educated on where Saskatchewan is), Cook worked with a core team to secure a historic and oversubscribed C$120 million private placement in May 2021. And she did it all virtually, with a newborn on her lap, days after her second son was born.

Raising capital not the be-all and end-all

While raising capital is a lucid dream for most entrepreneurs, Cook’s advice, paradoxically, is to not do it.

“A lot of tech companies look at raising money as the end. Raising money is a means to an end, it's a means to a greater milestone of your career,” she says.

Instead, start-ups should focus on boosting sales by creating a product people enjoy and want to pay for.

“Venture capital should accelerate that, not replace that. And that’s the thinking a lot of tech companies are missing,” she says.

“Everyone wants to be the next success story and follow in the footsteps of the Atlassians, AirBnBs, and DoorDashes of the world. Yes, there is a lot of money sitting around but that doesn’t have value until you put it to work and create value with it.”

In her mentoring initiatives, Cook often reminds aspiring founders to try and solve “real problems” rather than create technology first and then figure out if it’s useful.

“Get to know the problem space deeply rather than the solution space. Become an expert. People pay for you to solve a problem, they don’t necessarily pay you for a product. Raise money from your customers by obsessing about their problems more than anyone has the patience and drive to,” she says.

Check metrics: The ultimate guardrails for growth businesses

Another important business lesson from Cook is that founders, executives, and investors shouldn’t be hoodwinked by “north star metrics” (NSM).

NSMs have become increasingly popular among companies, especially in technology. They usually denote an indicator of revenue, customer value, and measurement of progress. As an example, Airbnb’s NSM is “number of nights booked” as it correlates to profitability and usage of its short-term rental platform by hosts and guests.

But NSMs can be misleading. As an example, if Airbnb ran a promotion offering homes for $1 a night, then usage would surge but revenue would decline, though it might feel delightful for a CEO to say - and investors to hear - that the number of nights booked jumped when in reality profit margins sunk.

That’s why Cook advocates that NSMs should be linked to “check metrics” which act as guardrails to ensure key business goals are achieved in a sustainable way and prevent strategies designed to game them.

“Are customers buying a million units of a $1 item compared to one unit of a $1 million item? Those are check metrics of one another - one captures quantity, generally, and one captures value,” she says.

“For us, we measure the total value of the products and services being purchased through the Vendasta platform and marketplace, measured by Gross Merchandise Volume, and our check metric is the total transactions, which is the factor of the number of small businesses and the products and services they purchase. 

“The first captures value, the second captures volume and if more local businesses are buying products and services, then agencies and vendors are proving their value and our whole ecosystem is growing.”

Sport, travel, and Barack Obama

For someone who’s not even hit age 40, Cook has racked up a stellar list of achievements.

She’s part of the C-suite at a booming technology company, she’s raised eye-watering amounts of capital and won one of Canada’s most prestigious leadership awards - all while becoming a proud mother to two children, and a wife.

But those are just her main gigs. On the side, Cook has served as a board member for non-profits including Recess Guardians, which aims to reduce bullying in Canada, and Care & Share Saskatoon, which supports inner-city children by funding sports and literacy programs.

Cook is also a founding board member of Co.Labs, Saskatchewan’s first technology accelerator. She and her husband have invested in over 10 startups across Canada and dedicate their own time to mentoring, judging local competitions, and speaking at events.

It’s hard not to be inspired by what she’s done. So what can young professionals and business students do to follow in her footsteps? For a start, pick up a sport and go travel (when it’s safe to do so of course).

She attributes much of her career success to soccer and exploring the world, describing herself as “not a model student” and someone who didn’t get “straight As” while studying commerce at the University of Saskatchewan.

Regrets and missed opportunities

As good as the journey has been, Cook has some regrets and a strong message for students undertaking post-secondary education.

Though she came back to finish her degree, she feels she didn’t make the most out of her time at university in social and extracurricular contexts, lamenting that she didn’t have more of what she calls “accidental collisions.”

“An accidental collision about opening yourself up to something that's outside of your norm, so meeting people that are outside of your sphere of influence and going places that you wouldn't always,” Cook says.

Students need to realize that university is a one-way escalator. It keeps going, and once at the top floor, there’s no going back for all the things one wishes they could have done.

“Your time in university - you blink and it's over. So get out of your comfort zone in as many dimensions as you possibly can because there’s so much of the world that you don’t know, and this is the time to explore and play with that before you jump into the next 30 years of your career,” she says.

“Because if you squirrel around too much, then you're not actually creating depth in your career. University allows for you to iterate your passions as much as you can in that timeframe.”

A bright future for local businesses and agencies

While she’s proud and thankful for her accomplishments, Cook’s attention is squarely on the future, which she believes is bright for local businesses and the digital agencies who serve them. And Vendasta’s sole goal is to fuel their success.

The pandemic remains an ongoing issue, but underlying demand at a global level is strong and unemployment is falling, which puts SMBs in a good position to benefit when consumers eventually return to shops, restaurants, and salons in droves as health restrictions ease.

However, the reality is the way people are buying things and interacting with local businesses is changing, and Cook says agencies need to play a leadership role in helping SMBs adapt to evolving and increasingly digital purchasing habits.

“Local businesses are the lifeblood of our economy and we want to work with agencies to help business owners adapt to digital ways of doing business and win,” she says.

“Being the best in the world at understanding their problems is where agency owners will succeed. They should know deeply what their customers’ problems are, and then match the appropriate technology to what that business needs.”

As for will 2022 finally be the year when Vendasta becomes Saskatchewan’s first prairie tech unicorn? “Watch this space,” Cook says.