Entrepreneurial example of love what you do

Winnipeg-based Stone HR Strategies celebrates decade of helping lift small-, medium-sized businesses across continent

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Others might have been reaching for a beer, but Derek Rolstone was thinking about work.

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Others might have been reaching for a beer, but Derek Rolstone was thinking about work.

While watching the Toronto Blue Jays compete against the Los Angeles Dodgers in Game 3 of the World Series last week, the Winnipeg-based human resources professional looked at Barbara, his wife of 25 years, and said he was going to do some work while taking in the rest of the game.

“‘I have so much work to do,’” Rolstone recalls telling his wife.

Her response: “‘Yeah, but you love it.’”

MIKE SUDOMA / FREE PRESS
‘Success to me is when people actually are so buttoned down on the HR stuff that they don’t need to call us anymore,’ says Stone HR Strategies founder and president Derek Rolstone in his office on Fort Whyte Way.
MIKE SUDOMA / FREE PRESS

‘Success to me is when people actually are so buttoned down on the HR stuff that they don’t need to call us anymore,’ says Stone HR Strategies founder and president Derek Rolstone in his office on Fort Whyte Way.

The 56-year-old founder and president of Stone HR Strategies is passionate about what he does. Rolstone brings nearly three decades of experience to the business, a full service human resources consulting organization with more than 200 clients across North America.

Rolstone believes in strategic HR that is bottom-line driven and committed to attracting, retaining and engaging employees. The company works primarily with small- and medium-sized organizations.

Need assistance recruiting employees, setting up a new benefits plan or building a stronger team? Rolstone and the 15 subcontractors he works with can help.

Looking for someone to write a job description, an offer letter or performance review form? They can assist you there, too.

Do you need to do a detailed reference check, come up with a holiday party policy or outline an orientation program? It’s Rolstone to the rescue.

Some have called Stone HR Strategies their Swiss army knife, others describe the company as a security blanket and a few have called Rolstone a fixer — all ways of saying he and his subcontractors bring expertise and are adaptable.

The variety is one of the things the father of two and one-time Jeopardy! contestant most enjoys about his work. “Every day is different and we never get bored,” he says.

MIKE SUDOMA / FREE PRESS
Stone HR Strategies is located at 100-105 Fort Whyte Way.
MIKE SUDOMA / FREE PRESS

Stone HR Strategies is located at 100-105 Fort Whyte Way.

Born to a father who worked in textiles and a mother who was a homemaker, Rolstone grew up in the Charleswood neighbourhood of Winnipeg. He earned a degree in political science at Western University in London, Ont., and then an MBA at the University of Victoria.

Rolstone took a few human resources courses at UVic and then was thrown into the HR deep end during a practicum at Kleysen Group Ltd. in Winnipeg. Roger Ramsay, then-vice-president of human resources at the trucking company, tasked Rolstone with devising a new compensation system for the business.

During a time before internet searches and ChatGPT, Rolstone headed to the library at the University of Manitoba’s business school to figure out what a broadband pay system was and how to implement one.

By the time the practicum was over, Kleysen Group was preparing to adopt the system and Rolstone had something he could write about for his master’s thesis.

After graduation, Rolstone worked as the HR director at a number of companies, including Pepsi Bottling Group, Suncor Energy and TransX. He also worked in politics for a few years, serving as chief of staff for B.C. premier Gordon Campbell from 2003 to 2005 and as Winnipeg mayor Sam Katz’s policy adviser in 2011.

By 2014, Rolstone had transitioned to teaching human resources at Red River College Polytechnic. He started Stone HR Strategies as a side hustle that year after finding there were many business leaders — former high school classmates, people he played squash with, neighbours on his street — who had 10 or 30 employees but no HR help.

So, he started helping them.

“You don’t need a full-time HR person until you have maybe 80 employees (and) you don’t need a part-time one until you have maybe 50,” Rolstone says. “So there’s that place in the middle where (people) need help.”

In 2018, Rolstone left RRC Polytech to focus on his company full-time. The move did not surprise Ramsay, who has been a mentor to Rolstone ever since that practicum at Kleysen Group.

“I think it’s in his nature to be an entrepreneur,” Ramsay says.

MIKE SUDOMA / FREE PRESS
Rolstone (right) and HR consultant Sara Baldwin outside Stone HR Strategies at 100-105 Fort Whyte Way in the Eye for Business centre.
MIKE SUDOMA / FREE PRESS

Rolstone (right) and HR consultant Sara Baldwin outside Stone HR Strategies at 100-105 Fort Whyte Way in the Eye for Business centre.

When Rolstone was working for other companies, Ramsay always got the sense that he was looking for “the leeway of an entrepreneur.”

“Then he decided to go independent and be an entrepreneur and I remember thinking, ‘Finally, he’s the boss,’” Ramsay says. “And the rest is history.”

In addition to working for businesses such as Old Dutch, Farmery and Winter’s Collision Repair, Stone and his team are the in-house HR consultants for Sport Manitoba and also work with numerous arts and religious non-profits.

Talent acquisition management accounts for about 50 per cent of what the company does, Rolstone says. To do that, he works with Theresa Bolton of Customized Recruitment. Stone HR Strategies has done more than 1,700 searches and is the biggest user of Indeed.ca in Manitoba.

Bolton says she reached out to Rolstone when she started her business five years ago because she saw a natural synergy between his HR consulting work and her background in professional recruitment.

“Success to me is when people actually are so buttoned down on the HR stuff that they don’t need to call us anymore.”

“Together, we’re able to provide fractional HR and recruitment support — being there when our clients need us without adding headcount to their organizations,” Bolton says.

Rolstone is well-connected and respected in Winnipeg’s business community, she adds.

“Derek strikes the perfect balance between being an HR professional and a business-minded strategist,” Bolton says. “HR often involves identifying risk and liabilities, which can sometimes make business decisions challenging. Derek brings a thoughtful perspective that considers both the human and business sides, helping organizations make sound, well-rounded decisions.”

Rolstone says, ultimately, everything the business does circles back to helping companies attract, retain and engage quality employees. While working with clients, he aims to teach them along the way so they can do human resources work themselves.

“Success to me is when people actually are so buttoned down on the HR stuff that they don’t need to call us anymore,” he says.

Rolstone celebrated his company’s 10th anniversary last year with a party at Little Brown Jug Brewing Co. As he looks to the future, his main goal for Stone HR Strategies is to keep doing what the company has always done.

“We just want to help as many organizations as we can implement better HR practices,” he says.

aaron.epp@freepress.mb.ca

Aaron Epp

Aaron Epp
Reporter

Aaron Epp reports on business for the Free Press. After freelancing for the paper for a decade, he joined the staff full-time in 2024. He was previously the associate editor at Canadian Mennonite. Read more about Aaron.

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