The Olympic gold and silver medallist counts rowers Marnie McBean and Silken Laumann, as well as speedskater and cyclist Clara Hughes among the guides of his competitive life.
"They were always there when I needed to ask a question," Whitfield said Tuesday in Toronto.
Whitfield wants to take on that role for the next generation of Canadian athletes.
The four-time Olympian has joined boxer Mary Spencer, sprinter Bruny Surin, soccer player Kara Lang, wheelchair racer Josh Cassidy and kayaker Mark de Jonge in a venture that provides both money and mentorship for the Canada's aspiring Olympians.
CIBC has launched a $2-million, three-year "Team Next" program. Sixty-seven athletes can each apply for $15,000 in grants and will be matched with one of those veteran athletes during the three years.
"They've been given a grant for the next three years which should help them in the transition as they move from one level of competition to a higher level of competition," Whitfield explained. "It's unique in that it gives them an opportunity to use us as sounding boards, mentors."
Spencer, a world champion boxer and 2012 Olympian from Windsor, Ont., expects to be counselling up to a dozen athletes from different sports.
"I think I'm going to be surprised with whatever ones I get," she said.
"I know I wouldn't be where I'm at without the mentors I had. I look back and there were other athletes who weren't that fortunate to have those mentors. It's a really critical phase when you're an up-and-coming athlete. You really need all the support you can have."
Whitfield and Spencer won't train with their apprentices, but will help them navigate life as a high-performance athlete.
CIBC is a sponsor of the 2015 Pan American and Parapan Games in Toronto, so the Team Next program dovetails with that sponsorship strategy.
Athletes who want into the program must be nominated by their sport federations. AthletesCAN, an association of national-team athletes, and the Canadian Sport Institute Ontario will administer the selection process. Athletes from across Canada can apply.
Prospects competing at a top provincial level or who are on a national development team will be given consideration, according to AthletesCAN executive director Jasmine Northcott.
"It's targeted at our up-and-coming athletes and athletes under the radar right now," Northcott explained. "Canadians don't know who they are and they're not on your senior national teams yet, so their access to funding is quite limited."
Northcott referred questions about financial compensation for Whitfield and the other mentors to CIBC. A bank spokesman said "we do not disclose terms."
Spencer is still competing, but Whitfield is no longer racing internationally. The 38-year-old from Kingston, Ont., says mentorship and working with a major bank has helped him adapt to his new life.
"It's a difficult transition and to be given this opportunity, to be frank, I haven't had a lot of that support in the last year," Whitfield said.
"I've created a lot of different business ventures for myself that I'm working on, but CIBC stepping forward and helping me through that transition has meant a tremendous amount. I've gone running with employees, I've been to different branches. I've had lots of different opportunities to meet with executives."
There are so many athletes based in Victoria, where he and his family live, that Whitfield expects to spend a lot of mornings in coffee shops talking with them.
"I benefited a lot through mentors throughout my career, so this is a chance to do that," he said.