Helen Radford does the same for Jamie Murphy's team from Nova Scotia.
Female coaches at the Tim Hortons Brier are a recent development and this is believed to be the first year there are two. Both Montgomery and Radford are coaching teams at the Brier for the first time in their careers.
Montgomery played third for Saskatchewan's Sherry Anderson at the 1994 and 1995 Canadian women's curling championship. Radford was third for Colleen Jones at the 1997 Scotties Tournament of Hearts.
Both agreed a female coach at the Brier would have been unheard of in the mid-1990s.
"Absolutely at one time it was," Montgomery said. "It's new for the Brier to have female coaches in the competition, absolutely."
Said Saskatchewan skip Scott Manners: "We might be the first Saskatchewan team to ever have a female coach, but I don't know that for sure. We might be."
It would be easy to chalk up their presence here to a change in the men's attitude, but it's also been a matter of getting women qualified to coach at this level. Montgomery, 56, is a nationally certified coach and has a masters degree in psychology.
"There's still room for more women," she said. "I was out at Scotties too and I believe there were only two women on the coach's benches there. We're working hard to increase the numbers."
Radford, also executive director of Curl Nova Scotia, says the introduction of curling at the 1998 Winter Olympics amplified the role of the curling coach.
The demands of the sport now are such that four players and an alternate need both a critical mind to assist in decision-making and an assistant to help manage the demands of a marathon like the Brier.
"I think coaching itself has become a little bit more in the forefront for a lot of teams," Radford said. "They're starting to use coaches for various reasons. I think teams are starting to recognize there's a lot to the game now, they have a lot of responsibility, so it's helpful to have somebody with experience who can help them out."
Added Montgomery: "All across the board, teams are looking for skilled coaches whether they're male or female. Teams want to represent at the highest level they can, so they're looking for skilled coaches, but I don't think gender comes into it."
Montgomery seems to have more input with Saskatchewan when they're debating their next shot than the 43-year-old Radford, who says she prefers to stay under the radar.
"She's definitely a good facilitator and helpful in putting together our schedule this week and keeping things on track," Murphy says of his coach. "From a strategy perspective, we're pretty good on our own, but it doesn't hurt to have a set of eyes from behind the scoreboard to give us some influence sometimes."
Nova Scotia's record was 4-4 and Saskatchewan's was 2-7 following the 13th draw on Wednesday afternoon.
The major difference between men's and women's curling is men have more power to execute big-weight shots and they strategize with that in mind. Women play more of a finesse game, so Montgomery says she's adjusted her thinking to how a man might play a shot.
"I come off of the women's playing field and that's the very first thing I have to do when I walk out to a timeout, is reflect what their thoughts are and what they're thinking in the situation," she explains.
"I'm not telling them the shot to make, but I'm helping them problem-solve. They come with a different set of skills than the women do, although having said that women now are working so hard to bring that power to their game. Men do have more explosive, muscle-power than women so that plays out in the game."
As much as the Manners and Murphy teams are learning in their first Brier, so are their coaches.
"You can't learn it any other way other than stepping out there and putting yourself on the line, taking the risk and seeing where the chips fall," Montgomery said. "I'm learning every bit as much as these gentlemen."