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Tim Jennings: determined, inventive, inclusive
Shaw's executive director Tim Jennings. Supplied

The executive director and CEO of the Shaw Festival has had a challenging five years in the job. He has helped lead the transformation of the festival’s performance vision, its return to fiscal health and an almost military-like campaign to fend off the COVID-19 pandemic.

But Tim Jennings seems inspired by the challenges.

“Some of my colleagues are saying: ‘It’s great finding extra time to do things, very useful,’ ” says Jennings, 50. “I don’t think I’ve worked less than 80 hours a week since March.” 

He says it proudly. At age 12 his parents brought him to see the 1981 production of “Cyrano de Bergerac” at the Shaw. He was so enthralled by the production, he vowed not only to find a career path to manage theatres in general, but the Shaw Festival specifically. 

“It was very inspiring. It was beautiful. It was poetic. It really solidified my interest in the theatre as a potential career.”

Everything in his educational and career lives has pointed him toward Niagara-on-the-Lake and the Shaw Festival.

Jennings grew up in Georgetown, Ont., the son of the acting provincial deputy minister of energy. It was, in his own words, a quite well-off family.

“My parents started to take me to theatre at about the age of seven,” he says. “I can remember going to the Young People’s Theatre. I think “Curse of the Werewolf” was my first production.”

The young Jennings had virtually no television growing up. “My parents were committed to us reading. Plays and art were part of our life. Sometimes I read two books a day.”

Jennings’ great-great grandmother, Elizabeth Warren (Mrs. H. D. Warren, he makes sure to clarify how everyone knew her), had a profound effect on his life. “She was the only female founding board member of the ROM, the AGO, the U of T School of Social Work. And she instilled in the family the importance of philanthropy.”

“I was around a lot of people who gave a lot of money to charity. So, I thought I could probably get quite good at this. As a result, I developed an interest in an inclusive theatre environment.”

His odyssey into the theatre had a rocky start.

At age 17, when he decided to go into the theatre, his father effectively kicked him out of the house, refusing to pay for school.

“So, I moved out to Toronto, putting myself through Humber College, working weekends backstage in theatres. I was the first and only graduate of Humber’s short-lived stage management program.” 

He and his father reconciled early in his career. 

“He apologized,” remembers Jennings. “I think it as the only argument we ever had of any significance. In fact, he became quite a big fan of the work I was doing.”

Jennings’ early career saw him in teaching and stage technical roles at Humber and Ryerson. Over the last 20-plus years he has held senior management positions in Guelph, Toronto, Seattle and Minneapolis, running the Children’s Theatre Company in Minneapolis-St. Paul, just before taking up his role at Shaw in 2015. 

Along the way, he developed a robust consulting practice helping smaller theatres realize their production and touring aspirations. And he attended over 200 arts marketplaces around the world, peddling Canadian theatre on behalf of the federal government.

Jennings is married to Truly Carmichael, an award-winning costumer and milliner with a master of fine arts degree in theatre costume technology and design, specializing in historic garments. She often works as a costumer for Shaw productions.

“She is a very rare cat,” Jennings says proudly. “Very talented.”

They have a 20-year-old son, who is studying IT and data security.

Jennings’ drive to run the Shaw Festival wasn’t just about his devotion to theatre management, he admired Shaw the man, his approach to theatre and to Fabian socialism.

“In college my friends would make fun of me because I carried around a copy of Shaw’s “Man and Superman” and Mao’s “Little Red Book,'' in my back pocket,” he chuckles. “I was a bit more socialist than most people.

“As only kids that come from well-off families can, I started to think there was a line between socialism and charitable function that made sense to me. 

“I’ve carried that with me. It’s a big part of who I am.”

Jennings describes the biggest Shaw challenge in his tenure, prior to the pandemic, as pivoting against the mandates of earlier leadership.

“We decided that there wasn’t a strict mandate. Rather, we had a vision that we were being provoked by the civic period of GBS to create theatre that was relevant, exciting, entertaining and more inclusive than it had been.

“And we would do that, any way we felt like.’

Jennings admits the 58-year-old theatre festival took a lot of risks. 

“It was hard,” he says with an audible sigh. “We were taking big risks and I would lose sleep at night thinking we're going to alienate 40,000 attendees. But hopefully we’ll get 60,000 back in the door.”

“And we did. It resonated somehow in this current moment and that has been terrific,” he says.

“It paid off: 2018 and 2019 were the two best financial years in the history of the theatre. I think people felt more connected.”

Along came the pandemic.

It’s well-documented that Shaw Festival has survived through the pandemic, largely because Jennings and his team had the foresight to purchase pandemic performance interruption insurance. And not single show interruption, but for all 750 shows in their season.

“It allowed us to make some different kinds of decisions,” says Jennings. “It allowed us to keep our company going all summer. We continued to employ 99 per cent of our company until the end of August.

“Our duty was to keep the people whole. My number 1 job is making sure the artists and artisans and arts workers have a stable place to work from.”

“I’ve always focused on the people, not the buildings. Anything else can be rebuilt.”

It’s not hard to imagine that many of his peers think he is a bit of a guru. “Literally everybody I talk to in the industry says, ‘I wish I was with you guys.’ ”

And he is also considered a bit of a grant-whisperer. Not only can he smell a new government support program from a long way off, he has the connections and the creativity to find ways to take advantage of the opportunities.

He gives most of the credit for turning grants into actionable programs to artistic director Tim Carroll and his associate artistic director, Kimberley Rampersad.

“If I find a grant, Tim and Kimberley jump to it and figure out a way to work with it — how are we going to make something beautiful and make it a part of what we are?”

This fall's free outdoor music concerts are a case in point.

Jennings was able to convince the federal government that because the festival was healthy and local tourism businesses were not, it should sponsor a series of what will be more than 40 concerts this autumn.

“We were able to show that for every dollar someone spends on theatre tickets, they spend $3 to $8 more being here. For food, accommodation, tours, bike rentals and so on.”

Jennings is hesitant to give too much away, too soon, about the 2021 season. He has already presented ideas about moving forward to the festival board.

“We’re not just remounting the 2020 season. We’ve come up with a version of it that will include some of the things we were planning on doing and a couple of small new things,” he says.

“We’ve budgeted in way that assumes some physical distancing at the start of the season that would lighten up as it gets toward the end. And we’ve changed or reduced the number of performances.”

He expects details of the 2021 season to be announced in mid-October.

Underpinning all Jennings’ thoughts, remains a current of optimism.

“2020 should have been the next step in our fiscal and creative evolution. I am saddened we are delayed. But I am happy whatever we do from here is growing momentum.”

“The Shaw Festival is a kind of beautiful attitude and stick-with-it-ness that is derived from our provocateur, Mr. Shaw,” he says.

“We are in a really good position to move forward out of this.”

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