Canadian Underwriter

Culture Continuity

November 1, 2012   by Daryl Angier and Regan Reid

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Baird MacGregor Insurance Brokers sits on the corner of Queen Street East and Empire Avenue in Toronto in a heritage building full of character, intentionally removed from the bustle of the downtown core. It’s just one of a number of things that makes the brokerage a unique place to work.

Since its inception, management at the brokerage has been committed to creating a welcoming environment for its employees that fosters loyalty and achievement. Philomena Comerford, the firm’s president and chief executive officer, credits the commitment to this culture as part of her own successful transition from senior manager to full owner. Moreover, ensuring this culture is maintained will be a key priority in her eventual succession plan. 

Committed to Culture

Creating a distinctive work environment was an important goal for the founders from the beginning. Jack Baird and Harry MacGregor opened Baird MacGregor Insurance Agency on April 1, 1979 (choosing the date deliberately) with the goal of establishing something different from the large brokerage they had both left behind. “We decided that we were going to have an environment that we would enjoy, because we weren’t happy with the environment that we [had] left,” says Baird. The brokerage began as a joint venture with Kopas Wray and Cameron Insurance Agency Limited, before becoming Wray Baird MacGregor Insurance Brokers Limited in 1981 and eventually Baird MacGregor Insurance Brokers in 1988. Comerford had previously worked with Baird and MacGregor at Tomenson Saunders Whitehead.

Her career began in claims before moving into TSW’s commercial department. She notes that a number of people who apprenticed there went on to have successful careers, many becoming brokerage owners themselves.MacGregor and Baird recruited her to join them in 1980. “Jack was very technical in his approach and Harry was a great relationship builder. I was probably somewhere in between the two of them, but we worked very well together over the years,” says Comerford. One of the firm’s first clients was Somerville Car and Truck Rental—a client they still represent today—and commercial transportation has remained an important part of Baird MacGregor’s business ever since. Today, roughly 95% of the firm’s business comes from a diversified commercial lines portfolio, with a significant portion of it made up of rental fleets, long haul trucking, dealerships, and limousine and taxi fleets.

I didn’t want to get thrown into some maelstrom where you’re put into a situation that’s not a good fit culturally.

As Baird MacGregor’s business continued to grow, the founders’ commitment to providing an inviting work environment remained the same. In 1989, the firm moved to its current home, a 20,000 sq ft, two-storey redbrick century building in Toronto’s east end. “It was [Harry and Jack’s] vision to say, let’s be a little bit different. Let’s get out of the steel and glass and go into a little more eclectic environment,” says Comerford. And Empire House, as the building is known, is certainly eclectic. The second floor of the office is home to a gym and large 1950s-style diner, equipped with blue leather booths, a jukebox and lunch counter. The diner serves as both an employee lunchroom and party venue. Every September since 1991, the office celebrates a themed black tie event for the “Survivor’s Club,” recognizing  all employees who have been with the company for more than four years. Comerford says this celebration has become a cherished tradition of the firm.

In addition to its out-of-the-ordinary amenities, Baird MacGregor has developed a distinct work atmosphere. “I think that our culture is quite unique,” says Comerford. “It is a very open environment, very communicative and everybody works hard, but they have a lot of fun.” The company has flexible hours, easy access to management, and profit sharing for every member of the company. “We would try to impress upon [the staff] the reality that we were an entrepreneurial firm and that every wasted dollar was going to cost them money and every earned dollar was going to make them money,” says Baird. The firm now has 80 employees, many of whom have been with the company for decades and many younger staff members are the children of these long-term employees.


From the very beginning of the company, the two founding partners were unconsciously building a succession plan into the management structure of the firm. Baird says that he and MacGregor were sales people first and foremost. The two recruited Comerford to help run the business and look after the aspects of management they were less inclined to deal with.

“[Comerford] wasn’t oriented or inclined to sales at the time, but she wanted to join us as the technical backup,” says Baird. “We also hired a number of other people over the years, most of whom she had some previous background with. So she knew the people, she knew the accounts, she knew us. There were  very few people that could handle us, I suppose. We asked her a number of times to take over as president, because neither Harry or I saw ourselves as that kind of person.”

Throughout the ‘80s, Comerford continued to develop her business acumen while becoming quite active in the insurance industry at the same time. She served as chair of the Insurance Institute of Canada, had sat on many of its boards, and had developed good relationships with many underwriters. The respect she earned helped her when she became a coordinator with the Insurance Community Action Network to fight the Ontario NDP’s plan to make auto insurance a government program. She helped organize a rally at Toronto City Hall to oppose the plan, which attracted thousands of people and significant media attention.

Comerford finally accepted the role of president of Baird MacGregor in 1990. Though both the founding partners continued working with the company for another 17 years, they knew that the company needed a long-term a plan. MacGregor and Baird felt at the time that it was unlikely that their children would take over the business. “We thought that the right thing to do [was] to be totally objective about it. She was the best person so we appointed her,” says Baird. “Not only was she a terrific manager, she was also very effective in terms of developing new business on her own, but also helping other people develop their business and through that process teaching them.”


Comerford’s stewardship of the company ensured the culture MacGregor and Baird first created would flourish and grow. Nevertheless, key elements of the firm’s succession plan still needed to be put in place: a plan for the transfer of ownership and the financing to facilitate it.

While Comerford had been appointed president in 1990, she did not become formally integrated into the ownership structure until 2000. In that year, after a number of potential investors had approached the brokerage and been rebuffed, the partners entered into an agreement with Federated Insurance Agencies, a division of Co-Operators. Federated bought 50% of the firm’s equity and the remaining half was split equally between Baird, MacGregor and Comerford. Though partnering with an insurance company could pose certain concerns to other insurance companies, Baird insists there was absolutely no condition that the firm had to place any business with Co-Operators. “It allowed us to honestly be able to say to clients, ‘We’re not in anybody’s pocket. We have outside investors, and they’re absolutely, totally passive,’ ” he says.

When the management of Co-Operators changed in 2004, the Bank of Montreal provided the funding for Baird, MacGregor and Comerford to buy back Federated’s 50% share, making them three equal partners in the firm. “That was a good solution because the ownership structure of the company is very important from the perspective of the marketplace and our clients, too,” says Comerford. “[It] was very acceptable to our markets, that we were buying back as opposed to having the consolidator coming in, or insurance company investment.”

When Baird and MacGregor retired in 2007, Comerford brought in an equity partner to buy out their interest and complete the succession process. “I thought it would be good to have an equity partner capital source,” she says, as completing the buyout of her partners was daunting for her to take on by herself. “I thought it was a heart attack on a platter. It was a pretty big number.” Comerford took an assignment letter to every market to let them know she was bringing in Newport Partners, an income trust, as her partner. “One of those meetings was with George [Cooke of The Dominion] and he said, ‘I’m sure glad it’s not an insurer, because as much as I like you, I wouldn’t be doing business with you.’ ” Comerford says Newport respected the partnership and allowed her to continue running the business as she saw fit. But she did have to adapt to its strict financial reporting requirements. “That was very good for us,” says Comerford. “Our internal controls, financial reporting and budget processes became much more formal [and there was] significantly more engagement from all the department heads.”

Newport had also invested in another brokerage, Hargraft Shofield LP, first established in 1874. In 2009, after some administration changes at Hargraft, Newport asked Comerford to take over the brokerage. On September 30 of that year, Hargraft came under the management of Baird MacGregor.

Eventually, Newport’s involvement in the financial services sector began to wane and Comerford again had to think about finding another financial partner. “They wanted to pay down their debt and they were buying out some of their other minority partners of their other businesses,” she says. “I guess I was a bit of a neophyte that I didn’t realize that equity capital has a lifespan and they quite often like to redeploy their capital somewhere else,” she says. In July 2011, Comerford again partnered with BMO and bought back Newport’s interest in Baird MacGregor as well as Hargraft, making her the sole owner of both firms, and allowing her to retain full control of the business on her own terms. “A lot of what drove that decision was how we feel about our culture. I didn’t want to get thrown into some maelstrom where you’re [put] into a situation [that’s] not really a good fit culturally [and] with how you see yourselves going forward,” she says. 

Looking Forward

When it is time for Comerford herself to move forward she knows she must plan to preserve all that makes Baird MacGregor unique. “I really [feel] a passionate commitment to sustaining what I think is a really good culture,” she says. Comerford notes that her executive committee has begun long-term strategic planning, and an important agenda item is choosing an appropriate successor. Finding the right person to maintain that commitment to staff, open atmosphere and team environment will be a challenge.

“Power is a double edge sword; in the wrong hands it can be a very damaging thing,” she says. “Finding people who  will take the mantle of that responsibility, with a degree of maturity—who  will use whatever authority goes with that role wisely is critical, because that’s what keeps an organization healthy.”

Keeping the best interests of the company and its employees in mind is important, but her successor must also be able to be handle all aspects of the business. “One day  I’m working on a complex claim file, the next  I’m talking [to] the bank…. The next , I’m out doing a presentation on a new program we’re putting together. The next day  the staff is asking me [about] a directional or tactical issue. It’s that range of skills an entrepreneurial leader needs to sustain the organization’s momentum. Finding someone who  has the scope  to be able to calmly deal with all of these things is key.” She says the company is now working on developing its younger talent while continuing to mentor senior seasoned staff and will look  to promote from within, but knows that whoever eventually takes over will need time to grow into the role.

“There are no shortcuts, it takes time to develop the skill sets needed to lead the firm, the confidence and the maturity to work effectively through the challenges and capitalize on the opportunities that move the organization forward.”


Copyright 2012 Rogers Publishing Ltd. This article first appeared in the September 2012 edition of Canadian Insurance Top Broker magazine.

This story was originally published by Canadian Insurance Top Broker.