Pride and prejudice with industry veteran Christopher Ashby

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When Mary and Joseph tried checking into that famous inn over 2,000 years ago, they failed to take into account one major strategy: booking in advance. As the world knows, they eventually found….other accommodations.

According to veteran hotel sales and marketing executive Christopher Ashby, whose current role is director of sales and marketing at Old Mill Toronto Hotel, some things really haven’t changed that much while other elements of hospitality have wholly transformed.

Old Mill Toronto Hotel

Ashby says that hotels are typically very traditional environments.

“What’s changed is the ornateness, the size and the number of services offered, “ he says, “but the fundamentals haven’t changed that much at all.”

A major player in the accommodations industry for over 40 years and a board member of the Hospitality Sales and Marketing Association International (HSMAI), Ashby has fulfilled various roles with over 16 hotels throughout his career. He’s been charged with opening three hotels, closing one, and rebranding another. He’s done taskforce work for an additional three hotels, and worked for both independents and major chains, with most of his career spent in the luxury sector. Throughout the years, there have been peaks and valleys, successes and losses, and Ashby’s been a keen observer of and participant in many of these highs and lows.


The journey to management began with an auspicious debut—shortly after a young Ashby was hired for a role at L’Hotel he felt a certain degree of vulnerability, and this compelled him to out himself before starting the job. “The corporate office’s actions made one believe that homosexuality didn’t exist within the executive level and it was a very male-dominated environment,” he says. “The only women in executive roles were housekeepers.”

Things began to shift in the 1980s with the corresponding rise of HIV / AIDS, he says. “The next generation was much more liberal. The tide’s not completely turned but there’s been substantial social change.”

Ashby notes that women and gay men were both facing a glass ceiling in the accommodations sector back then and shared experiences of prejudice and facing roadblocks in their career development.

Fortunately, that changed over time, and Ashby now sees being gay as an asset to his role. “It’s provided opportunities,” he says. “Human resources spends hours trying to be responsive to different audiences because diversity is now front and centre in the HR world.”

As a manager, Ashby has leveraged his position to be a lightning rod for staff sharing stories of perceived obstacles, while in turn creating leadership opportunities for his charges.

After many setbacks, the LGBTQ2S+ community is now fairly well represented and accepted within the accommodations industry, at all levels, and this has generated positive business outcomes as demonstrated by the willingness of hotels to market themselves as inclusive, welcoming and safe spaces for LGBTQ2S+ travellers. Not only that, but gay travellers seem to have more disposable income, a fact not unnoticed by savvy hotel marketing specialists.

In a 2015 study conducted by Global Marketing, the behaviour of gay male travellers differed from lesbian travellers in several ways: gay men were more likely to travel with other adults, visit gay bars, and have more disposable time and income; lesbian travellers were more likely to travel with family, be more interested in child-friendly rather than LGBTQ2S+ friendly environments, and have travel preferences and budget constraints more closely aligned with people who are not LGTBQ2S+ than to gay men. People who are transgender might be more likely to travel for medical reasons, seeking high-quality and affirmational medical and surgical care.

A more recent impact on the sector has been navigating the devastating blow to the industry caused by COVID-19. Overnight thousands of people lost their jobs. “Restaurant staff who had been on the job for 25 years were now gone,” he says. “I was one of those casualties.” During the pandemic, many who lost their jobs transitioned their skills into new roles outside of the hotel industry and when the smoke had cleared it became difficult to find new talent to fill old roles.

“Housekeeping roles were difficult to fill and they were one of the first teams needed to return when the industry started its recovery,” Ashby notes.

And while the economic effects of COVID-19 are still being felt, both the industry’s profits and people’s travel patterns are gradually returning to pre-pandemic levels.

Building a sense of ‘destination’ in the city

Located in Toronto’s west end, the Old Mill Toronto Hotel currently stands near the original site of Toronto’s first sawmill, built in 1793. A series of fires destroyed subsequent mills, the last one in 1881. Its ruins stood on the property until 2000. In 1914 The Old Mill Tea Garden restaurant was opened by developer Robert Home Smith next to the mill’s ruins. Over the following decades, 16 banquet rooms were added, and during the 1980s, a wedding chapel. In 2001, the hotel was added on the grounds of the Mill’s ruins, using the original stones to create the lower level of the grand Tudor-style hotel which now stands adjacent to the 1914 restaurant as a kind of homage to times past.

Today the Old Mill Toronto Hotel, now owned by OMT Hotel Management Inc., is a luxury boutique accommodation that boasts 57 rooms of varying styles and suites, a spa and a setting surrounded by nature, steps from the Humber River.

One of the newer additions to the hotel’s repertoire is the recent acquisition of its sales and marketing director.

“The Old Mill is something out of a storybook,” says Ashby. “It’s a destination within the city. This is a place where memories are made.”

“I love the diversity of the job,” he continues. “Every day offers new areas to play in and you’re impacting people’s lives in a positive way. It’s what’s kept me going year after year.”

Career Highlights

Christopher Ashby has held various marketing and operational positions across the hotel industry including sales manager, general manager, director of marketing, consultant and board member with renowned organizations including:

Dymon Group of Companies

• Marriott International

• Shangri-La Hotels and Resorts

• Courtyard by Marriott Downtown Toronto

• InterContinental Hotels Group (IHG)

• The Sutton Place Hotel Toronto


• Windsor Arms Hotel Toronto

• Four Seasons Hotel Toronto

• HSMAI Ontario

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