Upon meeting Bobby Bissessar, you will be struck by his poise, professionalism, and plain old friendliness, which makes sense since he’s built a successful career in customer service and experiential marketing. From the time he was a young child growing up in Trinidad and Tobago, Bobby knew the hospitality sector was where he wanted to be. His schooling and career ultimately led him to the Central Okanagan and he wouldn’t have it any other way.

Bobby - Cropped Headshot

Bobby Bissesar at Central

After graduating from the University of Victoria on Vancouver Island, Bobby worked in various marketing roles in Victoria, Vernon, Vancouver, and Kelowna. This experience led to his current role as the Marketing & Sales Manager at The Shore owned by national real estate developer RISE Commercial, Canada’s first true ‘flex-stay’ hospitality model catering to short-, mid-, and long-stay guests. The development is conveniently located across from Boyce-Gyro Beach and close to numerous amenities, making it easy to explore the best of Kelowna. 

In addition, to starting his new role at The Shore, Bobby was also recently elected to the Board of Directors of the Kelowna Pride Society and has taken on the role of Director of Communications. The volunteer position is exciting for him, as he gets to help plan events, share LGBT2Q+ stories, and execute a vision for the future of the society, as well as for the continued openness and understanding of LGBT2Q+ rights and issues in the community. 

As a proud member of the LGBT2Q+ community, Bobby was adamant that Kelowna celebrates Pride this year, even if that meant pushing back the dates and coming up with creative solutions on how to execute. “Pride is like a big hug—everyone is welcome and it’s a time and place for everyone to feel free to be who they are.” 

That’s the feeling Bobby had while attending his first ever Pride in Vancouver in 2016, with legendary BC drag queen, Joan-E. “It was an eye opening experience that showed me that everyone has a place,” Bobby said as he reflected on the day. And that is the message he and the rest of the Kelowna Pride team want everyone to hear: We are welcoming, we see you, you are valued. 

Pride 2020 kicks off September 18 —including events like an outdoor rainbow market, and pedal / motor / water parades—and culminates with the reveal of Kelowna’s Next Drag Superstar and the Pride Festival on September 26. For more information on all events click here

Now that you know a bit about Bobby, let’s find out what he ALWAYS suggests when hosting friends or family, or when someone asks for his Kelowna recommendations:

Art of the Cocktail


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Kelowna’s downtown revitalization, including the cocktail culture that is sprouting up, is something that is very exciting to this cocktail aficionado. A few of Bobby’s favourites are: 

Vegetarian and Vegan Food Galore


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Since coming back to Kelowna from Vancouver, Bobby is blown away by the quality of the vegetarian and vegan options here and says it rivals any big city options he’s tried. Don’t miss:

Wine, Wine, and More Wine


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Of course, a visit to Kelowna is not complete without wine touring. Recently, Bobby explored wineries in Kelowna and area that he hadn’t tried before and was so excited to share his favourites:

  • Mirabel Vineyards recently opened a new tasting room in southeast Kelwowna and Bobby left with a case of their 2017 Rose. 
  • At The View Winery, Bobby was blown away by the customer service. During their tasting, Crystal was so on point with her recommendations and tasting notes, he couldn’t believe it was her first day on the job.  
  • One other recent stop was at Frind Estate Winery in West Kelowna. He loved their immaculate grounds along the shores of Okanagan Lake with a lovely garden, private dock and lakeside seating.

Connect with Bobby on Instagram @strategistbobby