Senior Regional Sales Manager

1 week ago

Whitby Ontario, Canada Cottage Dream Vacations Full time $75,000 - $150,000 per year

Senior Regional Sales Manager – High-Ticket Real Estate Training & Hospitality Expansion


On-site at Head Office – 701 Rossland Rd East, Whitby, ON


$75,000 base salary + overriding commission (uncapped)

At Cottage Dream Vacations (CDV), we help Canadians build wealth through real estate investing — and we're looking for a Senior Regional Sales Manager who's hungry to lead high-performing teams, inspire clients, and crush targets.

CDV empowers people to design lifestyle freedom through high-ticket real estate training programs and luxury vacation experiences. As we continue to grow, we're expanding into the resort and hospitality space, and we need a proven sales leader ready to take ownership of results, mentor a talented team, and evolve into our Director of Sales.

What You'll Do

  • Lead, coach, and motivate a team of Sales Leaders and Closers to exceed targets.
  • Oversee the sales cycle for our high-ticket real estate and lifestyle programs.
  • Collaborate with marketing to optimize lead flow and conversions.
  • Prepare to lead our expansion into the hospitality and resort sector.
  • Develop future leaders and shape a culture of excellence.

What We're Looking For

  • 5+ years in sales leadership (real estate, coaching, or high-ticket programs).
  • Proven track record of scaling and mentoring high-performing teams.
  • Strong CRM and data-driven management experience.
  • Entrepreneurial mindset with ambition to grow into a Director of Sales role.

If you're ready to lead a powerhouse sales team and help Canadians create real estate freedom — we want to meet you.

Apply now and join a company where sales leadership meets lifestyle vision.

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