Account Executive - Hypergrowth Luxury Short-Term Rental Tech Firm - Sell to Property Management Firms

August 22, 2025

Our staffing agency represents a privately-held AI-powered luxury short-term rental company that combines the quality of a luxury hotel with the comfort of a private vacation home. This 160-employee, Series A firm ($48 million in venture funding), which has earned a 94% guest satisfaction rate, is seeking an Account Executive to close net-new partnership agreements with property management firms of all sizes. This is a remote role, although you must be located near a major Canadian airport. SolutionOur client is transforming the $1.3 trillion (and growing) lodging industry with a guest experience that merges the best of both worlds in hospitality – and pulls demand from both markets. Their mission is to help people find their happy place. Their vision is to create the infrastructure for people to experience the world. And their home operations team is the link between both ideas and the unit that brings homes to life through maintenance, upgrades, and smart home technology. Role* Individual contributor role, working from your home office in a preferred metro area.* $80k USD base salary, $189k OTE. Uncapped comp plan with accelerators.* Top candidates have a background in luxury real estate or property management, with proven success in B2B sales and business development* If you have an existing network within the Canadian property management or luxury real estate industry, you are at the top of our list.* You have at least 3 years of experience succeeding in a remote role. Self-starters who want to supercharge their career thrive here.* You must be willing to travel locally, regionally, and nationally to meet with prospects. * No order takers please; you are scrappy, gritty, driven, creative, and passionate about sales!* Bilingual capabilities (English/French) highly preferred. Culture* 5.0 Glassdoor, 100% Recommend to Friend. One employee says, “Extremely uplifting and supportive environment, everyone in each department helps each other.”* There are 9 AEs currently in this role, and they are thriving. We are expanding the team to keep up with demand!* Head of Sales is an industry veteran who previously scaled up high-performing teams at HomeAdvisor and Angi.* Fortune 500-quality marketing organization; weekly content delivered on YouTube, LinkedIn, Instagram, and their blog. Official Job Description About the RoleWe are a growing startup specializing in luxury home rentals catering to an upmarket demographic of guests who expect five-star hotel experience in a short-term rental. We are looking to hire a full-time Account Executive to spearhead our expansion into the Canadian market by building strategic partnerships with property management companies. This is an exciting opportunity to join a fast-paced team at a rapidly-developing company, where you'll be the driving force behind our Canadian growth strategy while working with some of the most prestigious properties across the country! Required Qualifications<ul><li>Background in luxury real estate or property management highly preferred, with proven success in B2B sales and business development</li><li>Self-directed and motivated with a strong sense of personal ownership and accountability</li><li>Ability to generate and qualify leads through research and networking within the Canadian property management sector</li><li>Comfort with cold-calling, emailing, and attending industry events to network and meet in person</li><li>Ability to create compelling presentation materials, generate partnership proposals, and close deals with property management companies</li><li>Proven ability to foster long-term relationships with partners, identifying upselling and expansion opportunities</li><li>Detail-oriented with strong time management and organizational skills</li><li>Team player with a positive attitude and strong work ethic</li><li>Willingness to travel up to 50% of the time across Canada to meet with prospects and partners</li><li>Interested in long-term employment and career development at a growing company with a tight-knit culture</li></ul> Preferred Qualifications<ul><li>Confident & resourceful, strategic thinker & collaborative problem solver</li><li>Experience working with product and engineering organizations to help roadmap new feature developments based on partner needs</li><li>Bachelor’s degree in business, Real Estate, Communication or a related field</li><li>3 to 5 years of relevant sales or business development experience in luxury real estate or property management</li><li>Strong communications skills, both written and verbal</li><li>Existing network within Canadian property management or luxury real estate industry</li><li>Bilingual capabilities (English/French) highly preferred for French Canadian markets</li></ul> Responsibilities<ul><li>Through targeted outbound outreach, identify and secure partnerships with high-end property management companies across Canada</li><li>Qualify leads from marketing campaigns and convert them into strategic partnership opportunities</li><li>Conduct proactive outreach to property management companies, contacting key decision makers through calls, emails, and in-person meetings</li><li>Travel extensively across Canada to meet with prospects, conduct property tours, and build relationships with property management partners</li><li>Nurture prospects, discover their needs, offer relevant resources, and articulate why our partnership model is the right fit for their portfolio</li><li>Utilize targeted and insightful questions to speak knowledgeably with property managers and owners, providing content and service information while demonstrating how we can enhance their property performance</li><li>Maintain strong knowledge of our luxury home standards, technology platform, and concierge processes</li><li>Document all partnership activities and maintain detailed partner information in CRM system</li><li>Work closely with marketing, product management, and operations teams to ensure successful partner onboarding and ongoing relationship management</li><li>Provide market insights and feedback to inform product development and Canadian market strategy</li></ul>

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