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Toronto, Ontario, Canada
Remote only
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Founder in Residence based in Canada.
As a Founder in Residence, you’ll have the opportunity to build a new business from the ground up within an AI-first environment. You’ll identify a meaningful opportunity in the short-term rental industry, validate it directly with customers, and turn it into a scalable product or business vertical. Rather than starting with a blank balance sheet, you’ll have access to engineering, AI, product, design, distribution, funding, and executive support. You’ll own the venture’s strategy, growth, customer outcomes, and financial performance. The role combines entrepreneurial autonomy with the resources of an established platform. If successful, you’ll grow into the long-term leader of the business you create.
Identify high-potential opportunities within the short-term rental market and assess their potential to become new products, services, or business verticals.
Conduct customer research and maintain direct conversations with property managers and rental operators to validate problems, needs, and potential solutions.
Define the venture’s product vision, business strategy, positioning, and go-to-market approach.
Work closely with engineering, product, design, and AI specialists to rapidly prototype, build, launch, and iterate new solutions.
Recruit, develop, and lead a multidisciplinary team as the venture progresses from validation to growth.
Own key business outcomes, including product adoption, customer success, growth, recurring revenue, and financial performance.
Use customer feedback, market signals, and business data to make decisions, test hypotheses, and continuously refine the venture.
Communicate progress, opportunities, challenges, and strategic decisions directly to founders and executive leadership.
Build a scalable business that can ultimately become a dedicated division or potentially operate as an independent company.
Establish the operating model, culture, priorities, and execution practices required for sustainable growth.
Strong entrepreneurial mindset with a clear bias toward action, experimentation, and measurable outcomes.
Exceptional problem-solving skills and the ability to turn ambiguous opportunities into structured plans and executable strategies.
Strong product and commercial intuition, with an understanding of how customer needs translate into viable products and businesses.
Comfort operating with significant autonomy and creating structure in environments where priorities and answers are not yet defined.
Excellent communication, influencing, and leadership capabilities, with the ability to work effectively with customers, executives, technical teams, and business partners.
Demonstrated ability to recruit, inspire, develop, and lead high-performing teams.
Strong analytical and execution skills, with the ability to use data and customer insights to guide decisions.
Deep customer orientation and a strong focus on creating products that deliver meaningful value.
Willingness to operate across product, sales, marketing, operations, and strategy as the venture requires.
AI-native mindset and enthusiasm for using emerging AI technologies to build products, automate workflows, and accelerate experimentation.
Previous experience as a startup founder, early-stage employee, product leader, operator, or investor is highly valued.
Experience in short-term rentals, hospitality, property technology, or related markets is an asset.
Ability to pursue ambitious goals, work at high speed, and maintain strong ownership through uncertainty.
Opportunity to build and lead a new business venture from the ground up.
Access to established engineering, AI, product, design, and go-to-market resources.
Funding and strategic support to validate and scale your ideas.
Direct access to experienced founders and executive leadership for mentorship and decision support.
Ability to recruit and build your own multidisciplinary team as the venture grows.
Significant autonomy over the venture’s strategy, product direction, and execution.
Competitive salary and performance-based incentives.
Long-term career opportunity to become the General Manager and leader of the business you build.
Remote work flexibility with the role available across Canada and multiple international locations.
Opportunity to work at the intersection of entrepreneurship, AI, and the rapidly evolving short-term rental industry.
