We are looking for a powerhouse Head of Sales to transform our early momentum into a scalable revenue engine. As our first senior sales hire, you will be a "player-coach" who isn't afraid to lead from the front, closing our most strategic property management accounts while simultaneously building the playbooks, quotas, and culture of our sales organization. You understand that selling AI to the property management industry requires a mix of high-touch relationship building and data-driven persistence. You will be a key strategic partner to the CEO, responsible for defining our commercial strategy and ensuring we dominate the HOA and multifamily markets.
This position is based in
North York and is currently full-time in-office. This position is ideal for someone who thrives in a collaborative, high-energy environment and enjoys building teams in person.**
Tasks- Sales Strategy & Playbook Design: Define the end-to-end sales process, from initial lead handoff from marketing to final closing, creating the scripts, decks, and objection-handling guides the team will use.
- Revenue Generation: Own the company's revenue targets, personally managing and closing high-value "Tier 1" accounts while building a consistent pipeline of mid-market deals.
- Team Expansion: Lead the recruitment, onboarding, and continuous coaching of our Account Executives (AEs) and Sales Development Representatives (SDRs) as we scale.
- Pipeline Management & Forecasting: Implement rigorous CRM hygiene (HubSpot/Salesforce) to provide leadership with accurate weekly and monthly revenue forecasts.
- Cross-Functional Feedback Loop: Act as the "eyes and ears" on the ground, translating customer feedback into actionable insights for the Product and Engineering teams to refine our AI assistant.
- Contracting & Negotiation: Oversee the negotiation of complex contracts, ensuring favorable terms that balance rapid growth with long-term profitability.
Requirements- The 0-to-1 Track Record: 8+ years of sales experience, with at least 3+ years in a leadership role at a high-growth B2B SaaS startup (PropTech or Real Estate experience is a massive bonus).
- Elite Closer: A proven history of consistently exceeding multi-million dollar quotas and navigating complex, multi-stakeholder sales cycles.
- Strategic Builder: You have experience building sales departments from scratch-you know how to set commissions, define territories, and implement a sales tech stack.
- Communication Mastery: Exceptional ability to present to owner-operator executives, making the value of AI feel tangible and urgent.
- Data-Driven Leadership: You manage by the numbers, using CRM data to identify bottlenecks in the funnel and pivot strategy in real-time.
- Startup Grit: You thrive in ambiguity and are excited by the challenge of selling a cutting-edge product into a traditional, relationship-based industry.
Benefits- Competitive salary
- Comprehensive health, dental, and specialist benefits.
- Company Macbook.
- Free parking and shuttle service to the office.
- Extra PTO during occasional US holidays.
- Company events, in-office restaurant, and building-wide perks.
- Unlimited ping pong and espresso!
If you're passionate about AI and ready to disrupt a massive industry, we want to talk to you!
