Head of Sales

STAN AI; Toronto; Hybrid; CAD 180,000 - 260,000; Full time

Benefits offered by this job

Competitive salary

Comprehensive health benefits

Company Macbook

Free parking and shuttle service

Extra PTO during US holidays

Company events, in-office restaurant

Unlimited ping pong

Espresso perks

Job summary

STAN AI is seeking a Head of Sales to transform early momentum into a scalable revenue engine. As the first senior sales hire, you will lead from the front, closing strategic property management accounts while building playbooks, quotas, and the culture of our sales organization.

This North York-based role is hybrid in-office, ideal for someone who thrives in a collaborative, high-energy environment and enjoys building teams in person. You will drive revenue growth in HOA and multifamily markets.

Qualifications

• 8+ years in sales, including 3+ years in leadership at a high-growth B2B SaaS startup.
• Proven multi-million dollar quota track record and complex, multi-stakeholder sales cycles.
• Experience building sales departments from scratch, including commissions and territories.

Responsibilities

• Define end-to-end sales process with playbooks, scripts, and objection guides.
• Own revenue targets and close high-value Tier 1 accounts while building pipeline.
• Recruit, onboard, and coach Account Executives and SDRs as we scale.
• Maintain CRM hygiene and provide weekly/monthly forecasts.
• Translate customer feedback to product/engineering insights.
• Oversee contracting and negotiations to balance growth and profitability.

Skills

Sales leadership

Strategic selling

Enterprise closing

CRM analytics

Team building

Tools

HubSpot

Salesforce

Job description

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 hybrid in-office. This position is ideal for someone who thrives in a collaborative, high-energy environment and enjoys building teams in person.**

About Us

STAN is the largest provider of AI solutions for HOA and Condo Property Managers. We are using cutting-edge and patented artificial intelligence technology to build solutions that enhance life for residents of more than 2.5 million+ homes across North America. And, we are on a mission to build the world’s first AI property manager. Want to come along for the ride?

STAN is also an award-winning platform, having been recognized by Rogers, FedEx, George Brown College, StartUp Canada, the Waterloo Accelerator Centre, and more!

To learn more, feel free to visit us at www.stan(.)ai

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!