Head of Sales

Stay22 Technologies Inc; Montreal; Hybrid; CAD 200,000 - 225,000; Full time

Job summary

A leading travel technology company in Montreal is seeking a Head of Sales to drive new business acquisition and lead a high-performing sales team. This role requires extensive experience in sales leadership, a deep understanding of pipeline management, and comfort with modern sales tools. The candidate will play a crucial role in shaping the sales organization and achieving top-line growth. The company offers a hybrid work model and a supportive office culture.

Benefits

Health & dental benefits

Retirement plan

Learning and development opportunities

Pup-friendly office

Flexible schedule

Qualifications

• 5+ years of successful sales leadership experience.
• Proven experience building and leading high-performing B2B sales teams.
• Familiarity with CRM systems and modern sales tools.

Responsibilities

• Drive top-line growth through effective sales strategies.
• Lead, coach, and motivate the BDM team to exceed targets.
• Own sales forecasting and reporting for accurate insights.

Skills

Sales leadership

Team management

CRM proficiency

Coaching

Pipeline management

Communication

Job description

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Job Description

Job Title : Head of Sales

Salary : $200,000 - $225,000 OTE

Location : Montreal - Hybrid (2-3 days at the office per week)

About Stay22

At Stay22, we’re revolutionizing how people convert online. Our AI-powered affiliate platform helps publishers, ticketing platforms, and content creators unlock new revenue streams while enhancing their audience's user experience. Our partners don’t just earn more—they deliver more. Join us and be part of something big that’s shaking up the affiliate world.

Position overview

As we scale our GTM engine, we’re looking for a Head of Sales to lead, inspire, and execute on new business acquisition—while building a world-class sales team focused on performance, accountability, and growth.

Key responsibilities

1. New Business Acquisition: Drive top-line growth through effective sales strategies and execution.
2. Team Leadership: Lead, coach, and motivate our BDM team to hit (and exceed) targets.
3. Goal Setting & Tracking: Implement performance targets and ensure team alignment through pipeline reviews and check-ins.
4. Sales Process Excellence: Establish and refine sales frameworks using MEDDIC, Mutual Action Plans, and proven qualification methods.
5. Forecasting & Reporting: Own sales forecasting, reporting, and CRM hygiene for accurate insights.
6. Recruitment & Onboarding: Hire, train, and ramp new sales team members as we grow.
7. Strategic Deals: Engage in high-stakes deals when needed.

Requirements

• 5+ years of successful sales leadership experience
• Proven experience building and leading high-performing B2B sales teams
• Deep understanding of pipeline management and performance accountability
• Familiarity with CRM systems, social selling, and modern sales tools
• Comfortable managing frameworks like MEDDIC and MAPs
• Strong coaching skills—getting the best out of people
• Excellent communication, resilience, and outcome focus
• Experience in tech or travel is a major plus
• Knowledge of adtech, affiliation, or web technologies is a bonus
• Existing network in the US publishing space is a strong asset

What to Expect from our Hiring Process

We know your time’s valuable. Here’s what to expect:

1. Screening call with our Talent Acquisition Partner (30-45 mins)
2. Interview with the Hiring Manager (30 mins)
3. Digital exercise
4. Panel interview with the Executive team (90 mins, in-person)
5. Final interview with our CEO (30 mins)
6. Offer & onboarding

Note: The process may change based on team requirements.

Why join Stay22?

• Support Travel Creators: Empower travel creators to explore and increase passive income.
• Empower Your Growth: We hire champions and promote growth, skipping levels.
• Lead with Impact: Make a real impact in the Stay22 universe.
• Location: Bright, vibrant Montreal office in Plateau Mont-Royal.
• BYOD - Bring your own dog: Pup-friendly office.
• Be Yourself: Come-as-you-are dress code and flexible schedule.
• Benefits: Health & dental, retirement, learning, retreats, and more.

Stay22 is an equal opportunity employer. For accommodations, contact us at [e-mail].

Seniority level

Executive

Employment type

Full-time

Job function

Management and Sales

Industries

Software Development

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Additional roles include Sales Director, VP of Business Development, Director of Sales, and more.

Additional info

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