Head of Sales

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

Job summary

Stay22 is seeking a Head of Sales to lead new business acquisition and build a high-performing sales team. The role emphasizes strategic deal management, team leadership, and performance accountability in a dynamic environment. Located in vibrant Montreal, this position offers a competitive salary and benefits. Join us to empower travel creators and make a significant impact in the affiliate marketing landscape.

Benefits

Health & Dental Benefits

Retirement Plans

Flexible Work Schedule

Bring Your Own Dog (BYOD) Policy

Learning & Development Opportunities

Team-building Activities

Qualifications

• 5+ years of successful sales leadership experience.
• Proven experience building and leading high-performing B2B sales teams.
• Strong coaching skills with excellent communication.

Responsibilities

• Drive top-line growth through effective sales strategies.
• Lead and motivate the BDM team to surpass targets.
• Implement clear performance targets and facilitate team alignment.

Skills

Sales Leadership

Pipeline Management

Team Coaching

Communication

CRM Familiarity

Strategic Deal Management

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 levelling up their audience's user experience. At Stay22, 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

• New Business Acquisition: Drive top-line growth through effective sales strategies and execution.
• Team Leadership: Lead, coach, and motivate our BDM team to hit (and exceed) individual and team targets.
• Goal Setting & Tracking: Implement clear performance targets and ensure team alignment through regular pipeline reviews and performance check-ins.
• Sales Process Excellence: Establish and refine sales frameworks using MEDDIC, Mutual Action Plans, and proven deal qualification methods.
• Forecasting & Reporting: Own sales forecasting, reporting, and CRM hygiene to provide accurate insights to leadership.
• Recruitment & Onboarding: Hire, train, and ramp new sales team members as we grow.
• Strategic Deals: Roll up your sleeves and jump into 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 tooling
• Comfortable managing a team using frameworks like MEDDIC and MAPs
• Strong coaching skills—you get the best out of people
• Excellent communicator, resilient, and laser-focused on outcomes
• Experience in tech or travel is a major plus
• Knowledge of adtech, affiliation, or web technologies is a nice 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, so here’s the quick rundown of what to expect.

• Screening call with our Talent Acquisition Partner (30-45 minutes)
• Interview with the Hiring Manager (30 minutes)
• Digital exercise
• Panel interview with the Executive team (90 minutes - in-person)
• Final interview with our CEO (30 minutes)
• Offer & onboarding
  
  

Please note that this process is subject to change at any point, based on additional requirements from the team.

Why join Stay22?

• Support Travel Creators: Be part of a team that empowers travel creators to explore the world by increasing their passive income potential.
• Empower Your Growth: We hire champions and give them the opportunity to excel, skipping levels and honing their superpowers.
• Lead with Impact: We empower our team members to take charge and make a real impact in the Stay22 universe.
• Location, Location, Location: Enjoy our bright and vibrant office in the heart of Montreal’s Plateau Mont-Royal, surrounded by the best shops and restaurants.
• BYOD - Bring your own dog: our office is pup-friendly. Whether it's a quick belly rub or a midday walk, your furry sidekick is welcome here.
• Be Yourself: Embrace a come-as-you-are dress code and a flexible work schedule.
• Comprehensive Benefits: We offer health & dental benefits, retirement plans, learning & development opportunities, and social & team-building activities, including exciting retreats.
  
  

(Stay22 is an equal opportunity employer. All qualified applicants are given consideration. If you have a disability or particular need that requires accommodation, please contact us at careers at stay22.com)

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Management and Sales

• Industries

  Software Development

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