Head of Sales

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

Job summary

Stay22 is seeking a Head of Sales to lead and inspire a high-performing sales team in Montreal. This role encompasses driving business growth, overseeing team performance, and establishing effective sales strategies. The ideal candidate will have extensive sales leadership experience, particularly in B2B environments, and will thrive in a hybrid work setting.

Benefits

Health & dental benefits

Retirement plans

Learning & development opportunities

Pup-friendly office

Flexible work schedule

Team-building activities

Social retreats

Qualifications

• 5+ years of successful sales leadership experience.
• Proven experience in building and leading high-performing B2B sales teams.
• Strong background in pipeline management and performance accountability.

Responsibilities

• Drive top-line growth through effective sales strategies.
• Lead, coach, and motivate the BDM team.
• Establish and refine sales frameworks using proven methods.

Skills

Sales Leadership

Coaching

Pipeline Management

Communication

Tools

CRM Systems

Sales Frameworks (MEDDIC, MAPs)

Job description

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 on a mission to revolutionize the travel media industry. Using cutting-edge AI-powered solutions, we empower travel media companies and content creators to unlock fresh revenue streams and seamlessly monetize their platforms. With us, you’re not just enhancing your income—you’re elevating travel experiences for your audience. Join our vibrant team and be part of a journey that’s making travel media more rewarding for everyone.

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
  
  

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)