Sales Development Representative

About Stay22

Stay22 is a Montreal-based company that helps ambitious creators and high-intent digital platforms turn their existing traffic into additional revenue through technology that operates quietly in the background. More than 6,500 creators and platforms rely on the platform, which processes over $1 billion in annual transactions. While the business started in travel, it now supports partners in retail, lifestyle, publishing, events, and transportation as it continues building monetization infrastructure for today’s creator economy.

Role overview

As a Sales Development Representative (SDR), you will be responsible for creating qualified meetings and building pipeline for the SMB to mid-market sales team, with a primary focus on online publishers and adjacent verticals such as ticketing, creators, and platforms. You will use tools such as Similarweb and a structured outbound approach to develop targeted prospect lists, run effective outreach sequences, and start conversations with the right decision-makers. This opportunity suits someone who enjoys inventive prospecting, is driven by results, and thrives in a fast-paced startup setting.

Responsibilities

• Identify and target prospects by building and maintaining strong account and contact lists using Similarweb and other sources, while keeping CRM records accurate and clean.
• Create, launch, and refine multi-step outbound sequences across email, LinkedIn, social channels, and phone to secure qualified meetings.
• Assess fit by checking factors such as traffic, monetization setup, intent, and the decision-making process, then hand over qualified opportunities to the appropriate Account Executive with clear notes.
• Support event-driven pipeline generation by preparing prospect lists in advance, booking meetings ahead of events, and following up quickly during and after events.
• Continuously improve outreach performance by A/B testing messaging and sequencing, tracking outcomes, and sharing insights to raise reply and meeting rates.

Requirements

• Demonstrated success in generating leads, with a consistent record of producing qualified meetings or pipeline through outbound activity.
• Hands-on experience building and managing outbound sequences, including email and multi-channel outreach, along with examples of testing and performance improvement.
• Strong writing and messaging ability, with the creativity to craft compelling angles and personalized outreach that earns responses.
• 1 to 2 years of experience in an SDR, BDR, or other outbound-focused role; experience in SaaS, affiliate, adtech, martech, or publishing-related environments is an advantage.
• Strong research skills and comfort using tools such as Similarweb, LinkedIn Sales Navigator or similar platforms, and CRM systems.
• Well-organized, consistent, and able to work effectively in a startup environment where priorities can shift quickly.
• Multilingual ability is a strong advantage in an international business environment.
• A startup mindset and the ability to thrive in a dynamic, fast-moving scale-up setting.
• Strong English communication skills are required for day-to-day interaction with international clients and colleagues.

Hiring process

The selection process includes a screening call with the Talent Acquisition Partner, a virtual interview with the Hiring Manager, a digital exercise, an in-person interview with the Head of Sales at the office, and a final interview with the CEO, followed by an offer and onboarding. The process may change depending on team needs. Your application will be reviewed by Mariel, the internal recruiter.

Why join Stay22

• Be part of a team that helps travel creators grow their passive income while exploring the world.
• Join a company that invests in strong talent and supports growth, skill-building, and progression.
• Have a direct impact by taking ownership and contributing meaningfully to the company’s evolution.
• Work from a bright, lively office in Little Italy, close to popular shops and restaurants.
• Enjoy a relaxed dress code and flexible work hours.
• Benefit from comprehensive coverage including health, dental, retirement, learning and development opportunities, social activities, team-building events, and retreats.

Additional information

Stay22 is an equal opportunity employer and reviews all qualified applications. If you have a disability or specific accommodation needs, you can reach the company at [email protected]. The company also encourages candidates who do not meet every requirement but are excited about the role to apply.