Sales Development Representative

Stay22•Montreal, QC

15d•Onsite

About The Position

Based in Montreal, Stay22 helps ambitious creators and intent-rich digital platforms turn their existing traffic into incremental revenue, with technology that works quietly in the background. Today, more than 6,500 creators and platforms rely on Stay22, with over $1 billion in annual transactions flowing through the platform. Originally built for travel, the company now supports partners across retail, lifestyle, publishing, events, and transport as it expands its monetization infrastructure for the modern creator economy. As a Sales Development Representative (SDR) at Stay22, you will generate qualified meetings and pipeline for our SMB to mid-market sales team, with a focus on online publishers (and adjacent verticals like ticketing, creators, and platforms). You’ll use tools like Similarweb and a structured outbound motion to build targeted prospect lists, run high-performing sequences, and start conversations with the right decision-makers. This role is for someone who enjoys creative prospecting, is metrics-driven, and thrives in a fast-moving startup environment.

Requirements

Demonstrated track record of consistently creating qualified meetings or pipeline via outbound.
Hands-on experience building and running outbound sequences (email and multi-channel), with evidence of iteration and performance improvement.
Strong copy and messaging instincts, with an ability to craft compelling angles and personalization that drives replies.
1–2 years experience in an SDR/BDR or outbound-focused role (SaaS, affiliate, adtech, martech, or publishing-adjacent is a plus).
Strong research skills and comfort using tools like Similarweb, LinkedIn Sales Navigator (or similar), and CRM systems.
Organized, consistent, and comfortable in a fast-paced startup environment with changing priorities.
Multilingual: Strong asset given our international presence.
Thrives in a fast-paced, startup setting and comfortable with the dynamic demands of a scale-up environment.
English proficiency is required for daily communication with international clients and colleagues.

Nice To Haves

Publishing-adjacent experience is a plus.
Multilingualism is a strong asset given our international presence.

Responsibilities

Build and maintain high-quality target accounts and contact lists using Similarweb and other sources; keep CRM data clean.
Build, launch, and optimize multi-step sequences across email, LinkedIn, social media and phone to generate qualified meetings.
Confirm fit (traffic, monetization setup, intent, decision process) and hand off qualified opportunities to the right AE with crisp notes.
Pre-build event prospect lists, book meetings ahead of time, and run fast follow-ups during and after events.
A/B test messaging and sequencing, track outcomes, and share learnings to improve reply and meeting rates.