Sales Strategy & Operations Manager

About Stay22

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.

Position Overview

We are building the sales pillar of RevOps, and we want someone who has actually carried a sales number before, not just reported on one. This is a senior, high ownership seat that sits next to sales leadership, not behind a dashboard. You will own territory planning, pipeline forecasting, and the deal desk end to end, and you will be the person sales leaders call first when a number does not add up.

You will be a founding member of the GTM pod on the RevOps side, working alongside Partner Success Ops and Marketing Ops to build one coherent revenue engine.

Key Responsibilities

• Territory planning: build and maintain rep productivity, quota attainment, and territory and pod performance tracking.
• Projections: own pipeline governance, CRM hygiene, and forecast accuracy for sales, end to end, across all AE pods and SDRs. Run and improve the pipeline commit cadence and deal reviews, and speak to the health of any deal on demand.
• Deal desk: be the first point of contact for deal desk questions, exceptions, approvals, and deal structuring.
• Design and operate the sales funnel stages, exit criteria, and qualification frameworks in HubSpot.
• Proactively surface pipeline risk, forecast variance, and process breakdowns before they escalate.
• Ensure clean, reliable handoffs between sales and partner success.
• Turn ambiguous leadership asks into scalable frameworks: a structured recommendation, not just the first idea executed.
• Over time, help shape sales process design and comp/incentive mechanics alongside RevOps leadership.

Cross-Functional Collaboration

You'll operate at the center of the revenue engine, dedicated to sales but never in a silo. You'll partner closely with:

• Sales leadership, as a frontline performance partner.
• Senior RevOps leadership, for direction and priorities.
• A RevOps Analyst, for deeper modeling and performance analysis.
• A Systems Ops teammate, who owns tooling, automation, and infrastructure.
• Marketing Ops and PS Ops, to keep the full revenue lifecycle aligned end to end.

Requirements

• 4+ years in RevOps or sales operations, with real ownership of pipeline, forecasting, and deal desk, not just support of them.
• Real sales experience: time spent as an account executive, sales manager, sales engineer, or in another deal-facing role, not only supporting sales from an ops seat.
• A track record of building or owning forecasting methodology, territory design, or a deal desk process, not just running someone else's.
• Comfortable holding your own with a sales leader in the room: structured pushback, not just a data pull.
• Sharp analytical instinct: you know when a number is off before anyone points it out, and you go find out why.
• Strong HubSpot fluency; comfortable with CRM architecture decisions, not just hygiene.
• High ownership: you flag the problem before you're asked to fix it.
• Comfortable in a fast-moving environment where the revenue model is not SaaS.
• English proficiency, strong curiosity, and a real alignment with Stay22's values.

What to Expect During Our Hiring Process

We know your time is valuable, here is a quick look at the next steps:

• Call with our Talent Acquisition Advisor (30 min).
• Interview with the hiring manager (45 min).
• Technical interview and live case with members of the RevOps team (in person, 60 min).
• Panel interview with other members of the team (60 min).
• Final interview with our CEO (30 min).
• Offer and onboarding

Note: this process may evolve based on the team's needs.

Why Join Stay22?

• Prime Montreal Location : Work from our vibrant Little Italy HQ with a cafeteria allowance, full gym access, and a rooftop terrace complete with a seasonal basketball/pickleball court & hockey rink.
• Comprehensive Benefits: Health & dental coverage, RRSP matching, fully paid STM pass', and regular team socials, events, and retreats.
• Flexibility That Works: Flexible schedules, work-from-anywhere opportunities, year-end shutdown, and flex days.

(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 View email address on click.appcast.io)

Your application will be reviewed by Nayo, our internal recruiter - even if you don't meet every requirement but you're excited, let's talk.