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Added 1 hour ago
GC
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- Full-time
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Added 2 hours ago
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Added 2 hours ago
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Added 5 hours ago
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Added 7 hours ago
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Stay22

Chief of Staff

Montreal, QC, Canada

Full-time

Apply on LinkedIn About employer

Applications open in a new tab.

Job details

Job type: Full-time
Apply by: Apr 3, 2027
Experience: 5 ans et plus d'expérience en stratégie, en consultation ou en opérations, dont au moins 2 ans comme Chief of Staff ou dans un rôle similaire auprès de la haute direction
Posting language: English · French
Posted: Oct 5, 2026

Original job description

English section of this bilingual listing.

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

As Chief of Staff, you'll be a strategic partner to the executive team and help turn company priorities into results. You'll run the company's operating cadence, lead high-impact projects across teams, and make sure leadership has the information, alignment and follow-through it needs to make good decisions quickly. You'll work across Commercial, Product, Engineering and Finance. It's a high-visibility role for someone who wants to understand how the whole company works and help shape where it goes next.

Key Responsibilities

Strategy and execution: Partner with the executive team to set company priorities and OKRs, track progress, and hold teams accountable for outcomes.
Supporting Key Initiatives: Leans in and supports operationalizing strategic initiatives across the organization, starting with operationalizing the new CRO Commercial plan.
Operating cadence: Own the leadership rhythm, including leadership meetings, business reviews, so decisions are made, documented and acted on.
Cross-functional alignment: Connect revenue teams with the rest of the company, unblock work, and keep communication clear across departments and levels of leadership.
Company events: Shape the agenda, content and sessions for company retreats and kickoffs so they advance our strategic priorities.
AI-first operations: Lead how AI is built into the company's operating system: find high-value workflows to automate, set standards for adoption, and scale tools across teams.

Requirements

5+ years in strategy, consulting or business operations, with at least 2 as a Chief of Staff or in a similar executive-facing role
Scale experience: you've worked as a Chief of Staff at a company with 200+ employees and $100M+ in revenue
Proven operator: you've taken complex, cross-functional projects from idea to impact
Montreal-based: you can work hybrid from our Montreal office
Global experience: you've supported a leadership team spread across countries and time zones (Asset)

Qualifications

Strong strategic thinking and problem-solving skills, with the judgment to prioritize what matters most
Excellent written and verbal communicator who can turn messy inputs into clear priorities, recommendations and execution plans focused on delivering outcomes.
Highly organized and able to execute, comfortable juggling many priorities in a fast-moving environment
A high level of discretion with sensitive information
Strong business sense across commercial, product and financial areas; comfortable with data and KPIs
Enthusiasm for AI tools and new ways of working
Lives our values: Care (puts the team and Stay22 first), Curiosity (challenges the status quo and keeps learning), and DWIFT (has a bias for action, owns outcomes and finds a way to win)
Nice to have: an MBA, or experience in technology , affiliate marketing, or travel tech

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 minutes)
Hiring Manager call (30 minutes)
Panel Interview with cross-functional team members (45 minutes)
Psychometric Assessment - completed at home
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?

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 careers@stay22.com)

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

Read the full bilingual original

À propos de Stay22

Basée à Montréal, Stay22 aide les créateurs ambitieux et les plateformes numériques à forte intention à transformer leur trafic existant en revenus additionnels, grâce à une technologie qui fonctionne discrètement en arrière-plan.

Aujourd’hui, plus de 6 500 créateurs et plateformes font confiance à Stay22, avec plus d’un milliard de dollars en transactions annuelles transitant par la plateforme. Initialement conçue pour le secteur du voyage, l’entreprise accompagne désormais des partenaires dans les domaines du commerce de détail, du lifestyle, de l’édition, des événements et du transport, alors qu’elle poursuit l’expansion de son infrastructure de monétisation pour l’économie moderne des créateurs.

Aperçu du poste

En tant que Chief of Staff, tu seras un·e partenaire stratégique de l'équipe de direction et tu aideras à transformer les priorités de l'entreprise en résultats concrets. Tu piloteras le rythme opérationnel de l'entreprise, mèneras des projets à fort impact entre les équipes et t'assureras que la direction a l'information, l'alignement et le suivi nécessaires pour prendre de bonnes décisions rapidement. Tu travailleras avec les équipes Commercial, Produit, Ingénierie et Finance. C'est un rôle très visible, parfait pour quelqu'un qui veut comprendre comment toute l'entreprise fonctionne et contribuer à définir la suite.

Responsabilités principales

Stratégie et exécution : Travailler avec l'équipe de direction pour établir les priorités et les OKR de l'entreprise, suivre l'avancement et responsabiliser les équipes face aux résultats.
Soutien aux initiatives clés : S'impliquer à fond dans la mise en œuvre des initiatives stratégiques à l'échelle de l'organisation, en commençant par l'opérationnalisation du nouveau plan commercial du CRO.
Rythme opérationnel : Prendre en charge le rythme de la direction, y compris les rencontres de direction et les revues d'affaires, pour que les décisions soient prises, documentées et mises en action.
Alignement interfonctionnel : Faire le pont entre les équipes de revenus et le reste de l'entreprise, débloquer le travail et garder une communication claire entre les départements et les niveaux de direction.
Événements d'entreprise : Façonner l'agenda, le contenu et les sessions des retraites et des kickoffs pour qu'ils fassent avancer nos priorités stratégiques.
Opérations axées sur l'IA : Piloter l'intégration de l'IA dans le fonctionnement de l'entreprise : repérer les processus à forte valeur à automatiser, établir les standards d'adoption et déployer les outils dans toutes les équipes.

Exigences

5 ans et plus d'expérience en stratégie, en consultation ou en opérations, dont au moins 2 ans comme Chief of Staff ou dans un rôle similaire auprès de la haute direction
Expérience à grande échelle : tu as été Chief of Staff dans une entreprise de plus de 200 employé·es et de plus de 100 M$ de revenus
Opérateur·rice aguerri·e : tu as mené des projets complexes et interfonctionnels de l'idée jusqu'à l'impact
Basé·e à Montréal : tu peux travailler en mode hybride à partir de notre bureau de Montréal
Expérience internationale : tu as soutenu une équipe de direction répartie dans plusieurs pays et fuseaux horaires (un atout)

Qualifications

Excellente pensée stratégique et solides habiletés en résolution de problèmes, avec le jugement pour prioriser ce qui compte vraiment
Excellente communication écrite et orale : tu sais transformer des informations éparpillées en priorités, en recommandations et en plans d'exécution clairs, axés sur les résultats
Très organisé·e et orienté·e vers l'action, à l'aise pour jongler avec plusieurs priorités dans un environnement qui bouge vite
Grande discrétion avec l'information confidentielle
Solide sens des affaires dans les volets commercial, produit et financier ; à l'aise avec les données et les KPI
Enthousiasme pour les outils d'IA et les nouvelles façons de travailler
Tu vis nos valeurs : Care (tu fais passer l'équipe et Stay22 en premier), Curiosity (tu remets en question le statu quo et tu continues d'apprendre) et DWIFT (tu passes à l'action, tu assumes les résultats et tu trouves une façon de gagner)
Un plus : un MBA ou de l'expérience en technologie, en marketing d'affiliation ou en travel tech

À quoi t'attendre dans notre processus d'embauche

On sait que ton temps est précieux, alors voici un petit résumé de ce qui t'attend.

Appel de présélection avec notre partenaire en acquisition de talents (30 minutes)
Appel avec le ou la gestionnaire d'embauche (30 minutes)
Entrevue en panel avec des membres de différentes équipes (45 minutes)
Évaluation psychométrique, à faire à la maison
Entrevue finale avec notre CEO (30 minutes)
Offre et intégration 🎉

Note : ce processus peut évoluer selon les besoins de l’équipe

Pourquoi rejoindre Stay22 ?

Emplacement de choix à Montréal : Travaillez depuis notre dynamique siège social situé dans la Petite-Italie, avec une allocation pour la cafétéria, un accès complet au gym, ainsi qu’une terrasse sur le toit comprenant un terrain saisonnier de basketball/pickleball et une patinoire de hockey.
Une gamme complète d’avantages sociaux : Couverture santé et dentaire, contribution de l’employeur au REER, titre de transport STM entièrement payé, ainsi que des activités d’équipe, événements et retraites réguliers.
Une flexibilité adaptée à votre réalité : Horaires flexibles, possibilités de travailler de n’importe où, fermeture des bureaux en fin d’année et journées flexibles.

(Stay22 est un employeur garantissant l’égalité des chances. Toutes les candidatures qualifiées seront examinées. Si vous avez un handicap ou des besoins particuliers nécessitant des aménagements, contactez-nous à careers@stay22.com.)

Ton CV sera lu par Mariel, notre recruteuse interne, même si tu ne coches pas toutes les cases, on aimerait quand même te rencontrer.

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

As Chief of Staff, you'll be a strategic partner to the executive team and help turn company priorities into results. You'll run the company's operating cadence, lead high-impact projects across teams, and make sure leadership has the information, alignment and follow-through it needs to make good decisions quickly. You'll work across Commercial, Product, Engineering and Finance. It's a high-visibility role for someone who wants to understand how the whole company works and help shape where it goes next.

Key Responsibilities

Strategy and execution: Partner with the executive team to set company priorities and OKRs, track progress, and hold teams accountable for outcomes.
Supporting Key Initiatives: Leans in and supports operationalizing strategic initiatives across the organization, starting with operationalizing the new CRO Commercial plan.
Operating cadence: Own the leadership rhythm, including leadership meetings, business reviews, so decisions are made, documented and acted on.
Cross-functional alignment: Connect revenue teams with the rest of the company, unblock work, and keep communication clear across departments and levels of leadership.
Company events: Shape the agenda, content and sessions for company retreats and kickoffs so they advance our strategic priorities.
AI-first operations: Lead how AI is built into the company's operating system: find high-value workflows to automate, set standards for adoption, and scale tools across teams.

Requirements

5+ years in strategy, consulting or business operations, with at least 2 as a Chief of Staff or in a similar executive-facing role
Scale experience: you've worked as a Chief of Staff at a company with 200+ employees and $100M+ in revenue
Proven operator: you've taken complex, cross-functional projects from idea to impact
Montreal-based: you can work hybrid from our Montreal office
Global experience: you've supported a leadership team spread across countries and time zones (Asset)

Qualifications

Strong strategic thinking and problem-solving skills, with the judgment to prioritize what matters most
Excellent written and verbal communicator who can turn messy inputs into clear priorities, recommendations and execution plans focused on delivering outcomes.
Highly organized and able to execute, comfortable juggling many priorities in a fast-moving environment
A high level of discretion with sensitive information
Strong business sense across commercial, product and financial areas; comfortable with data and KPIs
Enthusiasm for AI tools and new ways of working
Lives our values: Care (puts the team and Stay22 first), Curiosity (challenges the status quo and keeps learning), and DWIFT (has a bias for action, owns outcomes and finds a way to win)
Nice to have: an MBA, or experience in technology , affiliate marketing, or travel tech

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 minutes)
Hiring Manager call (30 minutes)
Panel Interview with cross-functional team members (45 minutes)
Psychometric Assessment - completed at home
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?

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.

Apply on LinkedIn About employer

More about this job

Responsibilities

Partner with the executive team to set priorities and OKRs, manage leadership meetings and business reviews, and ensure decisions are documented and followed through. Lead cross-functional strategic initiatives, align revenue teams with other departments, shape company events, and scale AI tools and workflow automation across the organization.

Requirements

Requires 5+ years of experience in strategy, consulting, or business operations, including at least 2 years as a Chief of Staff or in a similar executive-facing role, plus experience at a company with 200+ employees and over $100 million in revenue. Candidates should have led complex cross-functional projects, be based in Montreal and able to work hybrid, and demonstrate strong strategic, communication, organizational, business, data, and discretion skills; international leadership experience is an asset.

Skills

Strategic Planning
Business Operations
Executive Partnership
OKR Management
Project Management
Cross-Functional Leadership
Operational Cadence
Stakeholder Alignment
Commercial Strategy
AI Operations
Workflow Automation
Data Analysis
KPI Management
Written Communication
Problem-Solving
Change Management

Benefits

Cafeteria Allowance
Gym Access
Rooftop Terrace
Health Insurance
Dental Coverage
RRSP Matching
Fully Paid STM Transit Pass
Team Socials
Company Events
Company Retreats
Flexible Schedules
Work-From-Anywhere Opportunities
Year-End Office Shutdown
Flex Days

Visa sponsorship

Not detected in the job text

Keywords

Chief of Staff
Strategy
Business Operations
Executive Leadership
OKRs
Commercial Plan
CRO
Operating Cadence
Business Reviews
Cross-Functional Alignment
Strategic Initiatives
AI Operations
Artificial Intelligence
Workflow Automation
AI Adoption
Revenue Operations
Product
Engineering
Finance
KPIs
Data-Driven Decision-Making
Creator Economy
Affiliate Marketing
Travel Technology
Technology
MBA

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Work requirements

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