Executive Operations Associate

Stay22; Montreal; Hybrid; CAD 80,000 - 100,000; Full time

Job summary

A dynamic technology company in Montreal seeks an Executive Assistant to support the CEO and Chief of Staff. This hybrid role involves managing the CEO's calendar, booking travel, and handling operational tasks. Ideal candidates will have 5-10 years in a fast-paced environment, be organized, proactive, and comfortable with various tools. A competitive salary and comprehensive benefits are offered.

Benefits

Health & dental benefits

Retirement plans

Learning & development opportunities

Social & team-building activities

Qualifications

• 5-10 years in a fast-paced, dynamic environment.
• Thrive in fast-moving environments where priorities shift.
• Comfortable juggling multiple projects, details, and deadlines.

Responsibilities

• Manage CEO's calendar to optimize time.
• Book travel and plan company events.
• Prepare materials and drafts for communication.

Skills

Organized

Proactive

Reliable

Detail-oriented

Multitasking

Tools

Google Workspace

Slack

Asana

Notion

Job description

About Stay22

At Stay22, we’re revolutionizing how people convert online. Our AI-powered affiliate platform helps publishers, ticketing platforms, and content creators unlock new revenue streams while levelling up their audience's user experience. At Stay22, our partners don’t just earn more, they deliver more. Join us and be part of something big that's shaking up the affiliate world.

Position Overview

We’re looking for someone who thrives on getting things done. This role is all about enabling leaders to move faster, stay focused, and make better decisions by taking care of everything else that would slow them down. You’ll support our CEO directly while also reporting to our Chief of Staff. In this hybrid role, you’ll take on high-impact operational tasks across Finance, People Operations, and Office Management playing a critical role in keeping the company running smoothly and enabling our leadership to operate at their best. This is a high-growth role with direct exposure to business operations at the leadership level.If you're someone who notices problems and quietly fixes them before anyone else sees them, you'll thrive here.

Key Responsibilities

Executive & Calendar Management

• Manage CEO’s calendar to protect time for focus, travel, and priorities.
• Ensure meetings are purposeful with agendas, context, and clear outcomes.
• Take notes and track follow-ups when needed.
• Book meeting rooms, venues, catering, and restaurant reservations.
  
  

Travel & Events Logistics

• Book flights, hotels, trains, and car rentals for leaders, teams, and company events.
• Create detailed itineraries with all key info (times, contacts, addresses).
• Adapt quickly to last-minute changes.
• Plan and coordinate company events, retreats, and celebrations.
  
  

Communication & Information Support

• Monitor CEO inbox, flag priorities, and draft/edit key communications.
• Prepare materials, briefs, and research for meetings, partners, and events.
  
  

Task & Project Coordination

• Maintain prioritized task lists in tools like Notion, Asana, or Trello.
• Track progress and follow up on cross-functional projects to ensure nothing is missed.
  
  

Office & People Ops Support

• Support onboarding logistics (equipment, workspace setup, candidate travel).
• Keep office stocked, organized, and guest-ready.
• Liaise with building management on facilities.
• Manage access cards, parking, and gym passes.
• Maintain first aid readiness (training, supplies).
  
  

Requirements

• 5-10 years in a fast-paced, dynamic environment
• You’re organized, reliable, and proactive. You don’t wait to be told.
• You thrive in fast-moving environments where priorities shift.
• You’re comfortable juggling multiple projects, details, and deadlines.
• You follow through on everything you commit to.
• You handle sensitive info with discretion and professionalism.
• Familiarity with tools like Google Workspace, Slack, Float, Asana, Notion.
  
  

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 (30-45 minutes)
• Interview with the Chief of Staff (30 minutes)
• Interview with the CEO (30 minutes)
• Final in-person interview with the Executive Team (60-90 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?

• 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
• 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)

Compensation Range: CA$80K - CA$100K