Chief of Staff

Job Title: Chief of Staff to the COO

About Stay22

At Stay22, we’re on a mission to revolutionize the travel media industry. Using cutting-edge AI-powered solutions, we empower travel media companies and content creators to unlock fresh revenue streams and seamlessly monetize their platforms. With us, you’re not just enhancing your income—you’re elevating travel experiences for your audience. Join our vibrant team and be part of a journey that’s making travel media more rewarding for everyone.

Job Summary

The Chief of Staff will play a critical role in supporting the COO and ensuring the seamless alignment and coordination of managers across all departments. As the central hub for operational efficiency, this person will help drive collaboration, streamline processes, and maintain consistency in our strategic objectives.

Key Responsibilities

• Manager Alignment and Support:
  • Act as the primary point of contact between the COO and department managers, ensuring clear communication and alignment on priorities.
  • Facilitate regular check-ins with managers to monitor progress on KPIs, projects, and operational goals.
  • Identify bottlenecks or cross-departmental issues and propose solutions.
• Operational Planning & Coordination:
  • Assist the COO in the development and execution of operational strategies and plans.
  • Coordinate cross-functional initiatives, ensuring deadlines, resources, and deliverables are effectively managed.
  • Maintain an operational calendar to track critical dates, events, and milestones.
• Process Optimization:
  • Support managers in documenting, analyzing, and improving workflows and processes.
  • Help implement operational tools and software to enhance efficiency.
  • Conduct follow-ups to ensure processes are adhered to consistently across departments.
• Meeting Coordination & Facilitation:
  • Prepare agendas, presentations, and summaries for leadership and operational meetings.
  • Facilitate meetings to promote productive discussions and actionable outcomes.
  • Ensure all tasks and action items are tracked and followed up on.
• Data Analysis & Reporting:
  • Gather and compile data from department managers for reports to the COO.
  • Support in analyzing operational performance and recommending improvements.
  • Assist in preparing materials for board or stakeholder updates.
• General Administrative Support:
  • Manage communications, scheduling, and other administrative needs for the COO.
  • Handle ad hoc tasks and special projects as assigned.

Requirements

• Bachelor's degree in Business Administration, Operations Management, or a related field (or equivalent experience).
• 2–4 years of experience as a Chief of Staff or in any similar role, ideally in the travel tech or tech startup industry.
  
• Strong organizational and multitasking abilities with exceptional attention to detail.
• Excellent communication and interpersonal skills to manage relationships across all company levels.
• Analytical mindset with the ability to synthesize data and make actionable recommendations.
• Proficient in project management tools (e.g., Asana, Trello) and office software (e.g., Excel, Google Workspace).
• Proven ability to work under pressure and manage competing priorities.
• A collaborative and team-oriented attitude, with a knack for solving problems proactively.
• Knowledge of scaling operations in a fast-growth environment (an asset).

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)