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Stay22, based in Montreal, helps ambitious creators and digital platforms monetize their traffic through background technology. The company serves 6,500+ creators and platforms with over $1 billion in annual transactions, operating across travel, retail, lifestyle, publishing, events, and transport sectors.
As Chief of Staff, you will be a strategic partner to the executive team, translating company priorities into concrete results. You will own the company's operating cadence, lead high-impact cross-functional projects, and ensure leadership has the information, alignment, and follow-through needed for rapid decision-making. You will work across Commercial, Product, Engineering, and Finance teams in a highly visible role.
Key Responsibilities:
- Partner with the executive team to establish company priorities and OKRs, track progress, and hold teams accountable for outcomes
- Support operationalization of strategic initiatives across the organization, including the new CRO Commercial plan
- Own the leadership rhythm, including executive meetings and business reviews, ensuring decisions are made, documented, and acted upon
- Bridge revenue teams with the rest of the company, unblock work, and maintain clear communication across departments and leadership levels
- Shape the agenda, content, and sessions for company retreats and kickoffs to advance strategic priorities
- Lead AI integration into company operations: identify high-value workflows to automate, establish adoption standards, and scale tools across teams
Requirements:
- 5+ years of experience in strategy, consulting, or business operations, with at least 2 years as a Chief of Staff or similar executive-facing role
- Scale experience: prior Chief of Staff role at a company with 200+ employees and $100M+ in revenue
- Proven operator who has taken complex, cross-functional projects from concept to impact
- Montreal-based and able to work hybrid from the Montreal office
- Global experience supporting a leadership team across multiple countries and time zones (asset)
Desired Qualifications:
- Strong strategic thinking and problem-solving skills with judgment to prioritize what matters most
- Excellent written and verbal communication; ability to transform complex inputs into clear priorities, recommendations, and execution plans
- Highly organized and action-oriented; comfortable managing multiple priorities in a fast-moving environment
- High level of discretion with sensitive information
- Strong business acumen across commercial, product, and financial domains; comfortable with data and KPIs
- Enthusiasm for AI tools and new ways of working
- Alignment with company values: Care (team and company first), Curiosity (challenge status quo, continuous learning), DWIFT (bias for action, ownership of outcomes, finding ways to win)
- Nice to have: MBA or experience in technology, affiliate marketing, or travel tech
