Head of Innovation Operations

Stay22 • Montreal, QC

14d • Onsite

About The Position

The Head of Innovation Operations is a high-impact, high-trust role working directly with our co-founder and Chief Innovation Officer (CIO) to build and scale Stay22’s next chapter. You will lead a multidisciplinary team of innovators while establishing the structures, processes, and operating models that turn ideas into outcomes.
Blending strong people leadership with hands-on operational involvement, you will guide the team through ambiguity, shape the Innovation roadmap, and translate vision into clear, actionable plans. As a trusted partner to the CIO, you will drive alignment with business goals, communicate progress and risks to stakeholders, and remove blockers- ensuring innovation moves quickly, delivers real impact, and extends beyond the team itself.

Requirements

• English proficiency is required for daily communication with international colleagues and direct reports.
• Bachelor's or Master's degree in Business or a related field (or equivalent experience)
• Proven ability to lead, coach, and develop diverse team members. You excel at managing innovators with different specializations, from systems engineers to product-focused generalists, providing constructive feedback and helping individuals grow in their careers
• Excellent communication and interpersonal skills. Comfortable collaborating with cross-functional teams (Product, Design, other Engineering squads) and translating complex technical details into clear, actionable insights for stakeholders
• Creative and pragmatic problem-solver with a knack for navigating complex challenges. Able to make sound architectural decisions that balance immediate product needs with long-term platform health and scalability
• Demonstrated experience balancing hands-on technical involvement with high-level leadership. You take ownership of outcomes, ensure high quality standards, and have a track record of driving projects to successful completion. Experience in a fast-paced, agile startup/scale-up environment is highly valued

Nice To Haves

• Bonus experience in software development, including experience building scalable, reliable systems

Responsibilities

• Strategic Partnership
• Act as a force multiplier to the CIO, translating vision into clear priorities and executable plans.
• Drive alignment across leadership with visibility into progress, dependencies, and outcomes.
• Proactively identify and resolve risks, bottlenecks, and opportunities.
• Innovation Execution & Operating Model
• Build and run the Innovation engine, defining the operating model, processes, and rhythms that turn ideas into scalable outcomes.
• Lead initiatives end-to-end—from ideation and rapid experimentation to successful transition into core teams.
• Champion a “ship-to-learn” approach, using high-signal experiments to validate concepts before scaling.
• Ensure successful solutions are production-ready and can be integrated without rework.
• Team Leadership & Culture
• Build and lead a high-performing, multidisciplinary team of engineers, operators, and product thinkers.
• Hire and develop “0-to-1” talent who thrive in ambiguity and prioritize speed-to-learning.
• Foster a high-trust, high-performance culture where experimentation is encouraged and failure is treated as data.
• Empower teams to operate independently while removing organizational and technical friction.
• Governance, Enablement & Resources
• Establish lightweight governance that balances speed with accountability and makes innovation measurable and repeatable.
• Define clear signals for what to scale, iterate, or stop.
• Manage budgets, external partnerships, and key operational levers to maximize impact.
• Provide architectural guardrails, tooling, and resources to enable fast, high-quality execution.
• Internal and External Impact
• Act as the primary interface between Innovation and the broader organization, managing stakeholders and shielding the team from unnecessary process overhead.
• Bridge emerging technology with real user needs through direct customer engagement and data insights.
• Translate customer pain points into technical experiments and high-fidelity, design-forward prototypes.
• Maintain a focused Innovation roadmap by prioritizing high-impact opportunities over distractions.

Benefits

• 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 Little Italy, surrounded by great 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 11-50 employees