Chief of Staff & Corporate Development Lead

About Us

Canary Technologies is changing the game for hotels with modern software powered by Canary's hospitality-specific AI platform.

Canary is utilized by 20,000+ hoteliers in 100+ countries to equip hoteliers with the technology they need to work smarter and wow their guests. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western trust Canary to deliver results.

Canary was named a 2024 Deloitte Technology Fast 500™ company, a Most Innovative Company by Fast Company and a Hotel Tech Report  Best Place to Work — and is backed by top Silicon Valley investors like Y Combinator, F-Prime, Brighton Park Capital and Insight Partners.

We are seeking a highly analytical, execution‑oriented Chief of Staff & Corporate Development Lead to work directly with the CEO and drive the company’s most critical strategic and operational priorities. This role combines a close day‑to‑day partnership with the CEO and ownership of corporate development initiatives, including M&A and long‑term strategic planning.

This is a high‑impact role designed for someone with a strong foundation in investment banking or management consulting who is eager to apply that skill set in an operating environment and take meaningful ownership of outcomes.

• Chief of Staff to the CEO – Act as a trusted thought partner to the CEO on strategy, prioritization, and execution.
• Help set and manage the CEO’s agenda, ensuring focus on the highest‑impact initiatives.
• Assist in the preparation of Board materials, investor updates, and key executive communications.
• Drive alignment, accountability, and follow‑through across the executive team.
• Own and execute cross‑functional initiatives spanning all parts of the business.
• Identify risks, gaps, and opportunities early, and proactively recommend solutions.
• Serve as a point of leverage between the CEO and the broader organization.
• Manage the CEO’s EA.
• Corporate Development & Strategic Initiatives – Own and execute corporate development efforts, including M&A strategy and evaluation, financial modeling, valuation, and strategic analysis, diligence coordination and transaction execution, post‑merger integration planning and execution, support long‑term strategic planning, capital allocation decisions, and growth initiatives, and assist with international expansion and new product line strategy as needed.

• 7+ years of total professional experience.
• At least 3 years of experience at a top‑tier investment bank or management consulting firm.
• Prior operating experience in a company environment (post‑banking or consulting).
• Strong experience in financial modeling and strategic analysis.
• Prior exposure to technology, SaaS, or high‑growth companies (preferred).
• Experience supporting or executing M&A, corporate development, or strategic initiatives (preferred).
• MBA not required, but a plus.

• Strong written and verbal communicator; able to influence senior stakeholders.
• High ownership mentality — treats company outcomes as personal responsibility.
• Able to operate comfortably at both 30,000 feet and in the weeds.
• Highly organized and detail‑oriented.

• Direct, daily partnership with the CEO.
• Broad exposure across strategy, operations, finance, and leadership.
• Meaningful ownership of high‑impact initiatives and decisions.
• Opportunity to help shape the long‑term direction of a category‑leading company.
• Strong pathway to expanded leadership responsibility over time.

Base Salary Range: $175,000–$300,000 annualized salary. This is subject to standard withholding and applicable taxes. Actual compensation will be commensurate with the candidate’s skill level, experience, and specific work location. The role may also include the opportunity to earn a discretionary bonus and/or equity.

• Canary Days – Company‑wide days off each month to ensure at least one extended weekend or day off.
• Self Improvement Club – Monthly meetings to share personal goals; budget for purchases that help achieve these goals.
• Professional Development Chats – Budget for cross‑functional professional development conversations.
• Travel Reimbursement – Travel stipend for visiting offices in New York, San Francisco, or Dallas.
• Personal Travel Reimbursement – Credit toward stays at partner hotels.

Canary Technologies is an equal opportunity employer. We recruit, employ, train, compensate and promote talent regardless of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information or any other protected characteristic.