Senior Mid-Market Implementation Manager

About Us

Think about your last hotel stay. Did you skip the front desk line with mobile check-in? Message the staff for extra pillows? Order a late-night snack with a tap on your phone? Then you’ve likely run into Canary in the wild.

Canary Technologies is the leading agentic AI platform for hotel and guest management, powering the digital infrastructure for more than 20,000 hotels in 125+ countries. The world's most renowned hospitality brands, including Marriott International, Four Seasons and Wyndham Hotels & Resorts, partner with us to increase revenue, improve operations and elevate the guest experience.

We’ve executed the largest deployment of autonomous AI systems in hospitality, building technology that fundamentally redefines how guests and hotels interact. It’s made us one of the top-funded hotel technology companies in the world, with nearly $200M raised to date.

Canary has been recognized as a 2024 and 2025 Deloitte Technology Fast 500™ company, Inc. 5000 fastest-growing company, and swept the 2026 HotelTechAwards, including Best Place to Work, #1 Guest Experience Platform, and the Hotelier’s Choice Award. We’re scaling our team to bring innovation to life faster than ever.

We're growing quickly, and we're looking for people who are passionate about their work, want to grow with us and are ready to take on more responsibility along the way. We value rigor and velocity in equal measure: high standards, fast pace, real ownership. If that's the environment you're looking for, this is the place for you.

Come join us! Let’s shape the future of hospitality together.

About the Role

The Senior Mid-Market Implementation Manager owns the onboarding and go-live of Canary's most complex, higher-value hotel and hotel-group clients. This is a portfolio position: you will run multiple mid-market deployments in parallel, each with several stakeholders, custom configurations, and integrations to property systems (PMS, payment, and other third-party platforms). You will set mutual success criteria up front, coordinate cross-functional and vendor teams, and keep timelines moving through complexity, escalations, and change while identifying and driving expansion of the Canary relationship. This is a high-visibility, customer-facing role for an experienced implementation professional who can operate independently, navigate ambiguity, and act as a trusted advisor to senior hotel operators.

What You’ll Do

• Own end-to-end onboarding for a portfolio of mid-market and multi-property clients — from kickoff through go-live and initial adoption — running several deployments in parallel without letting timelines slip.
• Scope, configure, and deploy Canary's full product suite to each property's operational setup, including complex, non-standard configurations across hotel groups and portfolios.
• Lead integrations to customer systems (PMS, payment, and other third-party platforms): scope technical requirements, coordinate internal technical teams and outside vendors, and keep the project moving when integrations are delayed or complex.
• Establish mutual success criteria and a joint deployment plan with the customer up front, then drive product adoption to ensure those goals are measurably met.
• Manage senior and multi-stakeholder relationships- navigate pushback, reset expectations, resolve escalations, and maintain trust and momentum toward go-live.
• Identify and drive expansion opportunities during onboarding, partnering with Sales and Customer Success to grow the relationship beyond the initial deployment.
• Coordinate cross-functionally (Product, Support, Engineering, Sales, CS) to unblock issues and deliver a seamless customer experience in a resource-constrained environment.
• Track milestones, risks, and portfolio health in internal systems; forecast go-live timing and flag at-risk deployments early.
• Partner with Customer Success Managers to ensure a clean handoff into long-term account management.
• Contribute to and improve mid-market onboarding playbooks, best practices, and tooling; help mentor and raise the bar for the broader Implementation team.

What We’re Looking For

• Bachelor's degree (BS/BA).
• 2-3 years of proven experience in account management or customer success, preferably within a B2B SaaS environment.
• Excellent communication abilities and presentation skills, capable of building trust and rapport with diverse stakeholders
• Proven track record managing a portfolio of concurrent implementations and delivering to go-live on time.
• Charisma + consultative mindset: sets success criteria up front, drives adoption, and spots expansion opportunities.
• Ability to manage multiple accounts simultaneously and prioritize tasks effectively.
• Collaborative nature, adept at working with cross-functional teams including Product, Marketing, Sales, and Operations
• Proficiency with technology and adaptability to dynamic environments
• Hands-on experience scoping and managing third-party systems and coordinating technical teams and external vendors
• Highly organized and rigorous about time management and prioritization across competing deadlines.
• Hospitality and/or travel tech experience a plus.

Compensation

Target cash compensation ranges from $104,000 - $127,000, including a fixed annual salary and a performance-based bonus paid quarterly.

This role also includes a stock option grant, subject to board approval.

Actual compensation will be commensurate with the candidate's skill level, experience, and specific work location.

Perks & Benefits

We work hard to make Canary a fun, rewarding, and high-energy place to work. Here’s how we take care of our flock:

Time Off

• Unlimited PTO: Take the time you need to truly rest and recharge.
• Holidays + Canary Days: Standard holidays plus monthly company-wide days off for a guaranteed long weekend.
• Birthday Holiday: A dedicated day off to celebrate you!

Travel & Office Flexibility

• Office Exchange: A travel stipend to visit the team in person at our SF, NY, or Dallas hubs.
• Canary Hotel Experience: Staying at a Canary hotel? We’ve got you covered with a credit toward your stay.
• Preferred Hotels Discount: Enjoy a minimum 30% off the best available rate at select partner hotels globally.

Growth & Community

• Self Improvement Club: A monthly budget to help you smash your personal goals.
• Professional Development: Level up your career with a dedicated learning stipend to fuel your skills and cross-functional connection.
• Referral Program: Help us grow the flock and score a cash bonus for successful hires.