Senior Mid-Market Implementation Manager

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 HotelTechReport Best Place to Work — and is backed by top Silicon Valley investors like Y Combinator, F-Prime, Brighton Park Capital and Insight Partners. Join us in shaping the future of hospitality! 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. Responsibilities 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. Qualifications 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. We also work hard to ensure Canary is a fun and exciting place to work! Here are some of the additional benefits: Canary Days: As a company we want to ensure that the team has time to recharge. Each month we provide company wide days off to ensure there is at least one extended weekend or day off. Self Improvement Club: We meet each month and share our personal goals for the month. Each individual is provided a budget towards any purchases that help us achieve these goals. Professional Development Chats: We provide budget to help drive cross functional professional development conversations across the organization. Travel Reimbursement: Team members are able to visit our offices across New York, San Francisco or Dallas when they choose, and are provided a travel stipend for doing so. Spend time working with the team in their office, and use the rest of your time exploring a new city! Personal Travel Reimbursement: If you stay at a hotel that Canary works with, we provide a credit towards your stay. 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.