Senior Mid-Market Implementation Manager

About the role

The orchestrates the complete lifecycle of complex mid-market hotel group deployments, ensuring timely and successful go-lives that meet strategic business objectives. This role owns the end-to-end delivery for some of the most sophisticated hospitality technology implementations, requiring a blend of technical acumen and executive presence. You will serve as the primary internal conductor, aligning product, engineering, and support teams to deliver seamless experiences for hotel groups managing numerous properties. The position demands a high degree of ownership, where you will troubleshoot intricate workflow challenges and translate ambiguous requirements into clear, actionable plans. You will act as a strategic partner to hotel executives, guiding them through digital transformation initiatives powered by AI. This role is critical for reinforcing Canary's position as a trusted, innovative leader in the global hospitality technology landscape. You will leverage deep expertise to drive adoption, resolve cross-functional dependencies, and ensure that each deployment reinforces long-term customer loyalty.

Key facts

What you'll do

• Lead intake sessions to define the scope of large and complex hotel portfolios, capturing detailed requirements and success metrics.
• Design configuration blueprints that align with each property's unique workflows, ensuring seamless integration with PMS, payment gateways, and other third-party platforms.
• Coordinate with cross-functional and vendor teams to resolve issues and sustain deployment progress across multiple concurrent projects.
• Map data migration routes to ensure property records remain accurate, consistent, and reliable during live cutovers and go-live events.
• Drive user training programs tailored to different hotel stakeholder groups to ensure confident adoption and achievement of activation goals.
• Monitor usage data and system analytics to identify expansion opportunities and present strategic growth options to clients.
• Conduct stress testing of integrations with payment platforms and external systems to identify and mitigate risks before go-live.
• Produce comprehensive handover documents, runbooks, and operational procedures that support smooth transitions and future compliance audits.
• Establish clear success criteria at the outset of each deployment and maintain rigorous tracking against timelines and deliverables.
• Act as a trusted advisor to senior hotel executives, operating with independence and navigating uncertain situations with calm professionalism.
• Manage the end-to-end project timeline, including scoping, scheduling, resource allocation, and risk management for the portfolio of mid-market clients.
• Collaborate with product and engineering teams to provide feedback from the field, influencing product improvements and future feature development.
• Ensure all implementation activities adhere to Canary's quality standards, best practices, and brand promise across every engagement.
• Proactively communicate status updates, risks, and dependencies to internal stakeholders and external client leadership.
• Support the development of implementation playbooks and methodologies to standardize and scale the deployment process.

Requirements

• Must have two years of experience implementing hospitality technology in mid-market environments, with a proven track record of successful deployments.
• Requires a solid understanding of how property management systems interact with payment platforms and other third-party hospitality technology ecosystems.
• Must be capable of overseeing several hotel groups at once while maintaining precise documentation for each deployment stage.
• Requires effective communication skills to convey complex technical concepts to both senior hotel leaders and technical integration specialists.
• Must handle ambiguity well and adjust plans quickly when integrations, timelines, or scope change unexpectedly during live projects.
• Requires the ability to manage multiple priorities in a fast-paced environment without compromising on quality or client satisfaction.
• Must demonstrate strong problem-solving skills when troubleshooting configuration, data, or workflow issues during implementation.
• Requires a commitment to maintaining data integrity and operational continuity throughout the entire implementation lifecycle.

Nice to have

No specific additional skills or tools are listed for this role. Details regarding the application process should be verified Practical notes