Senior Mid-Market Implementation Manager

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.