Project Manager
About The Position
Guesty is the all-in-one platform for hospitality businesses to automate and optimize every aspect of their operations. With purpose-built technology, industry-wide expertise, and an R&D team of 200+ engineers, Guesty ensures that hospitality businesses can streamline and achieve growth, while delivering the best value to guests. With a complete suite of features and 150+ industry partners, including major booking OTAs like Airbnb, Vrbo, Booking.com, Tripadvisor, Expedia, Hopper, Google Travel, and many more, Guesty is transforming the hospitality industry with innovative solutions.
Today, Guesty has 15 offices and 800+ team members across the globe.
In Guesty, we use the latest technologies and frameworks and handle complex business operations, promoting open-mindedness, creativity, and self-reliance.
As a Project Manager on the Professional Services team, you will be responsible for leading the successful delivery of onboarding and implementation projects for our strategic and enterprise customers in North America. This role is key in ensuring projects are delivered on time, within scope, and with high quality, while maintaining exceptional communication with both internal and external stakeholders. You’ll collaborate closely with consultants, product, and technical teams to ensure a structured, well-governed onboarding experience that aligns with customer expectations and business goals.
Responsibilities
- Project Ownership & Planning: Own the full project lifecycle from SOW sign-off to post-onboarding handoff. Develop and manage detailed project plans including timelines, milestones, dependencies, and risk assessments.
- Cross-Functional Coordination: Align internal stakeholders across Professional Services, Product, CX, and Sales to ensure deliverables are met on schedule and with quality.
- Client Communication & Relationship Management: Serve as the primary point of contact for project updates, planning, and coordination with strategic and enterprise customers. Maintain open, clear, and timely communication throughout the onboarding process.
- Project Governance: Implement and maintain project governance standards, including change control processes, risk and issue tracking, documentation, and client sign-off management.
- Escalation Management: Proactively identify and manage project risks and roadblocks. Lead internal and customer-facing escalations and drive timely resolution with relevant stakeholders.
- Stakeholder Management: Act as the central liaison between internal teams and the customer, ensuring alignment around timelines, product readiness, integrations, and client expectations.
- Reporting & KPI Tracking: Monitor and report project performance against key metrics, providing transparency to both internal teams and customer stakeholders.
Requirements
- Experience: 3–5 years of experience in project management or implementation roles, ideally within a B2B SaaS or Professional Services environment. Proven experience managing strategic or enterprise-level customers with complex onboarding requirements.
- Project Management Skills: Demonstrated ability to lead cross-functional projects with accountability for outcomes. Skilled in managing timelines, dependencies, stakeholder communication, and risk. Experience with project management tools such as Rocketlane, Asana, Monday.com, or Jira. PMP or equivalent certification is a plus.
- Communication Skills: Excellent verbal and written communication skills, with the ability to effectively communicate with executive-level stakeholders. Comfortable leading high-stakes meetings and managing sensitive conversations.
- Technical Acumen: Ability to understand software configuration, APIs, and data migration workflows. Experience collaborating with technical and product teams on deliverables.
- Ownership & Accountability: Strong attention to detail with the ability to manage multiple projects simultaneously. High sense of ownership and a proactive approach to problem-solving.
- Customer Focus: Professional and customer-centric demeanor. Committed to delivering value and long-term success to customers through structured project execution.
- (Bonus) PMS Industry Knowledge: Familiarity with the Property Management Software (PMS) industry or the short-term rental (STR) technology ecosystem is a plus.
**Please note that this is a Remote position - must be located in Canada**
Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.