Professional Services Project Manager

Guesty; Montreal; On-site; CAD 70,000 - 100,000; Full time

Job summary

A fast-growing global startup seeks a Project Manager for its Professional Services team in Montreal. The successful candidate will lead onboarding and implementation projects for enterprise clients, ensuring timely and high-quality project delivery while collaborating with various internal teams. Required skills include strong communication, project management experience in a SaaS environment, and familiarity with project management tools.

Qualifications

• 3–5 years of experience in project management in a SaaS environment.
• Proven ability to manage strategic customers with complex onboarding.
• Experience in leading cross-functional projects and managing stakeholder communication.

Responsibilities

• Own the full project lifecycle from SOW sign-off to post-onboarding handoff.
• Serve as the primary point of contact for project updates with customers.
• Monitor and report project performance against key metrics.

Skills

Project Management

Communication

Cross-Functional Coordination

Risk Management

Education

PMP or equivalent certification

Tools

Rocketlane

Asana

Monday.com

Jira

Job description

Guesty is the all-in-one platform helping hospitality businesses around the world automate, optimize, and scale their operations. We’re a fast-growing global startup that’s transforming how the industry works — from guest experience to business growth.With a powerful suite of features and integrations with 150+ industry partners — including Airbnb, Vrbo, Booking.com, Expedia, Google Travel, and many more — Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven operations.We’re proud to have over 800+ team members across 16 countries worldwide, all working together to build the future of hospitality technology.If you’re looking to grow your career in a dynamic, global, and impact-driven environment, we’d love to hear from you.

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 professional services consultants, product, and technical teams to ensure a structured, well-governed onboarding experience that aligns with customer expectations and business goals.

*MUST RESIDE IN ONTARIO*

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:

• 3–5 years of experience in project management or implementation roles within SaaS 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.

A self-starter who can work independently and collaborate in a fast-paced team environment