Technical Program Manager

Guesty; Montreal; On-site; CAD 110,000 - 150,000; Full time

Job summary

Guesty in Montreal, Canada, is seeking a Technical Program Manager to partner with customers, applying deep knowledge of the Guesty product to navigate complex technical challenges and guide advanced use cases.

You will drive product adoption, translate customer requirements into scalable solutions, train users, and collaborate with Customer Success to align product development with client needs, while acting as the Voice of the Customer.

Qualifications

• Minimum 4 years of technical experience in SaaS or tech-driven environment.
• API literacy and strong problem-solving skills.
• Strong communication and presentation abilities to engage clients and cross-functional teams.
• Ability to work independently and collaborate across teams.

Responsibilities

• Lead advanced consultations for complex customer use cases across Guesty domains.
• Translate business requirements into sophisticated technical solutions for clients.
• Provide high-impact training to empower users to be hands-on with the Guesty product.
• Drive proactive product adoption by optimizing client workflows and increasing stickiness.
• Identify opportunities to leverage AI tools and automated workflows to scale operations.
• Partner with Customer Success Managers to manage a shared book of business, aligning technical excellence with client health and retention.
• Act as the internal Voice of the Customer to feedback roadmap priorities for Product teams.

Skills

Technical Aptitude

Strategic Problem-Solving

Communication & Training

SaaS Product Advocacy

Proactive Drive

Analytical Thinking

Adaptability

AI Proficiency

Market Knowledge

Accounting Knowledge

Tools

API literacy

AI Tools

LLMs & Automation

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 900+ 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 Technical Program Manager, you position yourself as a key technical partner to our customers, leveraging a deep understanding of the Guesty Product to navigate their complex technical challenges. You will provide advanced guidance for our customer use cases and lead the resolution of intricate technical hurdles.

In addition to addressing immediate technical complexities, you will take a proactive approach to driving product adoption. You will ensure our clients achieve the technical optimization necessary for long-term retention and growth. This role requires a close, strategic partnership with the Customer Success Management team to analyze workflows and identify opportunities for deeper product utilization.

Internally, you serve as the definitive "Voice of the Customer." You will advocate for real-world client needs to ensure Guesty’s product development aligns with the features that drive value and revenue.

Key Responsibilities:

• Serve as the technical product expert across all Guesty domains by leading advanced consultations for complex customer use cases.
• Translate business requirements into sophisticated technical solutions, making complex concepts easy for clients to understand and implement.
• Empower client proficiency through high-impact training and guidance, ensuring users are hands-on and self-sufficient in the Guesty Product.
• Drive proactive product adoption by identifying opportunities to optimize client operations and improve workflows to increase product "stickiness."
• Identify opportunities to leverage AI tools, AI agents, and automated workflows internally and externally to scale operational efficiency and client enablement.
• Partner strategically with CSMs to manage a shared book of business, aligning technical excellence with overall account health and retention.
• Act as the internal "Voice of the Customer," translating real-world client needs into actionable feedback and roadmap priorities for Product teams.
• Meet or exceed expectations in KPI attainment and professional development.

Requirements:

Key Skills:

• Technical Aptitude: A solid background in navigating complex SaaS environments and a natural ability to master intricate technical use cases.
• Strategic Problem-Solving: The ability to analyze customer configurations and workflows to provide optimal, scalable solutions.
• Expert Communication & Training: Exceptional presentation skills with a talent for translating dense technical concepts into simple, actionable guidance for both clients and internal teams.
• SaaS Product Advocacy: Experience collaborating with Product organizations to vocalize feature requests, provide tangible feedback, and advocate for impactful roadmap releases.
• Proactive Drive: High level of initiative to identify adoption gaps, improve customer setup, and collect meaningful product feedback.
• Analytical Thinking: The ability to identify trends across account cohorts and use data to track evolving product needs.
• Adaptability & Evolution: A proven ability to thrive in a fast-paced environment and a proactive embrace of change—whether adopting new internal tools, evolving systems, or leveraging developing automations to improve efficiency.
• (Bonus) AI Competency & Operational Transformation: Practical experience leveraging modern AI tools, LLMs, and intelligent automations, paired with a proven ability to help evolve traditional business workflows into scalable, AI-first operations.
• (Bonus) Market Knowledge: Familiarity with the short-term rental market, the OTA landscape (Airbnb, Vrbo, etc.), and the property management software ecosystem.
• (Bonus) Accounting Knowledge: A foundational understanding of trust accounting, including experience with ledgers, reporting, and bank reconciliations.

Qualifications:

• Minimum of 4 years of technical experience within the SaaS software industry or in a technology-driven environment
• API literacy
• Demonstrated problem-solving skills and creative thinking
• Strong communication and presentation skills
• Ability to work independently and collaborate with cross-functional teams
• Demonstrated proficiency with modern AI tools, agentic workflows, or LLM-driven automation

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.