Technical Program Manager

Guesty; Canada; On-site; CAD 110,000 - 140,000; Full time

Job summary

Guesty is seeking a Technical Program Manager to partner with customers, translating complex SaaS use cases into actionable technical solutions and guiding adoption of the Guesty product. You will train users, collaborate with Customer Success, and shape product priorities by voicing real-world needs.

This is a fast-paced, global role with opportunities to influence AI-enabled workflows. Ideal candidates have 4+ years in SaaS, API literacy, and strong communication skills.

Qualifications

• Minimum of 4 years of technical experience in 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.

Responsibilities

• Lead advanced consultations as technical product expert across Guesty domains.
• Translate business requirements into scalable technical solutions and implementable guidance for clients.
• Provide high-impact training to enable client hands-on product use.
• Drive proactive product adoption by optimizing client operations and workflows.
• Identify opportunities to leverage AI tools and automated workflows to scale operations.
• Partner with Customer Success Managers to align technical excellence with account health and retention.
• Advocate for customer needs to Product teams and translate feedback into roadmaps.
• Meet or exceed KPI expectations and pursue professional development.

Skills

SaaS tech depth

Strategic problem solving

Communication training

Product advocacy

Adoption & ops

Analytical thinking

Adaptability

AI/automation experience

Market knowledge

Accounting basics

Job description

Technical Program Manager

• Onboarding
• Canada
• Mid- Senior

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.

Responsibilities

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.