Head of Customer Success

Vancouver, British Columbia, Canada · Customer Success

About Us

Operto Guest Technologies, the world’s leading property automation and IoT operating system for vacation rentals, hotels, and serviced apartments, is revolutionizing guest stays and hospitality management. Through technology that connects teams, guests, owners, and smart devices; Operto addresses common friction points to provide fully seamless and personalized stays - creating greater efficiency, guest satisfaction, and more revenue.

Role Overview

We are looking for a strategic, customer-obsessed leader to join Operto as our Head of Customer Success. This is a senior leadership role responsible for owning and scaling our entire post-sales customer journey—including Customer Success Managers (CSMs), Onboarding, and Support. You will lead and inspire a high-performing team that is laser-focused on driving customer outcomes, increasing product adoption, reducing churn, and growing revenue through renewals and expansions.

You’ll work cross-functionally with Product, Sales, Marketing, and Engineering to represent the voice of the customer and ensure we deliver an exceptional experience throughout the customer lifecycle. This is a critical role in shaping the future of Operto’s customer success strategy and operational execution.

If you're a passionate customer champion who thrives in a fast-paced, scaling SaaS environment, we want to hear from you.

Role Responsibilities

• Own the strategic vision, execution, and performance of the entire CS organization, including Onboarding, CSMs, and Support.
• Establish the overall customer success strategy to drive retention, expansion, and customer satisfaction. Define and track team OKRs and KPIs.
• Design and implement scalable programs that reduce churn, increase renewals, and promote upsell and cross-sell opportunities.
• Champion the voice of the customer across Operto and define the customer journey from onboarding through renewal.
• Implement processes, tools, and metrics to improve CS efficiency, visibility, and scalability across all functions.
• Recruit, coach, and develop a global team of CSMs, Onboarding Specialists, and Support professionals. Foster a high-performance and customer-first culture.
• Partner with Product, Engineering, Sales, and Marketing to align around customer needs, product feedback, and go-to-market strategy.
• Maintain strong relationships with key customers and executive stakeholders to ensure alignment with their goals and continued success.
• Oversee and resolve high-priority customer issues while reinforcing processes to prevent recurrence.

Required Qualifications and Skills:

• 4+ years of progressive leadership experience in Customer Success, with at least 2 years in a senior management role within a SaaS or tech company.
• Demonstrated success owning customer retention, onboarding, and support functions at scale.
• Proven ability to lead high-performing teams and drive measurable results through strategic planning and hands-on execution.
• Strong analytical, problem-solving, and decision-making skills.
• Exceptional communication skills with the ability to influence stakeholders at all levels.
• Experience working cross-functionally in a high-growth, agile environment.
• Bachelor’s degree in Business, Technology, or related field. MBA or advanced degree is a plus.

Preferred Qualifications:

• Experience in a SaaS environment.
• Hospitality Experience is a huge asset!
• Familiarity with creating and managing Confluence documentation.
• Background in implementing customer feedback processes and improving support operations.
• Experience using tools such as Salesforce, Fullstory, Stripe, Dialpad, Outreach and Jira is an asset.

What does Success look like?

• Customer retention and satisfaction scores improve quarter over quarter.
• The CS team is engaged, accountable, and aligned to business goals.
• Scalable onboarding and support models are implemented and delivering measurable impact
• The voice of the customer is reflected in company-wide decision-making.
• Expansion revenue is growing through customer success-led initiatives.

Why We Love Working Here

• A modern office in a central location with free snacks/drinks and fun activities
• We have a top Health and Dental plan! We work to ensure we have one of the best plans for our team members.
• We’re champions of diversity. Our diverse backgrounds, skills, and abilities make us stronger. We work hard to make Operto a place where everyone feels welcome, respected and supported.
• We have regular team get-togethers, parties, and believe in celebrating our wins and having fun
• We are a hybrid environment that combines the energy and connections of being in the office with the benefits and flexibility of working from home. We currently require a minimum of three coordinated days in the office per week.

Operto is an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin or disability status. We are committed to providing accommodations in all parts of the hiring process. Upon request, we will work with you to meet your needs.

We thank all applicants for their interest, however, only those candidates selected for an interview will be contacted.