Head of Customer Success (CSM)

About the Company

Rezdy, together with sister brands Checkfront and Regiondo, powers more than 20,000 businesses and supports over $10 billion in bookings globally. Our technology helps operators thrive while delivering unforgettable moments to travelers. We operate across North America, Europe, and Asia‑Pacific, united by bold goals, a bias for action, and an unwavering commitment to our customers. We value self‑starters who take ownership, embrace challenges, and raise the bar for themselves and those around them.

About the Role

We are looking for a Head of Customer Success, North America to lead our Customer Success organization across Rezdy and Checkfront and build a high‑performing, commercially minded CSM function across the region. This hands‑on leadership role sets strategy while staying close to the work, owning retention, growth, and deepening relationships with North American customers, and creating operating discipline, talent, and engagement models needed to scale.

Responsibilities

• Lead the North American Customer Success organization across Rezdy and Checkfront, setting the strategy, expectations, and operating rhythm for the region.
• Own retention and growth outcomes across the North American customer base, with clear accountability for gross retention, net revenue retention, churn, expansion, and overall customer health.
• Build a consistent CSM operating model across both legacy brands, bringing greater clarity to segmentation, coverage, engagement expectations, customer health, and account planning.
• Develop a high‑performing, accountable CSM team through strong coaching, clear expectations, regular performance conversations, and thoughtful talent development.
• Stay close to our customers: build relationships with strategic accounts, join critical customer conversations, support escalations, and help the team navigate complex retention and growth opportunities.
• Establish a strong operating cadence around customer health, renewals, churn risk, expansion pipeline, forecasting, and account strategy, ensuring early identification of opportunities and risks.
• Build a proactive approach to retention, moving beyond reactive account management toward clear success plans, measurable customer outcomes, and meaningful ongoing engagement.
• Strengthen the commercial capability of the CSM organization, ensuring the team can identify customer needs, communicate value, and confidently uncover and progress expansion opportunities.
• Partner closely with Sales and Onboarding to create strong customer transitions, clear ownership, and alignment on expectations from the beginning of the customer lifecycle.
• Work with Support and Product to surface recurring customer challenges, product gaps, and opportunities to improve the overall customer experience.
• Use customer and business data to understand trends, prioritize action, and continuously improve how we manage and grow our customer base.
• Represent the voice of the North American customer internally, bringing clear, actionable insights to leadership and cross‑functional teams.
• Help shape the broader global Customer Success strategy by sharing what works, challenging what does not, and building practices that can scale across regions.

Qualifications

• Significant experience leading Customer Success, Account Management, or a similar post‑sale organization, ideally within a B2B SaaS or technology company.
• Proven experience leading and developing CSMs and customer‑facing leaders, with a track record of building high‑performing, accountable teams.
• Strong commercial instincts and demonstrated ownership of retention, renewals, expansion, churn, and net revenue retention.
• Experience managing a varied customer portfolio and developing segmentation and engagement strategies appropriate for different customer sizes and needs.
• A hands‑on leadership style; comfortable setting strategy and equally comfortable getting into an account, joining a customer call, reviewing a renewal, or coaching a CSM through a difficult conversation.
• Strong operational discipline and experience building scalable processes around customer health, forecasting, account planning, renewals, and performance management.
• A data‑driven mindset with the ability to turn customer and commercial data into clear priorities and action.
• Strong executive communication skills and the ability to build trusted relationships with senior customers and internal stakeholders.
• Experience leading through change, particularly bringing together teams, processes, or customer motions that have historically operated differently.
• The ability to partner effectively across Sales, Onboarding, Support, Product, Marketing, and Operations while maintaining clear accountability for Customer Success outcomes.
• A bias for action, strong judgment, and comfort operating in a fast‑moving environment where not everything is already built for you.
• Experience in travel technology, reservation software, vertical SaaS, or the tours and activities industry is a plus, but not required.

What You Can Expect

• High trust, real impact: autonomy and expectation to lead with ownership, tackle problems end‑to‑end, and make decisions that move the business forward in meaningful ways.
• Curiosity with discipline: asking sharp questions, challenging assumptions, and exploring smarter ways to work; getting things done right for customers.
• One team, all in: collaboration beats ego, wins are shared, and we rally together when the work gets tough.
• Space to grow: supported and stretched, taking on challenges that build capability, sharpen judgment, and accelerate growth as a leader and problem‑solver.
• Progress with purpose: move fast, stay focused on what truly matters, and prioritize long‑term impact over quick fixes.