Head of Customer Success; CSM

Head of CSM, NA

At Rezdy, we’re builders, doers, and difference-makers, driven by a shared mission to reshape the tours, activities, and experiences industry. Alongside our sister brands, Checkfront and Regiondo, we power more than 20,000 businesses and support over $10B in bookings globally. Our technology helps operators thrive while delivering unforgettable moments to travelers around the world.

We work in an industry built on adventure, energy, and human connection, and that same spirit fuels how we show up every day. Spanning North America, Europe, and Asia-Pacific, our teams are united by bold goals, a bias for action, and an unwavering commitment to delivering for our customers.

Our success starts with people. Our teams are the engine behind everything we create. We value self‑starters who take ownership, embrace challenges, and raise the bar, for themselves and those around them. We believe in creating space to grow, take risks, and make a real impact, and we celebrate those who lead with curiosity, grit, and drive.

If you’re passionate about performance, hungry to learn, and ready to help shape the future of travel- this is your kind of place. Let’s build, grow, and win together.

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 is a hands‑on leadership role for someone who can set the strategy while staying close to the work. You will own how we retain, grow, and deepen relationships with our North American customers, while building the operating discipline, talent, and customer engagement model needed to scale.

You will bring together teams and ways of working across our brands, creating greater consistency in how we manage customer health, drive adoption, identify risk, deliver value, and uncover opportunities for growth. You will partner closely with Sales, Onboarding, Support, Product, and other leaders across the business to create a connected customer journey and ensure our customers see measurable value from their partnership with us.

• 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 we identify opportunities and risks early.
• Build a proactive approach to retention, moving the organization 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…