Head of Customer Success, North America

About Us

We are Rezdy, Checkfront, and Regiondo—three leading brands united under one mission: empowering experience providers worldwide to grow, thrive, and deliver unforgettable moments. Fueled by teamwork and the combined strength of our brands, we are dedicated to equipping tour, activity, and experience providers with the tools they need to succeed.

We believe experiences shape who we are—creating lasting memories, fostering connections, and offering fresh perspectives on the world. With this vision at our core, we help 20k businesses globally, processing more than $10 billion in bookings to date. Our solutions enable operators to streamline operations, manage online bookings, boost sales, and enhance customer experiences—whether it’s simplifying the booking process, expanding reach through multiple sales channels, or giving providers the freedom to focus on creating memorable experiences.

With teams across North America, Europe, Australia, and beyond, we are a fast-growing organization passionate about technology, creativity, and collaboration. Our strong foundation and deep industry expertise allow us to deliver reliable, scalable, and customer-centric solutions that empower businesses and transform the way people experience the world.

Joining us means becoming part of a dynamic, hard-working, global team shaping the future of the tours and activities industry.

We live by three core values:

• Be a Trusted Guide: Support our customers and each other with expertise and integrity
• Shape the Future: Drive innovation and improvement in everything we do
• Be Proud of the Journey: Celebrate successes and learn from challenges along the way
  
  

Join our team to be part of a dynamic company that is transforming how businesses in this sector operate and succeed.

We look for people who…

• Do the right thing, lead by their personal integrity
• Are truly customer-focused and proactive with support
• Can execute strategic and meaningful customer interactions
• Go above and beyond - adapt and be flexible in their thinking and processes
• Love team collaboration, knowledge sharing and aren’t afraid to learn
  
  

About The Role

We’re looking for a strategic and people-first leader to head our Customer Success team and shape the next phase of our client experience strategy. This role is central to building long-term, high-value relationships with our customers, driving retention and growth, and evolving our team into a world-class customer success function.

As the Head of Customer Success, you’ll set the vision, lead the team, and implement the infrastructure needed to scale client outcomes across all segments—from SMBs to enterprise. You'll partner closely with leaders across Sales, Product, and Marketing to ensure our clients succeed, grow, and stay with us long-term.

What you’ll do

Team Leadership & Strategy

• Lead, coach, and grow a high-performing Customer Success team with a focus on accountability, collaboration, and measurable outcomes
• Set the long-term strategy for the function, aligning client success initiatives with company-wide goals and revenue targets
• Build team structure and operating models that support scale while ensuring a high-touch experience across a diverse customer base
• Invest in team development and leadership pipeline, identifying future leaders and supporting career growth within the team
  
  

Client Retention & Growth

• Design and refine scalable success playbooks and engagement strategies tailored to client lifecycle stages and market segments
• Ensure the team identifies and pursues meaningful expansion opportunities across our product suite—renewals, upsells, and cross-sells
• Work with Sales and Product Marketing to align messaging and drive seamless transitions from onboarding to long-term value
• Oversee strategies that elevate Net Revenue Retention (NRR) and ensure performance consistently exceeds benchmarks
  
  

Client Experience & Relationship Management

• Champion a customer-first mindset across the organization by driving deeper engagement, satisfaction, and loyalty
• Build systems to maintain strong health metrics and early warning signals, ensuring proactive support before issues arise
• Step in to support strategic accounts when needed—whether for executive alignment, complex renewals, or client escalations
  
  

Operational Excellence & Insights

• Use data to inform decisions—from forecasting and performance reviews to customer health tracking and CSAT/NPS scores
• Define and monitor KPIs to assess team performance, identify gaps, and drive continuous improvement
  
  

Improve internal processes, tech stack usage, and reporting to make the team more efficient and impactful over time.

What we are looking for

• 7 years of experience in Customer Success, Account Management, or Sales within SaaS or tech-driven environments
• 5 years in a leadership role managing high-performing teams in fast-scaling organizations
• Proven success in driving customer growth strategies and building scalable success programs across multiple customer segments
• Comfortable with transactional selling within a CS framework—renewals, upsells, and expansion strategies
• A strong operator with experience building processes, defining success metrics, and using data to optimize performance
• Exceptional leadership skills with a passion for developing people, building strong cultures, and driving results
  
  

Executive presence and communication skills—you can influence across levels and inspire both clients and team members.

Perks and Benefits

• An environment that empowers you to learn, grow, and make a meaningful impact
• Be a part of a fast-growing, ambitious company where your work directly drives results
• Work with ambitious, driven, and like-minded professionals in a collaborative and dynamic environment
• A regionally competitive benefits package
• The chance to be a part of a dynamic and innovative company that is making a difference in the tour and activity sector
  
  

We’d love for you to join us on this exciting journey. Together, let’s shape the future of the leisure and tourism industry!

The pay range for this role is $90,000-140,000 USD Annual Bonus

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