Customer Success Team Lead - North America

Customer Success Team Lead, North America

About Us

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.

About the Role

We are looking for a Customer Success Team Lead, North America to run a pod of CSMs across our Rezdy and Checkfront customer base. This is a working lead role: roughly 70% of your time will be spent managing your own book of accounts and jumping into your team’s toughest calls and renewals, and 30% coaching, reviewing pipeline, and keeping your pod accountable to the goals set by regional leadership.

What you will do

• Lead a pod of Customer Success Managers (roughly 4-8), setting daily/weekly priorities, running team rhythm (pipeline reviews, forecast check-ins, account strategy syncs), and holding the team accountable to retention and expansion targets.
• Carry your own book of strategic or complex accounts, modeling the standard you expect from the team.
• Coach CSMs through renewals, escalations, and difficult customer conversations including stepping into calls directly when needed.
• Run regular 1:1s and performance check-ins with your CSMs; flag development needs and performance issues early.
• Apply the existing customer health, segmentation, and engagement framework consistently across your pod.
• Track your pod’s retention, churn, and expansion metrics and report trends, risks, and wins up to the Head of CSM.
• Partner with Sales, Onboarding, and Support at the account level to resolve handoff issues and smooth escalations for your team’s customers.
• Help onboard and ramp new CSMs joining your pod.

What we are looking for

• 2+ years leading a small CSM/Account Management team, or strong senior CSM experience with some team-lead or mentoring responsibility, ideally in B2B SaaS.
• Comfortable owning a personal book of accounts while also coaching others as this is a hands-on, working-lead role, not a pure people-management seat.
• Solid grasp of renewals, expansion, and churn mechanics, and the judgment to know when to step into a customer conversation.
• Experience following (not necessarily designing) a segmentation and account-health framework, and keeping a team disciplined to it.
• Comfortable with regular coaching conversations, performance check-ins, and giving direct feedback.
• A data-driven mindset;  comfortable pulling and acting on customer health and pipeline data, even if you’re not building the reporting yourself.
• Clear, confident communicator who can represent your pod’s work to senior leadership.
• Experience in travel technology, reservation software, vertical SaaS, or the tours and activities industry is a plus, but not required.

What we are looking for

• 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. You are 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.

 

When you join our team, you’re stepping into a culture built on momentum, ownership, and clarity of purpose. We move decisively, think boldly, and stay deeply connected to our customers and the people behind the work. Across all our brands, we believe meaningful impact comes from empowered teams, aligned priorities, and unwavering commitment.

Here’s what you can expect:

• High trust, real impact: You’ll have the 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: We value asking sharp questions, challenging assumptions, and exploring smarter ways to work. We don’t just get things done, but to get them done right for our customers.
• One team, all in: Collaboration beats ego, wins are shared, and we rally together when the work gets tough.
• Space to grow: You’ll be supported and stretched, taking on challenges that build capability, sharpen judgment, and accelerate your growth as a leader and problem-solver.
• Progress with purpose: We move fast, stay focused on what truly matters, and prioritise long-term impact over quick fixes.

You’ll be joining a global team committed to building something that truly matters—and enjoying the ride along the way.

We’d be excited to have you with us. Together, let’s shape the future of the tourism industry.