Customer Success Team Lead

Guesty; Montreal (administrative region); On-site; CAD 125,000 - 180,000; Full time

Job summary

Guesty is seeking a Customer Success Team Lead to manage our Mid-Market CSMs across the United States, Canada and Mexico. You will lead a team of 7 CSMs responsible for 500+ clients, driving retention, expansions, and overall account growth.

The ideal candidate will coach the team, analyze customer data for strategic initiatives, and collaborate with cross-functional teams to optimize the customer journey and outcomes at scale.

Qualifications

• Proven track record managing 3+ CSMs in B2B SaaS.
• Experience closing upsells and negotiating contracts.
• Excellent communication and cross-cultural collaboration.
• Able to de-escalate complex customer situations.
• Proficiency with CRM and BI tools, especially Salesforce.

Responsibilities

• Own team performance against retention, expansion, engagement, adoption and activity KPIs.
• Conduct weekly one-on-ones and provide coaching.
• Analyze customer data to identify opportunities for process improvement and strategic initiatives.
• Report on team performance and portfolio health to senior leadership.
• Manage high-level customer escalations and maintain relationships with key accounts.
• Work cross-functionally with Operations, Sales, Onboarding to resolve blockers.
• Continuously raise the bar on the Customer Success team with high-quality work and collaboration.
• Drive portfolio-management discipline across a high-volume Mid-Market book of business.

Skills

Team leadership

Customer Success

B2B SaaS

Upselling

Data analysis

Tools

Salesforce

CRM systems

BI tools

Job description

Guesty is the all-in-one platform helping hospitality businesses around the world automate, optimize, and scale their operations. We’re a fast-growing global startup that’s transforming how the industry works — from guest experience to business growth.

With a powerful suite of features and integrations with 150+ industry partners — including Airbnb, Vrbo, Booking.com, Expedia, Google Travel, and many more — Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven operations.

We’re proud to have over 900+ team members across 16 countries worldwide, all working together to build the future of hospitality technology.

If you’re looking to grow your career in a dynamic, global, and impact-driven environment, we’d love to hear from you.

We are looking for a Customer Success Team Lead to join our team.

If you're passionate about Customer Success, have a talent for developing high-performing teams, and thrive in a dynamic environment, we want to hear from you. Join us in ensuring success for our MM customers and driving strategic growth for Guesty.

We are looking for a Customer Success Team Lead to manage and develop our MM segment in the United States. The Team Lead will lead a team of 7 CSMs in the U.S., Canada and Mexico, responsible for 500+ clients across those regions, and be responsible for driving customer retention, upsells and overall account growth. This role will also support the Director in building scalable processes for the team, improving the customer journey, and coaching the CSMs on driving strategic conversations with clients.

Responsibilities:

• Own team performance against retention, expansion, engagement, adoption and activity KPIs; identify performance gaps early and develop individual and team-level action plans to improve results
• Conduct weekly one on ones and review client calls to provide ongoing feedback and coaching opportunities to the team members
• Analyze customer data and trends to identify opportunities for process improvement and strategic initiatives
• Report on team performance and portfolio health to senior leadership
• Manage high-level customer escalations and maintain strong relationships with key accounts
• Work cross-functionally with other teams (Operations, Sales, Onboarding) to resolve blockers for your team
• Continuously raise the bar on the Customer Success team with high quality work, proactive improvement suggestions and a high level of internal collaboration
• Drive portfolio-management discipline across a high-volume Mid-Market book of business, helping CSMs prioritize risk, growth opportunities, strategic engagements and proactive outreach.

Requirements:

• Proven track record of managing 3+ CSMs in the B2B SaaS environment
• Proven track record of successfully closing upsells, contract negotiations, and managing high amount of accounts in a B2B Saas environment
• Excellent communication and interpersonal skills, strategic thinking with the ability to align customer success strategies with business goals effectively across cultures and time zones
• Demonstrated ability to handle complex customer situations and de-escalations
• Effective at creating and delivering creative solutions to mid-market sized customers
• Proficiency in CRM systems, Customer Success tools and BI tools (Salesforce strongly preferred)
• Familiarity with the MM market and its unique challenges (preferred)
• Experience in the short-term rental industry is a huge advantage

Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.