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. 

The Head of CX Operations — AI, Automation, Billing & Payments is a unique opportunity to join a highly motivated, customer-centric team striving for operational excellence.

Guesty is shifting gears toward an AI-first approach in a super-fast-paced environment. Our goal is to make the customer experience a competitive advantage in the hospitality industry by ensuring our processes are not only well-defined, but supercharged by intelligent automation, data, and AI.

You will be a hands-on operational leader, designing and optimizing workflows using n8n, Make, and Claude; leading critical Billing and Payment, and owning a significant portion of Guesty CX’s day-to-day operations.

AI & Automation Architecture - Hands-on:

• Build & Deploy AI Solutions: Take a hands-on role in designing, building, and deploying AI-based solutions and automations that transform CX operations, reduce manual work, and improve the customer experience.
• Workflow Engineering: Utilize n8n, Make, Claude, and other emerging technologies to architect complex, scalable workflows integrating multiple CX and business systems.
• Client-Facing AI: Own the priorities, roadmap, and requirements for Guesty’s homegrown client-facing chatbot, built on AWS AgentCore and LangChain and leveraging multiple AI models.
• AI Agents Management & Orchestration: Build, deploy, monitor, and continuously improve a network of AI agents supporting different areas of CX Operations, including data analysis, knowledge management, training, support, quality, and operational workflows.
• Data-Driven Improvement: Own CX KPI reporting and partner with the BI team to continuously improve data quality, reporting, dashboards, and operational visibility.
• CX Tech Stack: Oversee the CX technology ecosystem, including Zendesk, Tymeshift, Airtable, and internally built tools, ensuring the stack supports scalable and efficient operations.
• Continuously evaluate emerging technologies, AI capabilities, and automation opportunities that can improve CX efficiency and customer outcomes.

Billing & Payment Operations:

• Own day-to-day Billing & Payment Operations, ensuring accurate, timely, and efficient execution across billing, payments, refunds, credits, subscription changes, and other operational processes.
• Lead the Billing & Payment Operations teams, setting clear priorities, managing capacity, monitoring performance, and ensuring consistent execution against operational targets.
• Define and own KPIs across Billing & Payment Operations, including productivity, SLA, backlog, accuracy, resolution time, quality, and customer-impact metrics.
• Establish operational controls and processes to reduce billing and payment errors, identify risks early, and minimize customer impact.
• Own escalations and complex operational issues, coordinating with Finance, Product, Engineering, Customer Success, and other relevant teams to drive timely resolution.
• Identify automation opportunities across Billing & Payment processes and lead initiatives to eliminate repetitive manual work and improve scalability.
• Drive root-cause analysis and continuous improvement, ensuring recurring billing and payment issues are identified, addressed, and prevented from repeating.
• Partner with Finance and other business stakeholders to ensure operational processes align with financial controls, business requirements, and customer experience standards.

Technical & Professional Expertise:

• AI Builder: Proven, hands-on experience building and deploying AI-based automations and solutions.
• Automation Expert: Deep, hands-on expertise with n8n / Make /Claude (formerly Integromat).
• Information Systems: Experience with information systems, workflow design, and process automation within a global or international company.
• Data Oriented: Strong analytical mindset with an ability to use data and KPIs to drive operational decisions.
• CX Operations: Experience managing CX or Back-Office operations is a strong advantage.
• Billing & Payments: Experience with billing, payments, financial operations, or SaaS subscription operations is a strong advantage.

Leadership & Mindset:

• High-Velocity Mindset: Ability to thrive in a super-fast-paced environment, manage multiple priorities, and maintain a positive, solutions-oriented approach.
• Hands-On Leadership: Comfortable getting into the details, building solutions yourself, and working closely with teams to drive execution.
• Team Management: Experience managing multidisciplinary teams, particularly small, high-performance squads.
• Cross-Functional Leadership: Strong ability to influence and collaborate with teams across the organization, without relying solely on direct authority.
• Communication: Fluent English with excellent written and verbal communication skills.
• Customer Focus: Tech-savvy with a strong understanding of the customer journey and the ability to translate customer needs into operational improvements.

Bonus Points:

• Experience in the hospitality, hotel, or travel industry.
• Experience in a global B2B SaaS company.
• Experience with billing, payments, subscriptions, or revenue operations.
• Experience working with AWS AgentCore, LangChain, LLMs, or AI agent architectures.

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.