Technical Support Specialist - Freelance, Remote

About the Opportunity Our client is a leading property management SaaS platform that empowers short-term rental hosts, co-hosts, and property managers to automate their operations across major booking channels like Airbnb, VRBO, and Booking.com. They provide an all-in-one solution featuring AI-powered guest communication, smart pricing, direct booking tools, and seamless integrations with smart home devices. Trusted by over 30,000 users worldwide, they're rapidly expanding their support team to maintain their reputation for reliability and exceptional customer care. Why does this role exist? As our client continues to scale their platform and serve thousands of property managers globally, they need a proactive, customer-focused Customer Support Specialist to ensure every user receives timely, accurate technical support. This role exists to be the frontline problem-solver who helps hosts troubleshoot product issues, resolve technical challenges, and maintain smooth operations across their rental businesses. The ideal candidate will combine strong technical aptitude with exceptional communication skills to deliver consistent, high-quality support that reflects the company's commitment to customer success—and shows strong potential to grow with the team as they expand in the coming months. Tasks and Responsibilities Customer Support via Live Chat (Primary Channel) Respond to customer inquiries through live chat with professionalism and speed Provide technical troubleshooting for product features, integrations, and platform functionality Handle phone and email support requests when needed to ensure comprehensive coverage Technical Issue Resolution & Troubleshooting Diagnose and resolve issues related to calendar syncing, channel integrations (Airbnb, VRBO, Booking.com), and smart device connectivity Guide customers through setup processes for AI auto-replies, dynamic pricing, and direct booking features Ensure timely and accurate resolutions while maintaining attention to detail in all interactions Documentation & Escalation Management Maintain detailed records of customer interactions, issues, and resolutions in CRM/ticketing systems Document recurring issues and system bugs, escalating them to appropriate internal teams Review and update customer information with strong attention to detail Communication & Tone Adaptation Adjust communication style based on customer needs—from patient and educational for new hosts to efficient and technical for experienced property managers Maintain a professional yet personable tone across all customer touchpoints Collaborate proactively with team members to resolve complex customer concerns efficiently Quality Assurance & Process Adherence Follow internal support procedures and quality guidelines to deliver consistent service Meet or exceed quality standards set by both internal teams and client assessments Demonstrate adaptability and willingness to learn new tools, processes,…