Remote Desktop Support Jobs in Naples, FL (NOW HIRING)

About the Role

The Technical Support Specialist serves as a critical point of contact for Rentvine clients, delivering expert-level assistance across accounting, operational, and platform-related inquiries. This role goes beyond basic troubleshooting — you\'ll be expected to develop deep product knowledge, identify patterns in customer issues, and contribute meaningfully to the processes that drive support quality across the team.

You\'ll manage inbound support across multiple channels (phone, email, and chat), own tickets end-to-end, and collaborate with Tier 2, Engineering, and Product teams to drive resolution. The ideal candidate brings hands-on experience in SaaS support or a related technical environment, a strong grasp of accounting or property management workflows, and the communication skills to translate complex issues into clear, actionable guidance for customers.

This is an opportunity to grow your career inside a high-velocity software company where your contributions are visible, your feedback shapes the team, and your path forward is real.

What You\'ll Do

Customer Support & Communication

• Own inbound customer inquiries via phone, email, and live chat — responding promptly, professionally, and with measurable impact on customer satisfaction.
• Serve as a trusted advisor to clients, guiding them through complex platform questions and helping them get maximum value from Rentvine\'s features.
• Create, manage, update, and resolve support tickets with accurate documentation and timely follow-through.
• Consistently meet or exceed established SLAs, CSAT targets, and team KPIs.

Troubleshooting & Technical Resolution

• Diagnose, investigate, and resolve software, accounting, and workflow-related issues with a structured, methodical approach.
• Identify recurring issues and escalate complex or high-impact cases to Tier 2 or Engineering with clear, thorough context.
• Document troubleshooting steps and resolution outcomes in a way that enables team-wide knowledge sharing.

Product Expertise & Customer Education

• Develop and maintain deep expertise in Rentvine\'s platform, including accounting modules, reporting tools, integrations, and operational workflows.
• Guide customers through best practices, configuration options, and system navigation to help them work more efficiently.
• Serve as an internal resource for team members on platform behavior and edge-case scenarios.

Documentation & Cross-Functional Collaboration

• Contribute to the continuous improvement of the knowledge base, internal SOPs, and customer-facing help content.
• Capture customer feedback to surface trends to Product, Engineering, and Leadership.
• Collaborate cross-functionally with Onboarding, Account Management, and Customer Success to ensure a seamless customer experience.
• Participate in team initiatives, process improvement discussions, and ongoing training programs.

Qualifications

• 2 years of experience in technical support, help desk, or customer success — ideally within a SaaS or software environment.

• Demonstrated ability to troubleshoot software issues methodically, with clear documentation of steps and outcomes.
• Strong written and verbal communication skills, with the ability to convey technical information clearly to non-technical audiences.
• Experience working within ticketing or CRM systems (Intercom, HubSpot, Zendesk, Salesforce, or similar).
• Comfortable managing multiple open cases simultaneously and prioritizing effectively in a fast-paced environment.
• Customer-first mindset with a genuine passion for helping people solve problems.

• This position is eligible for onsite hire for candidates local to SouthWest Florida/within commuting distance to Estero, FL. We will also consider remote hire for qualified candidates in greater Florida.

Even Better If You Have

• Bachelor\'s degree or equivalent experience in Accounting, Finance, Business, Property Management, Information Technology, or a related field.
• Hands-on experience supporting a SaaS platform with accounting or financial functionality.
• Proficiency with Intercom, HubSpot, Aircall, or comparable CRM/support platforms.
• Familiarity with property management software, real estate operations, or proptech.
• Experience contributing to knowledge base content, internal SOPs, or team training materials.
• Track record of identifying process improvements or contributing to support team projects beyond day-to-day ticket handling.

Schedule

• Core schedule: Monday–Friday, 9:00 AM – 5:00 PM ET
• Light weekend coverage: one weekend per month 
• One rotating extended weekday shift per week: adjusted to cover 5:00 PM – 8:00 PM ET

What Rentvine Offers

• Competitive base salary commensurate with experience, plus a full benefits package.
• A visible, high-impact role on a team where your work directly shapes the customer experience.
• Clear growth paths into Tier 2 support, Customer Success, Product, or other functions as the company scales.
• Professional development support, including ongoing training and access to industry resources.
• A collaborative, inclusive culture that values accountability, curiosity, and continuous improvement.
• The energy of a high-growth startup (#60 on the 2025 Inc. 5000) with the stability of a proven platform.

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