Location: Estero, FL, Remote - FL
Rentvine is the fastest-growing property management software company in the industry, ranked #60 on the 2025 Inc. 5000 list. Our powerful, cloud-based platform helps property managers streamline operations, reduce manual work, and deliver a better experience for tenants and owners. Behind that innovation is a team-first culture that puts people at the center. We care deeply about building a company where smart, driven individuals can grow, feel supported, and do the best work of their careers. Our people aren't just part of our success—they're the reason for it.
Please Note: Rentvine is unable to provide employment sponsorship now or in the future for this position.
#LI-Onsite #LI-Remote
The Technical Support Analyst (Tier 2) is a senior individual contributor on the Support team, responsible for owning the most complex, high-impact, and technically demanding issues that reach our support organization. You are the last line of defense before Engineering.
This role sits at the intersection of Support, Engineering, and Product. You'll investigate escalated issues from Tier 1, manage defects through to resolution, and serve as the primary bridge between customer-facing teams and the engineers building the platform. You'll also play a direct role in making the entire support organization smarter — enabling Tier 1 through training and swarming, surfacing product gaps to leadership, and building the documentation that raises the floor for everyone.
The ideal candidate has deep SaaS support experience, strong technical instincts, a working knowledge of accounting or property management workflows, and the communication skills to operate fluently across engineering, customer success, and executive stakeholders.
Advanced Troubleshooting & Defect Ownership
- Serve as the escalation point for complex, high-severity, and unresolved issues from Tier 1 — taking full ownership from intake through resolution.
- Conduct deep-dive investigations into product behavior, data integrity issues, integration failures, and accounting edge cases.
- Build, document, and manage defects in the appropriate tracking system with clear reproduction steps, impact assessment, and supporting evidence.
- Own the lifecycle of defect-linked tickets — tracking status, communicating updates to customers and internal stakeholders, and driving closure.
- Distinguish between user error, configuration issues, and true product defects with rigor and speed.
- Act as the primary liaison between Support and Engineering — translating customer-reported issues into precise, developer-ready documentation.
- Participate in defect triage and prioritization discussions, providing support-side context on customer impact, frequency, and urgency.
- Maintain clear, consistent communication on defect status and timelines across both engineering and customer-facing teams.
- Develop a working understanding of Rentvine's technical architecture, data models, and integration ecosystem to improve diagnostic accuracy over time.
- Provide real-time support to Tier 1 through swarming on active tickets and live troubleshooting collaboration.
- Conduct structured feedback loops on escalated cases — helping Tier 1 agents understand what could have been resolved at the first tier and how.
- Identify recurring escalation patterns and build training content, playbooks, or escalation decision trees to reduce future escalation volume.
- Serve as a go-to internal resource for platform behavior, accounting logic, and edge-case scenarios across the support team.
- Lead outbound communication on complex, high-impact, or time-sensitive customer issues via phone or scheduled meetings.
- Set and manage customer expectations around resolution timelines, workarounds, and defect status with professionalism and transparency.
- Identify when issues require broader account attention and engage Account Management, Onboarding, or Customer Success teams appropriately.
- Represent Rentvine's support organization at its highest level of expertise and responsiveness.
- Own and expand the internal knowledge base for Tier 2-level issues, integration behaviors, and complex accounting scenarios.
- Contribute to customer-facing help content in partnership with the Product and Training teams.
- Proactively identify workflow inefficiencies, tooling gaps, and product experience issues — and bring well-formed recommendations to leadership.
- 3–5 years of experience in technical support, SaaS support, or a related role with demonstrated advanced troubleshooting responsibility.
- Proven track record of owning complex customer issues end-to-end, including managing defect lifecycles in collaboration with engineering teams.
- Experience working directly with engineering or product teams in a liaison or escalation capacity.
- Strong analytical and technical problem-solving skills — comfortable investigating logs, data outputs, integration failures, or workflow inconsistencies without a defined playbook.
- Solid understanding of accounting principles, property management operations, or financial software workflows.
- Experience with defect tracking tools (Jira, Linear, or similar) and CRM/ticketing platforms (HubSpot, Zendesk, or similar).
- Excellent written and verbal communication skills, with the ability to operate clearly across technical and non-technical audiences.
- High degree of ownership, organization, and follow-through on long-running, multi-stakeholder issues.
- Bachelor's degree or equivalent experience in Accounting, Finance, Computer Science, Information Technology, Property Management, or a related field.
- Experience in a Tier 2 or escalation support role at a B2B SaaS company.
- Familiarity with REST APIs, webhooks, or data integration concepts — enough to investigate and document integration-related issues.
- Background in property management software, real estate technology, or fintech.
- Experience building or maintaining internal knowledge bases, escalation guides, or support training materials.
- Exposure to SQL or structured data querying for data validation and investigation purposes.
- Core schedule: Monday–Friday, 9:00 AM – 5:00 PM ET
- Light weekend coverage: one weekend per month (compensated)
- One rotating extended weekday shift per week: adjusted to cover 5:00 PM – 8:00 PM ET
- Competitive base salary commensurate with experience, plus a full benefits package.
- A high-visibility role with real influence over product quality, support effectiveness, and the customer experience.
- Clear growth paths into Engineering, Product, Customer Success Leadership, or Support Management as the company scales.
- Professional development support, including ongoing training, access to industry resources, and exposure to a modern, fast-moving tech stack.
- A collaborative, intellectually curious culture that rewards initiative, ownership, and direct communication.
- The momentum of a high-growth startup (#60 on the 2025 Inc. 5000) with a platform customers depend on every day.
