Account Success Specialist

About Rentvine 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. About the role We’re seeking an engaging and organized Account Success Specialist to deliver high-quality, in-person training for customers implementing and using our SaaS platform in the property technology (prop tech) space. This role is responsible for facilitating onsite training sessions, guiding customers through product workflows, and ensuring they feel confident using the system. This is a highly interactive, customer-facing role with approximately 20% travel. The ideal candidate enjoys working directly with customers, can adapt to different audiences, and is comfortable delivering structured training in a dynamic, real-world environment. What you'll do Facilitate engaging, hands-on training tailored to customer needs and use cases, in group and 1:1 setting Deliver onsite training sessions for customers, including new implementations and ongoing educationGuide users through product workflows, best practices, and real-world scenariosAdapt training delivery based on audience skill level and feedback in real timeSupport virtual training sessions as needed (e.g., follow-ups or smaller groups)Partner with customer success and implementation teams to align on customer goalsProvide feedback on training materials and suggest improvements based on field experienceEnsure a consistent, high-quality training experience across all customer interactions Travel Expectations: Approximately 20% travel, potentially 1 trip per month (may vary based on customer demand)Most trips are 1–3 days in length, with occasional longer engagementsTravel is within the U.S.Schedule is generally planned in advance, with some flexibility requiredAll travel expenses are covered, including flights, hotels, and mealsOpportunity to earn and retain travel rewards (airline/hotel points)Non-travel time is focused on preparation, follow-ups, and coordination with internal teams Qualifications 2–5 years of experience delivering training, teaching, or facilitating group sessionsStrong presentation and communication skills—you can confidently lead a roomAbility to explain software workflows clearly to non-technical usersComfort with frequent travel (approximately 50%)Strong interpersonal skills and ability to build rapport quicklyOrganized and able to manage multiple training engagementsAdaptable—you can think on your feet and adjust as neededOnsite - Estero, FL Even Better If You Have: Experience in SaaS, prop tech, or B2B softwareExperience with customer onboarding or implementationFamiliarity with training materials (guides, decks, exercises)Experience delivering both onsite and virtual training What Success Looks Like: Customers leave training confident and able to use the product effectivelyTraining sessions are engaging, organized, and tailored to customer needsStrong customer feedback and improved product adoptionClear communication and alignment with internal teams Locations: Estero, FL