Account Success Specialist at Rentvine

You're a mid-level professional with 2-5 years of experience delivering training or facilitating group sessions, comfortable explaining software to non-technica

Work type: onsite

Location: Estero, FL

Type: Full-time

Summary

You're a mid-level professional with 2-5 years of experience delivering training or facilitating group sessions, comfortable explaining software to non-technical users and accustomed to frequent travel. **What makes it worth a look...** Rentvine, a rapidly growing property management software company, is hiring an Account Success Specialist for an on-site role in Estero, FL. This position involves approximately 20% travel for customer training. **You might be a good fit if you...** * Have experience delivering software training or teaching. * Can clearly explain software workflows to non-technical users. * Are comfortable with frequent travel across the U.S. * Have experience in SaaS, prop tech, or B2B software.

Job Description

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.

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 education


• Guide users through product workflows, best practices, and real-world scenarios


• Adapt training delivery based on audience skill level and feedback in real time


• Support virtual training sessions as needed (e.g., follow-ups or smaller groups)


• Partner with customer success and implementation teams to align on customer goals


• Provide feedback on training materials and suggest improvements based on field experience


• Ensure a consistent, high-quality training experience across all customer interactions

• Approximately20% travel, potentially 1 trip per month (may vary based on customer demand)


• Most trips are 1–3 days in length, with occasional longer engagements


• Travel is within the U.S.


• Schedule is generally planned in advance, with some flexibility required


• All travel expenses are covered, including flights, hotels, and meals


• Opportunity to earn and retain travel rewards (airline/hotel points)


• Non-travel time is focused on preparation, follow-ups, and coordination with internal teams

• 2–5 years of experience delivering training, teaching, or facilitating group sessions


• Strong presentation and communication skills—you can confidently lead a room


• Ability to explain software workflows clearly to non-technical users


• Comfort with frequent travel (approximately 50%)


• Strong interpersonal skills and ability to build rapport quickly


• Organized and able to manage multiple training engagements


• Adaptable—you can think on your feet and adjust as needed


• Onsite - Estero, FL

• Experience in SaaS, prop tech, or B2B software


• Experience with customer onboarding or implementation


• Familiarity with training materials (guides, decks, exercises)


• Experience delivering both onsite and virtual training

• Customers leave training confident and able to use the product effectively


• Training sessions are engaging, organized, and tailored to customer needs


• Strong customer feedback and improved product adoption


• Clear communication and alignment with internal teams

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