Job Title: Account Success Specialist
Location: Estero, FL
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
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 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
Qualifications
- 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
Even Better If You Have:
- 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
What Success Looks Like:
- 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
Apply Now
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