Remote Customer Success Specialist | Real Estate Ops (Demos + Onboarding) 🏠🤝

Company Overview

OnSightPros provides independent property condition reports for rental homes. When a property manager requests an inspection, the team coordinates with residents, sends a trained technician to the property, and delivers a photo-rich report documenting the home’s condition.

These reports are used during move-ins, move-outs, lease renewals, and periodic property checks. Property managers rely on them to document damage, identify maintenance issues, reduce disputes, and keep property owners informed about the condition of their homes.

Your Role

This role exists to help customers clearly understand how the inspection service works and to ensure their first inspections run smoothly.

You’ll lead service demos, help customers plan their first inspection cycle, and guide them through the early steps—from request submission to receiving their first reports. Success in this role means customers quickly understand the process and begin using the service with confidence.

You’ll:

• Run service demos tailored to property managers’ workflows

• Walk prospects through real inspection reports

• Help new customers plan their first inspection cycle

• Lead kickoff calls and guide onboarding steps

• Explain scheduling, tenant coordination, and turnaround timelines

• Write clear follow-up notes customers can reference later

• Turn recurring questions into guides and simple documentation

• Share customer feedback that helps improve the process

You Bring:

• 2+ years in a customer-facing role (customer success, onboarding, support, or implementation)

• Experience explaining workflow-heavy services or products

• Excellent spoken and written English communication

• Confidence leading demos or structured walkthroughs

• A tech-savvy, process-oriented mindset

• Ability to simplify complex workflows for customers

• Strong organization and follow-through

• A patient, supportive approach with customers

Bonus Points:

• Familiarity with property management workflows

• Experience with field services, inspections, or scheduling operations

• Experience creating onboarding documentation or FAQs

What’s Offered:

• Fully remote contractor role

• Open to candidates across the Americas

• Work aligned with U.S. Central Time business hours

• PTO included

• Competitive USD compensation (based on experience)

• Direct collaboration with the CEO and operations team

• Opportunity to shape onboarding and demo processes

Interview Process

1️⃣ Discovery call — background and communication approach

2️⃣ Short challenge — record a brief Loom explaining a workflow

3️⃣ Team interview — discuss customer scenarios and judgment

4️⃣ Final conversation — expectations and next steps