Customer Escalations Representative

Lessen Inc.

Job Overview

Location

Remote, AZ or IL

Job Type

Full-time

Full Job Description

📋 Description

• As a Customer Escalations Representative at Lessen Inc., you will play a critical role in resolving complex customer issues that require specialized attention, ensuring high satisfaction and retention among property owners, managers, and service providers using Lessen’s platform.
• Day to day, you will triage and manage escalated customer inquiries via phone, email, and chat; investigate root causes of service disruptions or vendor performance issues; coordinate with internal teams (operations, vendor management, and product) to implement timely resolutions; document all interactions and outcomes in the CRM; and follow up to confirm customer satisfaction and prevent recurrence.
• Lessen is a venture-backed, tech-enabled property service provider transforming real estate operations through its platform that connects over 30,000 vetted vendors with clients managing over 1 million properties and completing 3.5 million work orders annually. Headquartered in Scottsdale and Chicago, the company leverages data-driven insights to improve efficiency and scalability across the real estate ecosystem.
• In this role, you will develop advanced conflict resolution and customer advocacy skills, gain deep exposure to property service operations and vendor management workflows, and build expertise in using CRM and ticketing systems to drive process improvements—positioning you for growth into senior customer experience, operations, or client success roles within the proptech industry.

🎯 Requirements

• Minimum 2 years of experience in customer service, technical support, or escalations management
• Strong communication skills with ability to de-escalate tense situations and convey solutions clearly
• Experience using CRM or ticketing systems (e.g., Zendesk, Salesforce, Freshdesk) to track and resolve customer issues
• Ability to work remotely with reliable internet and a distraction-free workspace
• Familiarity with property management, real estate services, or vendor coordination is a plus
• Bachelor’s degree or equivalent practical experience

🏖️ Benefits

• Fully remote work flexibility with option to work from Arizona or Illinois
• Competitive salary with performance-based bonuses
• Comprehensive health, dental, and vision insurance plans
• 401(k) retirement plan with company match
• Paid time off and company holidays
• Opportunity to work with a growing, innovative proptech company backed by venture capital

Skills & Technologies

Remote

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Lessen Inc.

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About Lessen Inc.

Lessen provides technology-enabled property services for single-family rental operators and institutional investors. Its platform connects property owners to vetted contractors for maintenance, turn services, renovations, and inspections across the United States. Software automates scheduling, pricing, and quality assurance while analytics track portfolio performance and spending. Founded in 2019 and headquartered in Scottsdale, Arizona, the company manages millions of work orders annually, aiming to reduce vacancy times and operating costs for large-scale rental portfolios.

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