Director of Customer Success
Bitly
Customer Success Specialist
Lessen
full-time
Posted on:
Origin: • 🇺🇸 United States • Illinois
Visit company websiteJob Level
JuniorMid-Level
About the role
- Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.
- Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers.
- The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services.
- Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.
- Job Summary: The Customer Success Specialist plays a key role in driving successful onboarding, adoption and satisfaction among trade vendors using Lessen Pro, our SaaS Field Service Management (FSM) platform.
- This role serves as a trusted partner to new customers, guiding them through platform setup, training, and early adoption milestones.
- The specialist ensures a smooth onboarding experience, helping vendors quickly realize value from the platform and build confidence in its use.
- Key responsibilities include facilitating vendor activation, delivering training, addressing early-stage support needs, and monitoring engagement to proactively resolve issues.
- By building strong relationships and providing tailored support, the specialist improves vendor retention, reduces time to value, and contributes to the overall effectiveness of Lessen Pro.
- Reporting to the Manager of Customer Support, this role has a direct impact on customer satisfaction, platform utilization, and operational efficiency.
Requirements
- Bachelor’s degree preferred, or an equivalent combination of education and relevant experience in customer success, onboarding, account management, or training—ideally within SaaS or Field Service Management (FSM) industries, with at least 2+ years of hands-on experience in a similar role.
- Experience working with SaaS products is highly desirable
- Experience with CRM and support tools (e.g., Salesforce, Zendesk) preferred.
- Strong written and verbal communication skills
- Ability to work independently and as part of a team
- Familiarity with field service operations or contractor networks is a plus
- Industry Knowledge (Preferred): Understanding of the residential repairs and maintenance industry or the real estate/construction verticals
