Customer Success Specialist

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.

Responsibilities:

Vendor Onboarding & Training:

- Serve as the primary point of contact for new vendors during onboarding, guiding them through the Lessen Pro setup process to ensure a smooth, efficient transition onto the platform.

- Lead kickoff calls, system walkthroughs, and setup sessions to guide vendors through platform configuration, and conduct comprehensive training to ensure a strong understanding of Lessen Pro’s features and functionality.

- Track onboarding progress and ensure timely completion of key setup milestones.

- Monitor early usage trends and proactively address adoption barriers.

- Create and maintain training materials and resources to support vendor learning.

Customer Support & Relationship Management:

- Provide timely and effective support to vendors via phone, email, and chat, addressing their questions and resolving any issues.

- Build and maintain strong relationships with vendors, fostering a positive and collaborative environment.

- Collaborate with Sales, Product, and Support teams to ensure a seamless customer experience.

- Act as a trusted advisor, understanding vendor needs and providing tailored solutions.

- Monitor vendor usage of the Lessen Pro platform and proactively reach out to vendors to offer assistance.

Problem Solving & Escalation:

- Troubleshoot technical and operational issues, escalating complex problems to the Manager, Customer Support when necessary.

- Document vendor feedback and issues, contributing to the continuous improvement of the Lessen Pro platform.

- Identify opportunities to improve the vendor experience.

Contribute to Growth:

- Identify opportunities for vendors to maximize their usage of the Lessen Pro platform.

- Inform the manager of any upselling or cross selling opportunities that are discovered while assisting vendors.

Role Specific Skills

- Ability to dissect full projects into individual components so as to ensure prioritization and timely completion

- Computer Skills: Intermediate proficiencies in: Microsoft Word, Excel, PowerPoint, Outlook preferred

Professional Skills

Customer Service / Relationships: Proactively engage with customers to build positive relationships, resolve issues, and coach others on effective customer interactions.

Verbal Communication: Clearly and effectively communicate information to individuals and small groups, adapting style to fit the audience.

Written Communication: Produce concise, coherent, and professional written communications, including emails and support tickets.

Teamwork: Collaborate effectively with team members to achieve shared goals and foster a positive team environment.

Role Specific Skills

Customer Service Excellence :

- A passion for providing exceptional customer service and building strong relationships.

- Excellent problem-solving and communication skills.

- Ability to remain calm and composed under pressure.

Technical Aptitude:

- Comfortable learning and using new software platforms.

- Ability to simplify technical concepts for non-technical users.

- Basic proficiency in Microsoft Office Suite (Word, Excel, Outlook).

- Familiarity with Salesforce or other CRM systems is a plus.

Minimum Qualifications

- 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

Why Lessen:

· Competitive compensation

· Health, Dental, Vision, Life, Disability options

· 401K retirement savings plan

· Paid vacation, federal and floating holidays

· Maternity/Paternity Pay

· Career advancement opportunities

· All the tools you'll need to be successful

Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.