Inside Sales & Customer Retention Specialist

Pay Range:

Base Salary: $75,000 USD annually, plus commission

Target Total Compensation: $100,000-$150,000 annually

This role offers a performance-based commission structure designed to reward successful sales results, including new Caseload Manager sales and eligible expansion opportunities within existing customer accounts. Total compensation will vary based on individual sales performance and achievement of commission plan objectives.

We're seeking an Inside Sales & Customer Retention Specialist to help strengthen relationships with existing Caseload Manager customers while growing our customer base.

A wholly owned subsidiary of the American Arbitration Association,  provides fast, fair online resolution for disputes ranging from $5 online purchases to $10,000 medical bill issues. We leverage cutting-edge technology and AI to create enduring resolutions, bypassing costly legal processes. Our employees also participate in a comprehensive benefits program that includes medical, dental, orthodontia, vision coverage, student loan repayment, 401(k) retirement plan with substantial company match, discounted pet insurance, and generous paid-time-off benefits.

Caseload Manager is a configurable case management platform built for dispute resolution professionals and organizations. Our software supports real-world workflows across mediation programs, ombuds offices, HR departments, law firms, and other organizations.

This is a dual-purpose role, split approximately 50% customer retention and account support and 50% inside sales and business development . You'll engage existing customers, support renewals and expansion opportunities, and help generate new business through prospecting, lead follow-up, discovery, product demonstrations, and consistent sales follow-through.

This is an excellent opportunity for someone early in their sales, customer success, or account management career who wants to develop expertise in both customer retention and technology sales . You'll receive structured processes, tools, product training, and ongoing coaching while working closely with experienced sales, customer retention, product, and marketing leaders.

• Build and maintain strong relationships with existing Caseload Manager customers through regular, proactive outreach.
• Conduct customer check-ins to understand satisfaction, product usage, training needs, emerging requirements, and potential concerns.
• Support customer communications, training follow-ups, renewal reminders, and retention campaigns.
• Track renewals and identify potential retention risks, escalating concerns when appropriate.
• Identify opportunities to expand customer relationships through additional products, services, users, departments, training, and use cases.
• Coordinate routine product demonstrations, training, and customer education.
• Answer basic product questions and help route more complex technical or customer issues.
• Maintain accurate CRM records covering customer activity, renewals, opportunities, risks, and next steps.

• Follow up on inbound leads and prospects generated through marketing, industry relationships, conferences, and other sources.
• Conduct proactive phone, email, and outbound prospecting to targeted organizations.
• Lead discovery conversations to understand current processes, needs, and pain points and determine where Caseload Manager can add value.
• Qualify opportunities based on fit, need, timing, budget, and potential value.
• Conduct practical product demonstrations tailored to each prospect's organization, workflow, and use cases.
• Progress qualified opportunities through the sales pipeline and partner with senior sales leadership on larger opportunities, proposals, pricing, negotiations, and closing.
• Identify new opportunities within the existing customer base.
• Maintain an accurate, organized sales pipeline and consistent follow-up cadence using CRM and marketing automation tools.

You'll also partner with Sales and Marketing to improve customer retention campaigns, outbound prospecting, sales messaging, demonstrations, collateral, prospect lists, and market-specific use cases. Customer and prospect feedback will help shape how we communicate Caseload Manager's value across mediation, ombuds, HR, legal, and other markets.

Success in this role means building strong customer relationships while…