Customer Success Manager

Customer Success Manager (CSM)

As a Customer Success Manager (CSM) at Renterra, you will own the customer journey from pre-onboarding through long-term success. Your primary responsibility is to get customers up and running successfully, ensuring they are properly set up, trained, and confident using Renterra in their day-to-day operations.

You will partner closely with customers during implementation and training, then continue to manage the relationship post–go-live to drive adoption, retention, and growth. This role blends onboarding, enablement, relationship management, and proactive support, and is central to delivering an exceptional customer experience. This is a Chicago-based, hybrid role.

• Partner with customers immediately post-sale to guide them through pre-onboarding and implementation
• Lead system setup and configuration alongside customers, ensuring Renterra is tailored to their business workflows
• Conduct live training sessions to educate customers on core functionality and best practices
• Ensure customers successfully go live and feel confident using Renterra in their daily operations
• Identify risks early in the onboarding process and proactively address them
• Occasionally assist with in-person, onsite implementations when necessary

• Own long-term relationships for a portfolio of customers and serve as their primary point of contact
• Proactively monitor customer usage, engagement, and health indicators
• Lead ongoing check-ins and success reviews with customers
• Respond to customer questions and coordinate with support, product, and engineering as needed
• Advocate for customers internally while setting clear expectations

• Manage renewals and work to maximize retention and long-term value
• Identify opportunities for expansion and execute upsells through additional products, features, or increased usage
• Gather and synthesize customer feedback to inform product improvements and roadmap decisions
• Partner closely with product and engineering teams to represent the voice of the customer

• 3+ years of experience in Customer Success, Implementation, Onboarding, or Account Management at a SaaS company
• Strong experience leading customer onboarding, setup, training, and go-live processes
• Excellent communication and presentation skills
• Proven ability to manage multiple customers and projects simultaneously
• Comfortable balancing customer success with commercial outcomes, including renewals, upsells, and cross-sells
• Comfortable working in a fast-paced, startup environment
• Strong problem-solving skills and a customer-first mindset
• Experience with SMB customers is a plus
• Familiarity with the equipment rental, construction, or asset-heavy industries is a plus, but not required
• Must be based in the Chicago area and able to work from the office in a hybrid capacity

• Competitive salary and equity
• Health, dental, and vision insurance
• Flexible PTO policy
• A supportive, customer-first team culture
• Direct ownership over customer outcomes from day one
• Opportunities for growth as the Customer Success organization scales

This is an opportunity to play a high-impact, end-to-end role in helping customers successfully adopt a modern rental software platform. If you enjoy onboarding customers, teaching software, building long-term relationships, and being hands-on with customers from day one, we'd love to hear from you.

Renterra is an Equal Opportunity Employer.