Customer Success Manager

Our mission at Renterra is to modernize the $100B+ equipment rental industry. Tactically, we are building an end-to-end platform that will massively improve the way rental companies run their businesses.

Renterra is a Series A–backed, venture-funded SaaS company serving hundreds of rental businesses across the U.S. and Canada. As we scale, customer success is a core pillar of our growth strategy and getting customers live, confident, and successful quickly is critical to everything we do.

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.