Customer Success Manager

Renterra; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Competitive salary

Equity

Health insurance

Flexible PTO

Team culture

Ownership of outcomes

Growth opportunities

Job summary

Renterra, a Chicago-based SaaS equipment rental platform, is seeking a Customer Success Manager to lead customers from pre-onboarding through long-term success. You will guide setup, training, and ongoing relationship management to drive adoption and renewals.

You will partner with customers during implementation, monitor usage and health metrics, and coordinate with support, product, and engineering to ensure a best-in-class experience. This is a hybrid, office-based role in Chicago.

Qualifications

• 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.
• 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.

Responsibilities

• 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.

Skills

Customer Success

Onboarding

Account Management

SaaS

Communication

Presentation

Project Management

Job description

About Us

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.

Job Description

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.

Key Responsibilities

Pre-Onboarding, Setup & Go-Live

• 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

Ongoing Customer Success & Support

• 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

Retention, Growth & Feedback

• 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

Qualifications

• 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

What We Offer

• 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.