Hybrid Chicago Customer Success Manager: Onboarding & Growth

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

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.