Customer Success Manager

Location: Chicago (remote) Type: Full-time

About Toro TMS

Trucking runs on pen and paper or software built decades ago, and most carriers are stitching together a half-dozen tools that don't talk to each other. We're replacing all of it.

Toro is a modern, end-to-end TMS built specifically for asset-based carriers — the companies that own the trucks and employ the drivers. Load management, dispatch, driver pay, invoicing: one system. More loads moved. Invoices out the door faster. Drivers paid correctly and on time.

About the Role

Toro TMS is looking for a highly organized, proactive, and relationship driven Customer Success Manager to join our growing team.

In this role, you'll manage a growing portfolio of trucking customers representing over $3 million in ARR . You'll be responsible for building strong relationships, driving product adoption, managing renewals, and identifying opportunities to grow existing accounts.

We're looking for someone who can balance strategic account management with a hands on understanding of our customers' day to day operations. The ideal candidate is a strong communicator, comfortable navigating challenging conversations, and capable of serving as a trusted advisor to business owners and key stakeholders.

Key Responsibilities

Account Management & Customer Relationships

Own and manage a growing book of business exceeding $3M in ARR, with accountability for customer retention, satisfaction, and revenue growth.

Build and maintain strong relationships with business owners, decision makers, and key stakeholders across assigned accounts.

Serve as the primary point of contact for customers, understanding their business needs, operational challenges, with a long-term goal of maintaining consistent customer engagement

Customer Retention & Revenue Growth

Lead annual renewal conversations, ensuring customers understand the value Toro delivers while securing continued long term partnerships.

Identify and execute revenue expansion opportunities, including add on features, additional truck capacity, and account overages.

Manage contract discussions, pricing adjustments, and renewal negotiations while balancing customer relationships with company revenue objectives.

Proactively identify churn risks and develop strategies to improve retention and protect recurring revenue.

Product Adoption & Customer Training

Become a subject matter expert on Toro TMS, with a strong understanding of trucking operations and customer workflows.

Lead customer training sessions to improve product knowledge, adoption, and operational efficiency.

Educate customers on new product releases, enhancements, and functionality relevant to their business.

Advise customers on implementing new features into their existing workflows to maximize the value of Toro.

Account Health & Risk Management

Conduct reviews of customer usage and engagement to identify adoption gaps, declining activity, and potential churn risks.

Develop proactive outreach plans for at-risk accounts and coordinate internal resources when additional support is needed.

Maintain accurate account records in Salesforce, including renewal dates, customer interactions, outstanding concerns, and expansion opportunities.

Prioritize competing customer needs while managing a large and growing portfolio.

Cross Functional Collaboration

Serve as the voice of the customer, acting as a conduit between customers and Toro's Product and Engineering teams.

Gather, document, and communicate customer feedback, feature requests, and workflow challenges to help inform product development.

Partner closely with Support, Implementation, Product, and Engineering to address customer needs and ensure a positive customer experience.

Communicate product updates, known limitations, and development progress to customers while setting clear expectations.

Qualifications

Required

3+ years of experience in Customer Success, Account Management, or a similar customer facing role, preferably within B2B SaaS.

Demonstrated ability to manage a large portfolio of accounts while maintaining strong customer relationships.

Excellent written and verbal communication skills, with the ability to confidently lead meetings and engage with business owners and senior stakeholders.

Exceptional organizational and time management skills, with the ability to prioritize multiple accounts, deadlines, and competing requests.

Experience managing customer renewals, identifying retention risks, and driving revenue growth.

Strong analytical skills and the ability to interpret customer usage data to identify trends and recommend action.

Comfortable learning software and translating technical functionality into practical solutions.

Proactive, resourceful problem solver who takes ownership of customer relationships and follows through on commitments.

Preferred

Experience in the trucking, transportation, logistics, or supply chain industry.

Familiarity with Transportation Management Systems (TMS), trucking operations, dispatch, billing, or fleet management workflows.

Experience negotiating SaaS contracts, renewals, pricing adjustments, and expansion agreements.

Experience working cross-functionally with Product and Engineering teams.

Familiarity with CRM platforms and customer success reporting tools.

Who Will Thrive in This Role

You're someone who enjoys building relationships but also understands that Customer Success is about delivering measurable business value. You're comfortable having difficult conversations, negotiating agreements, and managing competing priorities without losing sight of the customer experience.

You're naturally organized, take ownership of your accounts, and don't wait for customers to reach out before identifying opportunities to help them succeed.

Most importantly, you're interested in understanding how trucking companies operate and helping them use technology to run their businesses more efficiently.

Why Toro

Be part of a mission-driven team reshaping an essential industry

Real scope and impact: you'll work directly with customers and see your work move the needle

A culture that values clarity, warmth, and continuous improvement

Comprehensive medical, dental, and vision coverage

Unlimited PTO

401(k) policy managed by Empower

Toro TMS is an Equal Opportunity Employer. Toro TMS provides equal employment opportunities to all employees and applicants without regard to race, color, gender (including pregnancy), religion, national origin, ancestry, disability, age, sexual orientation, gender identity or expression, marital status, language, genetic information, veteran and/or military status or any other group status protected by federal or local law. If you require reasonable accommodation for the application and/or interview process, please notify a representative of the Human Resources Department.