Executive Assistant, Revenue

About Toro TMS

We are Toro TMS, a growth-stage startup building the modern operating system for trucking. Our mission is to deliver best-in-class, end-to-end transportation management software (TMS) for bulk commodity haulers.

About the role

As an Executive Assistant, you will be a trusted partner to Toro’s leadership team and revenue organization, ensuring they can operate at maximum effectiveness in a fast-paced, high-growth environment. You’ll go beyond traditional administrative support by anticipating needs, streamlining priorities, and proactively driving initiatives that keep our company aligned and moving forward.

This role is ideal for someone who thrives on being a strategic thinker, a problem solver, and a connector, someone who can balance tactical execution with big-picture awareness. You’ll be at the center of communication, organization, and decision-making, helping leadership focus on what matters most.

This is an in-office role out of Toro’s downtown Chicago headquarters 5 days a week (with flexibility as needed).

Responsibilities

• Provide proactive executive support, including project work and management of tasks in the revenue organization
• Anticipate needs and strategically prioritize tasks to ensure revenue organization executives are focused on high-impact initiatives
• Serve as a key liaison between leadership and external stakeholders, ensuring clear and timely communication
• Manage vendor relationships and ensure Chicago office operation 
• Identify opportunities to improve processes, workflows, and communication across the organization
• Handle sensitive information with discretion and maintain a high level of professionalism

Skills / Experiences

• 2+ years experience as an Executive Assistant, Chief of Staff, or in a high-level administrative role
• Strong organizational skills with the ability to manage multiple priorities and deadlines
• Excellent written and verbal communication skills; able to represent leadership with professionalism and clarity
• Strategic mindset with the ability to anticipate needs and proactively solve problems
• High emotional intelligence and interpersonal skills; able to build trust and strong relationships across teams
• Comfortable in a fast-paced startup environment, adaptable to shifting priorities
• Positive, resourceful, and solutions-oriented attitude

Benefits

• Comprehensive medical, dental, and vision coverage
• Unlimited PTO
• 401(k) policy managed by Empower
• FFC Gym Membership ($150+/month value)

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, ancestry, 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.