Leadership Support Specialist

At TransChicago Truck Group, we keep the trucks and people that power our economy rolling. We’re a full-service commercial truck dealership representing Freightliner and Western Star by providing sales, service, and parts for the trucks that keep goods on the road. We’re a family-owned, fast-growing dealership group that values curiosity, teamwork, and growth. If you’re the kind of person who likes to learn by doing and see the impact of your work every day, you’ve found the right spot.

We're looking for a Leadership Support Specialist who will provide support to our Corporate teams in this newly created role. This person will play a critical role in ensuring key priorities, communications, and meetings are executed smoothly across the organization. This is a great opportunity for someone who enjoys being creative creative and enjoy working within an entrepreneurial environment that is goal-oriented, purposeful, and client-driven. 

Essential Functions & Responsibilities:

• Provide day-to-day administrative and project support for the Corporate Team, ensuring proactive follow-through and clear communication with the team.
• Draft and format presentations, reports, and communications for leadership and cross-functional meetings.
• Prepare and submit expense reports on behalf of leadership team members.
• Arrange domestic and occasional international travel, including booking transportation and accommodations, building itineraries, and completing any other necessary preparation.
• Plan and set up in-person and virtual meetings (via Microsoft Teams or Zoom), including agendas, materials, note-taking, and action-item follow-up.
• Assist with planning and coordinating company-wide or high-priority customer events.
• Provide administrative support in coordinating recruiting activities such as new hire orientations or recruiting events.
• Maintain and distribute key pieces of business documentation, such as business licenses,
• Certificates of Insurance, annual dealer license plates, updated vehicle insurance cards, and more.
• Other duties as assigned.

Education and/or required experience:

• 3+ years of experience in a fast-paced administrative support role, preferably supporting senior leaders.
• Strong proficiency with Microsoft Office suite and other technology platforms.
• Proven ability to manage competing priorities and confidential information with discretion.
• Excellent written and verbal communication skills; ability to communicate across all-levels.
• Highly organized and detail-oriented, with strong follow-through and a proactive, solutions-focused approach.
• Comfortable working independently from start to finish on projects in an ambiguous, fast-moving environment.
• Willingness to work flexible hours as business needs require.

Compensation & Benefits:

• Compensation: $60,000-$80,000. Salary will be determined based on experience, competencies, certifications and education.
• Benefits:
  • Medical Insurance
  • Vision Insurance
  • Dental Insurance
  • Life and AD&D Insurance
  • Disability Insurance
  • Flexible Spending Account (FSA)
  • 401(k) with company match
  • Paid Time Off (PTO)
  • Paid Sick Time
  • Paid Holidays
  • Additional voluntary benefits: We also offer a variety of other benefits including an Employee Assistance Program (EAP), Accident Coverage, Critical Illness, Cancer Insurance, Pet Insurance, and Identity Theft Insurance

TransChicago Truck Group is committed to a diverse and inclusive workplace. TransChicago is an equal opportunity employer and does not discriminate based on race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.