Regional Charter Sales Specialist - Remote in Jacksonville, FL

Summit School Services companies share a strong commitment to provide the highest level of transportation safety, quality transportation, outstanding customer service and positive employee relations. Our corporate headquarters, located in Warrenville, Illinois, houses the administrative and corporate support functions for the organization. Our 250+ local customer service centers (CSCs) are supported by regional operations teams located throughout North America.

This role supports the East region, with a preference for candidates based in or near Jacksonville, Florida.

Outside Sales, Charter Business

Be an integral part of our growth initiatives for group charter transportation. This role will be responsible for generating new business and nurturing client relationships across schools, community organizations, corporate groups, and event planners. You will be tasked with the responsibility of daily prospecting, negotiating, and closing potential clients. You’ll promote safe, reliable, and cost-effective group transportation solutions using our fleet of school buses and charter vehicles.

This will be a remote position, located in the East Region and reporting to the Vice President Sales Innovation.

Responsibilities :

• Identify and pursue new sales opportunities through cold calling, networking, and attending industry events

• Build and maintain relationships with schools, sports teams, churches, tour operators, and corporate clients

• Conduct on-site visits and presentations to promote charter services

• Prepare and deliver customized quotes and proposals based on client needs

• Negotiate contracts and pricing to maximize profitability while meeting customer expectations

• Collaborate with dispatch and operations teams to ensure smooth execution of trips

• Track sales activities, leads, and performance metrics using CRM software

• Stay informed about industry trends, competitor offerings, and regional transportation regulations

The annual salary range is $80k - $90k plus a commission plan.

Qualifications

Requirements:

• Proven experience in outside sales, preferably in transportation, hospitality or logistics

• Bachelor’s degree or equivalent experience required

• 3 years in revenue generation experience required

• Experience in cold calling, transportation sales, deal closing

• Ability to quickly comprehend Organization’s processes and system’s utilization

• Adaptable work style with the ability to communicate effectively with various personalities and levels at Summit School Services

• Strong organizational skills and must be able to maintain detailed records of charter sales activity

• Strong working knowledge of MS Office, CRM Platforms and superior people skills

• Strong interpersonal and communication skills with a customer-first mindset

• Well-developed time management skills

• Knowledge of charter transportation logistics is a plus

Performance Goals

• Meet or exceed monthly and quarterly sales targets

• Maintain high client satisfaction and retention rates

• Expand market share within designated territory

Why Join Us?

You’ll be part of a purpose-driven team that values safety, reliability, and community impact. Our charter services help connect people to experiences—from field trips and sporting events to camps, weddings and corporate outings.

Summit School Services has a zero-tolerance policy on conduct that is incompatible with its policies and values, including sexual exploitation and abuse, harassment, abuse of authority, and discrimination. Summit School Services is committed to promoting the protection and safeguarding of all children and passengers.

We offer medical, dental, vision, basic life insurance coverage, holiday pay, and PTO accrual. Additionally, employees are able to enroll in a retirement savings plan.

At Summit School Services our goal is to be a diverse workforce that is representative of the communities we serve. All employment decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion, sex, pregnancy (including childbirth, lactation and related medical conditions), national origin, age, physical and mental disability, marital status, sexual orientation, gender identity, gender expression, genetic information (including characteristics and testing), military and veteran status, and any other characteristic protected by applicable law.

Summit School Services LLC’s independent subsidiaries and affiliates are an equal employment opportunity (EEO) employer

The pay rate range, along with most all of the other terms and conditions of employment, vary between different sites, geographical markets, customer/ contractual terms and positions.