Outside Sales Representative - FL New Orlando - Florida

WorldStrides, Inc.; Orlando (FL); On-site; USD 70,000 - 120,000; Full time

Benefits offered by this job

Mileage reimbursement

Travel stipend

Flexible work options

Health benefits

401(k) match

Paid time off

Job summary

WorldStrides is a global leader in educational travel seeking an Outside Sales Representative in the Orlando/Tampa metro area. You will partner with educators and administrators to design, promote, and sell student travel experiences for K-12 programs and beyond.

Responsibilities include prospecting, field presentations, relationship building, and managing a local travel schedule with regional events. The role offers a competitive base salary with uncapped commissions, mileage reimbursement,

Qualifications

• 3–5 years in outside sales and territory management.
• Experience selling into K-12 education is preferred.
• Must reside in the greater Dallas area (as per posting).
• Travel up to 70% locally, including evenings.

Responsibilities

• Prospect, qualify, and close new sales opportunities within regional school districts.
• Conduct field presentations with educators and district decision makers.
• Build and maintain a robust pipeline of educators and travel opportunities.
• Maximize retention through long-term relationships and repeat bookings.
• Manage a local travel schedule and attend events and conferences.

Skills

Outside sales

Territory management

Public speaking

Relationship building

CRM proficiency

Education

Bachelor’s degree in Business/Marketing/Communications

Tools

Microsoft Dynamics

Salesforce

Job description

WorldStridesis the global leader in educational travel and experiential learning. The company was founded in 1967 to provide middle school travel programs to Washington, D.C. and has grown to provide a wide range of programs for more than half a million students annually to over 100 countries around the world. WorldStrides offers experiential learning programs in educational travel, performing arts, language immersion, career exploration, service-learning, study abroad, and sports. Each of these experiences helps students to see beyond the classroom and to see the world – and themselves – in new ways.

Job Description:

We are seeking a dynamic, self-motivated Outside Sales Representative based in the Orlando / Tampa metroplex who wants to use their talents to make a real-world impact at WorldStrides. This role focuses on expanding our footprint in the educational student travel sector. You will be a consultive partner with educators, school administrators, and community leaders to design, promote, and sell life-changing travel experiences for K-12 and students.

Responsibilities:

• Drive Business Growth: Prospect, qualify, and close new sales opportunities within regional school districts. Develop and execute a strategic territory plan to systematically break into new schools and districts.
• Conduct Field Presentations: Conduct high-impact, face-to-face presentations and pitches with teachers, principals, and district decision makers. Effectively articulate the educational value, safety standards, and logistical ease of our travel itineraries.
• Build Educational Relationships: Navigate the unique landscape of K-12 school districts. Maintain a robust pipeline of educators and position yourself as a trusted travel advisor.
• Maximize Retention: Cultivate long-term relationships with past and current educators to secure repeat annual travel bookings, identifying opportunities to expand travel programs to other grade levels or departments.
• Manage Territory: Strategically manage a local travel schedule to maximize daily school visits and networking events, attend in person and evening parent information meetings, and represent the company at regional educational conferences.

Qualifications:

• Experience: Minimum of 3-5 years in outside sales and territory management. Experience selling into the K-12 education market is preferred.
• Local Expertise : Must reside in the greater Dallas area with deep knowledge and understanding of regional geography and school districts.
• Travel: Ability to travel locally up to 70% of the time, including occasional evening commitments for parent/school presentations.
• Communication: Exceptional public speaking, presentation, and interpersonal skills and comfortable presenting to both small and large audiences of parents, school board districts, administrators, as well as corporate executives.
• Education: Bachelor’s degree in Business, Marketing, Communications, or a related field preferred.
• Former experience in outside sales related to education or educational travel.
• Existing network of contacts within North Texas school districts (DISD, PISD, FISD, etc.).
• Proficiency with Microsoft Dynamics (or similar CRM) and Salesforce platforms to track pipeline activity.
• Must possess a reliable vehicle and valid driver's license.
• Competitive base salary with an uncapped commission structure tied directly to your territory’s growth.
• Comprehensive mileage reimbursement and monthly travel stipend and technology equipment including laptop and monitors.
• Extensive onboarding training on our travel products and educational sales cycle.
• Comprehensive health benefits: medical, dental, vision, life, AD&D, accident, critical illness, disability insurance, FSA/HSA options with employer HSA contributions, and a generous 401(k) match.
• Generous paid time off including 11 paid company holidays, 25 PTO days the first year (prorated), 1 paid volunteer day, 4 mental health days, and bereavement
• Professional development support, including up to $5,250 annually for tuition reimbursement and up to $1,000 for certifications annually
• Opportunities for paid and discounted travel
• Flexible work schedule providing on-site, remote, and hybrid office opportunities
• Encouraged participation in a wide variety of Employee Resource Groups
• Employee Assistance Program (EAP) and wellness resources, including fitness centers at select locations
• Paid parental, caregiver, and disability leave
• Team Member Discount Program
• Engaging, collaborative, and fun work environment

WorldStrides, a global organization, is committed to educate and serve communities worldwide. Our commitment is fueled by the passion of our team members and partners to make experiential learning accessible, while also being socially, environmentally, and ethically responsible. Together, we accomplish this by investing in initiatives to promote inclusion, diversity, and sustainability.

As an Equal Opportunity Employer, WorldStrides is committed to building a diverse workforce, supported by an environment that promotes inclusion and belonging. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

WorldStrides will only employ those who are legally authorized to work in the United States. This is not a position for which sponsorship will be provided. Individuals with temporary visas such as E, F-1, J-1, H-1, H-2, L, B, J or TN, or who need sponsorship for work authorization now or in the future, are not eligible for hire. Select seasonal roles may consider students on J-1 or F-1 visas.