Outside Sales Representative - FL

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.

Work Perks:

• 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

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.

Work Perks:

• 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