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Entrepreneurial Mentor Won Strategy LLC | Part-Time W-2

Employee Location:

Assigned schools and educational settings in Rhode Island / Southeastern Mass / Southern New Hampshire About Won Strategy Won Strategy is a veteran-owned business consulting and entrepreneurial development company helping individuals and organizations build skills, confidence, and practical pathways to success. Through our Why To How (W.T.H.) programs, students explore entrepreneurship, develop business ideas, strengthen workplace skills, and build financial knowledge through engaging, hands-on instruction. Position Overview We are seeking reliable, enthusiastic Entrepreneurial Mentors to deliver our approved curriculum and help students connect classroom learning to real-world opportunities. Mentors serve as instructors, facilitators, and positive role models. They lead student activities, support different learning needs, collaborate with school personnel, and maintain accurate program records. Assignments may include lead instruction, teaching assistance, and financial literacy instruction through: Why To How 101: Up to 10 class sessions per cohort. Why To How 201: Up to 10 class sessions per cohort. Why To How 301 — Cents to

Success:

Up to four class sessions per cohort. Key Responsibilities Instruction & Student Mentoring Deliver the Won Strategy Why To How curriculum with fidelity to approved content, learning objectives, and program structure. Facilitate engaging classroom instruction, discussions, projects, and hands-on student activities. Help students develop entrepreneurial thinking, communication, teamwork, problem-solving, independence, and work readiness. Differentiate instruction to meet students' abilities, needs, and learning levels while preserving curriculum objectives. Maintain a positive, respectful, and supportive classroom environment. Use instructional creativity to strengthen student engagement; obtain written approval before substantially changing curriculum content. School & Team Collaboration Collaborate professionally with teachers, administrators, Office of Rehabilitation Services (ORS) counselors, and other school personnel. Communicate student progress, classroom needs, and program concerns promptly. Participate in the required weekly team call, onboarding, training, coaching, and professional development. Participate in classroom observations, performance evaluations, and curriculum proficiency reviews. Documentation & Administration Complete student assessments, evaluations, attendance records, and progress reports accurately and on time. Maintain required program documentation and submit reports by established deadlines. Record all hours worked accurately in Workforce and submit timecards no later than the last day of each month. Protect confidential student, school, employee, and company information. Follow company policies, school requirements, safety procedures, and approved reporting processes. Qualifications Required Strong communication, organization, and classroom facilitation skills. Ability to explain business and financial concepts in accessible, practical ways. Ability to engage students with different abilities and learning needs. Professionalism, reliability, punctuality, and consistent follow-through. Comfort using digital tools for attendance, assessments, documentation, and timekeeping. Availability for assigned classes, required meetings, and training. Ability to travel to assigned schools and educational settings. Successful completion of required onboarding, training, and certifications. A valid Rhode Island BCI background check before assignment, renewed annually or as requested. Preferred Experience in entrepreneurship, business ownership, business management, education, mentoring, or workforce development. Experience working with youth, students with disabilities, or students receiving special education services. Experience facilitating hands-on learning, financial literacy, or career-readiness activities. Compensation Compensation depends on the assigned instructional role and program. AssignmentCompensation Lead Instructor — Year 1 $3,900 per cohort Lead Instructor — Year 2 $4,050 per cohort Lead Instructor — Year 3 $4,200 per cohort Lead Instructor — Year 4 $4,350 per cohort Teaching Assistant $150 per class Cents to Success Instructor $200 per class, up to four classes per cohort Formal, in-person Won Strategy training$50 per hour Lead Instructor cohort compensation is divided into 10 equal payments , paid through the company's regular payroll schedule. Mileage is not reimbursed. Employment & Student Safety This is a part-time, at-will W-2 employee position . Assignments and hours depend on program needs; minimum hours are not guaranteed. Mentors must maintain appropriate professional boundaries, follow child protection and school supervision policies, comply with applicable mandatory reporting requirements, and maintain required background clearances. What Success Looks Like Successful mentors deliver engaging, consistent instruction; help students make meaningful progress; build productive relationships with school partners; and complete documentation accurately and on time. How to Apply Submit your resume and a brief statement describing your experience in business, teaching, or mentoring, along with your availability and preferred geographic areas for school assignments.

Learn more:

www.wonstrategy.com Won Strategy LLC is an equal opportunity employer.

Pay:

From $390.00 per hour

Benefits:

Paid training

Work Location:

In person