High School Mentor and Curriculum Facilitator

Job Title: Pathways to Success Teacher and Mentor

Location: Poughkeepsie, NY Surrounding area

Position Type: Part-Time (10-Month Position – High School Calendar Year)

Overview:

, a dynamic and inspiring organization dedicated to empowering high school students through STEAM education and life skills development, is expanding! We are seeking a dedicated and enthusiastic Pathways to Success Teacher and Mentor to join our team. This role is pivotal in helping students build critical life skills and create pathways to their future success.

Who Are the Students You’ll Be Working With?

The high school students in our program are not just attending a class—they are actively building and managing their own racing organization. Each school has two specialized teams:

• The Build Team (≈15 students) works throughout the school year to build a Factory Five race car from the ground up. They apply real-world engineering and problem-solving skills, testing their design adjustments in a racing simulator, which mirrors the car they are building. Each month, schools compete in virtual races to earn points toward the championship.
• The Marketing Team (≈20 students) is responsible for telling the story of their build. They create newsletters, social media campaigns, commercials, logos, and mission statements—essentially launching a brand-new company. Their work is judged by industry professionals in branding, marketing, and business strategy.

Together, these teams compete against seven other schools to build the best overall racing organization. At the end of the year, professional race car drivers test the student-built cars on a real race track, and marketing professionals evaluate each team’s brand and strategy. The points are tallied, and the Winners Circle Project champion is crowned.

Beyond the competition, the learning is real: after the championship, each school is challenged to sell their car in the real world, generating revenue to sustain the program for future students.

Key Responsibilities:

Teach two 50-minute life skills classes per school/per month in each assigned high school across the Hudson Valley (3 to 4 high schools, depending on applicant).

Spend one full school day per month per school on-site, providing one-on-one and small-group mentoring to students.

Deliver pre-developed Pathways to Success curriculum with enthusiasm, engaging students in meaningful discussions and activities.

Act as a supportive, inspiring presence, guiding students to apply classroom lessons to their personal growth and future aspirations.

Participate in remote weekly check-ins with the Director of Enrichment and complete all necessary prep work to ensure impactful class delivery.

Attend a small number of additional events throughout the school year, including three field trips.

Collaborate with school staff and the Winners Circle Project team to foster an enriching learning environment.

Participate in training and shadowing sessions with the Director of Enrichment to gain a thorough understanding of the curriculum and role.

Compensation & Commitment:

$3,000 per month after training.

The position runs on a 10-month contract (aligned with the high school calendar year).

Compensation requires remote weekly check-ins with the Director of Enrichment, in-person school visits, curriculum prep, and participation in events/field trips.

Qualifications:

Proven experience working with high school students in a teaching, mentoring, counseling, or life coaching capacity.

Strong interpersonal skills, with the ability to connect with and motivate teenagers.

Enthusiasm for personal development and life skills education.

Professionalism, reliability, and a passion for making a positive impact.

Ability to travel between schools on designated dates and times in the Hudson Valley region.

Why Join Us?

At the Winners Circle Project, you’ll be part of an inspiring mission to shape the leaders of tomorrow. You’ll work in a collaborative, supportive environment, helping students unlock their potential and envision a bright future.

How to Apply:

Interested candidates are invited to send their resume and a brief cover letter highlighting their relevant experience and passion for teaching and mentoring high school students.

Join us in making a difference in the lives of students!

Job Type: Part-time

Pay: $2,800.00 - $3,200.00 per month

Expected hours: 3 – 8 per week

Ability to Relocate:

• Pleasant Valley, NY 12569: Relocate before starting work (Required)

Work Location: Hybrid remote in Pleasant Valley, NY 12569

Salary : $2,800 - $3,200