Workshop Facilitator (Contractor

Nonprofit

Published 3 days ago

Workshop Facilitator (Contractor)

Envision Your Pathway

On-site, Work must be performed in or near San Jose, CA

Job Type Contract / Freelance

Start Date August 28, 2026

End Date November 20, 2026

Final date to receive applications August 27, 2026

Experience Level Mid-level

Compensation USD $45 - $55 / hour

Cause Areas Children & Youth, Civic Engagement, Education, Job & Workplace

Job Description for Program Workshop Facilitator

Contractor (1099)

3-6 hours a week

Envision Your Pathway (EYP) is a workforce development nonprofit that empowers youth to build pathways of their own design that are aligned with their interests, passions, and values. EYP supports youth to gain dynamic skills to be civically engaged, self-determined, and confident in their competence so they may strive for their definition of success and persist beyond barriers. We are seeking a dynamic and passionate independent contractor to serve as a program workshop facilitator to lead and facilitate workshops within EYP’s Visionaries (cohort-based program) and Vista (standalone workshops), working directly with youth ages 15–24 in community-based settings.

The contract Facilitator will be responsible for delivering a range of educational, creative, and empowering workshops designed to engage participants, promote self-efficacy, and develop key skills for their future success. Most importantly, this contract Facilitator is someone who can build trust with young people, creating spaces where they feel seen and challenged, and helping them connect what they’re learning to real decisions about their future.

What This Role Looks Like In Practice

• Expectation of working 3–6 hours per week, depending on program needs
• Facilitating weekly workshops in person for cohorts of 10–25 youth in community-based settings (schools, libraries, housing sites)
• Adapting in real time to energy, engagement, and group dynamics
• Supporting youth who may be hesitant, distracted, or navigating real-life challenges outside the program
• Balance structured curriculum with your own facilitation style and presence
• Coordinate with EYP staff on logistics, materials, and session preparation
• Track attendance and basic program data to support outcomes and reporting
• Must be willing to travel to sites weekly for workshops (in San Jose or Morgan Hill)

Key Responsibilities (The Nuts And Bolts)

• Program Coordination:
  • Coordinate logistics with the Program Team for workshop delivery, including scheduling, location setup, materials preparation, and communication with participants, staff, and guest speakers.
• Facilitation:
  • Deliver EYP’s Visionaries Program and Vista Program workshops.
  • Lead engaging and interactive weekly workshops for participants, fostering a positive and inclusive environment.
  • Use your personal facilitation style while adhering to the primary learning objectives for each workshop.
  • Utilize a variety of teaching methods to accommodate different learning styles and keep participants actively involved.
  • Provide encouragement, feedback, and support to youth throughout sessions.
• Youth Engagement:
  • Build strong relationships with participants to encourage regular attendance, active participation, and growth.
  • Address and resolve any issues or concerns that may arise with participants, ensuring a safe and respectful space.
• Administrative Duties:
  • Track and maintain participant records, attendance, and other relevant data for both internal use and tracking grant outcomes.

Note:

There may be opportunities for additional hours or expanded scope based on program needs and fit.

Qualifications

• 2+ years of classroom experience or facilitating groups of young people (ages 15–24) in educational, community-based, or mentorship settings
• Strong group facilitation skills and engaging speaking style - both in person and virtually (Ex: You can read a room, adjust in real time, and keep energy moving)
• Experience working with 15-24 year olds and diverse audiences in an educational capacity while practicing cultural competency
• Passion for youth development and commitment to making a positive impact in the lives of young people
• Organizational skills with the ability to work independently
• Have…