Challenge Day Leader – Challenge Day (Concord, CA)

Organization and Position Overview

How Challenge Day Began

Motivated by memories of their own experiences of being teased and bullied in school, Yvonne and Rich Dutra-St. John created the award-winning Challenge Day program in 1987. As parents of four young children, their goal was to create a program that brought everyone together. "If we settle for tolerance, we have failed. Our goal is love," they said. In the last 30 years, Challenge Day has reached over a million people across the world and received numerous awards for this life changing work.

About Challenge Day

Challenge Day is a world leader in providing empowering and transformational workshops for teens as well as adults. Our life changing programs create a safe, open, and caring space for people to connect in a nurturing and fun environment, helping us realize that we are not alone in the issues we face (bullying, drugs, violence, abuse, poverty, prejudice, racism, etc.). Our programs provide real empathy and real hope and catalyzes us to “be the change” in the world. People often describe their experience with Challenge Day as “the best day of my life.”

Challenge Day provides a menu of programs for schools, businesses and adults.

Internationally recognized, Challenge Day has received numerous awards and has been featured in several documentaries and television programs in the U.S and abroad. Challenge Day was on The Oprah Winfrey Show and in the Emmy Award-winning documentary, “Teen Files: Surviving High School” and was the subject of the MTV series “If You Really Knew Me” and several seasons of the Dutch documentary series “Over de Streep.”

Challenge Day Program in Schools

Challenge Day’s signature program, Challenge Day, is a one-day program offered in high schools, junior high schools, middle schools, and youth organizations serving youth in the 7th through 12th grades. The 6½ hour Challenge Day program is designed for 100 students and 25 or more adults - including teachers, staff and family members, to build connection and empathy. The school programs successfully address issues seen at most schools - including cliques, gossip, rumors, negative judgments, teasing, harassment, isolation, stereotypes, intolerance, racism, sexism, bullying, violence, homophobia, hopelessness, apathy, and hidden pressures to create an image, achieve, and to live up to the expectations of others.

All of Challenge Day programs are a catalyst for creating positive change in schools, workplaces and communities; fulfilling our vision that every child lives in a world where they feel safe, loved, and celebrated.


Position: Challenge Day Leader
Supervised By: Leader and Training Department
Works with: Youth-centered organizations (high schools, middle schools, junior high schools, youth clubs, camps, and other clients as contracted.)

Job Purpose: Work in collaboration with Challenge Day team to bring healing, hope, connection, and love to teens and their communities by ensuring high quality program delivery and service to our clients. To be consistently committed to the practice of Challenge Day principles by self-evaluation and action including attention to one’s personal issues of social oppression, personal accountability and healthy emotional expression.

Essential Functions:

  1. Facilitate energetic and interactive youth programs in schools and other organizations.
  2. Reside in San Francisco Bay Area throughout entire Leader Training Process and for duration of employment as a program leader with Challenge Day.
  3. Be at least 25 years olddue to specific administrative requirements.
  4. Learn and effectively deliver program script; include personal examples and stories as they relate during program delivery.
  5. Travel by car and air within California and out-of-state (and possibly other countries)with all program-related equipment (up to 50 pounds per piece)to multiple locations an average of 3 weeks per month.
  6. Maintain valid travel documents, including a valid passport.
  7. Pass standard tests and background checks required tobe certified to workwith youth in schools:
  8. annual TB testing
  9. fingerprinting for FBI and Department Of Justice (LiveScan) background checks

The ideal candidate will also possess the following skills and qualities:

  • Open-minded and accepting of all forms of diversity including race, sexual orientation, gender identity, physical and mental disability, class, age, religion, spiritual beliefs, and lifestyles.
  • Demonstrated ability to work and connect with young people and teen issues.
  • Experience leading large groups of people (e.g. acting, performing, professional trainings, educating, presenting, etc.).
  • Demonstrated experience in leadership roles.
  • Excellent communication and facilitation skills; articulate, engaging and compelling.
  • Demonstrated ability in effectively reaching diverse groups of people with varied learning styles.
  • Self-motivated, organized, accountable, holding attention to detail.
  • Ideally will have education/training or equivalent experience in a related field.
  • Participated in some type of personal growth work OR counseling (individual or groups) OR 12-Step work OR other processes that may include understanding of intentional personal improvement
  • Understanding of social oppression issues. Previous personal or professional work in this area preferred.
  • Committed to living a life of integrity, professionalism; and to modeling compassion, patience and kindness.
  • Bilingual or multilingual is a plus – but not required

Primary Responsibilities:
Program Delivery (75% of time)

  • Co-facilitate the Challenge Day program in full partnership with a co-leader (typically a person of a different gender than you)
  • Actively upholdChallenge Dayprinciples.
  • Travel with all necessary program equipment and materials, to sites throughout the United States and/or Canada, possibly overseas.
  • Act as organization representative and ambassador for compassion and love in schools and all interactions.

Professional Development (15% of time)

  • Stay current and skilled in Challenge Day program scripts and delivery.
  • Committo continuous improvement of facilitation skills and knowledge.
  • Attend and participate in company-provided meetings, trainings, and retreats.

Completion of Paper Work (10% of time)

  • Work-related correspondences (email messages, phone calls, etc).
  • Required reports on conducted Challenge Day programs.
  • Submit expense reports within required time.

ENVIRONMENTAL CONDITIONS: Frequent air and automobile travel; facilitating energetic and interactive youth programs in enclosed spaces, often school gymnasiums for multiple hours;exposure to high volume music; and maintaining and transporting equipment.
Compensation & Benefits:

  • Daily rate per each Challenge Day program-day lead.

Note: Challenge Day programs run concurrently with the traditional school yearcalendar (September – May); limiting availability of work to those 9 months. (There may be less work during April and May)

  • Travel stipend: provided per day traveledas related to program delivery.
  • Food stipend: provided for all program days and travel days.
  • Health benefits, life insurance, short-term and long-term disabilityinsurance, 401(k) –on the first of the month following 30 days of employment

All Challenge Day Leaders must live in California’s San Francisco Bay Area (or be willing to relocate- at your own expense)before beginning work.

Regarding the Application Process:

  • In order for your application to be considered complete, please submit: a cover letter, resume, application and supplemental questionnaire, driving record, and a 2 minute video.
  • We will be keeping applications on file and conducting phone interviews as need arises.
  • After phone interviews, applicants may be invited to an in-person interview/audition. These are by invitation only and take place at the Challenge Day office in Concord, California (any needed travel and/or accommodations for auditions are at your own expense).

The Training Process:

  • The training process will take place April-August 2018, and there is no guarantee you will become a leader.
  • Based upon need, leaders who successfully complete the training process will start employment the 2018-2019 season. Any leaders chosen must be available to start on September 4, 2018.
  • Training will consist of a blend of coaching, group training, classes, and independent practice.
  • Classes will be held one to two times per week in the evenings.
  • In addition to classes, please expect about 20 hours per week of individual and group coaching.
  • The bulk of training will take place at our office in Concord, CA.
  • Further questions regarding the schedule may be addressed after your application has been accepted.
  • While we do our best to create a schedule that supports trainee needs and outside work, please keep in mind that there are several mandatory trainings throughout the course of the summer.

TO APPLY:

Download Leader Application at

Submit Resume and completed application to

CHALLENGE DAY is an equal opportunity employer.