Job Postings
Job Title: Program Facilitator-in-Training (full-time, year-round)
Supervisor: Program Manager
Location: Office in Troy (Monday), high schools in Detroit, Pontiac, Harper Woods, Hazel Park, and Warren, some work at home days (Tuesday-Friday)
Hours: M-F, 8:00 a.m. - 5:00 p.m. (During the school year there could be 7 a.m. start-times. Some evenings/weekends are required for events.)
Inspire and prepare teenagers to succeed by becoming a program facilitator-in-training with Winning Futures! We are looking to grow our team with an experienced individual to help us continue our mission. This position focuses on leading MOTIVATIONAL classes for high school students that focus on life skills, educational and career planning, and job readiness skills. Potential schools are Cass Tech, Communications & Media Arts, Community, Harper Woods, Hazel Park, and Warren Mott High Schools.
Winning Futures is a nationally recognized leader in empowering students, ages 14 to 23, to overcome obstacles and achieve their career goals. Its seven-year Workforce Prep Mentoring Program begins in 10th grade and continues through four years of college or trade school. Students are paired with volunteer Career Mentors from the business community who provide encouragement and real-world advice. Together they meet regularly during organized, staff-led, one-hour sessions focused on career exploration, skill development, and academic and career planning. Since 1994, Winning Futures has impacted more than 52,500 students and awarded $2.3 million in scholarships. Learn more at WinningFutures.org or watch our program video.
Culture: Winning Futures is a great company to work for! We have team activities and lunches, celebrate birthdays, work anniversaries, and heritage/awareness months, only respond to emails/texts/calls in off-hours if there is a major issue, health benefits, paid holidays including Juneteenth, paid time off (details provided in job offer), and 401(K) with a match. One employee shared:
“The atmosphere and energy of the company is something that I love. The people I work with are great, and everyone is extremely dedicated to their work and the cause. It is a well-organized and managed nonprofit, which has been wonderful to work for.”

Responsibilities:
As a Facilitator-in-Training, you will be learning your role by assisting the program facilitator, learning facilitation techniques, and job shadowing, with the goal that you will:
- Create a dynamic learning environment and deliver innovative training.
- Build strong relationships with school partners, set up/attend meetings throughout the year.
- Manage all aspects of the school relationships, which at times may be difficult if schools are lacking in communication skills and organization of the program.
- Research and stay up-to-date with the continuing education process.
- Customize PowerPoint presentations in conjunction with the Winning Futures curriculum templates for classroom teaching tools; develop creative facilitations and support materials.
- Support the program department.
- Support mentor recruitment (presentations, leads, intake, tracking, and scheduling).
- Manage and facilitate mentoring programs for high school students.
- Manage career mentors and students during programming to ensure participants meet developmental goals, attendance requirements, and program standards.
- Train and support career mentors.
- Follow-up and support career mentors and students when issues arise. Be flexible and willing to support them after normal work hours.
- Lead mentor retention activities including appreciation calls and notes, creating awards, and showing gratitude in class.
- Use social media to promote programs and appreciate volunteers.
Applicants Should Have These Qualities:
- COMMUNICATOR: You are an excellent communicator, in writing and verbally, and you are great at public speaking.
- DETAIL: You understand that “the devil is in the details” and meticulously pay attention to detail, especially when cleaning and entering data in Excel or databases.
- DIRECTION: You can take and follow direction, and when needed, give direction to others.
- FUN: You know that it’s important to get your work done and meet your goals, but you also know how to have fun along the way.
- GOALS: You are a goal setter who eagerly works to accomplish them, completely and on time.
- INCLUSIVE: You are committed to diversity and embrace a personal approach that values and respects differences in race, ethnicity, age, gender, sexual orientation, gender identity, religion, ability, and socio-economic circumstances.
- INITIATIVE: When you see a problem, you solve it. When you see an opportunity, you go for it. You don’t wait for others or try to avoid responsibility. You take the lead and own your projects and tasks.
- LOYALTY: You show appropriate discretion around confidentiality, decisions are for the good of the organization and not the individual.
- MICROSOFT OFFICE: You have good experience and know how to use basic Microsoft applications, like Word, Excel (sums, sort, filter), and PowerPoint. It’s an added bonus if you know MS Planner and MS Forms.
- ORGANIZED: You keep yourself and your work organized.
- POSITIVE ATTITUDE: You focus on the positive and avoid the negative and present yourself as such.
- PROFESSIONALISM: You always demonstrate a very high professional demeanor, even under pressure.
- PROJECT MANAGER: You prioritize your work and can manage multiple projects at one time, completing your work on or before the deadline.
- QUESTIONS: You aren’t afraid to ask questions or be asked questions.
- RELATIONSHIP FOCUSED: You want camaraderie with your co-workers. You are pleasant and helpful with stakeholders and get along well with others.
- SELF STARTER: Able to take initiative and work independently on projects.
- STUDENT FOCUSED: You are passionate about our mission and care about impacting our students.
- TEAMWORK: You jump in and help co-workers, give input without putting others down, and praise others.

Physical Demands and Work Environment:
- Standing/Walking: Frequently stands and walks through schools and classrooms for up to 4 hours.
- Lifting/Carrying: Occasionally lifts and carries boxes weighing up to 25 lbs.; setting up tables and chairs.
- Dexterity: Constant keyboarding and gross motor manipulation of controls.
- Environment: Commuting to high school schools and the office, working in high energy, noisy classes.
- Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions.
Education and experience:
- This position requires a bachelor’s degree and at least three years of professional experience in a role as a facilitator/trainer/teacher/presenter/speaker/broadcaster. This is not an entry level position.
Submit resume to: FacilitatorResume@Winningfutures.org. In your email, please put your full name in the subject line. In your email, please note your desired pay rate or range – be specific and do not say that you are negotiable.
Questions: Send any questions you have to FacilitatorResume@Winningfutures.org. Do not directly contact staff members regarding this position.


