Life Coach

Old Skool Cafe

Old Skool Cafe

Posted on Saturday, May 4, 2024

Who We Are

Celebrating our 20th Anniversary, Old Skool Cafe (OSC) provides life-changing support and opportunities for San Francisco’s most vulnerable youth. We train and employ at-risk youth, ages 16-22, to run all aspects of our supper club. Learning to be hosts, servers, cooks, and entertainers, we offer youth a solution for addressing their basic needs and break the cycle of poverty and incarceration. Our faith-based model provides a supportive environment to help youth maintain employment and be successful in all aspects of their lives. More than just a place for a fresh start, OSC is an anchor upon which their futures can thrive.

Our Culture and Values

Transformation is not a straight line. We know that change doesn’t happen overnight. We strive to maintain a culture where mistakes and failures are expected as part of the journey towards growth and transformation. We believe in second chances and learning from our mistakes.

OSC is a youth-run supper club. The youth are empowered to do the work of running the restaurant as adult mentors coach from the side. Adult staff actively seek out ways to empower our youth to push past their comfort zones, helping them grow in confidence and leadership.

We call out the gold in people. We look for the good, assume positive intent, and call out the best in one another.

We make lemonade out of lemons. We look for the good that we can find (or squeeze) out of every challenging situation, with a positive mindset. We look for the opportunity to learn and grow, rather than complain about what’s wrong.

Family starts with “yes” and “we.” There are no silos of work at Old Skool Cafe. “We” pull together as a team to find solutions and support each other to get the job done. We start with a spirit of “yes” to move mission-critical initiatives and projects forward.

We do the right thing. We understand that we are role models for our youth and our words and behavior carry weight that impacts others. Integrity is paramount as we work with excellence and honesty.

About the Role

The Life Coach is a key member of the OSC Program Team, providing youth with weekly check-ins to support them in goal planning and tangible steps toward achieving those goals. The coach also provides side-by-side training and support to participants on the floor and at events during restaurant service to help them navigate challenging circumstances in a healthy and positive way.

We seek a professional with experience working with at-risk youth, who truly loves and enjoys them. You value standards and working towards excellence and are eager to hold youth to account on their journey because you know they can achieve them!

You should apply if:

  • You are aligned with our core values and commit to living them out in the workplace: You naturally assume positive intent and see the gold in the people around you.

  • You want to make a tangible difference in the lives of youth: Your efforts will result in real-world impact— Through training and employment, we support our youth in finding their paths to self-sufficiency and a life filled with love and stability.

  • You’re energized by our opportunity: You are energized by getting your hands dirty while modeling professionalism and humility. We are a team of “do-ers” who jump in to ensure the success of our business and program. We do not shy away from hard conversations or hard work because we know our youth can meet the highest standards.

  • You want to be with the best: At OSC, we win together, celebrate together, fail together, learn together, and support each other. You will be surrounded by a high-caliber team of passionate leaders who will encourage you to do your best.

  • You are a servant leader: You naturally model excellence, professionalism, and acceptance. You don’t just enforce rules/standards, you provide accountability for your team and our youth. You see challenges as opportunities for creative thinking and teamwork, and mistakes as learning opportunities.

  • You have a flexible schedule: You are available to work all restaurant hours for weekdays and weekends, including closing on service days (Tuesday - Saturday, afternoons and evenings). Our hours need to accommodate youth school and work schedules, court dates, and special events (some occur on Sundays).

In this role, you will:

Restaurant anad Catering Operations:

  • Our training model is focused on our youth staff being the front line for our businesses. As a Life Coach you will provide a positive presence during restaurant hours. Help de-escalate conflicts that arise. Address interpersonal issues that arise with youth and help talk them through to a healthy resolution. You are a resource to youth staff and your operations team members.

  • On-the-job (OTJ) is integral to the OSC model and 1:1 meetings, and discussions that take youth off of the floor during service will only happen as a significant exception.

Training and Development:

  • Make every young person feel seen, welcomed, and cared for by listening, supporting, and encouraging them.

  • Participate in and at times facilitate life skills training for youth.

  • Weekly 1:1’s with youth to provide individual coaching. Assist the youth in setting and meeting personal goals based on OSC’s core competencies.

  • Through 1:1 and group meetings, provide actionable feedback to youth on their skill progression in the restaurant. This will be gathered from operational staff and documented.

  • Partner with the operations team to provide weekly feedback on the skill progression of youth staff. Identifying barriers and collaborating on methods to support the youth through these growth opportunities. Identifying challenges and partnering with the operations team and Program Manager to determine individual plans for success.

  • Track and document the learning progression of youth staff as they work their way through the program. Class completion, tests, and role completion/progression will all be documented in the case management system.

  • Meet and work closely with partner Case Managers to assist youth in completing their goals

  • Write letters of recommendation & support to the court when needed

  • Find resources in the community to help meet youth needs

  • Make appropriate referrals to community support partners.

  • Administer youth intake, surveys, and assessments

  • Manage youth paperwork and files.


  • This role is an independent contributor, but as a Life Coach, you will be a mentor and model for our youth.

  • Model a culture of formal and informal feedback and recognition, where the youth feel valued, motivated, and empowered to contribute their best work.

  • Provide accountability to youth staff ensuring they have all the information and tools required to meet the highest standards and are consistently meeting and exceeding these standards.

Requested requirements for the role:

  • 3+ years of experience working with at‐risk, foster care, or justice-involved youth

  • Ability to inspire youth to make positive changes in their life and community

  • Ability to cultivate a positive and safe culture that invites youth to let their walls down and grow

  • Professional training and coursework in Coaching, Counseling, and or Mentorship

  • Possess effective communication in person and in writing, strong listening skills, a polished appearance, and a professional demeanor

  • Available to work all restaurant hours for weekdays and weekends, including closing on service days (Tuesday – Saturday, afternoons and evenings and occasional Sundays)

  • Have a sincere, authentic desire to know the youth and be a support to empower them.

All life experiences matter! If you feel your experiences make you a good fit for our organization, please send us a cover letter with your resume sharing your perspective.

Old Skool Cafe’s Compensation Policy

OSC’s compensation program is designed to deliver Total Direct Compensation (based on role, level, and experience) that is aligned with the market. The range of base salary for this position is below. Please note that hourly pay offered may vary depending on factors including, job-related knowledge, skills, and experience.

$26 - $36/Hour USD


At OSC, you will make a positive and lasting difference in the world! Full-time employees receive a competitive benefits package including health, vision, and dental coverage, company-funded FSA, paid time off, 401k, and numerous professional development opportunities.

Equity and Inclusion

At OSC, we welcome everyone regardless of their background, race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, etc. We depend on the diverse and unique cultural and life experiences of our team to demonstrate examples of success for our youth. We are committed to increasing diversity across our team and ensuring that OSC is a place where people from all backgrounds can make an impact, and all of our youth have mentors and leaders who represent examples of success that they can see themselves in.


Old Skool Cafe is an inclusive work environment, and we are committed to ensuring equal opportunity in employment for qualified persons with disabilities. Please email accessibleinterviewing@oldskoolcafe.org or click here if you require any reasonable accommodations throughout the recruiting process.

Application Process

Applications, which will be reviewed as received, must include a cover letter describing your interest and qualifications, and your resume in Word or PDF format. Please send to jointheteam@oldskoolcafe.org or click here with “Life Coach” in the subject line.

Position open until filled. No telephone calls, please.