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Youth Development Specialist, Alpha

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Crossover
Full Time position
Listed on 2026-06-12
Job specializations:
  • Education / Teaching
    Youth Development, Tutoring, Teacher Assistant/ Paraprofessional
Salary/Wage Range or Industry Benchmark: 120000 USD Yearly USD 120000.00 YEAR
Job Description & How to Apply Below
Position: Youth Development Specialist, Alpha - $120,000/year USD

$120,000/year W2 salary, paid weekly; health, dental, and vision benefits starting day one.

On-site at an Alpha K-8 campus in the following locations:
Beverly Hills, CA;
La Jolla (San Diego, CA);
Palo Alto, CA;
Piedmont, CA;
South Bay (LA, CA);
Greenwich, CT;
Boca Raton, FL;
Fort Lauderdale, FL;
Miami Beach, FL;
Palm Beach Gardens, FL;
Chicago, IL;
Raleigh, NC;
Portland, OR (relocation support available).

Your role is not to teach. Your role is to motivate. The most meaningful support you can offer a student who reaches 99% of their target is to not accept it as finished. If that expectation feels uncomfortable, this role is not for you. If it energizes you because maintaining high standards signals your belief in a student's ability to meet them, read on.

At Alpha, academic learning happens through AI-powered applications. No traditional lectures. No textbooks. Approximately 60% of your time is spent facilitating one-hour life-skills workshops covering public speaking, focus, and the practice of giving and receiving constructive feedback. Roughly 30% of your time is dedicated to individual and small-group sessions, where you analyze student progress via Coachbot analytics and guide each student toward their weekly app targets.

The remaining 10% involves data analysis that informs your coaching strategy for the week ahead. You will not follow a rigid script; workshops serve as a foundation, and top performers in this role customize them and create new content when needed.

What You Will Be Doing
  • Facilitating one-hour life-skills workshops for K-8 cohorts covering public speaking, focus, feedback exchange, and other transferable skills, customizing the playbook and creating new sessions when you identify a need.
  • Conducting daily individual and small-group motivation sessions to drive every student toward their weekly app targets, leveraging Coachbot analytics, Alpha's incentive structures (school currency, leaderboards), and your rapport with each student to overcome resistance.
  • Administering Test2

    Pass (Alpha's mastery-based assessment) for each life skill, and providing coaching to students who do not pass until mastery is achieved.
  • Adjusting your coaching approach across a broad age spectrum, from kindergarteners requiring high energy and physical activity to 8th graders needing candid conversations and accountability.
  • Analyzing weekly cohort performance data in Coachbot, pinpointing students who are falling behind, and modifying your coaching tactics for the upcoming week based on data insights.
What You Won’t Be Doing
  • Delivering whiteboard lectures; academic content is managed by the apps, not by you.
  • Creating an entire curriculum from scratch; you begin with an established playbook and personalize it with your own style and narrative skills.
  • Passively monitoring students on computers; motivation in this role is active, individualized, and persistent.
  • Working through bureaucratic processes to secure resources for struggling students; if a student needs additional coaching time, you decide and implement the same day.
  • Grading assignments, conducting standardized test preparation, or managing parent outreach;
    Campus Leads handle parent-facing responsibilities, and the rest does not exist in this model.
Youth Development Specialist

Key Responsibilities

Guarantee that every student in your K-8 cohort reaches their weekly learning targets, achieves mastery in each life skill, and finishes the year expressing genuine appreciation for your impact.

Basic Requirements
  • Willing to work on-site at an Alpha campus in Beverly Hills, CA;
    La Jolla (San Diego, CA);
    Palo Alto, CA;
    Piedmont, CA;
    South Bay (LA, CA);
    Greenwich, CT;
    Boca Raton, FL;
    Fort Lauderdale, FL;
    Miami Beach, FL;
    Palm Beach Gardens, FL;
    Chicago, IL;
    Raleigh, NC;
    Portland, OR (relocation support available).
  • Bachelor's degree in any field.
  • At least 3 years of direct experience working with K-8 students (classroom instruction, coaching, tutoring, camp counseling, or youth program leadership).
  • A concrete example you can articulate of motivating a K-8 student toward a challenging goal: the objective, your actions, and the result.
  • Comfort with AI managing…
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