Youth Development Specialist, Alpha - $120,000/year USD

Crossover; Illinois; On-site; USD 102,000 - 138,000; Full time

Benefits offered by this job

Weekly pay

Day-one medical insurance

Day-one dental insurance

Day-one vision insurance

Relocation support

Job summary

Alpha is hiring a Youth Development Specialist to lead high-energy life skills workshops for K-8 students and coach them using Coachbot analytics to reach ambitious weekly goals.

You will focus on developing communication, resilience, and leadership, assessing mastery through Test2Pass, and personalizing coaching across ages, while partnering with campus leads to drive student progress and engagement.

Qualifications

• At least 3 years of experience working directly with K-8 students through youth development programs, teaching, coaching, tutoring, mentoring, or camp leadership.
• Willing to work in person at an Alpha campus in multiple U.S. locations including Chicago, IL.

Responsibilities

• Lead high-energy, one-hour life skills workshops for K-8 students.
• Coach students individually and in small groups using Coachbot analytics and motivation systems.
• Assess life skill mastery through Test2Pass and provide targeted coaching until mastery is demonstrated.
• Adapt coaching across elementary and middle school students to meet diverse needs.
• Analyze weekly student performance data to identify patterns and improve outcomes.

Skills

Youth development

Coaching

Public speaking

Mentoring

Education

Bachelor's degree

Job description

“All of my students came back in the top 1% for growth and achievement on their MAP scores.”

— Sam DePalo, Lead Guide, Alpha Fort Worth Texas

Alpha is hiring.

• $120,000/year W2 salary, paid weekly, plus day-one medical, dental, and vision benefits
• On-site at an Alpha campus in Bethesda, MD; Boca Raton, FL; Boston, MA; Chicago, IL; Greenwich, CT; Kirkland or Seattle, WA; Los Angeles, CA; Malibu, CA; Miami, FL; Miami Beach, FL; New York City, NY; Palm Beach, FL; San Francisco, CA; or Santa Barbara, CA (relocation support provided).

Most schools ask students to meet expectations. You'll teach them to exceed their own.

Every student has more in them than they believe. Most adults lower the bar when a student struggles. You do the opposite. You know confidence isn't built through praise. It's built by helping someone accomplish something they once thought was impossible. If you've ever refused to let a student, athlete, camper, or mentee quit on themselves, this is your kind of work.

Alpha has rebuilt school around a simple idea: AI is better at delivering academics, and exceptional humans are better at changing lives. Students complete core academics through adaptive AI-powered learning apps. Your job is to develop everything technology can't—discipline, resilience, communication, ownership, focus, and the belief that difficult things are worth doing. You won't spend your day delivering lessons or grading papers. You'll spend it coaching students through challenges, celebrating real progress, and helping them achieve goals they never thought they could reach.

About 60% of your week is spent leading energetic, one-hour life skills workshops on topics like public speaking, focus, leadership, and giving and receiving feedback. Around 30% is spent coaching students one‑on‑one or in small groups using Coachbot analytics to identify who needs encouragement, accountability, or a different approach. The remaining 10% is reviewing data, refining your coaching strategies, and preparing students for an even stronger week ahead. You'll start with proven workshop frameworks, then improve and expand them as you discover better ways to inspire students.

Success is objective. At least 90% of your students should consistently hit their weekly academic goals, demonstrate mastery of Alpha's life skills through Test2Pass assessments, and rate their experience with you at least 4 out of 5. Meet that standard consistently and you'll have a clear path to Lead Guide, coaching other Guides, and eventually Campus Lead, where you'll shape the culture and performance of an entire school.

This role isn't for people who want to lecture, follow a curriculum, or simply keep students busy. It's for youth development professionals, coaches, mentors, youth leaders, performers, tutors, and educators who measure success by what their students become. Every finalist spends a full day coaching real Alpha students before receiving an offer. If that sounds more exciting than another interview, we'd love to meet you.

What You Will Be Doing

• Leading high-energy, one-hour life skills workshops for K-8 students, developing communication, resilience, focus, leadership, and other durable skills while continuously improving the workshop experience.
• Coaching students individually and in small groups using Coachbot analytics, personalized accountability, and Alpha's motivation systems to help every student achieve ambitious weekly goals.
• Assessing life skill mastery through Test2Pass and providing targeted coaching until every student demonstrates genuine competence, not just participation.
• Adapting your coaching style across elementary and middle school students, knowing when a kindergartner needs movement and encouragement and when an eighth grader needs direct accountability.
• Analyzing weekly student performance data to identify patterns, remove obstacles, and continually improve outcomes for your entire cohort.

What You Won’t Be Doing

• Delivering traditional classroom instruction. AI handles academic teaching so you can focus on developing students.
• Grading homework, creating lesson plans, or preparing students for standardized tests.
• Watching students work silently on computers. Every day is active, interactive, and centered on coaching.
• Waiting for approvals before helping a struggling student. You have the autonomy to act quickly and do what's needed.
• Managing parent communication or administrative paperwork. Campus Leads own parent relationships so you can focus on students.

Youth Development Specialist Key Responsibilities

Build a cohort of students who consistently achieve ambitious academic goals, master essential life skills, and develop the confidence, resilience, and ownership to succeed long after they leave Alpha.

Basic Requirements

• At least 3 years of experience working directly with K-8 students through youth development programs, teaching, coaching, tutoring, mentoring, or camp leadership
• Willing to work in person at an Alpha campus in Bethesda, MD; Boca Raton, FL; Boston, MA; Chicago, IL; Greenwich, CT; Kirkland or Seattle, WA; Los Angeles, CA; Malibu, CA; Miami, FL; Miami Beach, FL; New York City, NY; Palm Beach, FL; San Francisco, CA; or Santa Barbara, CA (relocation support provided)
• Bachelor's degree in any discipline
• Ability to describe a specific example of motivating a student to achieve a difficult goal, including your approach and the outcome
• Excited to let AI deliver academics while you focus on coaching, motivation, and life skills development
• Authorized to work in the United States without current or future visa sponsorship

Nice-to-have Requirements

• Experience coaching youth sports, debate, theater, camps, after-school programs, or other performance-based activities
• Personal record of high achievement in academics, athletics, leadership, or another competitive field
• Strong stage presence and storytelling skills that can keep a room full of students engaged without relying on volume or discipline
• Demonstrated success helping disengaged, resistant, or struggling students become motivated, confident learners

About Alpha

Join the team building school around student growth

Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.

Roles with real student impact:

Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.

Education work that pays like it matters:

Alpha offers six-figure roles for people ready to help build a radically better school experience.

A culture built for builders:

Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.

Alpha is where you can do the most meaningful work of your career.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $120,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5607-US-Cook-YouthDevelopme.002