Demo

Youth Development Specialist, Alpha - $100,000/year USD

Crossover
Stamford, CT Full Time
POSTED ON 8/10/2026
AVAILABLE BEFORE 11/2/2026
  • On-site role in Springfield, MA (we provide relocation assistance)
  • $100,000 annual salary paid weekly. Full health, dental, and vision coverage from day one

Do you recognize when a student reaches 99% and feel compelled to ensure they finish? The most meaningful support for a child who achieves 99% of their objective is insisting they complete it. If that expectation unsettles you, this position likely isn't the right fit. If it energizes you because you understand that maintaining high standards demonstrates your belief in their capability, continue reading.

Alpha operates differently from conventional schools. Students complete a full academic day in roughly two hours using adaptive software. No traditional lectures. No physical textbooks. Your role addresses what technology cannot: developing Pre-K through 8th grade students' life skills including public speaking, concentration, and feedback exchange. You'll spend half your time facilitating hands-on workshops guided by structured curricula and narrative techniques. The remaining time involves working individually or with small groups, analyzing their adaptive learning progress via Coachbot analytics, and ensuring they achieve 100% of weekly objectives. Mastery is demonstrated through Test2Pass assessments rather than participation-based grading.

This is specialized work. During your first year, you'll become proficient in the core methodology: workshop facilitation, motivational coaching, mastery evaluation, and consistently holding every student accountable to 100% goal completion. Excel in this, and advancement to Lead Guide becomes available. You must bring warmth, strong presence, and unwavering standards. Submit your application now.

What You Will Be Doing

  • Facilitating one-hour life skills workshops covering public speaking, concentration, teamwork, and feedback practices, adjusting your delivery and intensity for Pre-K through 8th grade students
  • Conducting daily individual and small-group coaching sessions where you analyze student progress in adaptive learning platforms (via Coachbot analytics), establish objectives, and ensure they reach 100% of their weekly benchmarks
  • Overseeing and assessing Test2Pass evaluations to verify genuine mastery of each life skill rather than simple attendance
  • Providing focused interventions when students lag academically or in participation — identifying underlying issues and creating remediation strategies
  • Establishing authentic connections with every student so they trust you sufficiently to receive guidance through resistance, distraction, and uncertainty

What You Won’t Be Doing

  • Providing lectures or conventional academic teaching (core subjects are learned through adaptive applications, not direct instruction from you)
  • Creating lesson plans or original curriculum (Alpha supplies life skills frameworks; your responsibility is executing them with enthusiasm and narrative skill)
  • Handling parent communications or administrative duties (Campus Leads manage those areas; you concentrate on student development)
  • Evaluating homework or preparing students for standardized testing (these elements don't exist in this model)
  • Operating independently (you're integrated into a campus team including Lead Guides, Campus Leads, and colleagues who provide feedback and mutual accountability)

Youth Development Specialist Key Responsibilities

Guarantee that every student in your group develops a love for school, achieves mastery of critical life skills, and completes 100% of their academic objectives through adaptive learning technology.

Basic Requirements

  • Bachelor's degree in any discipline.
  • 3 years of direct experience with Pre-K–8 students (in teaching, coaching, counseling, or youth program management roles).
  • Demonstrated experience motivating or coaching Pre-K–8 students toward academic, behavioral, athletic, or extracurricular objectives, with at least one concrete example you can articulate (including the objective, your actions, and the result).
  • Willingness to embrace a coaching-focused model where the learning platform handles all academic instruction. Your function is motivation and guidance, not subject matter teaching.
  • Regular use of generative AI applications (e.g., ChatGPT, Gemini, Claude).
  • Availability to work on-site at Alpha's Springfield, MA campus (relocation assistance available).
  • Authorization to work in the United States without requiring visa sponsorship.

Nice-to-have Requirements

  • Background in youth sports coaching, camp management, or after-school programming where you held direct accountability for motivating children toward defined objectives.
  • History of notable personal accomplishment (academic distinction, competitive sports achievement, or leadership positions requiring consistent high performance).
  • Innate storytelling capability: you can maintain Pre-K–8 students' focus for an hour without elevating your voice.
  • Success engaging unmotivated or resistant students and converting them into active learners.
  • Experience supporting students who receive special education services.

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.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $50 USD/hour, which equates to $100,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5822-US-Stamford-YouthDevelopme

Salary : $100,000

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Youth Development Specialist, Alpha - $100,000/year USD?

Sign up to receive alerts about other jobs on the Youth Development Specialist, Alpha - $100,000/year USD career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$40,727 - $62,445
Income Estimation: 
$75,964 - $125,537
Income Estimation: 
$86,085 - $140,434
Income Estimation: 
$52,402 - $79,389
Income Estimation: 
$71,017 - $119,813
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Crossover

  • Crossover Providence, RI
  • "The sheer amount of time I get back from not having to make daily lesson plans and grade papers is huge." — Katie, Lead Guide, Alpha Denver Alpha is hirin... more
  • 1 Day Ago

  • Crossover Providence, RI
  • "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 hiri... more
  • 1 Day Ago

  • Crossover Las Vegas, NV
  • "We are never going to lower the standard for any kid — instead we're going to raise the support to help them get there." — Braden, Head Guide, Alpha Austi... more
  • 1 Day Ago

  • Crossover Las Vegas, NV
  • You went into private school leadership to shape how children learn, not to run capital campaigns and referee parent committees. There is a version of this... more
  • 1 Day Ago


Not the job you're looking for? Here are some other Youth Development Specialist, Alpha - $100,000/year USD jobs in the Stamford, CT area that may be a better fit.

  • Crossover Greenwich, CT
  • The most difficult aspect of this position is not instruction. You will sit with a frustrated six-year-old, and the correct response will rarely be to prov... more
  • 9 Days Ago

  • Crossover Stamford, CT
  • $120,000 annual W2 salary with weekly pay, plus medical, dental, and vision benefits starting day one In-person position at an Alpha campus located in Mali... more
  • 8 Days Ago

AI Assistant is available now!

Feel free to start your new journey!