Youth Development Specialist
$100,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Dorado, Puerto Rico
8am to 5pm, Monday to Friday
In-person
full-time (40 hrs/week)
Long-term role

Youth Development Specialist   $100,000 USD/year

Description

  • Location: Dorado, Puerto Rico (on-site) | Compensation: $100,000/year | Full-time: 40 hours/week

If you prefer structured lesson plans and predictable classrooms, this isn't the right fit. This position requires someone who can take charge of a room filled with 10–15 young children, maintain high energy throughout the day, and enforce rigorous standards without compromise. You'll be coaching behavior, attention, and accountability in the moment, and you'll demand mastery—not superficial engagement.

Alpha is an AI-powered private school founded on one core principle: children can achieve core academic competencies more rapidly through adaptive learning technology, freeing up time to develop the life skills that genuinely shape their trajectory. Your responsibility is to make this model effective for a K–3 cohort. As a Guide, you'll oversee one cohort band—either K-1 (Kindergarten–1st) or 2-3 (2nd–3rd)—and adjust your approach, tempo, and workshop design to match that band's developmental stage. You'll facilitate hands-on life skills workshops covering public speaking, concentration, and feedback exchange, while accelerating daily academic progress using Coachbot analytics, transparent benchmarks, and reliable motivation frameworks.

This is accountability-driven work. Success is measurable: 2x academic advancement per semester, 90%+ student satisfaction, and students demonstrating life-skill competency through Test2Pass. If you're prepared to coach with intensity, precision, and purpose, let's talk.

What you will be doing

  • Facilitate one-hour, experiential life skills workshops that incorporate narrative techniques, dynamic pacing, and hands-on practice to prepare students for Test2Pass
  • Leverage Coachbot analytics to identify obstacles early, establish daily and weekly benchmarks, and ensure every student maintains momentum within adaptive learning platforms
  • Conduct group check-ins that reinforce objectives, acknowledge achievements, and identify challenges before they compromise performance targets
  • Deploy motivation frameworks (school currency, leaderboards, incentive structures) to generate measurable improvements in focus, persistence, and productivity
  • Respond immediately when students encounter difficulty or lose focus, coaching them through problem-solving and self-correction on the spot

What you will NOT be doing

  • Delivering traditional academic lectures or serving as the main source of instructional content
  • Supervising children passively on devices while assuming progress will occur on its own
  • Reducing weekly performance goals to create the appearance of success
  • Facilitating workshops where students simply attend but fail to demonstrate competency afterward

Key responsibilities

This role ensures that a K–3 cohort reliably achieves 2x academic progress per semester while sustaining 90%+ student satisfaction and validated life-skill mastery.

Candidate requirements

  • Bachelor's degree in any field
  • Full fluency in English
  • At least intermediate Spanish proficiency to direct behavior, provide instructions, and engage with families
  • 3+ years of experience working with children ages 4–9 in dynamic, high-engagement environments (classroom, camp, coaching, or afterschool programs)
  • Experience actively leading and engaging groups of 10–15+ young children (not limited to supervision)
  • Exposure to structured goal-setting or progress tracking with children
  • Track record of receiving performance feedback and applying it
  • Willing to work in person in Dorado, Puerto Rico
  • Legal authorization to work in Puerto Rico without sponsorship

Nice to have

  • Experience facilitating structured workshops that incorporate an assessment or performance evaluation
  • Experience leveraging data or learning analytics to accelerate student progress (e.g., app dashboards, progress reports)
  • Direct experience implementing incentive systems such as points, currency, badges, or leaderboards in a youth environment

Meet a successful candidate

Watch Interview
Chris Hayes
Chris  |  L2 Guide
United States

Ever wondered if work is enhancing your life, or erasing it? After years of late nights as a fitness coach left him exhausted and disconnect...

Meet Chris

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.