Demo

Learning Guide, Alpha - $120,000/year USD

Crossover
Greenwich, CT Full Time
POSTED ON 4/15/2026
AVAILABLE BEFORE 5/14/2026
  • On-site at an Alpha School campus in one of the following locations: Piedmont, CA
  • Santa Barbara, CA
  • Santa Monica, CA
  • Greenwich, CT
  • Fort Lauderdale, FL
  • Palm Beach Gardens, FL
  • Chicago, IL
  • Boston, MA
  • Raleigh, NC
  • Charlotte, NC
  • Portland, OR
  • Seattle, WA
  • Annual compensation of $120,000 USD, distributed weekly. Comprehensive health, dental, and vision coverage begins on day one
  • Relocation assistance available. Teaching certification not required.

When a student achieves 95%, the most impactful response is to challenge them further rather than accept it as finished. If that principle feels wrong to you, this role isn't for you. If it resonates, you already share our mindset.

Alpha students don't absorb information through traditional lectures. They progress through academic content via AI-driven adaptive software at an individualized pace, frequently mastering an entire grade level within weeks. Your role encompasses everything the software cannot provide: guiding students through challenges, teaching them how to deliver feedback effectively, maintaining standards they never imagined reaching, and cultivating genuine enthusiasm for learning. You'll facilitate hands-on workshops focused on life skills including public speaking, concentration, and time management, followed by motivation sessions designed to inspire authentic engagement rather than simple compliance.

This environment doesn't resemble a conventional classroom. You'll support a small K-12 cohort where every student knows your name personally. Using Coachbot analytics, you'll monitor individual progress, identify when someone encounters obstacles, and teach them strategies to overcome those barriers independently. When your entire cohort achieves their weekly targets and 90% or more rate you positively in surveys, you'll have tangible proof the model succeeds because of your execution.

Guides who excel with their cohorts advance to Lead Guide positions—mentoring other Guides and influencing how an entire campus fulfills Alpha's mission. As Alpha expands with new campuses, today's standard-setters become tomorrow's leaders who scale excellence. If education wasn't previously on your radar but you believe you can transform a young person's future, this position turns that conviction into reality. Submit your application today.

What You Will Be Doing

  • Facilitating one-hour life skills workshops for K-12 students covering subjects such as public speaking, concentration, and feedback delivery: interactive, project-driven sessions where you engage and perform rather than lecture
  • Providing daily coaching to a small student cohort, leveraging Coachbot analytics and student profiles to establish personalized goals, monitor application progress, and drive every learner forward
  • Developing and administering mastery-based assessments (Test2Pass) that confirm students genuinely acquired the skill rather than merely attended the session
  • Building individual relationships with students: discovering their interests, identifying what drives each one, and tailoring your methods to fit
  • Maintaining performance standards: achieving 100% weekly goal completion across your cohort and securing 90% satisfaction ratings on student surveys

What You Won’t Be Doing

  • Instructing academic subjects. Math, reading, and science are delivered through adaptive applications. You won't stand before a whiteboard demonstrating long division.
  • Creating lesson plans from the ground up. Alpha supplies a structured life skills curriculum and implementation guides. Your responsibility is execution and delivery, not creation.
  • Handling traditional teacher tasks like grading papers, conducting parent conferences, or administering standardized tests. Report cards and state test preparation aren't part of this position.
  • Supervising students passively as they use computers. When learners encounter difficulties, you guide them toward self-resolution. Passive oversight contradicts this role entirely.
  • Compromising standards when students resist. The motivational framework depends on upholding high expectations, not accommodating pushback for comfort.

Learning Guide Key Responsibilities

Guide a cohort of K-12 students who thrive at school, accelerate their learning through adaptive software, and develop life skills via dynamic, hands-on workshops.

Basic Requirements

  • Bachelor's degree from an accredited institution in any discipline
  • Minimum of 3 years' direct experience working with K-8 students in professional or organized volunteer capacities (examples include coaching, camp counseling, or youth program leadership)
  • Availability to work on-site at an Alpha School campus in one of these cities: Piedmont, CA; Santa Barbara, CA; Santa Monica, CA; Greenwich, CT; Fort Lauderdale, FL; Palm Beach Gardens, FL; Chicago, IL; Boston, MA; Raleigh, NC; Charlotte, NC; Portland, OR; Seattle, WA
  • Authorization to work legally in the United States without requiring visa sponsorship

Nice-to-have Requirements

  • Background as a sports coach, theater director, debate coach, or camp program coordinator where you inspired children to excel, not simply participate
  • Demonstrated history of exceptional personal achievement (in academics, athletics, or professional domains) that earns respect from students and parents
  • Confidence presenting to groups: the type of presence that commands attention from a room of twelve-year-olds without needing to raise your voice
  • Experience with adaptive learning systems or educational technology platforms (such as Khan Academy, IXL, or DreamBox)

About Alpha

Want to join a learning rebellion that’s transforming the traditional classroom?

Alpha School is on a mission to reshape education with a bold approach that harnesses AI to accelerate learning and unleash student potential.

They don’t play by the old rules.

Alpha is creating a new paradigm where students master core academics in just two hours a day, freeing up time for hands-on, passion-driven learning that truly prepares them for the real world.

Alpha School is rewriting the rules of education.

Sounds too good to be true? It’s not.

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 $60 USD/hour, which equates to $120,000 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-5607-US-Greenwic-LearningGuide

Salary : $120,000

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 Learning Guide, Alpha - $120,000/year USD?

Sign up to receive alerts about other jobs on the Learning Guide, Alpha - $120,000/year USD career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$48,708 - $63,081
Income Estimation: 
$72,278 - $111,906
Income Estimation: 
$80,901 - $111,787
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 Washington, DC
  • On-site at Alpha School locations: New York City, NY Orange County (Lake Forest), CA San Francisco, CA Santa Barbara, CA $150,000 annual salary, distribute... more
  • 8 Days Ago

  • Crossover Kansas, MO
  • Most enrollment positions focus on volume. This one is designed to uphold standards. Alpha is developing one of the most forward-thinking school models glo... more
  • 8 Days Ago

  • Crossover Atlanta, GA
  • On-site position in Atlanta, GA; Las Vegas, NV; Nashville, TN; Park City (Salt Lake City), UT; or Spotswood, NJ. Annual salary of $150,000, distributed wee... more
  • 8 Days Ago

  • Crossover Chicago, IL
  • Many enrollment positions prioritize volume. This position exists to uphold standards. Alpha is constructing one of the most forward-thinking school models... more
  • 8 Days Ago


Not the job you're looking for? Here are some other Learning Guide, Alpha - $120,000/year USD jobs in the Greenwich, CT area that may be a better fit.

  • Crossover Greenwich, CT
  • Located on-site at an Alpha School campus (Chicago, IL Miami, FL Palo Alto, CA Piedmont, CA San Francisco, CA Santa Monica, CA Lake Forest, CA Greenwich, C... more
  • Just Posted

  • Crossover Greenwich, CT
  • On-site position at an Alpha School campus (Chicago, IL Miami, FL Palo Alto, CA Piedmont, CA San Francisco, CA Santa Monica, CA Lake Forest, CA Greenwich, ... more
  • 5 Days Ago

AI Assistant is available now!

Feel free to start your new journey!