Demo

Learning Guide, Alpha - $100,000/year USD

Crossover
Worcester, MA Full Time
POSTED ON 7/9/2026
AVAILABLE BEFORE 8/7/2026
  • On-site in Springfield, MA (relocation assistance available)
  • $100,000 annual salary, disbursed weekly. Full health, dental, and vision coverage begins day one

Do you recognize when a student reaches 99% of their target and refuse to accept that as completion? The most meaningful support you can offer a child who achieves 99% is to insist on the full 100%. If that expectation feels uncomfortable, this position is not the right fit. If it energizes you—because you understand that maintaining high standards demonstrates your belief in a student's capability—continue reading.

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

This is specialized work. Your first year centers on playbook mastery: facilitating workshops, conducting motivation sessions, overseeing mastery assessments, and demonstrating your ability to maintain 100% goal attainment across all students. Success in these areas creates advancement opportunities to Lead Guide. You must bring warmth, executive presence, and uncompromising standards. Submit your application now.

What You Will Be Doing

  • Facilitating one-hour life skill workshops covering public speaking, focus, collaboration, and feedback exchange, calibrating your delivery and energy for Pre-K–8 developmental stages
  • Conducting daily individual and small-group motivation sessions to review student progress in adaptive learning platforms (via Coachbot analytics), establish goals, and ensure 100% weekly target completion
  • Overseeing and evaluating Test2Pass assessments to verify genuine life skill mastery rather than mere attendance
  • Implementing targeted interventions when students experience academic or engagement setbacks — diagnosing underlying issues and creating recovery strategies
  • Cultivating authentic relationships with each student to establish the trust necessary for coaching through resistance, distraction, and uncertainty

What You Won’t Be Doing

  • Teaching traditional academic content or delivering lectures (core curriculum is managed through adaptive applications, not instructor-led sessions)
  • Creating original lesson plans or curriculum materials (Alpha supplies life skills playbooks; your responsibility is dynamic execution through storytelling and engagement)
  • Handling parent communications or administrative functions (Campus Leads manage these areas; your focus remains exclusively on students)
  • Evaluating assignments or preparing students for standardized testing (these elements do not exist in this model)
  • Operating independently (you function within a campus team including Lead Guides, Campus Leads, and colleagues who provide feedback and mutual accountability)

Learning Guide Key Responsibilities

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

Basic Requirements

  • Bachelor's degree in any discipline.
  • 3 years of direct experience with Pre-K–8 students (teaching, coaching, counseling, or youth program management).
  • 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 measurable results).
  • Comfort with a coaching-exclusive model where academic content delivery is entirely platform-managed. Your function is motivation and guidance, not subject instruction.
  • Daily utilization of generative AI tools (e.g., ChatGPT, Gemini, Claude).
  • Availability to work on-site at Alpha's Springfield, MA campus (relocation assistance provided).
  • Legal authorization to work in the United States without requiring visa sponsorship.

Nice-to-have Requirements

  • Background in youth sports coaching, camp leadership, or after-school programs where you held direct accountability for motivating children toward specific objectives.
  • History of significant personal accomplishment (academic distinction, competitive athletics, or leadership positions requiring sustained high performance).
  • Instinctive storytelling capability: you can command the attention of Pre-K–8 students for an hour without volume escalation.
  • Success re-engaging disengaged 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-Worceste-LearningGuide

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 Learning Guide, Alpha - $100,000/year USD?

Sign up to receive alerts about other jobs on the Learning Guide, Alpha - $100,000/year USD career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$42,051 - $54,727
Income Estimation: 
$42,691 - $53,255
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 Park, UT
  • $100,000 annual salary, disbursed weekly, including health, dental, and vision coverage from day one On-site placement at a single Alpha campus: Phoenix, A... more
  • 8 Days Ago

  • Crossover Peoria, AZ
  • You recognize that moment. A student stops fumbling through words and begins reading with purpose. They meet your eyes and realize, "I can actually do this... more
  • 8 Days Ago

  • Crossover Atlanta, GA
  • Trust is what keeps every campus running. This role ensures that trust is built, safeguarded, and delivered uniformly across the board. You will serve as t... more
  • 8 Days Ago

  • Crossover Pittsburgh, PA
  • LOCATION NOTE: This is an on-site position based at one of the campuses listed below, with regional travel required. If helping families navigate a fundame... more
  • 8 Days Ago


Not the job you're looking for? Here are some other Learning Guide, Alpha - $100,000/year USD jobs in the Worcester, MA area that may be a better fit.

  • Crossover Shrewsbury, MA
  • On-site in Springfield, MA (relocation assistance available) $100,000 annual salary, disbursed weekly. Full health, dental, and vision coverage begins day ... more
  • 7 Days Ago

  • Crossover Shrewsbury, MA
  • On-site in Springfield, MA (relocation assistance available) $100,000 annual salary paid weekly. Full health, dental, and vision coverage starting day one ... more
  • 11 Days Ago

AI Assistant is available now!

Feel free to start your new journey!