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

Crossover
Full Timemid
Greenwich, Connecticut, USPosted April 22, 2026

Job Description

  • On-site at an Alpha campus in Lake Forest CA, Palo Alto CA, Piedmont CA, San Francisco CA, Santa Monica CA, Greenwich CT, Chicago IL, Boston MA, New York City NY, or Chantilly VA (relocation assistance available)
  • $120,000 annual salary, distributed weekly. Health, dental, and vision coverage begins on day one
  • Daily instruction supported by AI-driven tools and adaptive learning platforms

You know that 20 minutes of diagnostically driven reading instruction outperforms 90 minutes of scripted lessons—and you have student outcomes to back it up. You've seen children move past phonics barriers because you identified the specific gap, not because a curriculum dictated the next step. If building lessons directly from live student data feels like professional autonomy instead of added burden, continue reading.

Alpha's reading instruction operates on a straightforward principle: every minute counts. Your workshops are 20-minute sessions designed around each student's actual needs, not a predetermined pacing calendar. You'll evaluate reading levels, organize targeted groups, and provide high-impact structured literacy instruction (phonics, fluency, comprehension) to students aged 4-7 that produces measurable weekly progress. AI-powered adaptive platforms work alongside you, producing performance data you'll analyze to modify tomorrow's lesson before today's workshop concludes.

This position evolves. During your first year, you're immersed in classroom instruction: facilitating workshops, leading motivational activities that convert hesitant readers into enthusiastic ones, and delivering detailed observations to the technology team refining Alpha's AI literacy platforms. As these platforms expand and your input shapes their development, your influence reaches beyond your immediate students. You'll contribute to building a reading program that functions across multiple campuses, transforming what you accomplish with 15 children into a framework that serves hundreds.

If you've built your career demonstrating that structured literacy delivers results and you're prepared to combine that expertise with technology that multiplies it, this is where your influence extends beyond a single classroom.

What You Will Be Doing

  • Creating and facilitating 20-minute reading workshops based on your own diagnostic evaluation of each student's reading level and specific gaps
  • Applying AI-generated student performance data to modify groupings and instructional focus between sessions, rather than waiting for quarterly reviews
  • Facilitating motivational sessions that cultivate intrinsic reading motivation, employing age-appropriate gamification and personalized goal-setting with K-2 students
  • Piloting and assessing AI literacy tools during live workshops, then delivering structured feedback to the technology team regarding effectiveness and areas for improvement
  • Monitoring measurable outcomes (fluency progress, decoding level advancement, accuracy improvements) and applying them to refine your instructional approach on a weekly basis

What You Won’t Be Doing

  • Implementing a scripted or packaged reading curriculum. You diagnose student needs and create instruction independently.
  • Conducting 60-90 minute lecture-based literacy blocks. Sessions are brief, targeted, and high-intensity.
  • Working exclusively with struggling readers. You'll teach all K-2 students across varying reading levels.
  • Functioning separately from technology. AI adaptive tools integrate into your daily workflow, not as an occasional supplement.
  • Delaying instructional adjustments until quarterly data reviews. You adapt in real time based on current data.

Learning Specialist Key Responsibilities

Advance early elementary students to grade-level reading proficiency through adaptive, AI-enhanced structured literacy instruction.

Basic Requirements

  • Bachelor's degree (any subject)
  • Master's in reading instruction OR structured literacy certification (Orton-Gillingham, Wilson Reading System, IMSE, CERI, LETRS, Neuhaus, UFLI, or equivalent)
  • 2+ years of full-time K-2 structured reading instruction in a school or clinical setting within the last 5 years, using systematic phonics or structured literacy
  • Ability to design your own reading lessons and clearly describe what you teach and how, without relying on a published program
  • Willingness to work in-person at an Alpha campus (Lake Forest CA, Palo Alto CA, Piedmont CA, San Francisco CA, Santa Monica CA, Greenwich CT, Chicago IL, Boston MA, New York City NY, or Chantilly VA; relocation support provided)
  • Willingness to use AI and adaptive learning tools daily and adapt as tools evolve
  • Legally authorized to work in the U.S. without visa sponsorship

Nice-to-have Requirements

  • Experience administering diagnostic reading assessments (e.g., DRA, DIBELS, AIMSweb) for creating differentiated groups
  • Documented history of measurable student reading gains you can articulate with specific data (e.g., advanced 12 students from Level C to Level G in one semester)
  • Experience partnering with edtech teams, product teams, or instructional designers on tool development
  • Background in a startup, micro-school, or non-traditional educational environment where you designed systems rather than implementing existing ones

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-5632-US-Greenwic-LearningSpecia

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