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Careers at Montessorium

Join Montessorium

New Texas School Blending the Montessori Teaching Method with 2 Hour Learning.

There are no public openings at Montessorium right now. However, new jobs are posted all the time — check back regularly for updates. In the meantime, Crossover also hires for many other companies with similar positions see all openings

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Holly Haygood
Holly  |  LL Guide and Reading Specialist
United States

Holly spent years helping students build skills that don’t always show up on a report card - confidence, planning, independence, and the belief that they can do hard things. But in public school, that kind of whole-child support was limited by paperwork & systems built for scale. Then she found Alpha - a school where every child is known well enough to be personally supported. Now she’s campus LL Guide & Reading Specialist at Alpha Scottsdale, helping students grow as readers, thinkers, & confident little people.

Meet Holly
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Carson Lehmann
Carson  |  Lead Guide
United States

He loved working with students, but Carson didn’t think education could give him a real career. AmeriCorps gave him purpose, but not stability. Google gave him stability, but not the work he loved. Then he found Alpha - a role that brought education, tech, mentorship, and leadership together in one place. Now he’s helping lead Alpha San Francisco and proving that the right school model can turn purpose into a real future.

Meet Carson
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Greg Annan
Greg  |  L3 Coach
United States

Greg knows what opportunity can do for a young athlete, and what happens when kids with just as much potential don’t get the same shot. After years split between elite soccer coaching and at-risk youth work, he found Texas Sports Academy. Now he’s an L3 Coach helping students train harder, think bigger, and build the kind of life skills that last long after the game ends.

Meet Greg
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Christie Ray
Christie  |  L1 Guide & Reading Specialist
United States

Christie spent her career trying to give teachers and students what they needed, until she realized the system set them both up to fail. After years as a teacher, mentor, principal, and district leader, she found Alpha - a school where kids get the right support, teachers get the right tools, and learning feels joyful again. Now she’s an L1 Guide helping students love school, and finally getting her own life back too.

Meet Christie
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Braden Pomerantz
Braden  |  Head Guide
United States

Braden knew he wanted to work with students. He just didn’t want the old version of the job. After years of coaching, debate, and searching for an education role built around motivation instead of lectures, he found Alpha. Now he’s a Head Guide helping grow the Guides who build trust, raise standards, and become the adults students remember.

Meet Braden
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Sam DePalo
Sam  |  Lead Guide
United States

After years of giving everything to education, Sam DePalo was done. Not because she lacked passion, but because passion alone couldn’t repair a broken model. Then she found Alpha. Now she’s a Lead Guide in Fort Worth, helping students grow faster, dream bigger, and learn the life skills traditional school never made time to teach.

Meet Sam
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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 disconnected from the people he loved, Chris Hayes found a different path at Alpha. Now he’s an L2 Guide in Miami, helping students build grit and confidence in a role that has given him a whole new kind of energy.

Meet Chris
Tyisha Brooks
Tyisha  |  L2 Guide
United States

As a teacher who once left the classroom for entrepreneurship, Tyisha longed for purpose-driven work again. Through Crossover, she joined Alpha, where she designed a preschool program that kids love, earned financial freedom for her family, and said ‘yes’ to a life-changing trip to Malawi—proving that education without borders is possible.

Read Tyisha's Story
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Katie Boye
Katie  |  Lead Guide
United States

She never wanted to just manage a classroom. Katie wanted to help students see what they were capable of. After years of trying to make that possible inside traditional K-12 systems, she found Alpha - a place where Guides are free to challenge, support, and believe in students every day. Now she’s helping build the future of school, one campus at a time.

Meet Katie
Julia Smolkina
Julia  |   AI-Driven Learning Strategist
Indonesia

As a single mom navigating life in Georgia (the country), Julia needed more than just a remote job - she needed purpose and flexibility. Discover how she found both through Crossover, leading groundbreaking AI education projects at Alpha School and 2 Hour Learning while traveling to 13 countries with her young daughter.

Read Julia's Story
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Andrew Poje
Andrew  |  Remote Coach
United States

Andrew competed in two Olympic Games before finding a new calling as a remote coach. Hit 'Read More' to see his tips for job applicants. Watch the video to hear more of his backstory, or read on for Andrew's tips about how it all works—and why it's such a great role for an elite sportsperson.

Meet Andrew
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Tristan Muniz
Tristan  |  Remote Coach
United States

What could be more important than inspiring the minds of the next generation? gt.school’s Remote Coach Tristan followed her calling from the top level of gymnastics, to a career in sales, to her dream job on Crossover.

Meet Tristan
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Lathan Lewis
Lathan  |  SVP of Software Engineering
United States

Lathan found an opportunity through Crossover’s remote job to move from Dallas, Texas to live on land in North Carolina, while still maintaining his career. Find out how he utilizes remote work async working with Trilogy to weave his work life around his personal life, and install the odd fence or two on his farm.

Meet Lathan
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Teague James
Teague  |  Product Knowledge Curator, Trilogy
United States

Teague James was recruited by Crossover to become a remote Product Knowledge Curator at Trilogy – which is really a fancy way of saying he can explain just about anything about any app to just about any audience.

Meet Teague
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Alex DeBrie
Alex  |  Dynamo DB Expert
United States

Alex now consults for Trilogy, where he coaches the world's top remote software engineers. He lives in Nebraska, USA.

Meet Alex
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Badri Varadarajan
Badri  |  EVP of Technical Product Management
United States

I get to be CTO of 150 different products. I can measure my impact and it is much higher here than it would be on any other job or anywhere else in Silicon Valley.

Meet Badri
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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.

Quotes

What Crossover recruits say about  the company...

Testimonial

We've developed an agentic team of AI engineers who create code, review it, and even manage repositories.

Tripti
2 Hour Learning
India
Research Analyst
Tripti Prakash Khetan
Testimonial

Being surrounded by smart and ambitious peers means I'm continuously learning, and becoming a domain expert.

Logan
Alpha
United States
Guide
Logan Higuera
Testimonial

The flexibility to manage my time plus weekly scheduled payments gives me both freedom and stability.

Stan
Trilogy
United Kingdom
VP of AI Center of Excellence
Stan Huseletov
Testimonial

Collaborating with AI to solve problems in domains I previously knew nothing about is incredibly exciting.

Phonn
IgniteTech
Thailand
AI Innovation Specialist
Phonn Kyaw
Testimonial

I was promoted into a higher position where my work was valued, and I could contribute in more meaningful ways.

Matewos
Trilogy
Ethiopia
AI-First Software Engineer II
Matewos Sima
Testimonial

I find work more sustainable and satisfying now because I'm given the space to focus deeply, solve meaningful problems, and work without constant interruptions.

Joseph
Alpha
United States
EdTech Evangelist
Joseph Marone
Testimonial

Using AI code analyzers to auto-generate actionable feedback has transformed our development process.

Praveen
Trilogy
India
Salesforce Developer
Praveen Kumar
Testimonial

Working at Trilogy through Crossover has been truly life-changing. The remote async work model has given me unmatched work-life balance, and the above-market salary has significantly improved my standard of living.

George
Trilogy
Romania
Product Manager
George Dita
Testimonial

This is not the right place for people who want an easy job. But I enjoy using 100% of my ability, and my pay increased 3X!

Megha
IgniteTech
India
AI Innovation Specialist
Megha Mondal
Testimonial

Getting full autonomy over my work with thorough team support creates the perfect balance.

Sofia
Trilogy
United States
Recruiting Director
Sofia Mastroianni
Testimonial

Using AI code analyzers to auto-generate actionable feedback has transformed our development process.

Priya
Upland
India
QA Analyst
Priya Sinha
Testimonial

It feels like I’m gaining valuable experience very quickly — and that’s incredibly motivating.

Mohammad
IgniteTech
Israel
AI Innovation Specialist - Software Engineering
Mohammad Mitwaly
Testimonial

Our AI copilots write reports for clients explaining what their child learned each week—it's amazing technology.

Soma
IgniteTech
Canada
Senior AI Innovation Specialist
Soma Konate
Testimonial

My proudest moment was achieving a seemingly impossible goal: 75% AI resolution rates across support.

Ciprian
Trilogy
Romania
L2 Customer Support Engineer
Ciprian Nastase
Testimonial

I love the hardcore technical challenges. People who find joy in building, improving and fixing will thrive here.

Nilo
Upland
Brazil
Software Engineer II
Nilo Soares
Testimonial

I get to work any hours that I'm comfortable with, allowing me to schedule my day freely.

Mohammed
Trilogy
Egypt
Customer Support Manager
Mohammed Amer
Testimonial

My favorite part is the relentless focus on exponential learning—we spend an hour daily updating our AI-powered second brain.

Sindy
GFI Software
Guatemala
Presales Engineer
Sindy Rodas
Testimonial

This job gave me the chance to go from Support Agent to VP in a few years.

Fernando
Trilogy
Malta
VP of Customer Support
Fernando Perez
Testimonial

Leading a tough project under tight deadlines pushed me to grow, and the positive feedback made it all the more rewarding.

Manuel
Trilogy
Brazil
Customer Support
Manuel Da Silva Junior
Testimonial

This role lets me learn and grow alongside an amazing team and a manager who truly sees me as a person, not just a resource.

Eugene
Trilogy
Serbia
AI-Augmented Full-Stack Principal Engineer
Eugene Dolgov
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