Careers at Waypoint Academy
Where rigorous academics meet outdoor adventure to build confident, self-directed future leaders.
The education Olympics
Salary without side gigs
Skills make the grade
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JOIN WAYPOINT ACADEMY
What if school was designed to build leaders instead of test-takers?
Waypoint Academy is reimagining education by combining accelerated academics, learner ownership, and adventure-based experiences that help students develop the confidence, resilience, and real-world skills needed to thrive.
- Students master academics in a fraction of traditional classroom time
- Nature and adventure become powerful tools for personal growth
- Learners take ownership of their goals, progress, and outcomes
- Every day is designed to develop leadership, grit, and independence
Join a movement proving that challenge, responsibility, and adventure create extraordinary young people.
Available Jobs
Find your place at Waypoint Academy...Inside the EdTech team experience
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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 & syst...
Meet Holly
School Meets Adventure
Most schools separate learning from real life. Waypoint Academy brings them together.
Students spend their mornings mastering core subjects through adaptive learning technology and their afternoons tackling hands-on challenges that build resilience, teamwork, leadership, and confidence. Learning happens both in the classroom and in the wild.
At Waypoint, education is measured not just by knowledge gained, but by character developed.
Learning at the Speed of Potential
Waypoint Academy believes every learner progresses differently. Instead of age-based pacing, students advance through mastery, responsibility, and demonstrated competence.
AI-powered learning tools personalize academic instruction, enabling students to progress faster while gaining deeper ownership of their educational journey. Guides act as mentors and coaches, helping learners think critically rather than simply providing answers.
The goal isn't compliance—it’s creating capable, independent thinkers who can direct their own future.
Building Humans, Not Just Students
Waypoint Academy was created around a simple belief: children are capable of far more than traditional education often expects.
Through outdoor challenges, meaningful projects, peer accountability, and real-world experiences, learners develop the habits and mindset required to navigate uncertainty, solve problems, and lead with confidence.
The ultimate outcome isn't better students—it’s stronger, more resilient humans.
Waypoint Academy's exclusive hiring partner
Waypoint Academy partners with Crossover to recruit high-performing people who can help bring their 2 hour learning model to life. Crossover’s hiring process looks beyond resumes, using structured screening, cognitive assessments, practical work samples, and interviews to identify candidates with the talent and judgment to make a real impact in education.
For applicants, that means a clearer path to show what you can do. For Waypoint Academy, that means finding people ready to do the innovative work modern education demands.
Lead the future of learning when you’re hired on Crossover.
2×
Faster learning with AI
2Hr
Core academics in just 2 hours daily
300+
Part of the Acton Academy network
20+
Countries with learners
How it works
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.
STEP 1
Chat-style screening interview.
STEP 2
Cognitive aptitude test.
STEP 3
Prove real-world job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Pass proctored test.
STEP 6
Accept job offer.
What Crossover recruits say about the company...
There isn't another platform purely focused on remote work like Crossover. The integration from recruitment to payday is unique.
Ben
DevFactory
United States
Product CTO
My proudest moment was achieving a seemingly impossible goal: 75% AI resolution rates across support.
Ciprian
Trilogy
Romania
L2 Customer Support Engineer
My salary has quadrupled since day one—no switching companies required.
Chintan
Trilogy
India
Customer Support
When a difficult challenge impacted my health, this job provided excellent support throughout.
Tyisha
Alpha
United States
Preschool Guide
AI is embedded in almost everything we do—it's not just a tool, it's how we work.
Tushar
IgniteTech
India
Senior Financial Analyst
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
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
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
Getting full autonomy over my work with thorough team support creates the perfect balance.
Sofia
Trilogy
United States
Recruiting Director
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
Working alongside experts who constantly push the boundaries of what's possible in AI keeps me inspired.
Samuel
Trilogy
Nigeria
Salesforce Support Agent
Using AI code analyzers to auto-generate actionable feedback has transformed our development process.
Priya
Upland
India
QA Analyst
Using AI code analyzers to auto-generate actionable feedback has transformed our development process.
Praveen
Trilogy
India
Salesforce Developer
Collaborating with AI to solve problems in domains I previously knew nothing about is incredibly exciting.
Phonn
IgniteTech
Thailand
AI Innovation Specialist
This job taught me the real value of async communication and gave me freedom to explore solutions independently with AI.
Nulad
Trilogy
Indonesia
AI-First Software Engineer
This job enabled me to afford treatment for a chronic health condition—and the chance to continue working and taking care of my family throughout.
Nitesh
Trilogy
India
AI-First Software Engineer II
I love the hardcore technical challenges. People who find joy in building, improving and fixing will thrive here.
Nilo
Upland
Brazil
Software Engineer II
My favorite part of my job is building high-level technical architecture for the latest possible innovations in the field.
Nilanjan
Trilogy
United Arab Emirates
SVP of Software Engineering and Operations
I get to work any hours that I'm comfortable with, allowing me to schedule my day freely.
Mohammed
Trilogy
Egypt
Customer Support Manager
It feels like I’m gaining valuable experience very quickly — and that’s incredibly motivating.
Mohammad
IgniteTech
Israel
AI Innovation Specialist - Software Engineering
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
The combination of a supportive team environment, excellent work-life balance, and world-class compensation makes this role truly exceptional.
Matthew
Trilogy
Turkey
Customer Support
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
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
Being surrounded by smart and ambitious peers means I'm continuously learning, and becoming a domain expert.
Logan
Alpha
United States
Guide
My proudest moment was learning python to automate a process from weeks down to hours.
Kelly
GT School
Portugal
EdTech Consultant
Highly ambitious and adaptable people can accelerate here with a speed and ingenuity that is electrifying.
Karina
Trilogy
Costa Rica
L3 Conductor
Remote work and flexible hours have given me the liberty to prioritize my social life, family time, and religion.
Kaitlin
GT School
United States
Associate Guide - Virtual
I feel welcomed, and appreciated for my level of expertise in the education field.
Julian
Trilogy
Colombia
AI-Driven Learning Strategist
This job has given me a much stronger sense of purpose in contributing to positive change and making a meaningful impact.
Joshua
2 Hour Learning
Philippines
Research Analyst
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
I like what I do. I like the team I work with, and I love the flexibility they give me.
James
Trilogy
United Kingdom
Inside Sales Representative
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
This job gave me the chance to go from Support Agent to VP in a few years.
Fernando
Trilogy
Malta
VP of Customer Support
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
Working with the smartest people in the world is my favorite part of the job.
David
DevFactory
Israel
SVP of Technical Product Management
My team is world-class: everybody is driven, deeply knowledgeable and kind.
Davi
2 Hour Learning
Brazil
AI-First Learning Strategist
The pay is way higher than what I could get in my country, translating to financial stability and the ability to dream bigger.
Daniela
Trilogy
Colombia
Research Analyst
I love the variety of working on short term projects with different tech stacks, using AI-based tools to solve problems.
Daniel
Trilogy
Brazil
Senior DevOps Engineer
Getting promoted and doubling my salary in a single week was a clear, immediate reward for delivering real results.
Csaba
Trilogy
Malta
VP of Customer Support
The difference we make in the kids' lives makes everything worth it.
Crystal
GT School
United States
Guide
My favorite part of the job is that you’re constantly learning something new every day. Just by being here and tackling real challenges, you grow into a better software engineer.
Chima
Trilogy
Nigeria
AI-First Software Engineer II
I've finally found a job that I'm passionate about, which offers the opportunity and trust to lean into my strengths.
Bruna
2 Hour Learning
Portugal
Research Analyst
This job has enabled me to build a solid financial safety net and pursue my long-term personal goals.
Braden
Alpha
United States
Lead Guide
Crossover brings in talented people and empowers them to operate within their strengths. There's a clear focus on outcomes, not micromanagement.
Benjamin
Studient
United States
VP, Regional Partnerships
Being AI-first is one of the best part of this job, AI has really elevated my capabilities.
Benito
Trilogy
Dominican Republic
Customer Support
My proudest moment was when my students learned more than 2x in the last school year.
Caleb
Trilogy
Philippines
AI-First Software Engineer III
I like the freedom of flexible working hours. It's always fast and easy to schedule a vacation, travel somewhere, or even relocate to another country.
Artyom
Crossover
Serbia
AI-Augmented Back-end Principal Engineer
AI lovers who are self-driven will thrive here.
Andrew
Trilogy
United States
Chief Operating Officer
I've rapidly developed expertise that usually takes years.
Andrew
Crossover
Lebanon
People Operations Manager
My favorite thing about working here is that there's little hand-holding, yet my colleagues are smart and helpful.
Andrew
IgniteTech
Uganda
AI Innovation Specialist - Sales
Making the money I deserve as an educator has really helped me and my family have less financial stress.
Anne
Alpha
United States
Preeschool Guide
Smart individuals who enjoy resolving complex issues and learning new technologies will love working here.
Ammar
Trilogy
Jordan
AI-First Software Engineer II
Working with bleeding edge AI is my favorite part of the job.
Akshit
2 Hour Learning
United Arab Emirates
AI Innovation Specialist
I'm earning more than double what I did in my previous role, significantly improving my quality of life.
Ajith
Contently
United Arab Emirates
Senior Account Manager
This job has given me a better work-life balance with fixed hours and higher income.
Abdul
Trilogy
Pakistan
AI-First Software Engineer II
If you think you are the best, this is the right place to prove yourself.
Ignacio
Virtasant
Mexico
Call Centre Concierge
I paid off my debt, got 2 new cars, and built my house within 7 months. The pay is so good, colleagues are friendly, managers are good listeners and opportunities for development abound.
Osazee
Virtasant
Nigeria
Call Centre Concierge
I love working with the best developers from all over the world. Crossover's open and standard pay Rates are great - I loved not having to negotiate with a HR person to get paid what I'm worth.”
Romi
Crossover
India
iOS Software Architect
“I am making 4x what I was paid on my last job, and with the extra money I was able to pay for my house. Thank you Crossover!”
Alexandra
Romania
Database Searchers 1
When you're paid 3x more than you ever have, tackling high expectations from Crossover leadership becomes a welcomed challenge.”
Frances
Philippines
Financial Analyst
“I work with some of the best talents from around the world. Only at Crossover is this possible!”
Virginia
Crossover
United States
Financial Planning & Operations Manager
Crossover is to Engineering what Formula 1 is to driving. You need talent, discipline, willpower, endurance and a thirst for learning.
Mircea
Crossover
Romania
SVP Engineering and Operations
The thing that drew me to Crossover was the forward-thinking vision of a 100% global remote workforce powered by the top 1% of talent. That vision is what keeps me desiring to continue my career here!
Jackie
Crossover
United States
Vice President of Sales Development
I started as a Software Engineer at Crossover and am now a Software Architect, doubling my earnings. I now look forward to progressing further up the career ladder Crossover offers.
Dimitrios
Crossover
Greece
Software Architect
This job has given me the motivation and opportunity to learn and broaden my perspective. I never imagined I'd be able to write scripts, explore databases with SQL, or create dashboards!
Ilma
Trilogy
Turkey
Research Analyst
This company is not for everyone. If you have high discipline, low ego, and are always hungry for learning and success, you will enjoy working here.
Milos
Trilogy
Serbia
VP of Technical Product Management
This role consistently encourages me to expand my knowledge and capabilities. The opportunity to work alongside top minds has been incredibly enriching.
Tushar
IgniteTech
India
Senior Financial Analyst
The exposure to talented people from across the globe is unique and rewarding. Meritocracy is at the heart of the company and that makes the work fulfilling.
Ajinkya
Trilogy
India
Strategic Analyst
It's incredibly demanding, but absolutely rewarding. I've been able to pay off financial liabilities, afford better health care and start some small investments.
Thabet
Trilogy
Philippines
Senior Software Engineer
That level of autonomy and global teamwork has been life-changing for me.
Rodolpho
IgniteTech
Brazil
Graphic Designer
It exceeds expectations and is by far the best job I've had. I love the flexibility in my schedule, good pay commensurate with my work, and belonging to a global team.
David
Trilogy
Nigeria
Operations Analyst
Some people think Crossover jobs are too good to be true. I found it hard to believe in the beginning!
July
IgniteTech
Indonesia
L3 C# Technical Consultant
My quality of life has improved significantly. I'm in the top 0.
Mohamad
Trilogy
Lebanon
SVP of Software Engineering
I bought a new house and put my kids through private school. Not everyone is cut out for this - but if you can keep up with the pace and challenges, you're going to do great!
Andrei
Trilogy
Romania
VP of Software Engineering
It's as exciting as a job gets. You have to continually learn, improve and enhance yourself as a professional.
Sebastián
IgniteTech
El Salvador
Inside Sales Representative
You are surrounded by amazing people so it keeps you on your toes. The learning curve is 3X better than any other job, and the pay is roughly 3-4X average pay in Egypt.
Mohammed
Trilogy
Egypt
L2 Customer Support Engineer
My favorite part of this job is working with awesome kids. I was so proud when they got excited about starting their own businesses!
Lethícia
IgniteTech
Brazil
L2 Professional Services
The ability to work from anywhere and be fully present and effective is truly unparalleled. What could be better than having the world as your office space?
Muhammad
Trilogy
Pakistan
Site Reliability Engineer
Better culture. Better pay.
Ailton
TelcoDR
Canada
VP of Product Management (Cloud Charging)
I became the primary provider for my family. The income I am receiving from Crossover is significantly higher than that of my peers or anyone at my age and level.
Joshua
Trilogy
Philippines
Research Analyst
We finally got our own place! The freedom to work from anywhere, anytime—nothing compares.
Venus
Trilogy
United States
Sales Development Representative
If it was easy, then it would be boring too. The best part of this company is the fast pace, continuous improvement, and trying to solve the biggest problems.
David
Crossover
Israel
Vice President of Inside Sales
In a developing country like Pakistan, this job is heaven-sent. The type of work & innovation we do is a learning experience of its own, and the remuneration is 10X.
Muhammad
DevFactory
Pakistan
Innovator (CodeNation)
If you're smart, independent and self-driven, this could be your dream job. Everyone I work with deserves their job based on merit.
Bernhard
Trilogy
Costa Rica
Strategic Analyst
No job has paid me even close to this. It was a thorough process of recruitment and challenging tests to get the role—and it was worth it.
Syed
Trilogy
Pakistan
Operations Analyst
The combination of a steep learning curve, remote work, and competitive salary is perfect for growth.
Xavier
Trilogy
Chile
Product Knowledge Curator
My billing rate has increased by 50% after working for 3 years. The job has more flexibility and a good work-life balance.
Naga
Upland
India
QA Manual Tester
It's helped me immensely to grow professionally and personally. The best part about this job is the constant learning and improvement.
Sandeep
IgniteTech
India
Senior Account Manager
I got promoted, made a lot of progress on paying off debts, and started investing for retirement.
Julius
Trilogy
Philippines
Sales Development Representative
The dynamic nature of the job and challenges have added a new and exciting dimension to my professional journey. I'm honored to be a part of it.
Khalil
Trilogy
Pakistan
Collections Agent
This is by far the best job I've worked at. All the brilliant minds are here.
Abhishek
Upland
India
Software Engineer - Java
People who are both ambitious and disciplined will love working here.
Foad
IgniteTech
Brazil
Java Architect
The best thing has been the ability to earn a US-level salary while working from home. It may seem too good to be true, but it's a real company, with real people working on real products!
Ben
Trilogy
Australia
SVP of Technical Product Management
I earn more than I ever did working in a corporate office job. It's hard but it's definitely worth it.
Marvin
Upland
Philippines
Customer Orders Associate
I have the freedom to work from home and spend more time with my family—plus better pay. I feel challenged in my role, which I like.
Leo
Upland
Kenya
Software Engineer
This is the most rewarding job I've had in my 25+ year career. I am much more satisfied and fulfilled with the work I am doing and the growth I am contributing to.
Brent
Trilogy
United States
M&A Principal
I am earning 5x more than in my previous job. People are wary that this is a scam.
Ludel
Trilogy
Philippines
Finance Manager
This is the best job I've ever had. I'm progressing and getting positive feedback all the time.
Álvaro
Upland
Brazil
QA Automation Engineer
Some people reached out to me asking if the compensation is real or fake. It most definitely is real!
Ricardo
Trilogy
Lebanon
Senior Software Engineer
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