Principal Architect
$800,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks ($400 USD/hour)

Not accepting applications on at this time.


Are you a tech industry veteran with a proven ability to become a domain expert in any field? Do you have a structured and algorithmic approach to technical problem solving? Are you able to communicate through clear, persuasive writing? If so, there’s a spot for you on Trilogy’s technical product leadership team!

In this role, you will be responsible for defining Trilogy’s most important technical strategies over the next 10 years, including cutting-edge cloud technologies, generative AI, and the future of education. To construct a durable technical strategy, you will become intimately familiar with cutting-edge products, develop a deep understanding of potential barriers to adoption, map key business problems to computer science fundamentals, and define solutions that leverage the best technology available in the market.

If you’re not already a domain expert in one of our core areas of interest, that’s all the better! We believe that outsiders’ fresh perspectives are often advantageous. As long as you’re excited by the challenge of solving abstract problems with technology and are not afraid to challenge the status quo, navigate ambiguity, and bet big on your own ideas, then we’re looking forward to meeting you.

What you will be doing

  • Technology evaluation. Diving deep on emerging cloud technologies and their applicability to our product portfolio
  • Product Roadmaps: Defining and scoping out the product specs required to bring a vision to life
  • Architecture Specs: Working on the most difficult product architecture issues escalated by more junior members of the team
  • Process Improvements: Designing process improvements for how our technical product and engineering teams operate
  • Work Reviews and Coaching: The quality bar for the work performed by the team begins and ends with you

What you will NOT be doing

  • Designing complex solutions for complex problems; we value the ability to develop simple technical strategies that are coherent and long-lasting, as opposed to setting random benchmarks that don’t drive the team toward a clear goal.
  • Folding in the face of ambiguity; most of the problems we solve have unclear solutions, timelines, and constraints. You will be expected to work through these obstacles, rather than coming up with reasons not to.
  • Following rules; we’re looking for someone who can think outside the box, challenge the status quo when necessary, and make everyone on the technical product management team better.

Key responsibilities

  • Design simplified product architecture through the most important technical decisions that define a product and its features for the next 5 to 10 years

Candidate requirements

  • A university degree in an Engineering field
  • 10+ years of experience building and delivering software products
  • 5+ years of experience being the most senior person responsible for architecture and design decisions on software projects
  • A grasp of AI, Large Language Models (LLMs), and prompt engineering, including Chain-of-Thought (CoT) prompting and Self-Consistency in CoT

Meet the hiring manager

Watch Video
Watch Video

Meet a successful candidate

Watch Interview
Steve Brain
Steve  |  EVP of Technical Product Management
United States  

What happens in tech when you follow the innovation? This outside-of-the-box thinker took unconventional risks all the way to the top. As Tr...

Meet Steve
How it works

Applying for a role? Here’s what to expect.

We’ve curated a series of steps that take the guesswork (and cognitive bias) out of recruiting the best person.

Pass Cognitive Aptitude Test.

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.

Pass English Proficiency Test.

Prove Real-World Job Skills.

Prove Real-World Job Skills.

Ace An Interview Or Two.

Ace An Interview Or Two.

Accept Job Offer.

Accept Job Offer.



Frequently asked questions

About the role

About Crossover

What you will learn

We believe in continuous growth and strive for constant improvement. As part of our team, you will learn new technologies, products, and industries daily, and our comprehensive suite of playbooks will equip you with the foundation to develop and enhance your existing expertise. 

We also provide a unique CTO Remote Camp for all new hires. This full-time, fully-paid training program covers all of the unique aspects of our Cloud Architecture and Design approach. You will get daily feedback to accelerate learning and growth far beyond typical classrooms or training programs throughout your training. Our curriculum includes several bite-sized training videos explaining how we design great software. Here’s an example of how to make and validate Important Technical Decisions.

Work examples

How do you enhance an application that is expensive to maintain? We believe that before adding features to a product, it is vital to ensure that it has a simple and strong core. When we acquire a product, we challenge ourselves to rebuild it entirely using today's cloud services and patterns in under 5,000 lines of code. This challenge helps us quickly get to the core and identify all the gems that can't be replaced with off-the-shelf software and services.

Our approach begins with writing the spec to build the existing product as-is. This "Technical Teardown Spec" aims to document what is core and why all the important technical decisions were made. Sometimes, historical decisions are made for great reasons that still hold true today. Often, we'd do things differently. While we write the teardown spec, we inject our opinions and insights alongside the facts we've learned. 

Once the technical teardown is complete, we write the rebuild spec that describes the important decisions necessary to rebuild the product in 5,000 lines of code.

These are examples of specs our organization has produced for Sococo:

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.