Portfolio CTO, Trilogy (Remote) - $800,000/year USD

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.

• 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

• 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.

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

• 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