Chief Technology Officer

Chief Technology Officer | Bloomy (YC S26)

San Francisco · Full-time

$200,000-$250,000 base salary, plus meaningful equity

About Bloomy

Bloomy is an AI-native academic system for K-12 schools, providing curriculum, AI teaching, and assessment. We help schools deliver personalized instruction in core academic subjects, identifying what each student needs and helping them master it.

Backed by Y Combinator, Reach Capital, Robinhood Ventures, and many more, Bloomy is growing rapidly, with early school partners and promising initial results for student learning. Founded by Alex Southmayd, a former teacher and Teach For America alum, Bloomy is built around the needs of students and educators across the country.

The role

We’re hiring a hands-on CTO to own Bloomy’s technology and build our engineering team. You’ll work directly with the founder to shape product direction, make technical decisions, and turn ambitious ideas into software that students and teachers use every day.

Today, the founder leads development using AI coding agents, supported by specifications, automated checks, and review. You’ll take ownership of the existing product and engineering operation, bringing the technical depth and judgment to improve how we build and prepare Bloomy for growth.

You’ll spend a substantial share of your time building: writing and reviewing code, working with AI agents, debugging production issues, and shipping across the stack. As the company grows, you’ll hire and lead a small engineering team and remain closely involved in the product and its architecture.

What you’ll own

• Technical direction and architecture. Make decisions across the application, infrastructure, data systems, and AI capabilities. Decide what needs investment now and what can wait, balancing product needs, reliability, cost, and speed.
• Product development. Build features across the student experience, teacher tools, assessments, and curriculum systems. Work with the founder to set priorities and take responsibility for delivering them.
• AI engineering workflows. Improve how we use agents to develop software and produce curriculum. Build the specifications, evaluation systems, testing, and review practices that make their output dependable.
• Learning and product intelligence. Connect student responses, tutoring interactions, and assessment results to improvements in instruction. Build the data infrastructure to understand where students struggle and evaluate whether changes help them learn.
• Production quality and trust. Own reliability, performance, security, and student data protection. Make Bloomy work well on school devices and networks, and establish practical monitoring and incident response.
• Engineering hiring and leadership. Work with the founder on hiring priorities, recruit strong engineers, and set clear standards for technical work. Build a team that takes responsibility for what it ships and stays close to users.
• Understanding classrooms. Spend time with teachers, students, and district partners. Turn their feedback into product decisions, including practical improvements to rostering, implementation, and everyday usability.

What we’re looking for

You’ve built and operated software that people rely on, and you’re ready to take responsibility for a company’s technology and engineering team.

• Strong engineering depth and recent experience shipping across the full stack.
• Experience owning technical decisions for a product, including architecture, delivery, and production operations.
• Substantial experience using AI coding tools, with the judgment to inspect their work, catch mistakes, and improve the systems around them.
• Experience building with LLMs in production, including evaluation, failure handling, and tradeoffs between quality, latency, and cost.
• Evidence that you can lead engineers, whether through hiring, managing, mentoring, or leading a significant technical effort.
• Strong product judgment and the ability to turn an ambiguous problem into a useful, well-built solution.
• Willingness to handle the details that make software work in schools, from roster imports to performance on older devices.
• A serious interest in improving student learning and measuring whether the product does so.

You may have been a CTO, founding engineer, technical lead, or senior engineer with substantial ownership. A previous CTO title is not required. Previous experience founding a company is a plus, especially in a hands-on technical role. Education industry experience is helpful but not required.

Our current stack

React, TypeScript, Vite, Tailwind, shadcn/ui, TanStack Query, Supabase, Postgres, and Vercel.

Compensation

$200,000-$250,000 annual base salary, plus meaningful equity. Compensation will reflect experience and the scope of responsibility.