VP of Engineering​/CTO

Autumn is a vertical AI company for hotels, starting with small independent properties.

Hotels run on a patchwork of 20+ disconnected systems across pricing, marketing, guest comms, ops, accounting, and more. Workflows are still highly manual and often require large back-office teams to manage. We're building toward a unified platform that helps hotels operate more efficiently and grow revenue.

We're live with hotels across North America and growing 20%+ month-over-month, acquired entirely through cold outbound while still in stealth. We close ~85% of cold prospect calls because we're solving a major, urgent problem, and we recently raised the largest seed round in hospitality tech, led by Bessemer.

We're looking for a CTO to own Autumn's technical strategy and execution, building the foundation for a category-defining product. We already have product momentum, customers, and a strong understanding of the market. What we're looking for now is a technical leader who can help us build the right long-term foundation.

You will partner directly with the CEO and take ownership of technical strategy, architecture, engineering culture, and team building.

This is a highly hands-on role. Our engineering team is lean but strong (we're currently four people), so in the near term you'll spend substantial time in the codebase. Over time, you'll help scale the engineering organization and build the technical systems needed as we mature.

What you'll do

• Set Autumn's technical strategy and long-term architecture.
• Remain hands-on in the codebase and help ship critical product initiatives.
• Build reliable systems for integrations, hotel data, workflows, and AI agents.
• Hire, develop, and lead an exceptional engineering team.
• Partner with the CEO, customers, and the broader team to shape product and company strategy.
• Establish strong standards for reliability, security, observability, and engineering quality.

• A hands-on technical leader. You are still close to the craft and comfortable moving between architecture, debugging, coding, hiring, and company strategy.
• Deeply product-minded. You think like a product leader, not only a technical leader. You start with customer problems and business outcomes, develop strong product judgment, and work closely with customers and the team to decide what to build—not simply how to build it.
• Fluent in modern product engineering. You have built and operated production software using contemporary web, cloud, and data technologies. You learn unfamiliar systems quickly, stay current with the evolving technology landscape, and make pragmatic decisions about when to adopt, replace, or simplify tools.
• AI-native in how you build. You are highly effective with AI-assisted and agentic development tools and know how to use them to improve engineering speed, quality, and leverage—not simply generate more code. You can establish thoughtful practices around context management, testing, code review, security, documentation, evaluation, and human oversight.
• AI-native. You have built meaningful LLM or agent-based systems in production and understand their reliability, evaluation, cost, and operational challenges.
• A strong team builder. You have hired and developed excellent engineers, or have demonstrated the leadership instincts to do so.
• Comfortable at the earliest stages. You operate well with ambiguity, move quickly, and know when to introduce structure without slowing the team down.

We are looking for someone who understands that production AI systems require more than model access and prompt engineering. Strong candidates will have experience with several of the following:

• Building and evaluating LLM-powered agents and workflows
• Agent orchestration, tool use, retrieval, and…