CTO / VP of Engineering

52 Limited; New York (NY); On-site; USD 240,000 - 420,000; Full time

Job summary

52 Limited is seeking a CTO to own technical strategy and execution for an AI-native hospitality platform in Williamsburg, Brooklyn. You will lead architecture, engineering culture, and product-driven decisions while staying hands-on in the codebase.

In this early-stage role, you’ll scale the engineering team, partner with the CEO and customers, and build reliable systems for hotel data, workflows, and AI agents to drive revenue and guest experiences.

Qualifications

• Hands-on CTO/VP-level experience in early-stage tech
• Proven ability to design long-term technical strategy and architecture
• Experience leading AI-native software products and data-heavy systems
• Strong hiring, team-building, and leadership skills

Responsibilities

• Define and drive the technical strategy and architecture
• Remain hands-on in codebase while shipping core initiatives
• Build reliable integrations, data workflows, and AI agents
• Hire, develop, and lead an engineering team
• Partner with CEO and customers to shape product strategy
• Establish standards for reliability, security, and observability

Skills

Hands-on leadership

Product-minded leadership

AI/NLP systems

LLM-powered workflows

System architecture

Cloud architecture

Hiring & mentoring

Security & observability

Tools

LLM platforms

Observability tooling

CI/CD pipelines

Job description

52 Limited is partnering with an innovative, venture-backed hospitality technology startup to find a CTO to join its growing team in Williamsburg, Brooklyn.

Our client is building an AI-native software platform that helps independent hotels, resorts, and boutique properties grow revenue, streamline operations, and deliver exceptional guest experiences. Backed by leading venture capital investors and founded by experienced entrepreneurs, the company is bringing modern technology and digital marketing capabilities to an underserved segment of the hospitality industry.

We're looking for a CTO to own [client]’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 company’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.

Who You Are

• 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.

AI Systems Experience

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 context management
• Human-in-the-loop systems, permissions, guardrails, and failure recovery
• Observability, debugging, testing, and versioning for AI systems
• Managing the cost, latency, and reliability of nondeterministic systems
• Measuring the product and business impact of AI-powered workflows

Who may be a fit

We are open to both:

• Experienced CTOs, VPs of Engineering, or senior engineering leaders who want to return to a highly hands-on environment.
• Exceptional principal, staff, or founding engineers who have demonstrated company-level technical leadership and are ready to build and lead an engineering organization.

Regardless of title history, you should be comfortable moving fluidly between company strategy, architecture, customer conversations, hiring, debugging, and shipping production code.

Nice to have

• Vertical SaaS/AI experience
• Marketplace or workflow software experience
• Complex integrations and data systems
• Hospitality, travel, or adjacent industry experience
• Experience scaling engineering teams from the earliest stages

Location & Requirements:

This is a full-time, onsite opportunity based in Williamsburg, Brooklyn, with an expectation of working in the office 4–5 days per week. Candidates must be authorized to work in the United States.

About 52 Limited:

52 Limited is a creative and technology staffing agency connecting exceptional talent with innovative companies nationwide. We specialize in opportunities across design, technology, marketing, and creative disciplines.