Chief Technology Officer (CTO)

Time To Hire; United States; Hybrid; USD 250,000 - 420,000; Full time

Job summary

Time To Hire is seeking a hands-on Chief Technology Officer to lead the technical vision and architecture of an AI-native platform for the insurance industry. You will co-own the product roadmap with the founders and build the engineering organization from the ground up in a fast-growing startup environment.

You will work across technology, product, people, and customers, balancing architecture with hands-on coding as needed, and drive reliability, speed, and scalability across 100+ insurer

Qualifications

• 8+ years of software engineering experience with meaningful CTO/engineering leadership exposure.
• Experience in early-stage startups (seed through growth).
• Proven track record of building and scaling engineering teams.

Responsibilities

• Own the technical vision and architecture of the AI agent platform.
• Co-own the product roadmap with founders and translate customer problems into tech requirements.
• Lead and develop an engineering team towards high ownership and accountability.
• Define AI agent evaluation, monitoring, and reliability metrics for production.

Skills

CTO experience

Python

AI/LLM systems

Architecture

People leadership

Customer interaction

Tools

Python

Job description

Chief Technology Officer (CTO) San Francisco, CA / Mexico City

• Full-time

About the Company

We’re building an AI-native platform for the insurance industry, using AI agents to automate complex back-office workflows that traditionally require significant manual work. Our agents use Computer Use - AI that operates software the way a person would - to work directly inside 100+ insurer portals, executing workflows such as quoting, collections, reconciliation, and claims end to end. We’ve reduced quoting turnaround from 2-5 days to under 2 hours and help brokers increase operational capacity by up to 10x without proportional headcount growth. The company is backed by a16z and is building the infrastructure for the next generation of insurance operations.

The Role

We’re looking for a hands-on CTO to become the most senior technical leader and help take the company through its next stage of growth. This is not a strategy-only CTO role. You’ll sit at the intersection of technology, product, people, and customers. You’ll own the technical vision and architecture of the AI agent platform, co-own the product roadmap with the founders, and build the engineering organization from the ground up. The engineering team is currently 9 people, with plans to grow to approximately 15, within a company of ~26. We’re looking for someone who can move comfortably between architecture, code, product decisions, hiring, and customer conversations in the same week.

What You’ll Do - Technology & Architecture

• Own the technical vision and architecture across AI agents, Computer Use, LLM orchestration, RAG, backend systems, and cloud infrastructure.
• Make pragmatic architecture decisions balancing speed, reliability, scalability, and technical debt.
• Stay technically close to the product and codebase, contributing hands-on when needed.
• Design systems capable of operating reliably across 100+ third-party insurer portals.

Product & Strategy

• Co-own the product roadmap with the founders.
• Translate customer problems and insurance workflows into technical and product requirements.
• Help determine what the company should build, what it shouldn’t build, and where technology can create the greatest business impact.
• Balance short-term customer commitments with long-term platform durability.

Engineering Leadership

• Lead and develop a team of ~9 engineers, with plans to grow to ~15. Recruit exceptional engineers and technical leaders as the company scales.
• Build a high-performance engineering culture centered around ownership, speed, quality, and accountability.
• Mentor engineers and develop future technical and people leaders.
• Establish the processes and standards needed to scale without unnecessary bureaucracy.

AI & Reliability

• Define how AI agents are evaluated, monitored, and improved in production.
• Establish metrics around agent accuracy, reliability, latency, and failure recovery. Build evaluation, monitoring, and human-in-the-loop systems.
• Stay ahead of the agentic AI frontier and determine what is ready for production versus what is still experimental.

Customers & Business

• Act as a technical voice with enterprise customers, partners, and investors.
• Clearly communicate what the technology can and cannot do.
• Partner with founders and GTM on enterprise opportunities, pricing, positioning, and technical requirements.
• Translate customer feedback into product and technical decisions.

What We’re Looking

• For 8+ years of software engineering experience, with meaningful experience as a CTO, VP Engineering, Head of Engineering, or equivalent.
• Experience in early-stage startups, ideally seed through growth.
• Proven experience building and scaling engineering teams from a small base.
• Strong architecture and systems design experience.
• Hands-on experience with AI/LLM systems, including agents, RAG, orchestration, prompting, evaluation, or related technologies.
• Strong proficiency in Python.
• Experience making technical decisions in highly ambiguous, fast-moving environments.
• Strong product judgment and the ability to connect technical decisions to business outcomes.
• Experience working directly with founders and customers.
• Excellent communication skills across both technical and non-technical audiences.
• Strong judgment around what to build, what not to build, and when to compromise. A builder mentality with the ability to move between strategy and execution.

Nice to Have

• Experience with Computer Use, browser automation, or agentic AI frameworks.
• Experience building evaluation frameworks for AI agents.
• Background in insurance, fintech, insurtech, healthtech, or another regulated industry.
• Experience handling sensitive financial or customer data.
• Familiarity with SOC 2 and enterprise security reviews.
• Experience supporting enterprise sales or customer implementations.
• Experience scaling an engineering organization from ~5-10 people to 15+.

The Ideal Profile

You’re the kind of technical leader who can design the architecture in the morning, review code in the afternoon, interview an engineer, and jump on a customer call with the founders before the day is over. You’ve already experienced what it takes to build a startup from an early stage, and you know how to scale both the technology and the people around it. You don’t need to be coding 80% of the time - but you still know how to build.

You’re equally comfortable discussing: architecture, product roadmap, engineering culture, AI reliability, hiring, and customer requirements.

Location

San Francisco preferred, Mexico City also considered. If you’re a technical leader who still loves building and wants to shape both the technology and the organization from the ground up, we’d love to meet you.