CTO — Settle

Settle is an AI-native enterprise data migration platform. We replace the manual schema mapping, transformation, and validation work consulting firms do by hand today.

Status: Paying mid-market customer in production. Active pipeline of enterprise and mid-market software companies in pilot. Pre-seed closing. Antler NYC residency.

From the founder

I spent 2.5 years at Deloitte watching Fortune 500 companies hire armies of consultants to do work that should take software hours. Enterprise data migration is one of the last great manual workflows — schema mismatches, transformation logic, and validation done by hand on every customer onboarding, M&A integration, and legacy system replacement.

We are building the AI-native version. The operating principle is simple: AI proposes, deterministic engines validate, humans approve. Correctness is the product. Eval rigor is the moat.

I am hiring the person who will own the technical side alongside me — CTO economics, CTO scope, full ownership of agent architecture and engineering culture from day one. Cash is below market through close, equity is generous, and I am transparent about what that trade means.

If you have shipped LLM systems in production, care about correctness more than novelty, and want to build the system that finally makes enterprise data migration work — let's talk.

What you will own

• AI agent architecture. Design and ship the agent loop, decomposition strategy, eval harness, and validation pipeline. This is the next 3–6 months and the centerpiece of the product.
• Engineering strategy. Technical direction, infrastructure decisions, architectural choices as we scale.
• Enterprise security and compliance. The technical face in customer security reviews. Drive SOC 2 Type II through the seed.
• Hiring and team building. Recruit and lead engineering from two to ten through Series A.
• Product and customer. Partner with me on roadmap. Talk directly to customers. Shape what we build.

This is not a role for someone who wants to write code in isolation. It is for someone who wants to build a company.

Stack

Next.js 14 App Router, TypeScript, Supabase / Postgres with RLS, Anthropic Claude API, Vercel.

Who you are

Must-have

• 5–12 years of engineering experience, with 3+ years shipping production systems used by paying customers
• Production LLM or agent system experience. Has built and deployed LLM-powered applications used by real customers. Knows prompt engineering, structured outputs, retries, evaluation, prompt regression testing. Non-negotiable.
• Strong backend and data fundamentals — Postgres at depth, schema design, SQL, async and queue patterns, idempotency
• TypeScript proficient. Next.js or Node ideal.

Strong preference

• Background in data engineering, integration, migration, or ETL — alumni from Snowflake, Databricks, Airbyte, dbt Labs, Fivetran, Hightouch, Census, Mulesoft, Workato, Informatica, or Talend will understand the problem viscerally
• Enterprise SaaS instincts — knows what SSO, RBAC, audit logs, and SOC 2 actually require
• Has built eval frameworks (Braintrust, Langfuse, Promptfoo, or homegrown). Phase 3 of our roadmap depends on this.
• Cloud-native production experience (AWS, GCP, Azure, or modern PaaS — Vercel, Supabase, Render, Fly.io)

Cultural fit

• Investigation-first — you read code before you change it
• Comfortable presenting in enterprise security reviews
• High agency. Decides and ships without direction.
• Direct communicator. Corporate-comms styles will not fit.
• Comfortable with startup pace. This is not a 9-to-5.

What we offer

• Title: CTO
• Equity: 5–10% common stock. 4-year vest, 1-year cliff. Range based on background and timing of join.
• Cash: $200K–$300K base. Range reflects timing of join and seed close. Ramp structure written into the offer.
• Optional structure: Portion of equity can be milestone-vested (Seed close, eval targets) for upside alignment.
• Location: NYC. In-person.