Founding Technical Leader: Head of Engineering / CTO Company: Newco (Stealth)
Role: Head of Engineering / Founding Engineer (Full-Time)
Location: Flexible (US, preference for NYC)
Stage: Pre-seed (Venture Studio backed)
Comp: Significant equity + competitive cash
Who We Are
Commerce is undergoing a fundamental shift. For the past decade, ecommerce has been built around static pages, manual optimization, and fragmented tooling: from analytics to experimentation to personalization.
Newco is building the AI-native intelligence layer for DTC commerce. Our platform interprets shopper behavior from the moment of ad click, scores intent in real time, and dynamically personalizes the on-site experience without requiring brands to rebuild their infrastructure. Every interaction compounds: the system learns, adapts, and improves outcomes continuously.
The result: higher conversion, stronger retention, and a lasting edge for brands competing in a signal-scarce, AI-native world.
What You'll Do
- Define system architecture from first principles and own it end-to-end
- Build the initial product hands-on (this is a 0 to 1 role)
- Design and scale the decisioning and personalization engine across data, infra, and product layers
- Work directly with the founder on product direction and technical strategy
- Hire and lead the early engineering team as the company grows
- Communicate technical tradeoffs and system design to non-technical stakeholders in outcome-oriented terms
Who You Are
- A builder-leader at the intersection of AI, product, and real-time systems
- Experienced in high-stakes, fast-moving environments: vertical SaaS, applied ML, or personalization/recommendation systems
- Comfortable working across backend, frontend, and product, not siloed
- Strong product intuition alongside technical execution
- Thrives in ambiguity and early-stage building
Key Technical Responsibilities
- Decisioning and Personalization Architecture Design and scale the real-time scoring and routing engine: interpreting incomplete behavioral signals, making decisions under uncertainty, and serving personalized experiences with low latency.
- LLM and Agentic Systems Build and maintain AI agent layers using frameworks like LangGraph or PydanticAI, including modular reasoning pipelines (RAG, ReAct, planner-executor) for CRO automation and content decisioning.
- Data Infrastructure Integrate event-driven pipelines, vector databases (pgvector, Pinecone), and structured data stores to support real-time retrieval, persistent memory, and behavioral pattern recognition.
- Evaluation and Observability Build tools for trace inspection, confidence scoring, and output validation. Develop evaluation loops and test harnesses to ensure reliability and consistency across decisioning outputs.
- Engineering Architecture and Delivery Define technical standards, development processes, and system architecture to support a scalable, maintainable product. Partner with product leadership to translate strategy into roadmap.
Core Skills
- 5 to 7+ years of full-stack engineering experience
- Experience building real-time systems, data pipelines, or decisioning / recommendation engines
- Familiarity with LLM agent development and frameworks (LangGraph, PydanticAI, or similar)
- Production-level experience with FastAPI, Docker, and cloud-native deployment
- Comfort with vector databases and retrieval-augmented generation patterns
- Proficiency in agentic IDEs (Cursor, Windsurf, Claude Code)
Bonus (not required)
- Experience in ecommerce, marketplaces, or personalization platforms
- Familiarity with event-driven or streaming architectures (Kafka, Kinesis)
- Shopify ecosystem knowledge
What This Is Not
- Not a pure infrastructure or platform role
- Not a maintenance or scaling role
- Not joining a large existing team
You will be building the foundation.
Why Join
- Significant equity + competitive cash
- True technical ownership: define the system architecture from day one
- Backed environment: venture studio with capital, operational support, and design partners already in market
- 0 to 1 opportunity: build a company, not just write code
Skills Required
- Experience with real-time systems, data pipelines, or decisioning systems
- Comfortable working across backend, frontend, and product
- Strong product intuition
What We Do
25madison is a New York City-based venture platform that incubates and invests in technology-enabled businesses, partnering with entrepreneurs to build companies from the ground up.
