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    25madison

    Venture Capital

    Founding Technical Leader (CTO/Founding Engineer), NewCo

    Any, United StatesOn-SiteFull-timePosted 1mo ago
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    Job description

    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

    Job details are sourced from the employer's original posting.

    Open job posting
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    About the company

    25madison

    25madison is a company builder that partners with entrepreneurs to launch and scale transformative businesses.

    View all 25madison jobs
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