Elayne helps families organize their assets, estate documents, and key contacts in one place, then guides them through life transitions as circumstances and priorities evolve. Like getting married, moving, having a baby, or losing a parent. Unlike traditional wealth management tools or online estate platforms that produce static legal documents, Elayne is dynamic, intelligent, and built not just to delight, but to comfort and guide you when it matters most.

I started Elayne after my mom passed away and I had to settle her estate, accounts, and affairs - essentially, I suddenly had to untangle all the details of her life. It was shocking how fragmented and opaque the process was and how I spent hundreds of hours chasing documents, coordinating accounts, filling legal gaps, and navigating unfamiliar systems, all while grieving and working full time. It shouldn’t be that way.

In the future, you could hire an attorney, download DIY legal forms, fax and mail physical documents, sync 10 different fintech apps, use a financial planner, spend thousands in fees, and hope it all holds together. Or, you could just use Elayne.

Backed by major investors like Y Combinator and Accel, we are now a 6 person team based in NYC.

About the Role:

Elayne is an Applied AI company reimagining how families organize, protect, and transfer their estates, from financial accounts and legal documents to digital assets and end-of-life wishes. We combine structured data, custom AI agents, and guided UX to make estate optimization and post-loss settlement fast, clear, and dignified.

We integrate with banks, insurance providers, legal systems, and data aggregators to create a real-time, intelligent view of an individual or family’s estate. Then we proactively adapt to life events (like having a child or losing a parent), and automate complex legal-financial workflows that typically take families years to finish.

We’re an Accel and YC-backed seed stage company, launched last year and we’re operating in a manual $260B TAM, with over $80T in assets expected to transfer in the coming decades. This is a greenfield market for AI, and we intend to define the category.

Your Mission:

As our Head of Engineering / CTO, you’ll own the architecture and execution of Elayne’s AI platform, spanning data ingestion, LLM-driven agents, and high-trust infrastructure. You'll move fast with the founding team to ship scalable, production-grade systems in a deeply complex and emotionally important domain.

You’ll lead technical strategy, scale the team, and be hands-on across system design, model integration, and rapid iteration. Your work will touch every surface area: product intelligence, retrieval, automation, and performance.

Most critically, your impact will be foundational. You’ll drive product evolution, enable customer success, and accelerate our path to becoming the trusted platform in this massive, untapped market.

What We’re Looking For:

• Builder’s mindset: you move fast, take full ownership, and are obsessed with solving real problems
• 8+ years of engineering experience: of which 2+ in technical leadership (Head of Eng, CTO, Staff+). If you come in as Head of Engineering, goal is for you to grow to CTO 
• Deep technical fluency in LLM workflows, backend systems, and AI infrastructure
• Strong experience with production AI systems: agents, RAG, prompt tuning, evaluation frameworks
• Skilled in building scalable full-stack solutions using TypeScript, NestJS, PostgreSQL, AWS and modern data tools.
• Thrive in ambiguity, urgency, and rapid iteration - ideally you’ve been part of a high intensity seed stage startup before (we work long hours, but have a lot of fun together)
• Based in NYC and excited to work in-person at our NoMad HQ

What You’ll Do:

• Lead and scale a world-class engineering team: recruiting, mentoring, and building the systems that drive excellence and growth
• Own technical strategy and execution: from infra and architecture to AI systems, model eval, and product performance 
• Design and scale production-grade AI features:
  • Architect and optimize RAG pipelines, LLM tool-use, and multi-step agent workflows
  • Implement memory/state strategies for long-lived agent sessions
  • Build LLM flows using LangChain or custom-built frameworks.
  • Integrate vector stores, embedding pipelines, and external APIs
• Lead prompt and model optimization efforts:
  • Build and test modular prompt frameworks
  • Drive model selection (OpenAI, Anthropic, OSS) and evaluation
  • Track latency, quality, hallucinations, and cost across use cases
• Own ML/AI infra and observability:
  • Deploy models across scalable infrastructure (AWS, serverless, GPU-optimized)
  • Define supervised feedback loops and retraining strategies
  • Monitor hallucination, trust, and LLM safety metrics

Current stack: React, TypeScript, NestJS, PostgreSQL, Redis, AWS, OpenAI, Auth0. Always iterating; stack decisions are grounded in performance, reliability, and developer velocity

We’ll be a great fit if you’re looking for:

• A rare chance to build an iconic company with actual human impact; not just another AI CRM or dev tool
• Full ownership of technical roadmap, team member development, culture, and growth
• YC, Accel, and mission-aligned investors backing a product with massive, untapped demand

Compensation:

Salary range $220k–$350k, depending on experience and qualifications

Meaningful equity package is included; final composition will be determined by level, scope, relevant experience, and cash vs equity preference. Benefits/PTO included. 

Additional detail.