Principal Engineer

What We Are Looking For

Exceptional Backend Engineering & Architectural Judgment — 8+ years of professional backend engineering experience at a Senior/Staff/Principal/Architect level, with exceptional hands-on development capability and significant production Java experience. Experience with Spring Boot, Spring Security and Hibernate/JPA strongly preferred.

Deep Relational Data Architecture Expertise — Proven ownership of complex production relational data models at real scale.

Strong System Design & API Architecture Capability — Demonstrated ability to design sophisticated production systems and REST APIs, understand distributed-system tradeoffs, with real experience improving an already-established codebase, not only building greenfield. Strong PostgreSQL experience (Cocoon currently uses Aurora PostgreSQL).

AI-Native Engineering Capability— Demonstrated ability to use modern AI-assisted development tools to materially improve engineering productivity and quality, while applying the technical judgment needed to critically evaluate AI-generated work.

Production Engineering Discipline — Strong understanding of application security, automated testing, observability, reliability, performance and maintainability. Builds systems designed to operate reliably in production, not simply function in development.

Technical Leadership & Independent Judgment — Experience directing senior engineers and serving as a trusted technical authority. Comfortable making consequential decisions with incomplete information, surfacing risks early, challenging assumptions, and recommending a clear path forward.

Production Applied-AI Experience (Highly Preferred) — Meaningful hands-on experience implementing and operating production AI, LLM, agentic, multimodal, or computer-vision capabilities, including architecture, evaluation, retrieval, reliability, and production operations

Strong Cloud & Production Infrastructure Fluency — Experience with AWS-hosted production systems (EC2, S3, RDS/Aurora, IAM, VPC networking), containers, CI/CD and modern cloud deployment architecture.

How You Work

Owner's Mindset, Professional Maturity & Communication

• Operates like an owner, not a ticket-taker.
• Takes responsibility for outcomes, moves quickly without sacrificing quality, disagrees productively, communicates clearly, and credibly represents Cocoon with technical and nontechnical stakeholders.

Genuine Engineering Craft

• Still loves building software and is comfortable operating without a large engineering organization around them.

Thrives in a Startup Environment

• Acts independently while collaborating effectively within a small team. Knows how to get things done and works quickly without requiring a high degree of oversight.

Core Responsibilities

Technical Architecture & Leadership

• Serve as Cocoon's primary internal authority on backend architecture, data architecture, system design and engineering quality.
• Own technical architecture and engineering decisions.
• Spearhead Cocoon's efforts to integrate AI-driven capabilities into its products, platform and engineering workflows.

Hands-On Backend Engineering

• Remain deeply hands-on in Cocoon's codebase and personally develop production software.
• Enter an established codebase, understand it quickly and determine what should be retained, refactored or replaced.
• Help shape product ideas and requirements alongside Cocoon team members before specifications are finalized.

Data Architecture

• Lead evolution of Cocoon's existing data architecture into a sophisticated relational domain model.
• Define schemas, relationships, data-access patterns and integrity standards.
• Develop safe migration strategies for evolving an active production database.
• Account for both structured and unstructured information as Cocoon's AI capabilities expand.
• Build a data foundation capable of supporting substantially greater intelligence, automation and scale over time.

AI-Native Engineering

• Be AI-native in how you work, actively using AI development tools to improve engineering speed and quality.

Infrastructure & DevOps Oversight

• Ensure infrastructure decisions remain aligned with Cocoon's application architecture.
• Maintain appropriate visibility into security, reliability, deployment architecture, performance & cost.
• Provide technical direction and oversight to Cocoon's outsourced AWS/DevOps engineer.

Enterprise & Partner Technical Leadership

• As required, represent Cocoon in technical discussions with insurance carriers, technology partners and other external stakeholders.

Why Join Cocoon

• Meaningful equity options and participation in the company's long-term success
• Direct working relationship with Cocoon's Founder & CEO
• Genuine ownership of Cocoon's technical architecture and engineering direction
• Opportunity to remain deeply hands-on while operating at the highest technical level in the company
• Small, senior team with substantial individual autonomy and impact
• Fully remote working environment
• Opportunity to shape how AI is embedded into both Cocoon's products and engineering organization

Compensation: Competitive compensation + equity options