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.

Projects

Cocoon connects property intelligence, homeowner engagement and service fulfillment to help homeowners better maintain and protect their homes while enabling insurance carriers and other partners to move from identifying property risk to addressing and verifying risk mitigation.

To take the next step in growing our business, we are seeking an exceptional Principal Engineer who will inherit our fully functional platform. We are looking for someone who wants to become a long-term member of Cocoon's core team, participate meaningfully in the company's success.

You will understand that system deeply, determine what should be preserved, identify what should be improved and lead the evolution of the platform's technical foundation in line with product and business strategy.

Serving as Cocoon's primary internal technical authority and source of technical truth, you will own technical architecture and engineering decisions in alignment with the company's product and business priorities.

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