Job Summary

Director of Engineering, Digital Platform Engineering

Lead the Transformation to AI-Native Engineering

We are seeking a visionary Director of Engineering to lead the evolution of our Digital Platform Engineering organization and redefine how software is built, delivered, and scaled in the AI era.

In this executive leadership role, you will drive the architecture and platform strategy behind our digital experiences while advancing an AI-enabled Software Development Lifecycle (AI-SDLC). You will champion multi-agent AI architectures, platform engineering excellence, and AI-native development practices that accelerate innovation, enhance developer productivity, and elevate delivery quality at scale.

This is a rare opportunity to shape enterprise-wide engineering transformation, build high-performing teams, and establish the foundation for the next generation of digital innovation.

Ready to lead the future of AI-native engineering? We'd love to connect. Apply today or reach out for a confidential conversation.

Director of Engineering, Digital Platform Engineering

About the Role

We are seeking a visionary Director of Engineering to fundamentally transform our Digital Engineering organization into an AI-native powerhouse. Sitting at the helm of our digital platform and software engineering teams, you will drive the architectural, solutioning and operational evolution of our core digital domains.

Your mandate is twofold. First, you will architect the the multi-agentic system architectures, harnesses, context layers, and platform engineering that transform our front-end digital experiences. Second, you will lead an internal evolution toward an AI-SDLC, equipping our software engineering & development teams with the AI-native tools and workflows required to exponentially increase developer experience (DevEx), delivery quality, and efficiency.

Key Responsibilities

Platform Engineering & Architecture

● Architect Platform: Direct the engineering teams responsible for the underlying platforms powering web engagement, Loyalty & retention systems, and CRM integrations, modernizing the cloud-native stack to adapt dynamically to changing conditions and execute tasks autonomously.

● Modernize Platform & Integrations: Design and deploy dedicated gateways to route, rate-limit, and secure digital traffic, ensuring highly available connections to backend models, agents and tools.

● Drive Multi-Agentic Architectures: Architect scalable multi-agent frameworks that natively orchestrate complex, multi-step customer journeys directly within the application layer.

● Establish repeatable Practices: Implement automated, policy-as-code guidelines across the platform to ensure all customer-facing AI features adhere to strict latency, security, data privacy, and brand-safety standards before reaching production.

Applied Context Engineering & The "Last Mile"

● Pioneer Context & Harness Engineering: Build the connective tissue (the harness) that dynamically retrieves, formats, and securely routes real-time context from our CRM, Loyalty, and web engagement to LLMs, guaranteeing highly personalized and grounded customer interactions.

● Embed acceleration in the Customer Journey: Engineer the application layer to deliver conversational commerce, intelligent product discovery, and dynamic personalization capabilities across all digital touchpoints.

● Align to Digital KPIs: Partner directly with digital product management to ensure all platform capabilities measurably drive E-commerce conversion, Loyalty program engagement, and CRM retention metrics.

AI-SDLC & Software Engineering Transformation

● Drive AI-Native Engineering: Lead the transition to an AI-SDLC; roll out AI-assisted coding tools, automated workflows, and AI-driven testing across the digital engineering organization to fundamentally change how we build software.

● Define Engineering Effectiveness: Measure and improve engineering velocity and platform reliability through DORA metrics, DevEx indicators, and operational transparency.

● Provide "Golden Paths": Unify the digital tech stack into a governed, self-service developer portal, giving software engineers paved roads to experiment with and deploy AI features safely, securely, and within budget.

Strategic Boundary Management

● Consume Core AI & Data Services: Act as the primary consumer and strategic partner to the Enterprise AI & Data organization. While they build the foundational data lakes and enterprise AI, digital platform orchestrates, builds the harness, securely routes, and applies those to the customer experience.

Qualifications & Technical Expertise

Experience

● 10+ years of progressive technology leadership experience, with a deep background in distributed systems, global API management, and high-traffic E-commerce architectures.

● 5+ years managing teams focused on platform engineering, SDLC automation, and full-stack software development.

● Proven track record of driving enterprise-scale technology transformations and successfully partnering with centralized Data or AI organizations in a matrixed environment.

Technical Skills

● Platform & API Ecosystem: Deep expertise in enterprise API management platforms, LLM gateways, internal developer portals, and cloud-native infrastructure (Kubernetes, serverless patterns).

● Digital Architecture: Strong hands-on architectural understanding of AI harness design, multi-agentic system architectures, enterprise context engineering, and RAG patterns.

● DevEx & Governance: Fluency with agentic-SDLC implementations, policy-as-code frameworks, CI/CD orchestration, and enterprise observability platforms to guarantee uptime for revenue-generating digital channels.

Core Competencies

● A profound product-engineering mindset; you view robust platform architecture as a direct lever for driving digital revenue, customer conversion, and loyalty.

● Exceptional executive communication skills, capable of translating complex multi-agent architectures and platform capabilities into tangible business value for non-technical stakeholders.

● Unrelenting focus on developer experience, identifying and eliminating friction in the software engineering process through AI and automation.

What Success Looks Like in Year One

1. AI-Native Engineering Culture: Engineering teams consistently deliver secure, reliable software faster, utilizing agentic-SDLC workflows to measurably improve DORA metrics and DevEx.

2. Architecture Enablement: Deployed a highly resilient AI harness, LLM gateway, and developer platform that allows E-commerce and CRM product teams to rapidly build and productionize applied AI features autonomously.

3. Revenue-Driving Personalization: Powered the launch of high-visibility, AI-driven features across E-commerce and Loyalty channels that measurably improve customer engagement, retention, and conversion rates.

4. Seamless Organizational Synergy: Established a highly functional operating rhythm, characterized by clear API contracts, shared SLAs, and zero duplicated engineering efforts.

NOTE: This position is eligible for hybrid working arrangements (requires on-site work from an Insulet office). #LI-Hybrid

Additional Information:

Compensation & Benefits: For U.S.-based positions only, the annual base salary range for this role is $205,800.00 - $308,700.00 This position may also be eligible for incentive compensation. We offer a comprehensive benefits package, including: • Medical, dental, and vision insurance • 401(k) with company match • Paid time off (PTO) • And additional employee wellness programs Application Details: This job posting will remain open until the position is filled. To apply, please visit the Insulet Careers site and submit your application online. Actual pay depends on skills, experience, and education.