Principal E-Commerce Engineer

Happy Health is revolutionizing sleep medicine delivery through their comprehensive telehealth platform. The Principal E-Commerce Engineer will have direct ownership of the architecture, implementation, and operation of customer-facing eCommerce systems, ensuring seamless and reliable purchasing experiences.

Responsibilities:

• Architect, build, operate, maintain, and evolve our eCommerce stack centered on Shopify and related systems to support customer-facing storefront experiences and internal operational workflows
• Lead the design, implementation, and ongoing operation of integrations, services, and workflows that support the full commerce lifecycle, including product catalog, checkout, payments, subscriptions, order management, fulfillment, refunds, and post-purchase experiences
• Establish and guide eCommerce engineering best practices across system design, observability, reliability, performance, maintainability, and security
• Provide hands-on technical leadership to other team members, contractors, and partners building on and supporting these systems
• Drive architectural decisions and cross-functional technical alignment across software, mobile, eCommerce, operations, DTC marketing, and partner-facing systems
• Help ensure security, compliance, and best practices are maintained across commerce systems and payment workflows, including integrations involving customer accounts, transaction processing, and downstream operational systems
• Own and help evolve the technical implementation and ongoing operation of attribution, analytics instrumentation, conversion tracking, and related data flows across the commerce funnel
• Partner with DTC marketing and related stakeholders to ensure landing pages, campaign tracking, event instrumentation, and attribution inputs are implemented reliably, maintained over time, and support accurate measurement of funnel and channel performance
• Monitor and improve the observability, reliability, and performance of commerce, payment, attribution, and analytics workflows in production, and proactively identify and resolve operational issues, platform gaps, and data integrity issues
• Identify technical risks, scalability bottlenecks, platform gaps, and analytics or attribution reliability issues early, and proactively drive solutions that support near-term commercial growth and long-term platform needs

Requirements:

• 8+ years of software engineering experience, with meaningful depth in ecommerce systems
• Significant hands-on experience with Shopify, including custom storefront development, APIs, app integrations, and platform limitations
• Strong experience with Stripe and production-grade payment processing systems
• Deep understanding of ecommerce architecture, including checkout flows, order lifecycle, refunds, subscriptions, discounts, taxes, and transaction edge cases
• Experience implementing, maintaining, and operating analytics instrumentation, attribution systems, event tracking, or related marketing technology integrations in production eCommerce environments
• Strong experience designing and operating reliable, scalable production systems
• Experience with modern web application architecture and performance optimization for conversion-sensitive customer experiences
• Experience integrating ecommerce platforms with third-party systems such as ERP, OMS, WMS, CRM, analytics, support, or marketing systems
• Demonstrated ability to lead major technical decisions across systems, services, and teams
• Strong communication skills and ability to work cross-functionally with both technical and non-technical stakeholders
• Proven ability to operate autonomously and set technical direction while remaining hands-on
• Experience with Shopify Plus
• Experience in high-growth direct-to-consumer or consumer health ecommerce environments
• Experience with subscription commerce and recurring billing models
• Experience with managing and simplifying diverse multi-vendor API integrations
• Experience with headless commerce architectures and evaluation of when they are or are not appropriate
• Experience with multi-store, multi-brand, or international ecommerce implementations
• Experience designing event-driven or asynchronous workflows for ecommerce operations
• Experience working in regulated, high-trust, or operationally complex environments
• Experience mentoring senior engineers and influencing engineering standards without direct people management responsibility