Director of Engineering
9 days ago
Miami Beach
Job DescriptionJob Title: Director of Product Engineering (AI & Platform Transformation) Location: Hybrid (Onsite in Miami, 33139) Start Date: ASAP Employment Type: Full-time, Direct Hire Compensation: ~$180K Benefits: Health, Dental, Vision, 401(k), PTO Work Authorization: Must be authorized to work in the U.S. This position is not eligible for sponsorship . About the Role We're looking for a hands-on engineering leader to own a full-scale platform rearchitecture and AI transformation as we enter our next phase of product-led growth (PLG). This is not a maintenance role. You'll lead all of engineering, own system architecture end-to-end, and guide a transition from legacy systems into a modern, AI-enabled, microservices-based platform. You'll partner closely with the SVP of Product to make the organization AI-forward by design—from how we build software to how the product delivers value to customers. Why This Role Exists We are actively replatforming: • Moving from legacy technologies (including VB.NET) to modern .NET architecture, • Evolving toward a microservices-based system, • Own the end-to-end architecture of the platform, • Lead a full replatforming effort (legacy → modern .NET, monolith → microservices), • Make high-impact decisions on system design, scalability, and long-term technical direction, • Ensure the platform supports a self-serve, PLG-driven product experienceAI Transformation, • Define and execute an AI-forward engineering strategy, • Drive adoption of AI tools across the development lifecycle, • Explore and implement AI agents and workflows to improve engineering output and product capabilities, • Partner with Product to embed AI into the customer experience and core product flowsProduct & PLG Execution, • Partner with Product and UX to build and optimize self-service user journeys, • Ensure systems support subscription workflows, payments, onboarding, and conversion funnels, • Translate business goals into focused, high-impact engineering initiativesTeam Leadership & Execution, • Lead all engineering (onshore offshore teams), • Act as a player-coach—comfortable going deep technically when needed, • Improve offshore team effectiveness (scope clarity, delivery quality, feedback loops), • Build and scale a lean, high-performing teamTechnology & Spend Ownership, • Own decisions across cloud (Azure), tooling, and vendor ecosystem, • Evaluate and optimize engineering spend, • Balance speed, scalability, and cost with strong business judgmentWho You Are (Must-Haves), • 10–15 years in engineering, with experience at Director / Head / VP level, • Proven track record leading a major replatforming or system transformation, • Deep experience in Microsoft stack (Azure, .NET), including modernization from legacy systems (e.g., VB.NET → modern .NET), • Strong architecture expertise—you've owned and redesigned complex systems, • Experience building or evolving microservices-based architectures, • Hands-on experience with AI in engineering (e.g., AI-assisted development, AI agents, or similar transformation work), • Strong understanding of PLG models and self-service product design, • Experience building systems that support subscriptions, payments, and customer lifecycle workflows, • Experience leading multiple teams, including offshore teams, • Willingness and ability to remain hands-on during a transformation phaseIdeal Background, • Experience in subscription-based, SaaS, or e-commerce environments, • Background in smaller or growth-stage companies, • Experience working on CRM-like systems or customer lifecycle platforms, • Familiarity with mobile ecosystems (iOS/Android), especially modernization efforts (Objective-C/Java → Swift/Kotlin)This role is best suited for someone who has:, • Successfully led a platform transformation in a PLG company, • Applied that experience in a new domain or industry, • Combined deep architectural ownership hands-on execution, • Assess architecture, team, and current platform constraints, • Build trust with engineering (onshore offshore) and product leadership, • Define initial replatforming strategy and priorities, • Align with leadership on PLG roadmap AI strategy, • Deliver early wins in architecture, velocity, or cost efficiency, • Establish a clear 6-month transformation roadmap, • Show measurable progress in AI adoption and engineering outputHow We Work, • Small, highly autonomous team, • Focus on pragmatic, high-impact decisions, • Value clear thinking, strong writing, and consistent shipping, • Treat AI as a core competitive advantage, not an experiment