Director of Product Engineering (AI & Platform Transformation)

Director of Product Engineering (AI & Platform Transformation)Location: Hybrid (Onsite in Miami, FL 33139) Start Date: ASAP Employment Type: Full-time, Direct Hire Compensation: $180-225K 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 RoleWe'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 ExistsWe are actively replatforming:Moving from legacy technologies (including VB.NET) to modern .NET architectureEvolving toward a microservices-based systemEmbedding AI-assisted development and AI-driven product capabilities across the stackWe need a leader who has done this before not just managed teams, but personally driven architectural transformation in a PLG environment.What You'll OwnArchitecture & Platform TransformationOwn the end-to-end architecture of the platformLead a full replatforming effort (legacy ? modern.NET, monolith ? microservices)Make high-impact decisions on system design, scalability, and long-term technical directionEnsure the platform supports a self-serve, PLG-driven product experienceAI TransformationDefine and execute an AI-forward engineering strategyDrive adoption of AI tools across the development lifecycleExplore and implement AI agents and workflows to improve engineering output and product capabilitiesPartner with Product to embed AI into the customer experience and core product flowsProduct & PLG ExecutionPartner with Product and UX to build and optimize self-service user journeysEnsure systems support subscription workflows, payments, onboarding, and conversion funnelsTranslate business goals into focused, high-impact engineering initiativesTeam Leadership & ExecutionLead all engineering (onshore offshore teams)Act as a player-coach comfortable going deep technically when neededImprove offshore team effectiveness (scope clarity, delivery quality, feedback loops)Build and scale a lean, high-performing teamTechnology & Spend OwnershipOwn decisions across cloud (Azure), tooling, and vendor ecosystemEvaluate and optimize engineering spendBalance speed, scalability, and cost with strong business judgmentWho You Are (Must-Haves)1015 years in engineering, with experience at Director / Head / VP levelProven track record leading a major replatforming or system transformationDeep 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 systemsExperience building or evolving microservices-based architecturesHands-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 designExperience building systems that support subscriptions, payments, and customer lifecycle workflowsExperience leading multiple teams, including offshore teamsWillingness and ability to remain hands-on during a transformation phaseIdeal BackgroundExperience in subscription-based, SaaS, or e-commerce environmentsBackground in smaller or growth-stage companiesExperience working on CRM-like systems or customer lifecycle platformsFamiliarity 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 companyApplied that experience in a new domain or industryCombined deep architectural ownership hands-on executionActively leveraged AI to change how teams build and ship softwareFirst 90 DaysMonth 1Assess architecture, team, and current platform constraintsBuild trust with engineering (onshore offshore) and product leadershipIdentify highest-risk areas in the current systemMonth 2Define initial replatforming strategy and prioritiesAlign with leadership on PLG roadmap AI strategyBegin implementing improvements in team execution and toolingMonth 3Deliver early wins in architecture, velocity, or cost efficiencyEstablish a clear 6-month transformation roadmapShow measurable progress in AI adoption and engineering outputHow We WorkSmall, highly autonomous teamFocus on pragmatic, high-impact decisionsValue clear thinking, strong writing, and consistent shippingTreat AI as a core competitive advantage, not an experiment