Director of Product Engineering (AI & Platform Transformation)

Location: Hybrid (Onsite in Tampa, FL 33626)
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.

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.

We are actively replatforming:

• Moving from legacy technologies (including VB.NET) to modern .NET architecture
• Evolving toward a microservices-based system
• Embedding AI-assisted development and AI-driven product capabilities across the stack

We need a leader who has done this before—not just managed teams, but personally driven architectural transformation in a PLG environment.

• 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 experience

• 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 flows

• 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 initiatives

• 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 team

• Own decisions across cloud (Azure), tooling, and vendor ecosystem
• Evaluate and optimize engineering spend
• Balance speed, scalability, and cost with strong business judgment

• 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 phase

• 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)

• 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
• Actively leveraged AI to change how teams build and ship software

Month 1

• Assess architecture, team, and current platform constraints
• Build trust with engineering (onshore offshore) and product leadership
• Identify highest-risk areas in the current system

Month 2

• Define initial replatforming strategy and priorities
• Align with leadership on PLG roadmap AI strategy
• Begin implementing improvements in team execution and tooling

Month 3

• Deliver early wins in architecture, velocity, or cost efficiency
• Establish a clear 6-month transformation roadmap
• Show measurable progress in AI adoption and engineering output

• 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