Job 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
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.
What You'll Own
Architecture & Platform Transformation
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
AI 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 flows
Product & 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 initiatives
Team 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 team
Technology & Spend Ownership
Own decisions across cloud (Azure), tooling, and vendor ecosystem
Evaluate and optimize engineering spend
Balance speed, scalability, and cost with strong business judgment
Who 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 phase
Ideal 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
Actively leveraged AI to change how teams build and ship software
First 90 Days
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
How 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