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