AI Product Engineering

Hunter Hillegas

Developer experience and AI product engineering leader building revenue-critical systems.

What I’m About

I turn ambiguous product and business problems into shipped software.
I own the full path from product discovery and architecture to hands-on implementation.
I build with MCP, RAG, LLMs, tool calling, agents, Codex workflows, and ChatGPT app integrations.
I care about reliable delivery for revenue-critical systems.

Over my career, I’ve built production software across Rails, mobile, e-commerce, course delivery, SaaS, and developer-facing AI systems. Recent work spans AI agents, Model Context Protocol, retrieval-augmented generation, large language models, tool calling, ChatGPT app integrations, React, SwiftUI, AWS, Docker, analytics, and production AI adoption.

Fun fact: I was the 903rd user to sign up for Twitter.

Get In Touch

Let’s work together

[email protected] GitHub LinkedIn @Hunter

What I’m Looking For

How I Plug In Quickly

Ideal teams

Product-focused SaaS, B2B, developer-experience, and AI teams that need a steady hands-on technology owner for ambiguous, revenue-critical work.

Currently based in Santa Barbara, CA, and partnering remotely across US-friendly time zones.

How I Can help

Technical leadership that turns product roadmaps into durable shipped systems.
Customer-facing AI coaching, search, summarization, and source-review workflows.
Revenue-critical Rails, mobile, e-commerce, SSO, course-delivery, analytics, and AWS/Docker platforms.

Leadership Roles

Chief Technology Officer

Mountain Goat Software (2016–Present)

Own technology strategy and hands-on implementation for a highly online training business where nearly all revenue depends on reliable digital systems. Built and maintain revenue-critical platforms across marketing, e-commerce, fulfillment, SSO, course delivery, internal systems, and AWS/Docker infrastructure. Built AI coaching and internal automation tools with RAG, MCP, tool calling, and agentic workflows for analytics, advertising, sales-call analysis, and operational support.

Co-Founder

EZ Golf League (2015-Present)

Co-founded a Rails and mobile golf league management platform serving thousands of players, captains, and league operators. Own the full technical surface across Rails, iOS, Android, hosting, APIs, scoring logic, DevOps, and customer-facing product workflows.

Director of Technology

Foraker Labs (2011-2016)

Led technology for a product consultancy building Rails backends, custom SaaS systems, iOS apps, and mobile/web products. Managed a product engineering team delivering software for Fortune 1000 clients and fast-moving small businesses.

Co-Founder

Liberation Media (1998-2010)

Co-founded a web product studio serving music-industry clients, building custom applications that helped bands sell millions of records. Served as principal engineer for product architecture, delivery practices, client communication, and durable web systems.

Recent Work

Projects & Case Studies

Enzo Reader for ChatGPT

Your RSS feeds, newsletters, and saved articles inside ChatGPT

Problem

RSS readers and newsletters hold high-signal material, but the workflow often lives outside the AI tools people use for research, recall, and synthesis.

Solution

Launched Enzo Reader for ChatGPT to connect Feedbin or NewsBlur, sync articles and tags, search with AI-powered recall, and ask ChatGPT for unread lists, summaries, or in-depth source reviews. Feed credentials stay encrypted and are never sent to any model.

Tech Stack

ChatGPT RSS Feedbin NewsBlur AI summaries Embeddings

OpenClaw Chief of Staff

Doing some of everything: Google Ads, analytics, competitive research and more

Problem

A small team wants to leverage AI to the max and get help with time-consuming and repetitive tasks.

Solution

Used OpenClaw to setup connectors to over 25 systems for gathering data, running ads, marketing tasks, system analytics, sales call analysis and more. Accessible via Slack, it's usable by the whole team when they need it. Massive team impact - these tasks are now done proactively and queryable at any time, from any device.

Tech Stack

OpenClaw OpenAI Codex MCP

AI-Powered Web Page Builder

Accelerating marketing while staying on-brand

Problem

Ability to move fast to create on-brand marketing and landing pages for an established product website.

Solution

Created an AI-powered tool that could analyze existing pages for style and structure and then apply that analysis to create new pages, with or without pre-existing copy. Reduced new page creation time from 2 weeks to 1 day, enabling a much higher rate of experimentation.

Tech Stack

OpenAI GPT-5 MCP Tool Calling Tailwind Rails AWS Postgres RDS

MGS AI Toolkit

Always-on coaching for training alumni

Problem

Mountain Goat Software training customers wanted access to 24x7 post-course resources to practice new skills and get answers to real-world questions without adding load to their training staff.

Solution

Built an AI toolkit with a RAG-powered agile coach, specialized story-splitting and backlog tools, and MCP integration so teams can use the experience inside their preferred chatbots. Achieved high user retention and moved from concept to beta in about 3 weeks.

Tech Stack

OpenAI GPT-5 MCP Pinecone Rails AWS Postgres RDS

Team Home Real-Time Learning System

Immersive live-online training at global scale

Problem

When COVID-19 hit, Mountain Goat Software needed to shift from in-person instruction to online training effectively overnight and needed a learning platform with custom exercises and simultaneous cohorts around the world.

Solution

We created Team Home, a suite of 75+ collaborative exercises with instructor dashboards to monitor progress and facilitate breakdowns. It has served thousands of learners and received rave reviews.

Tech Stack

Vue WebSockets Rails AWS

Other Notable Projects

Experimentation & Training

Fully interactive, real-time Planning Poker system for distributed software estimation sessions.
Video training platform with playback, AI-powered coaching, quizzes, and instructor analytics.

Platform & Identity

Custom SSO identity provider delivering unified login to more than 130,000 users.
AI-powered search platform blending semantic and traditional techniques for deeper, more personalized results.

Commerce & Data

Migration of a multimillion-dollar e-commerce business to a headless Shopify architecture.
Data warehousing and analytics stack combining a custom Rails/Postgres ETL, Mixpanel, Amplitude, and modern BI tooling.

Products

iOS, iPadOS, and visionOS Apps

I have been building native apps since the earliest App Store days, and that experience still informs how I evaluate product-engineering tradeoffs for today’s Web and AI platforms. The focus now is leadership and modern product systems, with native expertise serving as added proof that I ship real things.

Launched (2008) and re-imagined 1M+ download travel app VegasMate for iOS, iPadOS, watchOS, and visionOS.

Migrated from Objective-C to Swift (UIKit) and ultimately to SwiftUI.
Built the Rails backend and iOS app for EZ Golf League , delivering full league management plus Stripe-powered subscriptions.
Launched Enzo Reader for ChatGPT to bring RSS feeds, newsletters, Feedbin, and NewsBlur into ChatGPT for unread lists, summaries, search, and deeper reading.
Launched Enzo Reader , a visionOS RSS experience tailored for immersive reading.

Contact

Ready when you are

I’m open to full-time roles, fractional CTO work, and targeted engagements to ship AI-powered features or modernize product-engineering systems. Send a quick note that covers your company stage, what you need to ship in the next 6–12 months, and where you need the most help.

[email protected] LinkedIn X (Twitter) @Hunter

What to include

Your company stage or revenue profile.
The product or platform you need to ship in the next 6–12 months.
Where you need the most help: leadership coverage, AI delivery, system modernization, or all of the above.

Request CV