Building Products and Teams

Hunter Hillegas

CTO and product-engineering leader, currently open to new work

Availability

  • Full-time leadership roles: CTO, VP Engineering, Head of Product Engineering
  • Fractional or interim CTO engagements
  • Hands-on help shipping AI-powered features, experiments, and platforms

I help give product and engineering teams the technical footing they need to move faster. Sometimes that means tightening the parts of the system that slow everyone down. Often it means clearing the way for new ideas, experimentation, and AI-enabled workflows so the roadmap keeps shipping without chaos.

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

Get In Touch

Let’s work together
[email protected] LinkedIn @Hunter

What I’m Looking For

How I Plug In Quickly

Ideal teams

Product-focused SaaS and B2B companies and teams building pragmatic AI-assisted experiences, especially those who need a steady hand on product engineering.

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

How I help

  • Technical leadership that aligns roadmaps, rituals, and hiring with product goals.
  • Turning AI capabilities into practical copilots and assistants that keep teams moving faster.
  • Building experimentation platforms, real-time environments, and the data pipelines that feed them.
  • Coaching founders and product leaders through remote-team practices that keep velocity high.

Leadership Roles

Chief Technology Officer

Mountain Goat Software (2016–Present)

Lead the digital product, platform, and data strategy for a premier Scrum and agile training company. Translated course IP into software like Team Home, the MGS AI Toolkit, and experimentation tools that keep training experiences premium. Pair closely with the CEO and operations leads to align product-engineering hiring, rituals, and infrastructure decisions with the business roadmap.

Director of Technology

Foraker Labs (2011-2016)

Managed a product engineering team building web and native apps for Fortune 1000 clients and small business partners. Balanced discovery and delivery across mobile apps, custom SaaS builds, and modern Rails backends so launches shipped on schedule and on brand while the consultancy scaled responsibly.

Co-Founder

Liberation Media (1998-2010)

Liberation Media created custom web apps, primarily for music industry customers (musicians, record labels). In nearly 12 years operating, we built tools for bands helping to sell millions of records. I was the principal engineer responsible for architecting and building our products.

Recent Work

Projects & Case Studies

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 Retrieval-augmented generation, a technique for bringing enterprise content into an LLM session. agile coach, specialized story-splitting and backlog tools, and MCP integration Model Context Protocol, a common instruction set to integrate tools with AI. 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

Mountain Goat Software

Other Notable Projects

Long-running partnership driving digital transformation, experimentation, and operational tooling.

Experimentation & Training

  • Fully interactive Planning Poker experience for distributed estimation sessions.
  • Video training platform with playback, quizzes, and instructor analytics.

Platform & Identity

  • Custom SSO identity provider delivering unified login to more than 120,000 users.
  • AI-powered search platform blending semantic and traditional techniques for deeper 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 , 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.

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 My CV