Career highlights

Portfolio

The below include career highlights from past companies. They also include insights and learnings and other take-aways that cannot be gleaned from my resume.

Note, the companies are listed in reverse-chronological order from date of employment.

Lium AI

Oct 2025 – present CTO & Founding Engineer

lium.ai

Lium does real data work by conversation. It connects to whatever a team already has — databases, files, APIs, instruments, internal tools — indexes and profiles what it finds, then reasons across all of it at once: writing code, building reusable tools, blending sources, and returning an answer in plain language.

The interesting problems are the ones that never show up in a demo: bespoke formats, genuinely messy data, and terabyte scale. That is the work — geospatial and satellite imagery, energy, space, infrastructure monitoring, subsurface and geology, and scientific research.

As CTO and founding engineer I own both the architecture and the build: the integration layer that makes strange data legible, the agentic loop that writes and runs code against it, and the on-demand compute that provisions itself for heavy jobs so nobody has to think about infrastructure. Analyses and tools are saved as artifacts, so a team compounds its own work instead of redoing it.

Monster Orange, LLC

Current Founder & Owner

monsterorange.com

Monster Orange is the practice I run in my own name: technical advising for founders and executives, and the products I build myself. Engagements run from pre-raise through Series-raise and beyond, usually alongside a CEO and a head of engineering or product.

It is also where Wayfinder lives — a local-first retirement and life-scenario planner with a deterministic engine, a desktop app, and an MCP server so an AI agent can reason over a plan directly.

ShiftHealth AI

CTO Feb 2024 – Jun 2025 · advising since Technology Advisor · formerly CTO & Co-founder

AI-powered coach focused on helping people improve themselves through applied cognitive behavioral therapy leveraging LLM and agentic workflow to produce complex, conditional logic. Additionally, create digital fingerprint of consumer behavior to personalize and enhance AI coaching.

As CTO and founding engineer I singularly developed the entirety of both the mobile consumer experience (iOS/Android leveraging Flutter) and the back-end (Ruby on Rails, API, Postgres, redis) inclusive of administrative functionality (multi-tenant, fully localized, OAuth2). Setup of SDLC including CI/CD, automated testing (90% code coverage), monitoring, alerting.

I handed off the CTO role in June 2025 and continue as technology advisor.

Shift App

Our direct-to-consumer branded app for iOS (Android coming soon) that is purpose-built for everyone’s needs.

  • Delivers 24/7 in-the-moment coaching with empathetic support and actionable guidance
  • Guides users through structured, multi-week programs across nutrition, sleep, mental health, and more
  • Provides weekly check-ins to reinforce progress, identify blind spots, and drive lasting behavior change
  • Offers hyper-personalized daily tips based on individual patterns and coaching history
  • Enables life transformation by tracking micro-shifts and connecting effort to measurable outcomes

The Six App

A branded app for both iOS and Android that addresses the needs of first-responders. The Six has 48k+ hours working with first responders and veterans — elite coaching and programming to perform on and off shift.

  • Designed to challenge all musculoskeletal structures responsible for meeting the extreme demands of your job
  • See how your results match up vs. your peers, and track your progress over time
  • Schedule a physical therapy assessment or other rehabilitation services with our team
  • Perform like the 1% at 1% of the cost
  • Confidential in-the-moment coaching, available 24/7, and on-demand equipment-free workouts
  • Personalized coaching programs for all aspects of life including nutrition, sleep, stress & resiliency, PTSD, depression, anger, relationships, addiction, and leadership development

RealSelf

Jul 2019 – Jan 2024 CTO, CPrO & CMO

Joined at a time of dramatic traffic loss, arresting decline and clawing back much of the lost traffic through an entire site-wide re-design to apply best-in-class SEO inclusive of information architecture, DOM redesign, page performance, and improved page SEO density by massive reduction of long-tail low-equity pages. Organic traffic grew 7x after the refactoring.

Drove the strategic shift from passive ad-tech to active multi-sided marketplace, bringing together consumers, providers and brands.

Owned the entirety of the consumer-facing experience inclusive of technology (engineering, IT, analytics & data science), product & UX, consumer marketing, and customer support. Led globally distributed team of nearly 150 people across US, South America, and Europe with a mix of both onshore and nearshore full-time and long-term embedded contractors.

Varsity Tutors

2016 – 2019 CTO
IPO: September 21, 2021 at $1.4B EV (NYSE:NRDY)

We went from $50M to $125M in revenue in three years, while transitioning from a predominantly in-person experience to a fully-online learning experience on our own platform.

We did all this while transforming a classic monolithic Ruby on Rails app to an enterprise-grade, services-oriented architecture (SOA) with robust eventing, lambdas, and hyper-performant services.

SHS

Sears Home Services

2015 – 2016 Senior Director, Engineering

As head of engineering, I recruited and hired our engineering organization; growing from just myself to 30 souls in twelve months.

I was also responsible for creating the first few production services, software development lifecycle, continuous integration and deployment, along with AWS hosting with physical backbone connecting us to Sears’ data centers.

Xbox One

2012 – 2015 Senior Product Manager

I spear-headed the cloud-based console experience that powers all of Xbox One barring only a few services. From the home screen, to pinned favorites, to the online store; everything Xbox consumers interact with is powered by these services.

I brought together the Console, Editorial, and Services teams to move Xbox away from firmware-baked experiences to ones powered by cloud services, allowing us to move away from 6-month iterations to less than 2 weeks to change nearly any experience on Xbox One.

To this day, those services continue to power Xbox Series and even some of the PC experiences for games.

Amazon

2008 – 2011 Senior Software Engineer & Senior Product Manager

I launched AmazonTote, a pilot program in Seattle, in a matter of months. As its product manager, I worked with UX design, engineering, operations & logistics to create the customer experience, “hacked” our existing systems to meet our needs, and even ensured physical tote bags were designed, printed and shipped to us; all in under three months. Even on launch day, I rented and drove a truck to ensure our first customers’ orders were delivered on time.

I was one of the original senior software engineers involved with AmazonFresh while it was still a pilot program in the greater Seattle area. I was responsible for creating or modifying more than 80% of our bespoke warehouse management system (WMS). More than just writing code, we spent a considerable amount of time at our fulfillment center, working alongside folks to understand how the software we wrote impacted them, and therefore could be improved upon. I received 4 patents during my tenure on the program.

Boeing

2001 – 2008 Aerospace Engineer & Lead Software Engineer

I was the brain-child of a new generation of software to help analyze all flight regimes of Boeing airplanes to support long-standing regulatory requirements of airlines.

The software was a radical departure from command-line tools to a comprehensive application that allowed airline engineers to do massive computational studies of airplane configuration, runway and atmospheric conditions.

The short version

If you want the dates, degrees and numbers instead, the résumé has them.