Career highlights

Portfolio

Nine companies, one per slide — insights and learnings that cannot be gleaned from my résumé. Open the deck, or jump straight to a company.

01 / 9
Lium AI
Oct 2025 – presentCTO & 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.

02 / 9
Monster Orange, LLC
CurrentFounder & 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.

03 / 9
ShiftHealth AI
Feb 2024 – presentTechnical Advisor & Acting 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
04 / 9
RealSelf
Jul 2019 – Jan 2024CTO, 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.

05 / 9
Varsity Tutors
2016 – 2019CTO
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.

06 / 9
SHS
Sears Home Services
2014 – 2016Senior 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.

07 / 9
Xbox One
2012 – 2014Senior 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.

08 / 9
Amazon
2008 – 2011Senior 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.

09 / 9
Boeing
2000 – 2008Aerospace 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.

Lium AI
Major subsystems I built
Standards, architecture & oncall
Owner of the repository holding Lium’s cross-cutting standards, architecture and operational playbooks, plus Ephemeris, a dev-health dashboard tracking DORA proxies and cycle time.
140 of 179 commits 11 contributors largest contributor
Galaxy — developer platform
A local-first test platform built for the whole engineering org: synthetic browser, API smoke and k6 performance pillars, runnable against any environment.
388 of 602 commits 8 contributors largest contributor
Workspace & canvas model
Workspace copying, scoping, seeding and access control, plus the canvas targeting that puts agent output somewhere a person can use it.
18 of 32 commits 3 contributors largest contributor
Multi-tenancy, auth & audit
Tenant features and preferences, user management, billing administration, versioned terms-of-use consent, feature flags and the audit layer.
94 of 184 commits 11 contributors largest contributor
Web client
The Next.js product surface — workspace and admin features, artifact rendering, dialogs and modals — shipped in four languages.
425 of 879 commits 12 contributors largest contributor
API contract
An OpenAPI-generated TypeScript client, so the web app cannot drift from the backend it calls.
82 of 192 commits 10 contributors largest contributor
Agent & chat orchestration
The chat service, the tool executor that runs model-requested calls, an MCP client and an MCP tool server, and the versioned v1 API over all of it.
88 of 303 commits 15 contributors largest contributor
Tool system
Categorized tool definitions, dataset querying, visualisation and sequential-thinking, with tenant scope carried into every invocation.
36 of 175 commits 10 contributors largest contributor
1,624 of 4,683 commits on the default branches of 13 repositories, Oct 2025 – Aug 2026. Share is my commits as a proportion of every commit that touched that subsystem.
Monster Orange, LLC
Major subsystems I built
Wayfinder — retirement planning, web and desktop
Planning engine & service
The Python domain core: service layer, plan store, two engine generations, life-path overlays, entitlements and auth.
394 of 394 commits sole contributor
React application
Pages, components and API layer carrying the whole planning UI, internationalized on nearly every change rather than retrofitted.
445 of 445 commits sole contributor
Release & verification engineering
The most-touched file in the repository is the test runner; around it, a route-parity checker holding desktop and web to one API surface, conformance suites and CI.
502 of 502 commits sole contributor
Tauri desktop application
The shipped desktop product — UI, Rust host shell, notarised DMG packaging.
268 of 268 commits sole contributor
Rust store — crypto, licensing, persistence
The local-first data layer with encryption at rest and license verification; its test directory carries more commits than its source.
119 of 119 commits sole contributor
Rust engine-core compiled to WASM
The computation kernel held to golden Monte-Carlo reference fixtures, so desktop and web parity is proven to the cent rather than assumed.
51 of 51 commits sole contributor
MCP server
The plan model exposed to agents as callable tools — create, compare life paths, run Monte Carlo, solve for a goal.
41 of 41 commits sole contributor
Omnia Exterior Solutions — multi-brand CMS and lead generation
Lead capture & form engine
A lead wizard and declarative form renderer, with a coverage registry that proves every block’s form is actually reachable.
79 of 79 commits sole contributor
Content ingestion
Google Sheets and Docs become pages; the Lytho digital-asset library syncs into the CMS with its own browser and importer.
225 of 225 commits sole contributor
SEO & performance auditing
Lighthouse and JSON-LD audits as first-class models with their own jobs and history, plus sitemap refresh, redirects and cache warming.
41 of 41 commits sole contributor
Block-based page builder
An 845-line base class with 33 typed block subclasses, cloning, import and versioning, and a virtual builder for composed layouts.
238 of 244 commits 2 contributors largest contributor
Multi-brand tenancy
One platform serving several brands, each with a compiled asset bundle and generated CSS — brand identity as data, not a fork.
115 of 117 commits 2 contributors largest contributor
Test infrastructure
Cassette-recorded external calls and layered suites over controllers, models, services, jobs and integration paths.
538 of 549 commits 2 contributors largest contributor
2,407 of 2,424 commits on the default branches of two systems (99%), Jun 2025 – Sep 2026. Share is my commits as a proportion of every commit that touched that subsystem.
ShiftHealth AI
Major subsystems I built
Clinical feature extraction
Polymorphic, tenant-scoped feature records with pre-validation and fingerprinting, driven by declarative definition sets per program family.
131 of 134 commits 2 contributors largest contributor
Localization
Seventy locale files kept in step with every model, controller and view as the product grew — translation as part of the feature, not a later pass.
279 of 293 commits 4 contributors largest contributor
Multi-tenant identity & organizations
Every domain model scoped to an organization — 31 of them — with Devise authentication and OmniAuth.
279 of 296 commits 3 contributors largest contributor
Programs, assessment & evaluation
The content spine users move through — courses, programs, steps and scheduled actions — and the assessment instruments and scoring that measure the outcome.
193 of 208 commits 2 contributors largest contributor
Conversational AI pipeline
Message analysis, response generation, re-analysis, summarization and scoring — each an async job — plus speech-to-text, text-to-speech and the model client layer beneath.
235 of 281 commits 3 contributors largest contributor
Flutter SDK
A published client SDK with 18 typed API clients, cassette-driven system tests and a mock layer — the foundation the iOS and Android apps are built on.
413 of 490 commits 3 contributors largest contributor
2,886 of 5,191 commits across four repositories, Dec 2023 – Nov 2025 — including 2,283 of 2,756 on the platform itself (83%). Share is my commits as a proportion of every commit that touched that subsystem.