Matt Masteller | Fractional CTO / Agentic Engineer / AI-Native Systems & Custom Software

Matt
Masteller

Fractional CTO / Agentic Engineer / AI-Native Systems & Custom Software

Location
San Diego, CA

INTRO

I'm a Fractional CTO and Agentic Engineer with 30 years of experience building AI-native systems, custom platforms, and automation-first software. I work at the intersection of product, engineering, and business strategy—designing systems where autonomous agents coordinate workflows, reason over data, and replace manual processes across sales, ops, support, and analytics.


I've led startups, advised mid-market and enterprise teams, and shipped production systems where AI is the core operating layer, not a bolt-on feature. If you're trying to move fast, scale intelligently, and avoid brittle architecture, let's talk.

EXPERTISE

01
AGENTIC ENGINEERING & AI-NATIVE SYSTEMS

I design systems where autonomous agents coordinate workflows, reason over data, and augment or replace manual processes across sales, ops, support, and analytics.

02
FRACTIONAL CTO LEADERSHIP

Partner with founders and leadership teams to set technical strategy, architect platforms, and lead multi-million-dollar initiatives end-to-end.

03
FULL-BREADTH DEVELOPMENT

Full-stack execution across JavaScript, TypeScript, Python, and C#—from fast prototypes to production-grade, cloud-native systems.

04
INTELLIGENT AUTOMATION & DATA ENGINEERING

Automation-first software, data pipelines, and analytics that cut cost, unlock revenue, and improve operational efficiency.

05
CUSTOM PLATFORM ARCHITECTURE

Bespoke platforms and systems of record built to scale intelligently and avoid brittle, hard-to-maintain architecture.

06
PRODUCT & BUSINESS STRATEGY

Product thinking that connects technology decisions directly to business outcomes, roadmaps, and measurable results.

EXPERIENCE

2016 – Present

FitStack AI

Fractional CTO

San Diego, CA

Founded technology consultancy specializing in solving complex business and technology problems for startups to mid-market companies ($100M revenue) by designing and developing bespoke cloud-based software and integrating with best-of-breed platforms. Foster client relationships and identify business goals. Devise plans for projects valued at up to $1M. Oversee vendors and subcontractors. Drive solution development and management.

2019 - Present

UFC GYM

Fractional CTO

Newport Beach, CA

Rebuilt MarTech stack. Boosted conversions 20% and maximized marketing ROI by directing team of onshore and offshore designers and developers in modernizing customer-facing websites for multiple brands. Decreased website cloud costs 80% and elevated operational efficiency across multiple departments by building customized cloud-based applications and processes to integrate website, marketing automation, backend CRMs, and best-of-breed third-party platforms. Generated new revenue stream during massive brick-and-mortar shutdowns due to COVID-19 pandemic by designing and developing customized livestream and video-on-demand platform within 3 months.

2017 - Present

Next Ventures

CTO & Co-Founder

San Diego, CA

Technical co-founder of blockchain startup and investment firm with specialization in creating new products and services. Research new technologies and blockchain industries. Tested investment theses. Lead team of subcontractors.

2008 - 2015

New Evolution Ventures BPO

CTO & Co-Founder

San Diego, CA

Founded operating arm of private equity firm focused on fitness industry, establishing organization to act as back-office for portfolio companies. Crafted product roadmaps. Directed solution development, including design, coding, and deployment. Spun off SaaS software business and sold in successful exit.

2003 - 2008

24 Hour Fitness

VP Technology & Finance

Carlsbad, CA

Applied broad-based knowledge and experience to develop strategic improvement plans, identify performance gaps, develop, and support the implementation of a recommended plan of action to close the gaps.

2001 - 2003

CAS Venture Solutions

Software Architect & Co-Founder

Denver, CO

Provided venture consulting services; took ownership interest in client companies in exchange for software development, consulting, and business advisory services at discounted market rates.

1999 - 2001

Avanade (Microsoft/Accenture)

Software Architect

Denver, CO

Specialized in delivering custom Microsoft-based solutions that added value to client organizations.

1997 - 1999

Toros Development

Software Developer & Co-Founder

Denver, CO

Delivered value-added custom, internet-based distributed computing solutions for companies ranging from Startups to Fortune 500 companies. Advised Startups on business strategy and acquiring venture capital.

1994 - 1997

Prudent Man Investment Management

Software Developer & Portfolio Manager

Denver, CO

Developed mission-critical IT systems, custom applications, and portfolio management systems that quintupled productivity. Technologies included Advent Axys, VB, PERL, and HTML.

1994 - 1997

Arthur Andersen

Auditor

Denver, CO

Audited and prepared defunct savings and loan banks for purchase by the Resolution Trust Corporation (RTC), a temporary government agency.

EDUCATION

2021

Duke University

Specialization, Decentralized Finance (DeFi)

In this specialization, students develop the essential skills for understanding Decentralized Finance or DeFi. This includes an analysis of DeFi infrastructure and the problems that DeFi seeks to solve. Students also master the key primitives in this space such as blockchain mechanics, supply and ownership, and loans and swaps. Students also explore leading DeFi protocols including MakerDAO, Compound, Aave, Uniswap and dYdX. Finally, with any new technology there are risks. Students analyze smart contract risk, governance risk, scaling as well as regulatory issues.

2017

Johns Hopkins University

Specialization, Data Science

This Specialization covers the concepts and tools needed throughout the entire data science pipeline, from asking the right kinds of questions to making inferences and publishing results. In the final Capstone Project, skills learned are applied by building a data product using real-world data. At completion, students have a portfolio demonstrating their mastery of the material.

1995 - 1998

University of Colorado Denver

Master of Science Business Administration, Accounting & Finance

1988 - 1992

University of Denver

Bachelor of Science Business Administration, Finance & Economics

PROFILES

01

My most up-to-date profile—experience, background, and recommendations.

02

Open-source projects, experiments, and code I build.

PORTFOLIO

Coming Soon!

CONTACT

Let's build something.

I take on a small number of fractional CTO and agentic-AI engagements. If you have a project in mind, let’s talk.

Location
San Diego, CA

Matt
Masteller