Matt Stine

CV

Engineering executive. AI-native software delivery, reliability, and observability. Writer and symbolic practitioner on the side that doesn’t fit on a résumé, until now.

Near Memphis, TN (remote) · linkedin.com/in/mattstine · github.com/mstine · feralarchitecture.com

Summary

Engineering executive with 25+ years building platforms. I lead delivery, reliability, and observability engineering for CVS Health’s Enterprise Data & AI Platforms. For the past year I’ve shipped most of my work by directing parallel AI agents inside a regulated Fortune-10 enterprise, with human gates and independent verification on everything they produce.

  • Hands-on AI: shipped into 22 repositories through as many as 16 concurrent agent lanes, with every one of 1,301 agent plans independently verified. Writing O’Reilly’s report on governing AI-generated code.
  • Observability is the day job: shipped an LLM-backed on-call routing agent that cut mean time to acknowledge from 14.9 minutes to 35 seconds.
  • Pivots, not just scale: cloud-native transformation as Pivotal’s Global Field CTO; firmwide language and modernization strategy in JPMorgan Chase’s Chief Technology Office.
  • Storyteller and partner to product: author of two O’Reilly titles; former Spring product owner and senior PM.
  • Remote-first: my current org is fully remote across US and India time zones and runs on written norms and async decisions.

Experience

CVS Health

Executive Director, Delivery & Reliability Engineering · 2025–present

  • Lead a 29-person engineering and operations org. Split it into delivery engineering and incident management, gave each its own leadership seat, and developed four individual contributors into the leadership team.
  • Shipped an LLM-backed on-call routing agent to production. Mean time to acknowledge fell from 14.9 minutes to 35 seconds (97% faster), rolled out in shadow mode with humans reviewing model-written notes before write-back.
  • Built a CI/CD failure census across ~575 production applications and 7,000+ repositories, classifying ~130,000 workflow runs. Found that 57% of failures name no cause; one shared build-component change then reached 721 downstream consumers.
  • Showed that a consolidation effort framed as a several-hundred-repository migration was really three shared-component changes.
  • Run an AI-native delivery practice: 1,301 agent plans, 239 independent verification passes, 197 agent code reviews, and 81 human acceptance gates. Agents open pull requests; they never merge.
  • Wrote the six-category reliability scorecard, including toil and team health, with the rule that no metric judges performance until it has a baseline and a trend.

Executive Director, AI & Machine Learning Engineering · 2024–2025

  • Structured the platform organization into three delivery teams and wrote the promotion cases that moved two senior contributors up a level.

JPMorgan Chase & Co.

Principal Architect, Advisor & Investment Technology · 2023–2024

  • Built an architecture intelligence platform that turned static documentation into source-integrated visual models used in executive design reviews.

Principal Architect, Chief Technology Office — Firmwide Language & Modernization Strategy · 2020–2023

  • Owned programming-language ecosystem strategy across thousands of engineers in every line of business, without direct authority.
  • Designed and deployed OpenRewrite-based modernization automation for dependency upgrades at enterprise scale.
  • Chartered the firmwide governance council for language adoption and deprecation; onboarded Rust as a firm-supported language.
  • Standardized architecture-as-code (C4, Structurizr DSL) across divisions.

Executive Director, Architecture & Engineering — Wealth Management · 2019–2020

  • Led architectural direction across critical Wealth Management systems, keeping platforms able to scale and evolve with long-term enterprise strategy.
  • Product owner for a web-based C4 architecture model repository that standardized architectural visibility across distributed systems.
  • Introduced opinionated guidance for API design, database selection, caching strategy, and schema migration, and turned architecture from static documentation into an actively governed discipline.

Pivotal Software (now VMware Tanzu)

Global Field CTO · 2017–2019

  • Executive technical advisor to Fortune 500 CTOs on cloud-native transformation; defined reference architectures for financial services, retail, and healthcare.

Earlier at Pivotal: Product Owner, Spring Portfolio · Senior Product Manager, Spring Cloud Services · Platform Engineer, Cloud Foundry (BOSH)

Earlier career: VMware (Senior Consultant, Enterprise Modernization) · AutoZone (Technical Architect, International Expansion Systems) · St. Jude Children’s Research Hospital (Group Leader, Research Application Development)

Independent & Creative

  • Founder & CTO, RitualSync · 2025–present. Consumer AI products for symbolic-practice communities. Flagship: TarotPulse.
  • Architect & maintainer, Psyche · 2025–present. A personal AI cognitive system built as a set of MCP servers: cross-session memory, semantic recall, thread-based context. 3,100+ commits, built almost entirely with AI coding agents.
  • Co-host, Rewired with Jaye Anne Beringer. What happens when you leave the rigid belief systems and start finding what’s alive.
  • Creator, ARCÆON, a rock opera of the major arcana.
  • Workshop leader, Time as Oracle, Mystic South 2026. Tracking tarot patterns through the lens of personal cycles.
  • Archetypal tarotist and astrologer. Readings and coaching.

Selected Writing

Education & Skills

B.S., Computer Science — University of Mississippi

AI-native delivery: agentic coding workflows, MCP server architecture, LLM-integrated systems, AI/ML platform lifecycle

Platform & reliability: observability, SRE, CI/CD, paved-path platforms, Kubernetes, Terraform, AWS, Azure, cloud-native architecture

Languages & architecture: TypeScript, Go, Java, Python, GraphQL, OpenRewrite, C4 / Structurizr