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ThoughtfulBits Consulting · Kirkland, WA

AI-driven turnarounds for software companies.

Board-level operator and software CEO helping PE-backed companies convert AI disruption into product strategy, operating leverage, and shipped software.

01 · Practice areas

What I do

  • 01

    AI product strategy

    AI-native roadmaps and product repositioning for companies facing disruption.

  • 02

    Operating leverage

    Broad internal AI adoption across engineering, GTM, and back office — measurable cost and velocity gains.

  • 03

    Hands-on execution

    Technical architecture, executive recruiting, and sales support.

    “I still write and ship code every day.”

02 · Engagements

Current work

Luminate Capital

Innovation Partner

Board and operating-partner roles across eight software portfolio companies — every one now has AI-native product initiatives and broad internal AI adoption underway.

2024 — Present

Tailored AI

Chief Executive Officer

Building the Simple family of calm, evidence-first AI products — email intelligence, executive intelligence, and decision simulation.

tailoredai.solutions ↗

Engagements combine CEO judgment, AI strategy, product & GTM, executive recruiting, technical architecture, sales support — and daily hands-on coding.

03 · Operating history

Track record

  1. 2012 — 2024

    Polyverse Corporation Founder & CEO

    Cybersecurity company built on polymorphic defense. $10M+ cumulative revenue, sold to U.S. Government customers, including a NAVSEA SBIR Phase III — a parent program valued at up to $154M.

  2. 2010 — 2012

    AOL Executive Vice President & CTO

    Led global engineering, IT, and technology operations for the $2.2B public company, managing a 1,300+ person global workforce through AOL's post-spin turnaround.

  3. 1993 — 2010

    Microsoft Corporate Vice President

    Online Services Division CTO across Bing, MSN, and Microsoft Advertising; Technology Advisor to Bill Gates. Led 1,300+ engineers building platforms supporting $2.5B+ in annual revenue, and served as a key executive on 14+ acquisitions totaling $7B+.

  4. Early career

    Beginnings Founder & researcher

    Founded a grid-computing startup; worked at Los Alamos National Laboratory. Princeton University, BSE Computer Science, cum laude, 1993.

  • 200+ U.S. patents issued/pending
  • Princeton BSE CS · cum laude
  • Los Alamos National Laboratory
  • 30+ years building

04 · Publishing

Writing & video

05 · Open source

Free tools

ChatGPT, Codex, Claude & skills.sh

ThoughtfulBits Skills

Six free review and editing skills for B2B SaaS leaders: a reader-first editor for short- and medium-form social posts inspired by Nobunaga and Jonah Berger, screen-by-screen UI/UX action-loop testing, product and feature reviews, and board-deck audits. Install for ChatGPT Work, Codex, Claude Desktop, or compatible agents through skills.sh; MIT-licensed and open source.

v1.4.0 · Six skills · No ThoughtfulBits server

See all six skills →

07 · Contact

Taking a limited number of board and advisory engagements.