Fractional CTO & Technical Advisor · Central Massachusetts
I'm Rich Sadowsky, and I've been somebody's fractional CTO since 2022. Before that I had a long, diverse, and fruitful career. Some examples: I was employee #5 at TurboPower Software in 1987 and employee #7 at Jibo in 2013, Chief Architect at Affectiva, and Director of Emerging Technologies at Symantec — where I invented LiveUpdate. I work with a small number of founders and companies on the architecture, security and hiring calls that are cheap to get right early and brutally expensive to fix later.
The wall behind me on every call: Time's Best Inventions cover for a robot I helped build, a ComputerWorld Premier 100 plaque from 2002, a Forbes article about innovations at Affectiva, and some guitars.
Four decades, mostly at companies doing something new
Where I help
I do the work and hand it back to your team with the reasoning attached, so the next decision like it gets made without me. Four things founders keep calling me about.
Up to 50% of my capacity, owning technical direction: architecture, roadmap, build-versus-buy, and the engineering hires that will define your next two years. Built for teams with strong engineers and nobody who has done this at scale before.
I was Jibo's Security and Privacy Officer — a camera and a microphone sitting in a family's kitchen. Threat modeling, privacy by design, audit readiness, and an honest account of what your data practices actually expose you to.
For investors and acquirers, or for founders who would rather know first. I read the code, meet the team, and write the memo that says what is real, what is held together with tape, and what it costs to fix.
I started integrating machine learning into shipping products in the mid-1990s and put my first production integration in front of customers around 1998, as Director of Emerging Technologies at Symantec. Affective computing at Affectiva, robotics at Jibo, ML pipelines since. I can tell you which parts of your AI plan are real, which are decoration, and which will quietly become a data problem.
How it works
Every engagement starts the same way, and none of them start with a contract.
An hour, free, no slides. Tell me what's keeping you up. If I'm not the right help I will say so, and I usually know who is.
I go deep on one problem — architecture, security posture, delivery, team structure — and hand you a written assessment with a prioritized plan you can act on whether or not you keep working with me.
A predictable share of my week, direct access, and I'm in your Slack rather than booking a follow-up. Month to month — if it stops being worth it, it stops.
Receipts
The year I landed in California and started all this, in a computer store off Beverly Hills.
CTO and SVP of Technology roles, plus two VP/Head-of-Engineering posts.
Shipped my first production machine-learning integration — a quarter-century before the current AI wave.
ComputerWorld Premier 100 IT Leaders, for the LiveUpdate work at Symantec.
Symantec CEO Star Award, the company's top individual recognition.
Issued US patents as a named inventor, plus pending applications and a European filing.
Employee number 5 at TurboPower in 1987 and number 7 at Jibo in 2013 — taken from nothing to shipping product.
Selected work
The full history, back to a Beverly Hills computer store in 1984, is on the track record page.
Fractional CTO
Technology strategy and operations for passive thermal storage and edge computing that cuts energy use and emissions across the cold chain without bending on food safety. The technology works; the job now is turning it into a product customers love and a business that runs profitably at scale.
Architect of Server → Security and Privacy Officer
Nearly five years building the cloud behind the first social home robot, then owning its security and privacy posture — a networked camera and microphone sold into family homes in all fifty states, which is about as unforgiving a privacy problem as consumer hardware offers. I'm also a co-inventor of the robot itself. Hired as #7.
Chief Software Architect
Built enabling technology for the first two versions of the Affdex affective-computing platform and delivered it as a set of SaaS APIs, plus contributions to the Q Sensor wearable that recorded electrodermal activity. Founded by MIT's Rosalind Picard, PhD, and Rana el Kaliouby, PhD. Hired in first 10 employees.
CTO & SVP of Engineering
CEO Eric Rhoads wanted any web property to be able to run its own branded radio station without hiring a station's worth of people. I built the technology system that powered it: bespoke streams per customer through an interactive player, with calls to action carried as metadata inside the audio — fed to the streaming seed servers over a serial port from the music scheduling system and augmented with licensed detail about the song and the band. Integrated audio processing technology to deliver the best audio quality at 128kbps or lower. The original Lycos Radio, Earthlink Radio, About.com Radio and A&E Television Radio all ran on it. Three patent applications and $18M raised came out of the work.
Staff Software Engineer → Software Architect → Director of Shared Technology → Director of Emerging Technologies
I designed LiveUpdate, sold the idea company-wide, and drove it into Norton AntiVirus and every other Symantec product — the update infrastructure that kept hundreds of millions of machines current, at a time when the gap between writing a signature and getting it to every customer was the whole product. It issued as US Patent 5,790,796. Two CEO Star Awards and the ComputerWorld Premier 100 recognition came out of this work.
Senior Software Engineer
Where my career as a programmer soared, as the fifth employee. Co-author of the Jolt Cola award-winning Object Professional class library and of Async Professional; author of the company's swappable TSR technology and its NetBIOS, IPX and SPX network libraries. The customers were other programmers, which is the most demanding audience there is — and the code went open source and was still helping people decades later.
Invention
Named inventor on seven granted US patents plus a European filing, with further applications pending — spanning software distribution, boot recovery, remote uninstall, and affective computing. At two companies I also built and led the patent program itself: deciding what was worth filing, and getting engineers to write disclosures they'd rather not write.
Four of seven. The full list, including pending applications, is on the track record page.
The person you'd actually be hiring
I've been a musician since I was six and a programmer since not long after. There's a red Telecaster on the wall behind me on every call, two rescue dogs who are convinced they run the company, and a lake in central Massachusetts with a state forest on the far shore.
Forty years in, the pattern is consistent: the best work happened where the problem was genuinely hard, the team was better than me at something, and nobody was pretending. That's still what I'm looking for.
Get in touch
An hour on a call costs you nothing and I'll give you a straight answer, including the answer where you don't need to hire anyone. If there's a fit we'll both know by the end of it.