Every system decision you made was a good idea once.
Some of them still are.
Patterns you may recognize
It usually shows up like this:
- Your cloud bill goes up every quarter, and no one can say which line is buying you something
- A system everyone works around, because changing it feels riskier than living with it
- Build-versus-buy calls that were correct at seed stage and never revisited
- A stack assembled by whoever was available, in the order they were available
- Engineers who are busy every single week, on a roadmap that moves too slowly
- A vendor that started as one integration and is now load-bearing
This is normal
None of this is a failure of judgment. It’s what accumulates when a company is executing. Some of those calls were right. Some were the fastest thing available on a Tuesday. Some you inherited and have never had a reason to open up.
The question isn’t whether any of them were mistakes. It’s whether anyone has looked at them since.
What I actually do
A second opinion from someone with no stake in the original decision. Most of the work is sorting:
- Which costs are buying you speed, resilience, or optionality, and which are just still there
- Which systems are worth replacing now, and which ones will be cheaper to replace in a year
- What genuinely needs to be built, and what you are about to build because building is the reflex
I’m not going to hand you an architecture and leave. You’ll get the reasoning, the alternatives, and what each one costs you – and then you make the call, because you’re the one who has to live in it. I stay around only as long as you need me.
How I work
- One conversation first – no deck, no assessment phase
- Forty years across software, networking, and operations means I’ve usually watched your situation go both ways
- Straight answers about what I’d do and why, including when the answer is “leave it alone”
- Advice you can act on without hiring anyone
I take a small number of engagements at a time – advising the founder directly, or embedded with the team on one specific initiative, depending on what the situation calls for. Either way it’s judgment on the calls that are expensive to reverse, without the load of a full-time executive.
Who I work with
Founders, mostly at the point where the technical decisions have started to show up in the financials. Sometimes the CFO is in the room. Usually there’s already a team or a vendor – I’m not a replacement for either.
What I don’t do
That’s the whole scope: fractional CTO advice on cost, complexity, and what to build. Not networking support, not ongoing IT.
If two of those patterns sound like your last board meeting, that’s the conversation.
Boston based. Forty years across software development, networking, and operations, including CTO and VP Engineering roles at B2B SaaS companies through acquisition. I stay current on the tooling and the patterns so founders don’t have to.