Connect the stack.
Transform the work.
Optimize what stays.
Operator-led SaaS implementation, integration, sales effectiveness, and revenue operations. End to end. For SMB and middle-market teams who are done buying tools that don't earn their keep.
Three peer offerings. One operator behind them.
Most middle-market revenue and operations problems aren't tool problems. They're "we bought the tool but never finished the implementation" problems. Or "we changed the team but never changed the process" problems. Or "we hit a plateau and can't see why" problems.
We work in three places. Sometimes all three back-to-back. Sometimes one of them, deep.
Connect
SaaS implementation, integration, stack assembly. Roll the systems in. Wire them together. Get the platforms you already pay for actually talking to each other.
How Connect works →- "We bought Salesforce eighteen months ago and we're still using a spreadsheet."
- "Marketing, sales, and finance all have a number, and none of them agree."
- "Our integrations break every time someone updates a workflow."
Transform
Sales effectiveness rebuild, process redesign, org change, GTM redesign. CRO and GM-grade change work, sized for SMB and middle-market teams.
How Transform works →- "Our sales motion isn't working and nobody can tell me why."
- "We hired three new reps and none of them are ramping."
- "Forecasting is a fiction we update every Friday."
Optimize
RevOps tuning, dashboards, attribution that attributes, accountability mechanics. The operator scaffolding that keeps the gains in place after the change work is done.
How Optimize works →- "Our dashboards are pretty and nobody uses them."
- "We can't agree on what a qualified lead is."
- "We hit plateaus and can't see why."
And one thing we do above the operating layer.
For owners, boards, and PE sponsors, we serve as the steady technology voice in the room. Framing the next 12 to 24 months. Supporting diligence. Advising on where capital should — and should not — go in the stack. Sitting at the board table when it matters.
For founder-led companies, family boards, independent boards, and sponsor-backed companies who want a seasoned operator in the technology seat without hiring full-time for it.
Operate — fractional CRO or COO on retainer
For teams that need a senior operator in the room every week, not a project that ends. Operate is the recurring version of everything above: Connect, Transform, and Optimize work, delivered as an ongoing retainer.
Sized for SMB and middle-market teams that aren't ready to hire a full-time CRO or COO yet but can't afford to fly without one.
The first 90 days look the same.
Most engagements start with a paid two-week Diagnose. We map the stack, watch the sales motion, sit on a forecast call, look at the dashboards nobody's using. At the end you get a ranked punch list, a recommended sequence, and a fixed scope for whichever of Connect / Transform / Optimize you start with.
If we're not the right fit after Diagnose, you keep the punch list. We part friends.
Diagnose
What's costing you. Ranked.
Build
We pick one of Connect, Transform, or Optimize and ship it.
Stick
We stay close while the team takes ownership. Hand off cleanly.
After that you either go to Operate for ongoing support, or run on your own with a check-in cadence we set up before we left.
A boutique, on purpose.
Island CTO Group has been an LLC since 2012. The work hasn't always been called "Connect · Transform · Optimize," but it's been the same shape for a long time. Stand up the systems. Change how the work runs on them. Keep the gains.
One senior operator runs your engagement directly. One or two clients at a time, not a partner deck.
Twenty-five years in technology, revenue, and operations. Chris has carried the number as a Chief Revenue Officer, run the P&L as an EVP and general manager, and been the first employee on the ground building a business from zero. He has spent his career accountable for growth, not advising on it.
He has built go-to-market from nothing into a repeatable engine more than once: hiring and ramping the sellers, setting pricing and packaging, standing up the partner channel that fed the pipeline, and installing the forecast discipline that made the number predictable. He doubled the Google Cloud practice at 66degrees and was an EVP at 2nd Watch. He has run sales across North and South America, with hands-on delivery experience in Brazil.
The technical half is real. At AWS in the early days of enterprise cloud adoption, he ran some of the most complex migrations of that era, including Condé Nast. AWS named him Person of the Year for the work.
Island CTO Group is where that goes to work one client at a time. For teams that need a revenue leader now and can't yet justify a full-time CRO, Chris takes the seat himself: owning the number, running the pipeline reviews, coaching the sellers, and tightening the systems underneath the motion. For owners, family boards, and sponsors, he takes the technology seat in board conversations without the full-time hire.
Book a call →Start with a diagnostic. Two weeks. Fixed price.
You'll get a ranked punch list of what's costing you in your revenue and operating engine. If we keep going, the work shows up. If we don't, you keep the punch list.
Book a 30-min intro callTell us what's slowing you down.
Two weeks to a ranked punch list. Send a few details and we'll set up a 30-minute call.