Island CTO Group
// est. 2012 · operator-led · SMB + middle market

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.

Book a 30-min diagnosticHow we work →
// 25 years in tech + revenue + ops · CRO · GM · operator
// fractional CRO and COO · operator-led, not advisory
// trusted with SaaS rollouts, sales engines, and operating mechanics since 2012
// what we do

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.

01 · connect

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 →
You'll feel this when:
  • "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."
what we shipworking systems, mapped integrations, named owners, runbooks the team can actually use.
02 · transform

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 →
You'll feel this when:
  • "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."
what we shipa sales motion that runs without you in the room, pipeline discipline, forecast you can defend, a coaching cadence that sticks.
03 · optimize

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 →
You'll feel this when:
  • "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."
what we shipa real operating cadence, dashboards tied to weekly decisions, attribution you can argue about productively, accountability the team owns.
∞ · operate

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.

Talk about Operate
// how we work

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.

01 · diagnose · 2 weeks · fixed price

Diagnose

What's actually broken. Ranked.

02 · build · 8-12 weeks · fixed scope

Build

We pick one of Connect, Transform, or Optimize and ship it.

03 · stick · 4-8 weeks · light-touch

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.

ICG.
// about

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.

The practice is led by a senior operator with twenty-five years in technology, revenue, and operations.

  • Chief Revenue Officer and first-employee operator who has built go-to-market from zero into a repeatable engine.
  • EVP and General Manager roles scaling cloud and data consulting practices.
  • Hands-on delivery across SaaS implementation, cloud migration, and modern data platforms.
  • Sales and operations leadership across North and South America. Operator, not advisor.

The same senior operator runs your engagement directly. One or two clients at a time, not a partner deck.

Book a call →

Start with a diagnostic. Two weeks. Fixed price.

You'll get a ranked punch list of what's actually broken 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 call
// book a call

Tell us where it hurts.

Two weeks to a ranked punch list. Send a few details and we'll set up a 30-minute call.

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