Fractional CRO — Sydney & Global

Commercial clarity for organisations that can't afford to guess.

Greg Caleo steps in as a Fractional CRO to diagnose what's actually blocking revenue, rebuild the value narrative, and lead the team that runs it. No full-time cost. No theory. Just a commercial engine that works and a leader in the room to run it.

6-stepOperating model
8Core commercial services
AU + GlobalAvailability across time zones
What I Do

Senior commercial leadership, without the full-time cost or risk.

Most organisations don't fail because they lack ambition. They fail because they lack clarity. Complexity builds up, tools pile on, and momentum quietly drains away while revenue becomes harder to predict.

I work as your Fractional CRO: diagnosing the real commercial blockers, designing the revenue engine that fixes them, and leading the team on the ground to run it. It's hands-on leadership, not advisory theatre.

Cybersecurity SaaS AI MSPs Professional services Education NFP
How I Work

A six-step operating model, built to run without you needing to translate it.

Every engagement moves through the same disciplined framework, from first diagnosis through to board-level reporting.

1

Diagnose

Identify the real commercial blockers, fast.

2

Clarify

Define ICP, value narrative, positioning and GTM strategy.

3

Build

Create the revenue engine: sales motions, pipeline mechanics, commercial architecture.

4

Lead

Coach the team, lead deals, build real momentum.

5

Optimise

Improve deal velocity, close rates, pricing and packaging.

6

Report

Board-level clarity, forecasting and commercial governance.

Who I Work With

Founders, CEOs and boards in high-trust industries.

Cybersecurity

Technical credibility paired with a commercial story buyers actually trust.

SaaS

Predictable pipeline and pricing that matches how the product actually sells.

AI

Cutting through hype to a value narrative customers can act on.

MSPs

Repeatable sales motions that don't rely on one founder doing every deal.

Professional services

Positioning that reflects genuine expertise, not generic credentials.

Education

Commercial clarity for organisations balancing mission and revenue.

NFP

Revenue systems built around trust, not pressure.

Purpose-driven orgs

Growth that stays true to why the organisation exists in the first place.

Why It Works

Trust-first leadership. Hands-on execution. No corporate theatre.

Fast diagnosis

You get a clear read on what's actually blocking revenue in weeks, not a quarter of workshops.

Systems your team can run

No frameworks that live in a slide deck. Everything is built to be picked up and run by the people already in the room.

Commercial honesty

Straight talk and a real diagnosis. If something isn't working, you'll hear it plainly, with a plan to fix it.

Build the engine. Lead the team. Grow the business.

A short call is the fastest way to find out whether a Fractional CRO is the right move for where you're at.

Book a strategy call