When the Quarter Depends on a Handful of Big Deals

Late-quarter surprises almost always come down to untested assumptions.

I run a disciplined, Done-For-You deal inspection to pressure-test the deals that could make or break the quarter.

Built for Sales VPs responsible for six and seven-figure opportunities.

I lead the review
Your sales leader and rep bring the deal
We get clear on what has to happen next

You get clarity on where each deal really stands — while there’s still time to act.

Watch the 3-Minute Strategic Brief

For Sales VPs responsible for six- and seven-figure opportunities

A brief executive conversation to determine fit — no prep required

The Problem

Your Biggest Deals Aren’t Getting a Real Inspection

Most teams struggle because big deal reviews stay at the surface:

Deals get reported, not pressure-tested
It’s unclear who actually has the power to say yes — or no
There’s no real urgency from the customer’s side
The plan sounds fine, but nobody’s clear on what has to happen next
Sales leaders know how to run deeper reviews — they just don’t have the time

This isn’t a training problem
It’s a rigour + time problem

Most leaders simply don’t spend enough time inside their biggest deals.
They want to run deeper reviews, but don’t have the bandwidth to do it consistently.

That’s where a disciplined, done-for-you inspection makes the difference.

How the Done-For-You Big Deal Review Works

What I do

A Done-For-You deal inspection for the deals that move the number

I lead a structured review on your must-win opportunities—the ones that can make or break the quarter.

Not a pipeline review. Not a status update. A real inspection

We pressure-test:

What you know vs. what you’re assuming
Where the deal is exposed (and how early that exposure can be fixed)
Who matters, what they want, and what’s missing right now
The plan to win—and the next moves to prove momentum

I don’t teach your team how to sell.

I help you make sure nothing important is being missed.

“The process reminded us that being deliberate regarding our key “Must Win” deals is what will make us get the results we are targeting. A simple and effective approach for Big Deal inspection.”
Alex Talmor, President, GlassHouse Systems Canada

When a handful of big deals determines the quarter, it doesn’t take much for disciplined inspection to pay for itself.
Influencing just one must-win deal — or avoiding months of effort on the wrong one — can easily outweigh the investment.

Why Go Outside for Deal Inspection?

Your sales leaders are capable.
They know how to run deal reviews.

This work does not exist because leadership is weak.

It exists because big deals are inspected inside the system that owns them — and that creates blind spots.
Even when leaders intend to inspect deeply, time pressure and competing priorities almost always force reviews to stay high-level.

Optimism goes unchallenged.
Risk signals soften as they move up the forecast.
Fragile assumptions surface too late.

An external advisor sits outside that system by design.

No quota.
No reporting line.
No political downside.

The job is simple: pressure-test reality early enough to give leadership better options.

That’s why VPs go outside — not to replace their leaders, but to avoid being surprised by deals that matter too much to get wrong.

How It Works

The Big Rock Review

A disciplined, executive-level inspection of must-win deals

Each Big Rock Review gets leaders inside the deal — beyond status updates and into what’s actually happening.

Most experienced sales leaders already know what should be covered in a deal review.
The issue isn’t knowledge.

It’s time, structure, and consistency — especially when the deal is large and the quarter matters.

The Big Rock Review exists to create early, objective inspection, while there’s still time to change the outcome — not explain misses after the fact.

Your team brings the deal. I bring the rigor.

Rapid Assessment Review

(early signal and deal health)

The Rapid Assessment Review establishes baseline clarity.

It quickly answers:

Is this a deal worth deeper investment right now?
Are budget, authority, and timing validated?
Are key stakeholders being identified and covered
Where is early risk already visible?

This prevents leadership from spending time and political capital on deals that don’t deserve it — or from missing early warning signs on deals that do.

Sales Strategy Review

(depth, execution, and risk exposure)

The Sales Strategy Review goes inside the campaign.

This is where we pressure-test:

Solution fit and differentiation
Competitive positioning
Partner leverage
Political alignment and access to power
Customer success and adoption risk
Negotiation posture
The real next steps required to move the deal forward

This is not a presentation.
It’s a working inspection focused on what must be true for the deal to close.

What leaders get at the end of every Big Rock Review

Every review ends with:

A clear view of deal reality vs assumption
The top risks that must be addressed
A focused go-forward strategy
Concrete next steps, owners, and proof points

If a deal can be won, this process makes the path visible.
If it can’t, leadership finds out early — while options still exist.

This is not sales training.
It’s an executive-level deal inspection designed to protect the forecast.

How the Done-For-You Big Deal Review Works

Who I Help

If your quarter comes down to a few deals, this is for you

Built for tech sales orgs where:

5–15 deals drive the number
Cycles span multiple quarters
Risk exists long before it shows up in forecast calls
Managers are strong—but bandwidth is the constraint

Especially relevant for:

PE-backed and founder-led firms
Mid-market and enterprise selling motions
VAR / channel and services-led revenue models

Why It Works

Because Most Deal Reviews Happen Too Late

Most internal reviews rely on rep updates and optimism.
By the time leadership pushes, the deal is already baked into the forecast.

Better inspection leads to better decisions — and better outcomes

Big Rock Reviews are designed to happen early enough to:

challenge assumptions before they harden
surface risk while there’s still room to move
tighten strategy before the deal is locked into the forecast

The result: fewer surprises, cleaner commits, and more controllable execution.

I’ve brought Jeff’s deal execution to 3 different sales teams at 3 different organizations now and each time, we’ve seen a dramatic improvement in our big deal management and win rates.

— Greg Onoprijenko, Director of Cloud Sales, U.S. Ingram Micro Cloud

Jeff’s Big Rock Review is useful in “ruthlessly” qualifying opportunities and focusing your time on what will truly make you successful.
Benny Cifelli, General Manager, NetApp Canada

Jeff spreads infectious energy and is easy to listen to with a lot of insight.
Tom Schroeder, Head of Sales, CloudBlue, Germany

Why It Works Better Than What You're Doing Today

Typical Internal Review

The Big Rock Review™

Getting Started

Start by watching the short video explaining how the done-for-you Big Deal Review works.

This gives you a clear sense of the approach and when it’s most useful.

When you’re ready, book a 15-minute Executive Alignment Call to confirm fit and determine the right next step.

👉 Watch Video
👉 Book a 15-Minute Executive Alignment Call

No prep required.

3-Minute Strategic Brief

After watching the brief

I'm Here To Help

Jeff Goldstein | Strategic Deal Advisory

Your Biggest Deals Deserve More Discipline, Not More Work

After leading Canadian sales teams at HP, DG/EMC, NetApp, Veeam Software and advising global tech organizations, I know what disciplined deal execution looks like — and what happens when it’s missing.

If you want more control over must-win deals—and fewer forecast surprises—this is the fastest way to get there.

Accelerate and WIN More Big Deals