Stay in Command of Your Biggest Deals

Most big deals feel solid — until they slip.

I run Done-For-You strategic deal reviews your leaders don’t have the time or structure to execute consistently.

I lead the review.
Your sales team brings the deal.

Together, we pressure-test reality and build an execution plan your team can act on.

Better outcomes. Fewer late-stage surprises. Less wasted effort.

Watch the 4-Minute Strategic Brief
For Sales VPs managing complex six- and seven-figure opportunities

A brief executive conversation to determine fit — no prep required.

Stay in Command of Your Biggest Deals

Most big deals feel solid — until they slip.

I run Done-For-You strategic deal reviews your leaders don’t have the time or structure to execute consistently.

I lead the review.
Your sales team brings the deal.

Together, we pressure-test reality and build an execution plan your team can act on.

Better outcomes. Fewer late-stage surprises. Less wasted effort.

Watch the 4-Minute Strategic Brief
For Sales VPs managing complex six- and seven-figure opportunities

A brief executive conversation to determine fit — no prep required.

The Problem

Your Biggest Deals Aren’t Getting the Inspection They Deserve.

Most teams struggle with:

Inconsistent or shallow deal inspection
Hidden risks and blind spots
Missed political dynamics
Misaligned or weak strategy
Managers are too stretched to run deep reviews

This isn’t a training issue.
It’s a discipline and capacity issue.

Most leaders simply don’t spend enough time inside their biggest deals.
They often discover risk only after a deal has slipped — or when it’s already hard to challenge.

Your leaders want to run deeper reviews, but they don’t have the bandwidth to do it consistently.

That’s where I step in to help.

How the Done-For-You Big Deal Review Works

What I do

A Done-For-You Strategic Deal Review for Must-Win Opportunities

I run structured, high-discipline deal reviews for your most important opportunities — the ones that can make or break the quarter — so leaders can get inside the deal, not just rely on updates and summaries.

This is not training your team how to review deals.
And it’s not asking already-busy managers to do more work.

I lead the review.
Your sales team brings the deal.
Together, we pressure-test reality — separating confidence from evidence — and build a strategy your team can actually execute.

Together, we:

Ruthlessly qualify big deals early
Expose risks, gaps, and political dynamics that don’t show up in status updates
Build clear, winnable strategies
Strengthen competitive position
Bring evidence-based confidence to committed deals
Reduce wasted cycles

Your managers get better.
Your reps get sharper.
Your pipeline gets healthier.

“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.

How It Works

The Big Rock Review - A Structured, Battle-Tested Framework

Each Big Rock Review gets leaders inside their deal — beyond status updates and into what’s real.

Most sales leaders already know what a good deal review should include.

The problem isn’t knowledge.
It’s time, structure, and consistency.

The Big Rock Review exists to create a disciplined inspection process early enough in the sales cycle to change outcomes, not explain misses after the fact.

Your team brings the deal… I bring the rigor.

Designed for distributed sales teams and delivered virtually to maximize speed, focus, and consistency.

Phase 1: Rapid Assessment Review (3 steps – 30 minutes)
A fast diagnostic call with the sales leader and rep to validate:

Deal strength
Budget, authority, and timing
Early risks

Phase 2: Strategic Deal Review (7 steps – 60 minutes)
A deeper working session covering:

Solution fit
Competitive positioning
Partner leverage
Political alignment
Customer success plan
Negotiation strategy
Next-step execution plan

If a deal can be won, this process reveals how.

Every review ends with a clear strategy and a next-steps plan the team can execute.

How the Done-For-You Big Deal Review Works

Who I Help

Who is The Big Rock Review Designed For

This service is built for technology sales organizations where:

A small number of complex deals materially impact results
Sales cycles span multiple quarters
Deal risk exists long before it shows up in the forecast
Sales managers are capable — but stretched thin

It is especially relevant for:

Founder-led and PE-backed companies
Mid-market and enterprise technology firms
VARs, resellers, and service-led sales organizations

If your world is defined by must-win deals — this was built for you.

Why It Works

Why Disciplined Deal Inspection Changes Outcomes

The focus is the deal — not the people selling it.

Most deal reviews happen late — when deals feel good and confidence has already formed.

Big Rock Reviews are deliberately designed to get leaders inside the deal while there’s still time to shape the outcome — when:

Assumptions can still be challenged
Stakeholders can still be influenced
Strategy can still be adjusted

This works because the review goes beyond status updates and pressure-tests what’s real — not just what feels likely.

Fewer surprises
Cleaner forecasts
Stronger deal strategy
Less wasted time on unwinnable deals

Better inspection leads to better decisions — and better outcomes.

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

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™

How To Get Started

Start With a 15-Minute Executive Alignment Call

This is not a sales pitch.

It’s a short, focused conversation to:

Understand how deals are currently inspected
Identify where risk tends to hide
Determine whether a Done-For-You Deal Review makes sense

If there’s a fit, we’ll discuss next steps.
If not, you’ll leave with clarity.

Next Steps

WATCH VIDEO

BOOK CALL

DISCUSS REQUIREMENTS

RECEIVE GO-FORWARD PLAN

SCHEDULE PROGRAM

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 stronger strategies, better inspection, and fewer forecast surprises, a Done-For-You Big Rock Review is the fastest path to improving your team’s performance.

Accelerate and WIN More Big Deals