Most enterprise deals don’t fail.

They fade.

Not because of effort, but because somewhere inside the business, a real decision never formed.

I’ve spent decades in enterprise sales, including leadership roles at IBM, navigating procurement, legal, finance, and executive approval across complex organizations.

I’ve seen how deals actually get approved.

And how they quietly die.

What I saw consistently:

The people closest to the problem are rarely the ones who fund the solution.

Even when everyone agrees, the internal case often isn’t strong enough for someone to own the decision.

That’s where I work.

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What I do

I get inside late-stage, high-value deals and determine whether they can actually be decided.

If they can, we build the internal case that gets them approved.

If they can’t, we expose why before another quarter is lost.

I don’t train teams.

I work inside live deals where the outcome matters.

This means understanding:

• who can actually own the decision

• what financial case will stand up to scrutiny

• how the change impacts the business

• where alignment breaks down politically, including who can quietly block it

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How decisions actually get made

Every deal comes down to four conditions:

• A credible decision owner

• A defensible business case (revenue, cost, risk)

• A go-live plan that fits the business

• A cost of inaction the company can’t ignore

When those are in place, deals move.

When they’re not, they stall.

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What this looks like

• $380K ARR deal stalled 2 quarters → closed in 45 days after establishing a decision owner and quantifying $220K cost of inaction

• $520K deal aligned across finance, ops, and legal → approved after clarifying ownership and impact

• $700K deal deprioritized early when no decision owner emerged

Some of the most valuable work is identifying deals that look real but aren’t.

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Where this fits

• Enterprise deals ($100K–$10M+)

• Multi-stakeholder environments

• Late-stage deals that have slowed or gone quiet

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How work starts

Most clients start with a Deal Decision Audit on one live deal.

We determine quickly whether it can be decided, what’s missing if it can’t, and build the forwardable business case to get it approved.

This surfaces in days, not months.

On a larger deal, the value is measured in time saved and decisions made.

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Bottom line

Pipeline matters.

But decisions determine outcomes.

If a deal should have closed by now but hasn’t, there’s usually a reason inside the business.

I help surface it, fix it, or call it early.

If you have a deal like that, we should talk.