How I Sell.

Enterprise Sales · Philosophy · Process

Twelve years in. Here is what I know to be true about winning complex enterprise deals.

Belief 01

Trust closes deals. Everything else is just process.

Executives do not buy software. They buy the person standing in front of them. I have won deals against better-priced competitors and lost deals against inferior products. The variable in every case was trust. MEDDPICC tells you who to map. It does not tell you how to make a CFO believe you will still be solving their problem two years from now. That part is entirely human, and it is the part I have spent twelve years getting very good at.

Belief 02

No champion, no deal. Period.

I do not move opportunities forward without an internal advocate who can navigate politics I cannot see. A true champion is not someone who likes your product. They are someone whose career is better if you win. I spend more time building champion capacity than any other single activity in a sales cycle: and I qualify hard on it. A deal without a real champion is a deal I am about to lose slowly.

Belief 03

Discovery is the sale. The demo is just evidence.

Most reps rush to show the product. I stay in discovery longer than anyone is comfortable with. When I finally show the product, I am showing exactly three things that solve exactly the problems we already agreed are critical. The prospect does not feel sold to: they feel heard. That is the difference between a deal that closes and a deal that stalls in procurement for four months.

Belief 04

AI does not replace the rep. It exposes the ones who were never really doing the work.

I have run an AI-native sales motion at Vivify since 2024. What AI does well: research, personalization at scale, follow-up sequencing, pipeline hygiene. What AI cannot do: read a room, earn trust, handle a surprise objection on a Thursday at 4:45pm. The best reps I know are using AI to do more of what only humans can do. Everyone else is using it as a crutch: and that will show up in their numbers.

Belief 05

The 4am standard is not a flex. It is a filter.

I am up at 4am not to prove something to anyone. I am up because the reps who beat me will be up. The market does not care about my excuses. It cares about what I built. Every morning is a decision about the kind of professional: and person: I am going to be that day. That decision happens before most people are awake, and it compounds every day I make it.

The framework underneath

MEDDPICC.

Every deal I have run for the past twelve years has lived or died by these seven letters. This is not a methodology you learn in a workshop. It is a discipline you earn by losing deals you should have won and figuring out exactly why.

M
Metrics

Quantified business outcomes

Define the outcome in numbers. Revenue gained, hours saved, deals closed. If you cannot attach a dollar amount to the problem, you have not earned the right to the next conversation yet. Metrics are not the close — they are the foundation everything else sits on.

What failure looks like
You pitched features. They had no number to defend internally. The deal died in committee because nobody could answer: what does this actually cost us to not fix?

E
Economic Buyer

The person who can actually say yes

Not the champion. Not the committee. The person who signs the check and loses sleep over the ROI. You need to get in front of them or get your champion to carry your message into that room. Everything else is practice.

What failure looks like
You spent six months with the wrong person. They loved you. They had zero authority. The economic buyer picked a competitor they heard about in a board meeting.

D
Decision Criteria

The scoreboard they use to pick a vendor

If you do not know the criteria, you are guessing. If you do not shape the criteria early, you are losing to whoever does. Most reps discover the scorecard on the pricing call. That is already too late. Get in while the rubric is still being written.

What failure looks like
They used an evaluation framework you never saw. Your competitor helped build it. You showed up to a game where the rules were already set against you.

D
Decision Process

How they actually buy

Who approves. What Legal reviews. What triggers procurement. The steps between interest and signature. Every organization has a buying process they will not volunteer. Your job is to map it, respect it, and never get caught off guard by a step you did not know existed.

What failure looks like
Legal holds the deal for 90 days and you never saw it coming because you never asked. Your quarter ended. Their fiscal year reset. The deal reset with it.

I
Identify Pain

The wound underneath the symptom

Not the thing they mention on the first call. The problem that keeps the Economic Buyer awake at 2am and costs the company real money every quarter it goes unfixed. Symptoms are easy. Actual pain requires trust, patience, and the right questions. You are not selling relief — you are selling the absence of a problem they stopped believing could be solved.

What failure looks like
You sold to the pain they described instead of the pain that actually mattered. They signed a smaller deal, got partial relief, and renewed with someone else.

C
Champion

Your insider who wants you to win

Not just a fan. Someone with influence, real information, and a personal stake in your solution landing. Champions open doors, translate your message for internal audiences, and fight for you when you are not in the room. You build them, you do not find them. The relationship is the investment.

What failure looks like
Your champion could not defend the deal when it counted. They had no political capital. You lost to internal dynamics you never mapped and never saw coming.

C
Competition

Who else is in the deal and why

Who is in the deal. How the prospect sees them. What story is being told about you when you are not present. Competition is not just other vendors — it is the status quo, the internal build, the “do nothing” option. If you are not controlling the narrative, someone else is.

What failure looks like
You never asked. You assumed you were the only option. You were not. They picked the incumbent because nobody challenged the relationship early enough to matter.

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