We kept this edition simple. Things you should do. Things you shouldn’t do. And some hot discussions causing salespeople to argue as per usual.

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A lot of enterprise-level sales advice gets the job wrong online.

It treats big deals like small deals with bigger logos. Tighter discovery. Sharper objection handling. Better closing tactics.

This recent post shows that while that may ring true for some, the game isn’t always exactly that.

The Chris Schaum breakdown that is buzzing around r/sales this week is a 330-day playbook for a $4.6M Fortune 50 close. Read it carefully and you start to see that the skills that got the deal done weren't really “sales skills” as most people understand it.

Here's what you actually have to get good at to close 7-fig deals based on Chris’ write-up:

Understanding the company before you ever pitch.

Day 1 through 4 was straight research. Annual reports, investor presentations, conference talks. The IR section of a public company shows you how the executives talk about their own business. Your email must speak the same language they do. A cold-pitch to CEOs on your "innovative platform," is a losing game by default. They need to know how you tie to goals they've already committed to publicly.

Building coalitions, not just champions.

One champion gets you in, but a coalition drives it home. By day 41 he had the CEO’s number two, the R&D lead, and a paid test on the table. By day 301 he was sitting in five-hour engineering calls pulling junior engineers into the conversation in front of leadership. Every person you make look good is a person who picks up the phone when things stall.

Tying your product to their comp.

One of the sharpest moments in the entire post is when he asks the R&D team how they're measured on their performance reviews. Then quietly reinforces the project around hitting those goals. Bonus alignment. This is how you become an asset to their career and not just another vendor they don’t want to be rude to.

Knowing the deal will almost die three more times.

He says it twice. Every big deal almost dies more than once. Pricing pushback. Legal grinding. Sponsors going dark. Timelines slipping for reasons that have nothing to do with you. You can’t always prevent this, but you can stay calm and warn your execs ahead of time so they don't lose their minds on top of it all.

Patience that passes as persistence.

This particular deal had a 30-day ghost period. A 45-day reschedule. A near-blowup in a Target parking lot five days before Christmas. The reps who win these (like Chris) aren't sitting there screaming into their pillow as they wait. Send a competitor article. A market brief. Something actually useful. They stay in the conversation without making it weird.

Negotiation, but as a team sport.

When legal got stuck, he asked both sides for their top three must-haves and cleared six issues in twenty minutes. When the sponsor needed to shave price, he gave her a number that protected her bonus instead of his own ego. When a junior exec tried to push the start date into the next year, he didn't argue. He called the senior exec and let him handle it.

While you may be the one orchestrating the whole thing, deals this size are absolutely a team sport whether you like it or not.

The reason most reps never see a commission check like this is because they are simply optimizing for the wrong game. You can make more cold calls, run better demos, but the stuff above is what’s going to get deals like this across the line (and get you paid).

Think of it as more of “deal operating” vs. traditional “closing” and you’ll be better off.

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