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Daily
Every morning
Weekly
Tuesday recap
We've entered the era of The GTM Skills Crisis. Quota attainment is at historic lows. Sales cycles are getting longer. ACVs are small and tactical. Win rates are down. 3 reasons this happened: 1. The economy flipped overnight 2. The workforce went remote and got younger 3. GTM motions got more complex This isn't a skill gap. It's skill DEBT.
The single most underrated enterprise selling skill: Navigating decision dysfunction. Always assume that dysfunction is the status quo. And that it's your job to make it as functional as possible. That's why you get paid the big bucks in enterprise.
Enterprise sellers: Never let the types of deals you're closing today stop you from closing the types of deals you dream of closing. Good is the enemy of great: $50k deals are the enemy of $500k deals.
"Don't show the product on the first call" is a LIE. Sometimes a teaser demo OPENS discovery. Show just enough to get their mind spinning. Not too much. Not too little. Use it to spark questions and conversation. Discovery and demos can be happily married...
90% of AEs can’t build the cost of inaction. They ask generic questions: • How does this impact you? • What’s the cost of doing nothing? When you ask questions like that? You're not a trusted advisor. You're a manipulator. The best salespeople know something others don't:
Great sales calls start with planning. Before EVERY call, answer 3 questions: 1. What next step will I recommend? 2. Who will I recommend be involved? 3. Why this next step and why those people? If you can't answer these before the call, you're winging...
Getting access to power is one thing. Getting a 2nd or 3rd meeting with power is entirely different. Only sellers with sharp business acumen get the latter. "Continuity of power" is the ultimate metric nobody tracks. If you can't get meeting #2 with the...
Want access to the VP but stuck with a manager? Try this before your demo: "My goal with this demo is to get you so fired up that you're willing to sponsor a meeting between me, you, and your VP. Is that a...
The word "impact" feels manipulative to buyers. They've heard it from every seller. Replace it with "ripple effects." "Can you help me understand the ripple effects this challenge is having on the rest of the business?" Sounds more sophisticated. Signals business acumen. Gets 3x richer answers.
Weak sales managers manage calls. Average sales managers manage deals. Good sales managers manage forecasts. Great sales managers manage their people's skills & capabilities. Because they know one thing: Revenue is an outcome that expert-skilled sellers produce. Skill management = proactive management.
There's a book called The Inner Game of Tennis. I remember almost nothing except this: You can get better at tennis just by WATCHING great players. Your subconscious picks up their mannerisms and mimics them. Same in sales. Binge watch your best rep's Gong calls...
The difference between how good many sellers *think* they are vs. how good they actually are never ceases to amaze me. Arrogance caps your career and income.
Become a master wordsmith. Words trigger mental pictures. Mental pictures trigger emotions. Emotions trigger actions. Actions close deals. Stop paraphrasing your buyer. Stop putting your own twist on things. Use THEIR exact words back to them. That's how trust is built.
Pipeline generation isn't a quarterly sprint. It's a daily discipline. 2 hours every single day. No exceptions. No excuses. Your future self will thank you when everyone else is scrambling and you're closing deals from seeds you planted months ago.
There are two winners in every deal: 1. The seller who won 2. The seller who ejected early and didn't waste time Losing deals is NOT the enemy. Time spent on mediocre deals is the real income killer. The highest-paid sellers don't chase bad deals....
The best discovery question I ever learned: "What's going on in the business that's driving this to be a priority?" It sounds innocent. But it gets prospects to reveal the boardroom conversations that led to their budget approval.
Never ask: "What's your decision-making process?" Instead ask: "What steps does your company need to take to make a confident yes or no decision?" Same intent. Completely different depth of response. Then DON'T take their answer at face value.
Quote a $600,000 proposal with a straight face. That's a superpower. The best salespeople talk about money like it's nothing. "$600,000. Pass the salt." The worst salespeople tremble when price comes up. The turning point: realizing your value is a tsunami compared to the tiny...
The single most underrated enterprise selling skill: Navigating decision dysfunction. Always assume that dysfunction is the status quo. And that it's your job to make it as functional as possible. That's why you get paid the big bucks in enterprise.
3 years ago, almost to the day, I sat down for coffee in Los Altos with a man who earns $100M per year in SaaS. Yes, you read that right. 9-figures. Every year. Here’s what struck me:
Chet Holmes managed a magazine dead last in market share out of 15 competitors. He found 167 accounts drove 95% of industry revenue. He stopped pursuing the other 1,833. Cold turkey. Every 2 weeks: direct mail + phone call + fax. 4 months later:...
I’ve written 1,394 LinkedIn posts about Discovery. But according to the data… I still have more to learn: Last week, we released AI Skill Intelligence on a limited basis. It measures your proficiency against industry-standard revenue skills. So I ran my own discovery calls...
Sun Tzu said: "Fall like a thunderbolt." In sales, this means respond FAST. If you take 2 days to follow up after a demo, your buyer takes 2 days to respond. If you respond in 2 hours, they mirror that speed. Money loves speed. Speed...
