The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 24 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Enterprise Sellers Asking Basic Discovery Questions Will Fail
“If you are a seller today and you engage a potential buyer and you're wasting your time asking about what fucking CRM that they use or where they're located or who they do business with or how they make money, you're fucked. You just don't even call.”
Traditional Sales Discovery Is Dead and Replaced by Teaching Buyers
“Discovery as we know it is fucked, right? And what, when discovery, I took out the word discovery from the sales process and I inserted the word teaching. And words matter turns out. And what I would prefer my organization, what they do when they engage with a…”
Founders Should Not Build the Initial GTM Sales Playbook
“I would argue that that sheet music get created by a professional that has the pattern recognition that has seen it before. So I do not believe a founder should build that sheet music or playbook for how we're going to go to market.”
Combine CS and Account Management, but Separate New Logo Sales
“If I'm a founder right now, I would think about combining those roles a bit within CS and account management, but separate that from your new logo hunters, make sure that separate it.”
Heavy Customer Success Teams Signal Difficult Product Adoption to Buyers
“If you have a heavy people or human oriented customer success organization, Could be a red flag for the buyer.”
Brand Credibility, PMF, and Financial Trust Block Enterprise Software Scaling
“The three biggest hurdles in taking that holy grail of moving up into the enterprise, those massive ACBs, the sexy LTV to CAC, those sexy logos that you talk about, but the hardest problems. First, the credibility. No one knows who you are, especially in the e…”
The Worst Sales Deal Is One That Takes Too Long
“The worst deal is the one that takes too long. Drop your price and go get the fucking deal and move on. Just move on. Go get the next deal.”
Replace Underperforming Sales Reps Instead of Repairing Them
“The right answer is you move on and you bring in new talent.”
Best Practice Enterprise Sales Compensation Is a 5:1 Quota-to-Pay Ratio
“Best practice is a five to one ratio. So if I'm going to pay someone 200 pounds sterling, I want them to have a million quid as a goal or as a quota, right? So like thinking about what the what that ratio that you're willing to pay now in a startup, you may ha…”
Sales Friction Occurs Most With Product and Marketing
“Sadly it's product and marketing because salespeople they want a product that's applicable for everyone, right? So they complain about the product, which is wrong. And the second reason why sales wrong is on marketing. They want a fat pipeline of buyers that a…”
Enterprise Buyers Always Believe They Are Unique
“Because those big companies, they all believe that they're special snowflakes.”
Enterprise Clients Doubt Startup Financial Survival
“And third, your financial, because as you move up market, they just don't trust you. They don't trust that you can survive.”
CMOs Must Be Sellers and Sales Heads Must Be Marketers
“So the CMO, the marketer, must be very effective at selling and the head of sales must be very effective in marketing.”
Software Renewals Require Proving Time to Value Over ROI
“And we now must prove not just ROI anymore, but it's time to value what we're going to do differently for them.”
Trade Contract Discounts for Written Customer Reference Agreements With Early Clients
“Think very carefully on when you're negotiating these terms with your first 25, say, enterprise customers, give and gets. You're going to need their help to get this going. So give them the concessions that they need. Make it worth their while and get it in wr…”
Enterprise Price Cuts Should Be Trades for Marketing Value
“It's flexibility in negotiating terms. It's not necessarily just discounting the drop of your price, but go get something different. So as an example, if my price is a hundred K, I will do this deal for 60. And then Harry, what I expect from you is a story abo…”
90% of Initial Sales Prospects Cannot Sign Order Forms
“That happens nine times out of 10, and frankly, they are not the person that can sign the order form”
Belittling Competitors in Sales Rarely Works
“What I will say about with the competition and selling against your competition is when I'm directly the seller is to not belittle or throw mud at my competitors. It rarely works. If you roll around the pig, if you roll around in the mud with pigs, you just ge…”
Enterprise Expansion Yields Slower Returns on Speed Than SMB
“You need some capital to go into the enterprise and you won't get that immediate love. You won't. It takes time. It doesn't have the same return on speed as the SMB or mid market will have.”
Companies Fail Candidate Interviews by Asking Repetitive Questions
“What companies fuck up so often is that let's say there are three or four people that interview that candidate. They all ask the same damn questions. So you're not getting enough data from that candidate in the short time allowance that you do have.”
30-60-90 Day Plans Effectively Test Candidate Curiosity and Drive
“When I do take-home tests, it could be something as simple as what would be your 30, 60, and 90 day plan when you start with me. That could be it. So then you can grasp their intellectual curiosity. You can grasp their drive, their passion about your product a…”
Enterprise Sales Reps Take a Full Year to Fully Ramp
“If you're selling into the enterprise and let's just use an ACV of a hundred K, right? You want to let that rep ramp for about six months. Move slow in order to move fast later, but don't wait those six months to measure their performance. Have stage gates alo…”
Founders Mistake Waiting 18 Months to Evaluate Sales Reps
“In your sales process, you'll know within the first six months, if this rep is going to cut it in the enterprise or not, you should. And what I think founders make a mistake is they wait for how many deals that they get a year and a half later.”