The Ledger, every show

“So I say the mid-market doesn't exist, because what is a mid-market hire? It's either low end enterprise or upper end SMB. And if you bleed those two games, you're going to lose. They're so distinctly different.”

“Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of, you know swings to continue to stay in the number one, staying in the number one spots, the hardest part, right?”

“There's this running statement where a lot of VCs will say, don't go after tier one logos, go learn down market or go learn from like logos that don't necessarily carry a lot of weight. The ones that carry all the weight are the ones that are willing to take a…”

“Selling them as service, even though the technology is powering it on the back end, is the fastest way to get your foot in the door. It's what they know how to buy.”

“And there's only two entry points starting at the very, very tippy top, meaning going direct to the decision maker, the chief legal officer, or finding the individual that would be maybe one step removed. Okay. I personally, other people would argue with this.…”

“The most successful salespeople are not trained salespeople. That's why founders are so good at this.”

“A enterprise organization might reach out to you because they're going through a due diligence process to say, Hey, we'd love to see what you guys have built. Will you present this to four or five people? Don't do it. If you're either a checkbox and you don't …”

“The whole game is expansion. If you're not going from a hundred K or 250 K to three 50 or 500 the following year, it's not an enterprise motion.”

“Time box it to two or three days. Don't make it two weeks. Okay. I've done this enough times to say people will go in usually for half a day and get what they need out of it. Okay. Shorten your sales cycle by two weeks by doing two to 48 or 72 hours.”

“If you're selling a 100,000 dollar deal and you're pulling a Ford deploy, like your economics are, it's going to get messy.”

“Those are buckets to understand how to understand a weighted forecast, right? Like a proposal or something mid funnel might be weighted at 50% of the deal value for the for the pipeline. Something in contracting might be weighted at 80% and something in intro …”

“90%. Yeah. Because like enterprise sales is, it's mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process.”

“The win rate for enterprise, a good, healthy win rate. It's actually probably going to surprise you. It's not. Meaning of all sales qualified leads or opportunities with a healthy win rate is usually around 30 to 35%... 25 to somewhere between 25 and 35%.”

“If it's, if you, if your win rate is higher than that, your price is too low.”

“You need to vision cast. You need to sell to a gap. Don't sell to a problem. There's a very big difference between problem selling and gap selling. Problem selling is highly specific, more technical than not. And it's the way that every salesperson is going to…”

“And that's why founders are so good at selling because they, they're, they naturally go to vision selling and vision casting versus a typical trained salesperson is find the problem. You know, ask these questions and it just kills the vibe. It just feels like …”

“If you're venture backed, you can't be selling 10,000 dollar deals to the enterprise. You'll get killed. Or you've already lost the game because you're playing a small business game in, in the wrong sector.”

“Enterprise companies are very used to a land. When I say like the first initial contract, this is somewhere between 75 K and a 150 K. Very used to that. In fact, that's probably where you want to start”

“Design partners are incredible. They are the hardest logos to upsell, meaning go from design partner to full rollout customer. So like, don't expect these people to be your million dollar pipeline.”

“Most enterprises I'm talking to mention Gemini. Yeah, or Microsoft Copilot. So I don't hear much about Anthropic, to be honest.”

“So that's why the hundred K is such a safe zone because even for 10 K, you might have to go through procurement. So this is like the surest way to make sure that like you don't listen, I've seen 10 K take nine months to close.”

“A VP of sales at a large company, I would say they're best suited for a large company because one to 10, you're running through walls, right? You have to figure out, you know, you're doing a lot of convincing. You're doing a lot of educating. You're doing a lo…”

“Every single enterprise deal I have done, The deal is done. The deal is closed and pretty much done through text. It's not on email anymore.”

“And the thing about AI tools is they're all pulling from the same databases. So I'm like, I want to email someone not in the database that's getting hit by a million folks.”

“When a problem is truly being felt by the market, people will get on the call. People will respond. And there, you know, if I can compare two engagements at a time that we're running, I see one where it's a two percent interested rate, and then I'm seeing anot…”

“Everyone can keeps coming, always comes back to like, we have the sales problem. We have the sales problem. We have, you know, an outbound problem. And yes, there could be some technical things going on that you need to look at. Like maybe you've blasted, you …”

“I have this like theory that like, maybe you shouldn't hire any salespeople until series A. Right. Because seed is all about experimentation and proving out that experiment. And then obviously series A is about, you know, exploiting that learning, but I see so…”

“I would say 40 to 50% have to sell some form of service before they can sell a technology.”

“Even if you're selling a, if you sell a 100,000 dollar solution, it is the same exact process to sell a million dollar solution.”

“The enterprise organizations are more Sensitive to the process you take them through from a sales motion than they almost are with demoing the product.”

“Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable.”

“The fastest way to commoditize yourself is to go into some sales script, like budget authority, need timing, like that should be in the back of your brain. You never actually ask those questions.”

“Now, if you need something a bit more integrated and it, and it's a far more technical solution, what I'd highly recommend is do it for a month or two months, charge them for it, and then use that, that fee that you charge them for and credit it back to them i…”

“And I know every company is an ARR. Recurring revenue focus, but services is still the largest line item in budgets.”

“I've had clients say to me like, Hey, like, I don't know if we're in a position to do this. And I've straight up said to them, you are a liability, not closing this gap. And they're like, sometimes they just need to be like, again, you need to know if you're i…”

“Like so many people will create like AI reports that they can send to their clients or like AI imagery, or like, I dunno, you name your flavor. And it's like, anyone can do that. It just feels salesy.”

“In the age of AI, where it's all about Sucking the oxygen out of the room and winning the deal and getting your foot in the door as quickly as humanly possible before someone else tries to take that. You want to get to the enterprise as fast as humanly possibl…”

“Very, very hard now to go from those three users that you just priced them at a small business, in a small business way, turn, turn that into a hundred K because now it's documented what they're actually paying for this. So you're stuck. You've kind of like an…”

“That's very hard to defend a 10 X, 10 X jump. They're going to want to see 15 X value.”

“The problem with channel partnerships and why I don't believe in them is there are a hundred of you on this list, right? And you're expecting them to sell it on your behalf. Biggest no, no. They're not vision casters. They're not visionaries. They're consultan…”

“And don't be afraid to fire, like one in every two salespeople usually are fired. It's a very, yeah, it's like, it's a very high failure rate.”

“I will not get in on another call with someone because on the first call, it's either a yes or no. There's no in between.”

“I don't use a tool because I believe in the manual.”

“I don't think people realize how much of a competitive advantage the founder-led sales motion is for three kind of specific reasons. One is, is that the founder is the visionary. No one's going to be able to speak to it like they can. No salesperson, really no…”

“First and foremost is relevancy. I think that matters even more so than personalization right now, because I think it's so easy to personalize anything.”

“Cold calling, I never used to do this. It is one of the most the interest rates on cold calling are a lot higher than email in many cases.”

“And I think product market fit, when you start with the market first, it's accelerated, but I will say this, I think that it's also capped on the upside. Because you're starting with the market. Versus the Airtable and the Figma, which started with the technic…”

“You don't even need to talk about the solution. Here's that's like the big takeaway, which is if you get any sales email you get, what's the primary focus of that email? It's usually like, here's what we do. But I bet if someone reached out to you with like a …”