The Ledger, every show

“If you tell them you have a fully baked, ready to go product, they're not going to give you honest feedback. It's very hard to give, to say to a founder and look them in the eyes and say, Hey, we built this product. Can I show you what it is? You're just going…”

“Founder-led sales is more about, is not about revenue on day one. It is about learning as fast as humanly possible to get to that pulse. So that you can earn the right to sell. There's this concept that I talk about, which is like, you're going out to run sale…”

“On the first call, my fundamental belief is that the demo is a bit of the only carry you control in the sales process, right? Once they see it, it's kind of like, you know, pitching an investor. Once they take a look under the hood, that dream dreaminess in th…”

“Everyone that I know says they have a bottom of funnel problem. It's never a bottom of funnel problem. It's a top of funnel problem. I've actually never seen a bottom of funnel sales problem. It's always qualification, not qualification, which is a symptom of …”

“Interesting thing about legal. It's the largest budget line item in the enterprise kind of budget, right? Sometimes three to four times other budgets and it's forever. There's always more money for legal.”

“Most, most C-level executives don't respond to marketing. They might see your brand. They're not going to respond to a marketing campaign. Okay. It will respond one-on-one and the best individual to one-on-one to a corporate executive is the founder.”

“So as soon as the demo closes, you are texting the woman or the gentleman or whomever that has helped guide you to this point. How do you think that went? Can we grab, can I call you in like five minutes? I just want to, I want like a fresh debrief. They will …”

“There's always someone in the organization that's going to kill a deal. There's always somebody. You need to protect that as much as possible and make sure everyone is aligned and excited by what this is.”

“Try to hold out on talking about pricing until post demo, because you might, they might assume, oh, this is three times what I'm spending and not know why it's three times.”

“Your price should be predicated on your sales cycle, right? Like if you can get a deal done in 90 days for a hundred K, do that all the time. Right. If it takes nine months to get a deal done, you've got, you probably should be charging two 5300.”

“80%. Succeed post pilot. Correct. Yeah. Okay. Amazing. I find that. Yeah.”

“The red lines are extensive. See if you can get legal on a call live and just talk through them. That will accelerate your sales cycle versus a bunch of back and forth, a bunch of back and forth, get them on a call.”

“At this point, the deal will not fall apart. You just need to work closely with them to like, make sure they understand where you're coming from.”

“You don't really get taken seriously for 10 K. You get way more taken seriously for a hundred K's.”

“A really good salesperson, your commission on a 10 K deal. You're not going to get a great salesperson. They're going to want to do, they're going to want to be anchored to like, how can I sell a 250,000 dollar deal? How can I sell a half a million dollar deal…”

“I think it's about like, what game does the founder best understand? Are they like an incredible marketer and have some like competitive edge for how they can like win a massive audience? I would say go SMB and marketing led. Or are they a bit more you know, r…”

“And getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why, like, that executive needs to be involved. Because as soon as the executive picks up a phone and tries to ge…”

“Well, I, I'm a ten million dollar business. I'm like, in this small business space, you're zero dollars in enterprise. It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition. It's a different deal structur…”

“Yeah, because of the 50, 50% failure rate, I think that's exactly right. So yeah, even, even, even a taller order, go, order, go find two people that are good. But yeah, I think that that's right because, you know, one in two will fail.”

“Are you selling a 5000 dollar deal? It's gotta be marketing led to make that, to make the engine work. If you're selling a 100,000 dollar deal, you're doing outbound day one.”

“And founder led sales is really, really, really important because in the very, very, very early days, when there is no brand equity, when there is no marketing engine running, when there is limited to no reference ability, the founder is the product, right? Be…”

“Their day one market vision is never the same vision that takes them to product market fit.”

“Most startups are turning non-consumers into consumers, so that's why this kind of fits well.”

“I would say a healthy conversion rate from outbound probably sits around You know, when it's mature around five to seven percent, sometimes it could be two to three percent. Sometimes I've seen eight to 15% cause it's coming from the founder and they're solvin…”

“Before you buy any tool, don't even think about tools. I feel like people get, turn everything into this complicated mess with all of the tools that they start integrating. And then, you know, they're engineers. I get it. So they, now they start to engineer th…”

“Even if you're selling down market, mid market, or enterprise, volume comes once you've identified it and know the parameters. Parameters then allow you to do really strong enrichment with a clay. You now know the types of questions to give it. If you're not a…”

“One of the worst things someone can say to me is we're better than X product. Cause then I asked them to define that. And then I asked them like, okay, how do we measure that? And then I say, okay, should we give this company another year to like give them thi…”

“So I think the first is it has to be a growing and widening problem. No one's going to spend time fixing a pretty fixed problem because it's not necessarily really a priority anymore. It's maybe a pain in the butt, but like, it's not a priority if it's not gro…”

“Please, please, please do not ask questions. Like what keeps you up at night? If you had a magic wand you know, what are your pain points today? Cause I can guarantee you that answer changes every single day.”

“If they won't give you time on the calendar you could say, listen, great, like, feel free to email me. Maybe they're just being honest and they don't have their calendar available, but nine times out of 10, it's usually I don't have the heart to tell you I'm n…”

“You absolutely need to time box this. I would time box it as 90 days, and then what you can say in the next 90 days, we'll scope where we are and like what you need. Scoping out more than 90 days, listen, everything, so much is gonna change.”

“If you're selling a 3000 dollar tool, you absolutely want to be demoing as fast as humanly possible because it's a high volume game up market. When you're talking about hundreds of thousands of dollars, you want to slow that down as fast as possible.”

“So this is when you want to truncate contracts to a technology contract and a service contract. Service contract allows you to onboard them, get them prepped, come in and educate all of the users about what they're about to go through. So that then there's an …”

“The beauty with enterprise is once you're in, you beat out your competitor for a short period of time. There is a little bit of a moat there, but it's not forever. You all have intel that no one else will also have. Meaning, you're a part of conversations. You…”

“Discounting is great if you're getting, if they, if they're doing something for you far and beyond. Like for example, if they're a design partner if they're allowed, if they're going to be a reference for two years, if you're, if they're going to give you some…”

“Enterprises know that the process and the length to get the deal done is what costs more than the technology itself. Meaning the effort it takes to get through their system. That's why they're willing to spend so much, right? Like sometimes that's actually mor…”

“I would say anywhere between 50 to 200 K depending on the business unit you're selling to. That's kind of like sweet spot. Like they're used to something like in that realm.”

“It's so hard to give a founder hard feedback because they've just dedicated their life to this thing, right? Like who wants to be the bearer of bad news? And sometimes you just need to let that action speak louder than words.”

“Co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate. 99% of it.”

“Send a word document. Do not send a PDF. Cause they're going to always red line. Always send a word document of your paper”

“Another piece that's important with procurement is explaining exactly what you do and don't do. Because if you say you do a bunch of things and they can't really place you, they're going to send you to the kitchen sink of contracting and MSA. Which are, is goi…”

“If you're dealing with a highly regulated industry, Just know it's going to take a bit longer. Sometimes, 20 to 30% longer. So, like, a highly regulated industry, nine to 12 months on, like, conservative, on the conservative side.”