The Ledger, every show

“I can tell you no great VP of sales is ever going to take a job with a company that's dependent on an outbound go-to-market model. That's just, nope.”

“The entire outbound go-to-market SDR model has collapsed in the last five years, three years and it doesn't work anymore.”

“Like you should, discovery is five minutes. That's what discovery should be. And if you need more than five minutes to do discovery, then you really, you're not putting the work in to understand who your customers are.”

“I've never seen a sales resume that was a hundred percent honest”

“Versus like, oh, this guy was a sales force for 10 years. I won't ever hire that person in a startup generally, right? Because there's no, no comparable motion, right?”

“Ultimately, what AI does is probably get put the SDR function back under marketing.”

“For my first five sales hires, I would never hire somebody out of network.”

“Most of what we knew is off the books, has no relevance anymore to how we go to market, to how we build sales teams SDR teams, everything is, we're very much in a place where it's like, the more you can unlearn You're, the more that you can walk away from bad …”

“Investors are notoriously bad hiring recommenders. I'm sure I know you're different, but most, most investors and VCs like They make a recommendation, and my advice would be like, just, no.”

“DocuSign had just, that's all DocuSign did was go C-suite, Salesforce's endorsement, but there was all, there were two other layers of people, right? Evaluators and users that were, and then we just basically, Sam and I were like, yeah, And at that, at this po…”

“The team we had at EchoSign was so much better, by the way, there are some great people on our team at LinkedIn, by the way, phenomenal people that have had great success, but overall the team we had at EchoSign was way better. It was a way better team general…”

“I would guess probably eight in 10 startups probably fire or lose their first VP of sales inside of a year.”

“There's a thousand companies competing for attention from one buyer. When, you know, you go back 15 years ago, and that was five for 10 companies. And so, how are you gonna, like, mass produce some sort of out, quasi-personalized outbound go-to-market model th…”

“You talk to many, many founders, and the question I ask is like, why'd you start this company, right? What was the problem that you wanted to solve? And a lot of people can't answer, they can't answer the question.”

“You should know what their problems are and what their psychology is before you ever get on the fucking call, right? Like, that's just, that's zero point zero. Well, if you need to get on a call and spend two and a half hours doing discovery on your own behalf…”

“So it's like, usually there's like, maybe there's three different paths. What the opportunity or problem here is, is one of three paths. Or four paths, and you better know exactly what those look like and what every turnoff is on those paths before you ever ge…”

“Yeah, you should not hire a VP of sales as your first sales hire.”

“There's no comps there for like Salesforce or Oracle or Adobe or whatever, right? You don't ever have to make that kind of case there ever.”

“In the same way, like, if you're expecting to hire people off the street, expect their super high turnover rate, it's just, you know, there's a 98% chance that each hire is probably not gonna work out.”

“I believe in running, like, really, like, sort of a monthly, tight monthly Sort of process. No, Matt, really quite frankly, no matter what your ASP is, that's just what I believe in the startup is the right thing to do because it, it's, it makes it really hard…”

“If that's your philosophy and everyone's getting fired fast or first or whatever, then there's probably something wrong that's maybe not all them.”

“For me, it's all about taking the people that have proven they can do it for, in your company, in your system, with your customers, and letting them run, and then taking them as far as they can in their career.”

“Most of the time, you try to, like, overlay the strategic team and the failure rate is about 99%.”

“If you're a VP of sales and a, you know, you go to a startup or a growth company, you should have a good idea about who the people that you want to hire before you actually take the job. And if you don't, then you probably did something wrong.”

“I think there's some statistic that like, 90 plus percent of first VPs of sales hired at a startup turnover inside of 12 months or less than 12 months.”

“I would say most companies are probably higher, like a marketing leader, right? Like, you know, before sales leader, I mean, obviously in a startup, being able to hire a marketing leader, that's, that is an expert in driving sort of like top of the funnel, rig…”

“The sort of cold sort of outreach playbook, right, of like, let's just sort of spam the market with sort of quasi personalized communication is waning in effectiveness, right? You should do it, by the way. It's sort of table stakes. You have to do it. On some …”

“I don't want to, if we're making cold calls, we're doing something wrong, right? If we're blasting cold emails, we're doing something wrong.”

“You know, sort of, hey, let's tap into our investors, VCs, and they will help, but they're not going to continuously help because at some point they'll just say like, yeah, I made some interest for you, bro. Like, you know, the reason I invested in you guys is…”

“There is no one sales methodology that is going to answer you know, that is going to solve all the things in front of you, right? And so you see some people that are like, I subscribe to this theory, like, you know, band or solution selling or spin selling or …”

“Having some sales people that just absolutely crush it and are the highest paid paid people in the company is almost all net good, you know, from a, you know, they're probably, you're paying them a lot. Maybe they're even overpaid, but like, You know, that the…”

“The amount of like, you know, sort of sweat equity and intellectual capital that's been built there with that team is not replaceable most of the time.”

“Trying to like inundate the market with just this massive amount of like quasi personalized communication, right? Everyone's wise to it now, and you just can't mass produce that and have success, in my opinion, to expect to succeed all the way to the finish li…”

“I sort of ballpark it at about 30, 30 VPs of sales or CROs have taken their SaaS companies to fifty million in ARR plus. That's an unofficial number, so you can agree or disagree with that. But that's not a lot of people, and when you talk about hiring, ah, yo…”

“Equity, if a VP of sales candidate or a CRO wants, is passionate about the equity stake that they want, or that they want to get, I think that's a good sign, because that indicates their level of confidence that they can deliver for the company, versus maybe a…”

“A lot of companies are moving towards this account management model, which I believe is gonna be more, or, More risk for churn-centric environment”

“As far as collateral and content, you know, from a marketing standpoint, that's where I'm least interested in marketing, spending their time. So, certainly focusing on sort of demand gen, MQLs, et cetera, is what I want from my VP of marketing, and I'm happy t…”

“Sales playbooks need to be very, very rooted in what is the customer thinking? Not what is the customer thinking on behalf of a company, but what are they thinking? What is their personal what is their personal opportunity and fear and upside? And I've always …”

“Ultimately, the playbook the in ink should probably be written by the VP of sales, but yeah, you should have a, you know, sort of a loosely built playbook as a founder.”

“We closed a hundred percent, you know, we just became profitable in my startup. We close all of our own deals, myself and the co-founder. We don't have any salespeople.”

“If you don't have investors that can recommend good people, and you don't have your own network, I would get Advisors or influencers in your space, right? That have, you know, and make them partners, you know, give them equity and maybe pay them because their …”

“If what you sell today, if you, if that's not a compelling story, then why is it going to be compelling here? You know, and so we would have people that we were like, yeah, we really like this person you know, going through the interview process, and they woul…”

“I would say the Echosign model. Is a great model for times like this, right? Which was pay of really high percentage after they paid for the, after they paid for themselves, essentially, right?”

“You generally know in a quarter.”

“But like, yeah, I'd say a quarter, you know, a quarter plus some change, you should start to see things going, you know, and like, we would always say by the second quarter, you wanna, by the end of the second quarter, you wanna fully ramp salesperson.”

“And this is how I've run it in every company I've ever been in. And it's worked a hundred percent of the time with various, very, very types of sales cycles and types of products. But we had a, you know, everyone would have a monthly commit. Here are the deals…”

“Usually more, if there's like a three-day gap, and it's like a committed deal, and like maybe there's a contract in legal or whatever else, you're not closing that deal, right? Generally speaking, right? And so that's, that was one of the things that I would a…”

“Usually when you lose deals, it's not about, it's what you didn't do, you know, five steps prior, right? Or what you didn't establish or, you know, There's all sorts of stuff when you try to do a post-mortem on it, where you can look back and you can say, here…”