The Wisdom Wall

“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, you probably did something wrong.”

“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, um, an expert in driving sort of like top of the funnel, right? Because as you know, right, any sort of organic…”

“the sort of cold sort of outreach playbook, right, of like, let's just sort of, 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, it's sort of table stakes. You have to do it. On some level, but it's, it's the response rates are…”

“I don't, I don't want to, if we're making cold calls, we're doing something wrong, right? If we're, 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 you figure it out, right? They're not just going to be a…”

“There is no one sales methodology that is going to answer you, 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 value selling in you, right? In reality, like if you're…”

“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, they're probably, you're paying them a lot. Maybe they're even overpaid, but like, You know, that there's a, there's a, you know, cascading effect of…”

“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, and have success, in my opinion, to expect to succeed all the way to the finish line on the backs of that are not, it's not enough.”

“Equity, if a VP of sales candidate or a CRO, uh, 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 candidate that is, doesn't care about the equity and…”

“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 to create the content and collateral myself, ah, most times,…”

“you're not going to get where you want to go on the backs of, you know, sort of a single threaded go to market strategy or top of the funnel strategy.”

“some people shy away from that because they think it'll sort of drive, have them sort of unfocused off of like, well, I don't want somebody dreaming about being a VP of sales when they're an account executive today. But in my experience, uh, people with that kind of ambition, um, very rarely are they unwilling to put…”

“the most in-demand people, VPs of sales and CROs are tremendously risk averse. Most people don't understand this, right? They're not gonna put their, lean their, their chin out for you, most likely. And so, um, they're gonna do their due diligence really starting at no, right? So they're doing due diligence being like,…”

“I definitely think leaning into the partner, A partner sort of specific role earlier is like sort of a reality now. It's a, it's a smart thing to do, uh, because, you know, everyone's looking for, you know, a way to diversify, like I think Robert talked about, or diversify your top of the funnel and demand strategy.…”

“They're going to be really hard to get a really good sale, a really good sale, you know, salesperson to come in with no proof, right? Like, Hey, can I talk to a salesperson and sort of ask, you know, how much they may, you know, how much they've closed, how much they make. And you're like, well, we don't really have…”

“the problem is, is I viewed like these sales leadership roles are like sort of listing a house on the market, right? The longer it's on the market, the, the harder it gets to fill it because, you know, there's more community within the sales leadership community than ever, right?”

“If I were a founder looking for a VP of sales right now, I would be, and I didn't, you know, I didn't have, you know, a big network of sales leaders that I knew, or whatever, you know, whatever the terms of the scenario are, like, I would be meeting with people in a sort of unofficial way, you know, sort of like, uh,…”

“in my experience, most meaningful products that I've worked with or sold, there was a pretty, there was a behavioral change component to it. Right. Like it's not just, Hey, we do X just three percent better than Y.”

“I think realizing what your, not just what your strengths are, but what your weaknesses are, and then weaponizing that before your, your competitor exposes it as a liability, right? Taking, why do, why should we lose? Okay, we, if we know why we should lose and why they should yes, and we know that, you know, like…”

“What most companies do is they hire these huge advisory boards. Sometimes 1015, 20 people, of which you're not gonna get a lot of distilled feedback.”

“pick an executive search firm that specializes in sales leadership searches, and is not going to be so big that they can't give you the attention they deserve.”

“do they have a list of people that they would hire, um, when they came in as the, come in as the VP of sales? I'm huge on this, not everybody else is, but this is critical for me because, uh, one of my first sales jobs, I worked for a VP of sales that had this phenomenal resume, and he was always asking me for…”

“I think when you, you know, your first 10 sales hires are guys. It's going to be tough to diversify from there because there tends to be sort of a network effect of how you hire, and I think moving outside your comfort zone early on, and obviously you want to hire the best possible people for the job, but I think you…”

“great VPs of sales and CROs, they admire the work of their peers. Um, certainly Jennifer was somebody that I knew and respected even though she didn't even know me. When I reached, when I wrote a blog about the top five VP of sales and tech that are women, she didn't even know, I didn't even know her, so. But I…”