Opinion
Cassidy: EchoSign's early team was much better than LinkedIn's
“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…”
Assertion Not checkable as stated
Cassidy: 80% of startups lose their first sales VP in year one
“I would guess probably eight in 10 startups probably fire or lose their first VP of sales inside of a year.”
Insight
Cassidy: VPs of Sales must know their initial hires before accepting jobs
“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.”
Assertion Contradicted
Cassidy: 90% of first startup VPs of Sales turnover within 12 months
“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.”
Insight
Cassidy: Startups should hire a demand-gen leader before a sales leader
“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…”
Insight
Cassidy: Mass quasi-personalized cold outbound email is waning in effectiveness
“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 …”
Insight
Cassidy: Relying on cold outreach early is a mistake for B2B startups
“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.”
Insight
Cassidy: The vast majority of VCs will not continuously open doors
“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…”
Insight
Cassidy: Rigidly adhering to a single sales methodology will kill a startup
“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 …”
Insight
Cassidy: Making top sales reps highest paid employees is net positive
“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…”
Insight
Cassidy: Early sales leadership's institutional capital is rarely replaceable
“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.”
Insight
Cassidy: Mass-produced outbound emails no longer work as buyers grew wise
“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…”
Assertion Not checkable as stated
Cassidy: Only ~30 VPs of Sales have scaled SaaS to $50M ARR
“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…”
Insight
Cassidy: Sales leaders prioritizing equity over base salary signal higher confidence
“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…”
Opinion
Cassidy: Shifting Customer Success to Account Management Increases Churn Risk
“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”
Insight
Cassidy: Marketing should focus on demand gen over sales collateral
“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…”
Prediction Didn’t hold up
Cassidy: Justworks has an imminent IPO coming
“I mean, obviously Robert's got an IPO, imminent IPO at some level for JustWorks coming.”
Insight
Cassidy: Startups cannot scale on single-threaded top-of-funnel GTM strategies
“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.”
Assertion Not checkable as stated
Cassidy: Outbound SDRs cost $1,000 to $2,000 per qualified meeting
“And if somebody told me, I'm not sure how accurate is, but it seems accurate, you know, on average, like with an outbound SDR, it's like basically like a thousand, you know, somewhere between a 1002 thousand dollars cost per sort of qualified meeting.”
Insight
Cassidy: Do not shy away from hiring highly ambitious AEs
“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 people with that kind o…”
Insight
Cassidy: Top VPs of Sales and CROs are tremendously risk-averse
“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 chin out for you, most likely. And so they're gonna do their due diligence really starting at no, r…”
Insight
Cassidy: Startups should hire dedicated partner roles earlier to diversify demand
“I definitely think leaning into the partner, A partner sort of specific role earlier is like sort of a reality now. It's a smart thing to do because, you know, everyone's looking for, you know, a way to diversify, like I think Robert talked about, or diversify…”
Disclosure
Cassidy: CoSell pays sales advisors $500 a month to open doors
“It means, you know, put them on payroll, you know, so that's what we do. We pay them 500 bucks a month. They open a certain number of doors for us and you know, wet their beak a little bit, right?”
Insight
Cassidy: Top sales reps won't join startups without proven high earners
“They're going to be really hard to get 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 yo…”