Prediction Not checkable as stated
Cassidy: Top VPs of Sales will reject outbound-dependent startups
“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.”
Opinion
Cassidy: The traditional outbound SDR sales model has collapsed
“The entire outbound go-to-market SDR model has collapsed in the last five years, three years and it doesn't work anymore.”
Insight
Cassidy: Sales discovery calls should take no more than five minutes
“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.”
Opinion
Cassidy: No sales resume is 100% honest
“I've never seen a sales resume that was a hundred percent honest”
Prediction Not checkable as stated
Cassidy: Never hire 10-year Salesforce veterans for early-stage startups
“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?”
Prediction Not checkable as stated
Cassidy: AI will move the SDR function back under marketing
“Ultimately, what AI does is probably get put the SDR function back under marketing.”
Prediction Not checkable as stated
Cassidy: Never hire out-of-network for your first five sales roles
“For my first five sales hires, I would never hire somebody out of network.”
Insight
Cassidy: Sales playbooks older than 24 months are completely obsolete
“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 …”
Opinion
Cassidy: VCs are notoriously bad at making hiring recommendations
“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.”
Assertion Not publicly verifiable
Cassidy: DocuSign lost S&P deal by ignoring evaluators and end-users
“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…”
Insight
Cassidy: Market Glut Makes Mass Outbound Sales Models Ineffective
“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…”
Assertion Not checkable as stated
Brendon Cassidy: Many SaaS founders cannot articulate the problem they solve
“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.”
Insight
Brendon Cassidy: Reps shouldn't waste call time doing basic customer discovery
“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…”
Insight
Cassidy: VP of sales isn't good if customer paths aren't pre-mapped
“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…”
Insight
Cassidy: Founders should never hire a VP of Sales as their first sales hire
“Yeah, you should not hire a VP of sales as your first sales hire.”
Assertion Not checkable as stated
Cassidy: Reps at Salesforce and Oracle Never Need to Prove Problem Validity
“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.”
Assertion Not checkable as stated
Cassidy: Hiring sales reps off the street has a 98% failure rate
“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.”
Insight
Brendon Cassidy: Startups should run tight monthly sales cycles regardless of ASP
“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…”
Insight
Cassidy: High rep turnover and fast firing usually signal organizational failure
“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.”
Insight
Cassidy: Companies should promote proven internal talent rather than hiring externally
“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.”
Insight
Cassidy: Overlaying enterprise sales teams onto transactional orgs fails 99% of time
“Most of the time, you try to, like, overlay the strategic team and the failure rate is about 99%.”
Insight
Brendon Cassidy: Sales playbooks must target personal buyer motivations over corporate needs
“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 …”
Insight
Cassidy: VP of Sales Should Write Final Playbook, Not Founders
“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.”
Disclosure
Cassidy: My startup reached profitability with founders closing all deals
“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.”
