Mar 8, 2024 · 48m · news
Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, veteran sales leader Brendon Cassidy joins Harry Stebbings to outline why the traditional outbound SDR model has collapsed and provides an exhaustive, contrarian playbook for early-stage B2B sales hiring, playbook development, and high-velocity deal execution.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 7.1% of the talking time here. How this is scored →
Harry as informed peer 2.5 Guest teaching 4.5 Guest disagreement 2.7 Harry pushing back 1.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:37 Dismissing Long Discovery Calls
Brendon vehemently rejects lengthy discovery calls, arguing that reps who need hours to figure out customer problems shouldn't be on a sales team.
Hardest push from Harry ▶ 10:37 Challenging Pre-Call Customer KnowledgeHarry explicitly refuses Brendon's premise that reps should know customer pain points beforehand, asking how that's possible given how unique each customer is.
Biggest teaching moment ▶ 29:06 Debunking 'Fire Fast' DogmaBrendon reframes Harry's question about firing reps quickly, pointing out that immediate rep failures reflect poor leadership and onboarding rather than candidate fault.
Harry holds his own ▶ 15:27 Testing Jason Lemkin's Rep Hiring RuleHarry demonstrates deep familiarity with SaaS go-to-market frameworks by citing Jason Lemkin's two-rep hiring rule to test Brendon's perspective.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Early Career and Surviving the Dot-Com Crash | 1 | 2 | 1 | 0 | Harry opens with light conversational prompts about Brendon's career origins during the dot-com crash. Brendon describes surviving the bubble burst and having to adapt quickly. | |
| Unlearning Old Sales Habits and State of Sales Today | 1 | 3 | 2 | 1 | Harry asks broad questions about the current state of sales and what needs to be unlearned. Brendon asserts that spending ten dollars to make one dollar and outbound SDR models are completely dead. | |
| The Collapse of Outbound SDR and What Comes Next | 3 | 5 | 4 | 2 | Harry probes whether alternative channels or AI will replace traditional outbound SDRs. Brendon responds forcefully, stating no elite VP of Sales will join an outbound-dependent startup. | |
| Defining the Sales Playbook and the Pitfalls of Long Discovery | 4 | 6 | 6 | 5 | Harry directly challenges Brendon's view that discovery calls should be minimal, asking how reps can know pain points without asking. Brendon aggressively counters that buyer pain profiles are finite and standard. | |
| The Five-Minute Discovery Rule | 2 | 4 | 3 | 1 | Brendon advocates for a strict five-minute discovery rule and outlines how founders vs VPs of Sales should draft playbooks. Harry asks clarifying questions on playbook ownership. | |
| Your First Sales Hire: VP vs. Reps | 4 | 5 | 2 | 2 | Harry brings up Jason Lemkin's rule on hiring two sales reps at once. Brendon agrees with caveats, emphasizing that a startup's first five sales hires must come directly from a trusted network. | |
| Building a Sales Network via Advisors | 3 | 5 | 3 | 4 | Harry pushes on what founders without personal networks should do. Brendon suggests using domain advisors and dismisses VC hiring recommendations as notoriously unreliable. | |
| AE vs. SDR Hiring Characteristics | 3 | 5 | 3 | 1 | Harry asks if Brendon hires inexperienced reps with strong coaching potential. Brendon warns against hiring big tech enterprise reps for early-stage startups due to lack of comparable conditions. | |
| Sales Compensation and the EchoSign Profitability Model | 2 | 5 | 1 | 1 | Harry asks about sales incentive structures and whether reps are coin-operated. Brendon details the EchoSign compensation model where reps must pay for their operational cost before earning high commission tiers. | |
| Identifying Underperformance and the One-Quarter Rule | 3 | 4 | 2 | 2 | Harry asks how quickly a founder knows a rep isn't working out. Brendon explains that needing to step in and take over prospect calls is the ultimate telltale sign within one quarter. | |
| Debunking the 'Fire Fast' Philosophy | 3 | 6 | 4 | 3 | Harry asks if Brendon subscribes to the 'fire fast' mantra. Brendon pushes back, asserting that rapid rep turnover usually points to managerial and onboarding failure rather than rep incompetence. | |
| Why Strategic Enterprise Hires Fail in Transactional Orgs | 3 | 5 | 3 | 1 | Brendon notes that enterprise reps overlaid on transactional teams fail 99% of the time, then shares his rule that three days without prospect contact means a deal is dead. Harry prompts on deal review structures. | |
| Analyzing Lost Deals and Post-Mortems | 3 | 6 | 4 | 1 | Harry asks how to address lost deals. Brendon details a multi-threading strategy at EchoSign where his team beat DocuSign for the Standard & Poor's account by engaging every level of the organization. | |
| Quick-Fire: Timeless Tactics vs. Dead Outbound SDRs | 2 | 4 | 2 | 1 | Harry runs a quick-fire round on changing tactics. Brendon reiterates his thesis that AI will push outbound SDR functions out of sales and back into marketing. | |
| Impressive Sales Strategies: Rippling and Talkdesk | 1 | 3 | 1 | 0 | Harry asks which modern sales organizations impress him. Brendon highlights Rippling's talent density and Talkdesk's late-stage course correction before wrapping up. |
Statements from this episode (36)
Cassidy: AI will move the SDR function back under marketing
“Ultimately, what AI does is probably get put the SDR function back under marketing.”
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.”
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.”
Cassidy: Recruiting Fees Are First Expense Cut in Market Downturns
“And then recruiting became literally the first thing, you know, that's the first, oh, recruiting fees? Yeah, that's just, yeah. That's not even, there's not, that's a five second discussion.”
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 …”
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.”
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…”
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.”
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 …”
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…”
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…”
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.”
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.”
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.”
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.”
Cassidy: No sales resume is 100% honest
“I've never seen a sales resume that was a hundred percent honest”
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.”
Cassidy: Founders without networks should build 5-person advisory boards for hiring
“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 …”
Cassidy required unanimous panel approval for sales hires at Talkdesk
“And like, so a talk desk, We had like a panel as myself and like my first three sales hires, and we would listen to them pitch that. And we would say it has to be unanimous. All of us have to sign off on this person. And that was sort of how we would, you know…”
Cassidy: Having candidates pitch their current product is the best sales hiring test
“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…”
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?”
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.”
Cassidy: EchoSign's cost-first sales comp model fits current market conditions
“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?”
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.”
Brendon Cassidy: Sales leaders generally know within one quarter if a hire fails
“You generally know in a quarter.”
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…”
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.”
Cassidy: Sales reps should be fully ramped by end of second 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.”
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.”
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%.”
Cassidy: Monthly commit vs. best-case deal reviews work 100% of the time
“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…”
Cassidy: A three-day gap in customer communication usually dooms committed 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…”
Cassidy: Lost sales deals stem from skipped steps early in sales cycles
“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…”
Cassidy: Vendor partner recommendations signal skipped customer due diligence
“Because usually when a partner tells you to pick someone, It means that there's a level of due diligence you didn't really do.”
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…”