Apr 12, 2024 · 1h 15m · news
Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 · 20VC with Harry Stebbings
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In this episode of 20VC, veteran sales leader Sam Blond joins host Harry Stebbings to unpack the mechanics of building, hiring, and scaling a world-class sales team for early-stage startups. He provides highly tactical advice on founder-led sales, creative demand generation, in-person team dynamics, and diagnosing growth bottlenecks.
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 17.1% of the talking time here. How this is scored →
Harry as informed peer 3.3 Guest teaching 3.8 Guest disagreement 1.1 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 38:01 Sam rejects host's focus on conversion over demand
Sam forcefully rejects Harry's assertion that conversion rates are easier to improve than demand, arguing that rep behavior in lead-starved setups proves demand generation is the true bottleneck.
Hardest push from Harry ▶ 37:27 Harry directly pushes back on demand vs conversion focusHarry explicitly interrupts to challenge Sam's thesis, arguing that building a structured sales process and improving conversion is easier and less wasteful than burning leads.
Biggest teaching moment ▶ 43:30 Sam reveals counterintuitive AE vs SDR lead generation dataSam educates Harry with real data from Brex showing that AEs spending half their time on outbound generated far more closed revenue than full-time SDRs due to better deal intuition.
Harry holds his own ▶ 16:55 Harry challenges candidate profile as unrealistic for early startupsHarry demonstrates sharp business judgment by calling out Sam's ideal sales candidate profile as unaffordable and unrealistic for seed-stage founders, forcing Sam to clarify the math.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| 20VC Title Card | 1 | 1 | 0 | 0 | Harry welcomes Sam back to the podcast and asks a friendly introductory question about how Sam first got into tech sales. Sam warmly recalls joining EchoSign as an SDR through his brother's connection. | |
| The Hard Truth About Startups and Pick Importance | 1 | 3 | 0 | 0 | Harry asks what Sam knows now after 17 years in sales that he wishes he knew at the start. Sam shares the insight that company selection is the single most important factor defining a sales career. | |
| The Myth of the Sales 'Order Taker' in Hyper-Growth | 3 | 4 | 2 | 4 | Harry plays devil's advocate, asking if sales reps on hyper-growth startups are just order takers. Sam reframes the premise, explaining that huge performance variance exists even in high-flying startups. | |
| Sequencing the First Sales Hires | 5 | 3 | 1 | 3 | Harry asks how to sequence early sales hires and forcefully asserts that founders must sell and build the playbook first. Sam agrees with Harry's view and outlines exact customer threshold signals for hiring. | |
| The Candidate Profile for Early Sales Reps | 4 | 4 | 2 | 5 | Harry challenges Sam's candidate criteria, arguing that finding proven early-stage top performers is an unrealistic dream world for seed startups. Sam counters with the total addressable pool of reps across startups. | |
| Sourcing Sales Talent Through Personal Networks | 2 | 4 | 1 | 1 | Sam explains why founders should never use external recruiters for early sales hires and should instead rely on personal and investor networks. Harry listens as Sam shares how Brex sourced its first reps. | |
| Testing Sales Candidates and Tactical Pitching | 3 | 3 | 1 | 2 | Harry asks about candidate case studies and sales compensation structures. Sam advises having candidates sell their own prior company rather than the founder's business. | |
| Sales Onboarding and the Three Pillars of Success | 2 | 4 | 0 | 1 | Sam lays out three pillars for evaluating sales reps: performance, effort, and attitude. Harry asks about onboarding setup for early reps. | |
| Tracking Metrics in Long Sales Cycles | 4 | 4 | 2 | 5 | Harry challenges Sam on the difficulty of measuring effort in long enterprise sales cycles when CEOs have limited bandwidth. Sam explains that pipeline opportunity creation provides immediate leading indicators. | |
| Spotting Bad Hires and Red Flags Early | 5 | 3 | 1 | 4 | Harry boldly asserts that he knows within one week whether a hire is bad. Sam agrees that standard quarterly timelines are too long and shares common hiring mistakes. | |
| Diagnosing Growth Bottlenecks: Conversion vs. Demand | 2 | 5 | 1 | 1 | Sam reframes a common founder misconception, arguing that growth bottlenecks are almost always caused by demand generation deficits rather than conversion issues. | |
| The Danger of Lead Starvation and Rep Behavior | 6 | 5 | 4 | 7 | Harry explicitly pushes back against Sam's thesis, arguing that fixing sales processes and conversion is less wasteful than burning leads. Sam firmly defends his view, highlighting rep behavior in lead-starved setups. | |
| Niche Focus and Brex's Early Go-To-Market Strategy | 3 | 4 | 1 | 2 | Harry highlights horizontal positioning traps. Sam illustrates Brex's early strategy of positioning specifically as the corporate card for startups to dominate a niche. | |
| Accountability for Lead Generation: SDRs vs. AEs | 3 | 5 | 1 | 2 | Harry asks who bears responsibility for lead generation. Sam shares empirical data from Brex showing AEs outperforming SDRs in sourcing high-revenue deals due to better intuition. | |
| Why Traditional Outbound is Broken | 5 | 4 | 2 | 4 | Harry questions whether traditional SDR outbound is dead in a modern era of short-form content and inbound trust. Sam agrees traditional spray-and-pray outbound is broken. | |
| The Concentric Circles of Outbound Targeting | 1 | 5 | 0 | 0 | Sam details his concentric circles outbound framework, moving outward from personal and investor networks to targeted geographic awareness before attempting cold outreach. | |
| Creative Outbound and the SMB ACV Trap | 5 | 4 | 1 | 3 | Harry calls out startups that deploy enterprise sales stacks on low ACV products, warning of broken unit economics. Sam agrees that customer acquisition costs must match ACV. | |
| The Impact of AI on Outbound Sales | 4 | 4 | 1 | 2 | Harry asks if AI will flood prospects and commoditize outbound communication. Sam explains that AI automates efficiency but cannot replace human creativity in sales campaigns. | |
| The Late-Night Whiteboard Session | 2 | 4 | 0 | 1 | Sam describes using late-night whiteboard sessions to invent contrarian marketing ideas, citing Brex's guerilla tactics at SaaStr like keycard sponsorships and burritos. | |
| Rippling's Organic LinkedIn Strategy | 4 | 4 | 0 | 0 | Sam explains Rippling's creative strategy of offering gift cards for positive onboarding LinkedIn posts. Harry validates the effectiveness of job-change posts on social media. | |
| The Power of Brex's SF Billboard Campaign | 2 | 4 | 0 | 1 | Sam shares Brex's famous $300k San Francisco billboard campaign, explaining how blanketing the city catalyzed brand mindshare and outbound response rates. | |
| The Brex Restaurant Fail and Celebrating Failure | 5 | 2 | 2 | 6 | Sam confesses Brex's biggest mistake: opening a physical restaurant and lounge in SF. Harry bluntly calls it a world-class bad idea, while Sam advocates celebrating creative failures. | |
| Quick-Fire: The Strategic Role of Discounting | 3 | 4 | 1 | 1 | In a quick-fire round, Sam explains the tactical use of discounting to drive deal urgency, while warning against defaulting to price cuts. | |
| Quick-Fire: The Case for In-Person Sales Teams | 4 | 4 | 2 | 1 | Sam criticizes the laziness of remote sales reps working 30-hour weeks waiting for leads. Harry agrees, noting how easy it is to stand out when standard effort levels are mediocre. |
Statements from this episode (35)
Blond: Startups should prioritize startup experience over domain expertise when hiring initial AEs
“Where people over index is domain. If you are hiring your first AE, first big AEs number one and two, they need to have seen an early stage startup environment.”
Sam Blond: Picking the Right Startup Defines Career Success More Than Performance
“The reality is the importance of picking the right company it just really defines one's career. I attribute so much of my success to joining the right businesses. Now, like, I was able to perform within those businesses, and, you know, for context, we're talki…”
Blond: Parker Conrad Will Build a $100 Billion Business With Rippling
“I just wanted to join this guy's company because he was going to build a hundred billion dollar business. You know, we didn't realize that outcome with Zenefits. He's going to with Rippling.”
Blond: Top Sales Reps Outperform Bottom Reps 3x Even in Hyper-Growth
“But what happens seemingly universally, even at the best companies in the world, like Zenefits in 2014, is there are outlier performers That perform at something like three X to the bottom performer. And so you get a team of like 10 people, even when you're in…”
Blond: Startups should always hire two individual account executives first
“The way I start is hire two individual contributor account executives. Those are sales reps. Always start with two.”
Blond: Startups should not hire SDRs before hiring a sales leader
“I don't like hiring SDRs prior to hiring a sales leader. Because they need a lot of hands-on management.”
Blond: Startups must win non-friends customers before hiring sales
“You should have a handful of non-friends and family revenue-generating customers, and a process that you believe is repeatable in terms of generating more of these customers.”
Blond: Sales Reps Will Fail If Founders Cannot Close Deals First
“If you as the founder cannot close customers and generate revenue people that sort of specialize in sales will definitely not be able to. There is no one better qualified to acquire your first set of customers than you as the founder.”
Blond: Do Not Hire Initial Sales Reps From Salesforce or Rippling
“If you are hiring your first AE, first AEs number one and two, They need to have seen an early stage startup environment. Do not hire from an extreme example, be Salesforce, but gosh, even today, you know, don't hire from a rep who came from rippling. And join…”
Top sales talent avoids third-party recruiters
“Most of them do not go through a third party recruiter. They want to go somewhere where their reputation precedes them a little bit.”
Blond: Brex Never Used Recruiters to Source Sales Talent
“At Brex, we did not use recruiters, internal or external, to source candidates for the sales organization Ever.”
Blond: Test sales candidates by having them pitch their previous company's product
“Oh, I think the prior company is a really interesting one, because I think what's hard about sell me my company, meaning, you know, let's, let's say you sell me 20 VC, right? You're a 20 VC expert, and I'm not. So, you know how to pitch this product better tha…”
Sam Blond: Startup AE total comp ranges between $100K and $250K
“AE range, 100 to two 50 is, is like the AC is the total comp for a sales rep.”
Blond: Move on from underperforming sales hires who lack effort or attitude
“If the performance isn't there, you sort of default to, okay, what is the effort and the attitude like? And if either are lacking, this is either like a zero time or one time conversation with the person around performance.”
Blond: Effective sales hires improve leading pipeline metrics almost immediately
“If you make the right hires, there are metrics that you should start seeing improve almost immediately, regardless of how long the sales cycles are.”
Blond: Assessing early sales hires should take 30 days at most
“I, the number that was coming to mind for me, it almost doesn't matter how long the cycle is with these early hires in particular, I think, 30 days. And in here, you're probably closer to right with your week. Most, you know, many folks say a quarter, many fol…”
Blond: Having early performance conversations with a hire is a red flag
“If you're having sort of like performance expectation conversations really early on, you know, I think that is a bit of a red flag but you know, not it's not one size fits all, once again.”
Sam Blond: Generating demand, not conversion rate, is almost always the startup bottleneck
“And I just believe that demand masks a lot of other potential problems and almost all startups. The bottleneck to growing faster is demand. We are constrained by the number of opportunities that we are creating. We are misdiagnosing this as a conversion rate p…”
Sam Blond: Account executives must generate their own demand from day 1 to 1000
“Salespeople should absolutely be responsible for controlling their own destiny in a way, generating their own demand that often manifests through outbound. I think this is true on day one. This should be true on day 1000.”
Blond: Brex AEs Sourced More Revenue Than SDRs at $100M ARR
“When we were a relatively mature startup so let's call it 50 to a hundred million dollars of annualized revenue. One of the things that we noticed was that the AEs were sourcing far more of their own revenue than their SDR counterparts.”
Sam Blond: Startups Should Target Outbound in Concentric Circles
“I think the way that startups should be approaching this, first is on who you are targeting, and then how you target them. So who you are targeting, think about the universe in terms of concentric circles. And you want to start with the sort of like closest co…”
Sam Blond: Brex Scaled Outbound from Personal Networks to Billboards
“At Brex, we started with personal networks, we moved to investor networks, we moved to YC companies, we moved to former YC companies, we then put billboards up all over San Francisco, and we targeted companies that were headquartered in downtown San Francisco …”
Blond: Brex's Champagne Outbound Campaign Yielded Massive Response Rates
“And I've talked about a champagne campaign that I did at Brex where we sent founders a bottle of champagne early on and, you know, congratulated them on a recent fundraise. That's differentiated. It received a ton of responses.”
Stebbings: Enterprise Sales Teams for $10K ACV Products Rarely Scale
“And the ACV is a 10 K and it's like, ah, and they're like, ah, but it'll scale. It'll scale, Sam. It rarely scales. And so we're layering on this enterprise cost base for this very SMB PLG revenue base, which has really been born out of the PLG motion. And I'm…”
Sam Blond: AI Cannot Devise Creative or Unconventional Sales Campaigns
“I think what, at least today, AI does not accomplish that humans still do is this aspect of being creative. You know, the AI isn't going to tell you here is your contrarian or unconventional outbound sales campaign that is different from what everybody else is…”
Blond: Run late-night, small whiteboard sessions for contrarian sales ideas
“At a ten-person startup, Harry, you're the founder, you're gonna be in this meeting, the two sales reps are gonna be in this meeting, and then maybe we have, like, somebody in growth, that person's gonna be in this meeting. So we've got four people in this mee…”
Blond: Brex Hired TaskRabbits to Hand Out $4 SaaStr Breakfast Burritos
“We show up, we had task rabbits outside of the event in Brex t-shirts handing out Brexfist burritos to every single person that walked in the venue. So the first experience that they have at Sastra is they get a Brex burrito on when they walk in. Four bucks a …”
Blond: Brex Spent $300,000 on Its Initial SF Billboard Launch Campaign
“The very day that we launched in GA the product, we put billboards up all over San Francisco. And I think the campaign cost something like 300,000 dollars over three months, but we were everywhere. And that just made everything easier for us.”
Blond: Brex opened a San Francisco restaurant when under 100 employees
“We decided at a very early stage, we were less than a hundred employees, we decided that we were going to open a restaurant and lounge. And so we opened a in South park in San Francisco, we opened a Brex lounge on top of a South park cafe, which was a restaura…”
Blond: Opening a San Francisco Restaurant Was Brex's Biggest Mistake
“In hindsight, that was a big mistake. We should have focused on what was working, building a credit card company using our dollars to acquire things like customers, and not, you know, remodeling A hundred year old restaurant that was in dire need of a remodel.…”
Sam Blond: Startups should only offer discounts late in sales cycles to drive urgency
“I think where people make mistakes and salespeople in particular make mistakes is like just defaulting to discounting. This is something that happens very late in a deal and it happens with A very clear trade-off, which is driving urgency to close.”
Blond: In-Person Meetings Tripled Sales Conversion Rates at Brex
“We measured conversion rates at Brex. When we met a customer in person, we had three X the likelihood of closing that deal than if we didn't.”
Blond: Remote-only Zoom sales models are becoming obsolete
“And so like the days of working from home, doing Zooms only to meet with customers, not meeting customers and developing personal relationships those days, I think are going to be a thing of the past, if not already.”
Blond: Early-stage startups should build fully in-person sales organizations
“I think if you are starting a business today, I am very biased towards building the in-person both the, you know, the entire company, but also the sales organization.”
Blond: Modern Salespeople Are Lazy and Overdependent on SDRs
“Today's salespeople have gotten a little bit lazy. And I think they and we, cause I consider myself, you know, part of this community. Couple of things have happened. One, we have become overly dependent on marketing, SDR, anybody to source our own leads. We a…”