Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139
Sam Blond (guest), Harry Stebbings (host), Narrator, Narrator
In this episode of The Twenty Minute VC, featuring Sam Blond and Harry Stebbings, Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 explores sam Blond Reveals Why Startup Outbound Fails—and How To Fix It Former Brex and Zenefits CRO Sam Blond explains why most startups misdiagnose their sales bottleneck and dramatically underinvest in demand generation, particularly smart outbound. He argues founders must sell first, then hire two proven early-stage AEs, and obsess over opportunity creation rather than blaming missed quarters on slipped deals.
Sam Blond Reveals Why Startup Outbound Fails—and How To Fix It
Former Brex and Zenefits CRO Sam Blond explains why most startups misdiagnose their sales bottleneck and dramatically underinvest in demand generation, particularly smart outbound. He argues founders must sell first, then hire two proven early-stage AEs, and obsess over opportunity creation rather than blaming missed quarters on slipped deals.
He details how to hire, compensate, and ramp early sales reps, what profiles to avoid, and how to use personal networks instead of recruiters to source top performers. Blond also shares frameworks for diagnosing growth constraints, designing contrarian outbound and marketing campaigns, and aligning SDR/AE models to revenue, not activity.
Throughout, he emphasizes work ethic, attitude, in‑person relationship-building, and creative, highly targeted demand-gen plays—from champagne and billboards to Rippling’s NPS-powered LinkedIn posts—over spray-and-pray sequences and overbuilt, uneconomic sales orgs.
Key Takeaways
Founders must close the first non–friends-and-family customers before hiring sales.
If a founder can’t sell the product and define a repeatable process to win a handful of real customers, no sales hire will magically fix that; salespeople amplify existing motion, they don’t create it from zero.
Get the full analysis with uListen
Your first two AEs should be top performers from early-stage startups, not domain experts from big brands.
Prior success as one of the first ~10 reps at a startup, with similar deal sizes and buyer types, matters far more than industry familiarity; over-indexing on “domain experience” usually means trading away true selling talent.
Get the full analysis with uListen
Source early sales hires through personal and investor networks, not recruiters.
The best AEs rarely go through third-party recruiters; systematically working founders’ past companies, current team networks, and investor referrals yields higher-performing, culturally aligned hires and creates a virtuous referral loop.
Get the full analysis with uListen
Most startups’ real bottleneck is demand generation, not closing skills.
Founders tend to blame missed targets on a few slipped deals, but in reality calendars show AEs with only an hour a day of customer-facing time; doubling qualified opportunities is often far easier and more impactful than trying to 2x win rates.
Get the full analysis with uListen
Make AEs responsible for sourcing their own pipeline and tie SDRs to revenue, not just meetings.
AEs understand what a high-quality opportunity looks like, so their outbound often outperforms SDRs; shifting SDR comp and targeting to revenue and proven high-converting personas fixes this while preserving AEs’ outbound muscle.
Get the full analysis with uListen
Outbound is broken when it’s generic; start with concentric circles and contrarian tactics.
Rather than cold-blasting strangers, begin with founder/team/investor networks, happy customers, and tightly defined verticals, then use standout touches—physical mailers, gifts, events, or clever campaigns—so your outreach isn’t the 12th identical email that day.
Get the full analysis with uListen
Creativity and effort beat tools and automation in sales differentiation.
AI and sequencing platforms make it easier to send more messages, but not to design truly original campaigns (e. ...
Get the full analysis with uListen
Notable Quotes
“For almost all startups, the bottleneck to growing faster is actually around demand gen—opportunity creation.”
— Sam Blond
“If you, as the founder, cannot close customers and generate revenue, people that specialize in sales will definitely not be able to.”
— Sam Blond
“Where people over-index is domain… it’s already so hard to find an exceptional early-stage, track-record-of-performance sales rep.”
— Sam Blond
“Everybody is doing outbound wrong… they drop the universe into a seven-email sequence and it goes right into the trash.”
— Sam Blond
“Today’s salespeople have gotten a little bit lazy… we’ve become overly dependent on marketing and SDRs to source our own leads.”
— Sam Blond
Questions Answered in This Episode
How can a founder with no sales background practically structure their first 60–90 days of founder-led selling to reach that initial ‘handful’ of non–friends-and-family customers?
Former Brex and Zenefits CRO Sam Blond explains why most startups misdiagnose their sales bottleneck and dramatically underinvest in demand generation, particularly smart outbound. ...
Get the full analysis with uListen AI
If you’re already a few hires in and realize you mis-sequenced your sales org (e.g., hired SDRs too early, wrong AE profiles), what is the cleanest way to reset without blowing up morale?
He details how to hire, compensate, and ramp early sales reps, what profiles to avoid, and how to use personal networks instead of recruiters to source top performers. ...
Get the full analysis with uListen AI
What specific metrics and dashboards should a founder use monthly to distinguish a true demand-gen bottleneck from a genuine conversion problem?
Throughout, he emphasizes work ethic, attitude, in‑person relationship-building, and creative, highly targeted demand-gen plays—from champagne and billboards to Rippling’s NPS-powered LinkedIn posts—over spray-and-pray sequences and overbuilt, uneconomic sales orgs.
Get the full analysis with uListen AI
How can early-stage teams systematically run the kind of late-night, contrarian whiteboard sessions Sam describes without it becoming unfocused brainstorming?
Get the full analysis with uListen AI
In a world of AI-accelerated outreach and remote work, what concrete behaviors will distinguish the top 1% of salespeople over the next five years?
Get the full analysis with uListen AI
Transcript Preview
Where people over-index is domain. If you are hiring your first AE, first, like, AEs number one and two, they need to have seen an early stage startup environment. There are three things that I look for in terms of measuring the success of a sales hire. For almost all startups, the bottleneck to growing faster is actually around demand gen. Opportunity creation.
Ready to go? Sam, listen, I am so excited to have you back on the show. Wher- it was a while ago since we last made this happen. Hopefully I've improved as an interviewer. So thank you so much for joining me again today.
Arie, I'm pumped to be here. Thank you for having me. Last time we did this was, I think, a month or so after I joined Brex in 2018. The world is quite different six years, uh, later as we sit here.
I mean, six years ago, fuck me I'm getting old. But, um, I- I do have to start (laughs) on-
Yeah, but it's better than me.
Uh, uh, dude, you're ancient. I mean, you- you are just- I try. ... I mean. (laughs) Uh, I wanna start with the entry into sales before we dig into specifics. What was the entry point for you, and when did you realize that you loved sales?
I attribute a- a couple data points of luck to- it- to being in sales and in tech sales in the first place. So I graduated from University of Missouri in 2007, and, uh, wasn't considering, like, you- you know, but for my brother being in the Bay Area doing tech sales, as a graduate of the University of Missouri, that's not even on y- your radar. I got a job as an SDR at a company called EchoSign, so I sort of lucked into getting into tech sales in the first place because of my brother, and then I lucked into, um, joining a- a successful business like EchoSign that allowed me to progress my career. I didn't know what I was looking for at the time, and fortunately I found Jason Lemkin, who's a friend of both of ours that was leading this company, and joined as an SDR when it was effectively being run out of a- a garage, an actual garage in Palo Alto. The question around when did I sort of figure out that, uh, uh, you know, tech sales was for me, something like that, I was able to start differentiating myself from peers doing the same thing. The feeling of being successful was addictive, and so, uh, you know, it was- it was pretty evident to me early on that I had found something that aligned well with my skillset that- that, you know, eventually e- evolved into a tech sales career.
Dude, I think momentum and confidence are two of the most important things to have in a team, because as you said there, success is so addictive. I always think, "How do I create that momentum in teams?" Uh, you've been in sales respectfully then for, Christ, 17 years without aging you. Um, so with that in mind, what do you know now that you wish you'd known when you started 17 years ago in that garage with EchoSign?
Install uListen to search the full transcript and get AI-powered insights
Get Full TranscriptGet more from every podcast
AI summaries, searchable transcripts, and fact-checking. Free forever.
Add to Chrome