Salesperson

topic on 14 shows · 32 statements across 31 episodes

the Y Combinator Startup Podcast In Depth Startups For the Rest of Us We Live to Build Lenny's Podcast the Neon Show the Official SaaStr Podcast A Product Market Fit Show Capital Allocators Catalyst Top Founders the MAD Podcast the a16z Podcast 20VC

32 statements about Salesperson, every show

20VC Opinion
Degnan: AI will not make salespeople or SDRs obsolete
“You know, I'm thinking about, like, all these questions around, you know, people are saying the sales person will be dead, or SDRs will be dead. I just, I don't buy it”
Chris Degnan May 23, 2026 ▶ 1:09:04 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
IN DEPTH Insight
Enterprise products always face competition; reps claiming otherwise are bad at sales
“If you are selling a product that is worth anything, there's some competition that's trying to eat your lunch. You have to be hyper paranoid about that competitor. Like the worst thing is like, if you do a forecast review with a sales team and like, who's the …”
Chris Degnan Feb 26, 2026 ▶ 39:39 Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
Abel: Startups cannot hire top salespeople selling $10K contracts
“A really good salesperson, your commission on a 10 K deal. You're not going to get a great salesperson. They're going to want to do, they're going to want to be anchored to like, how can I sell a 250,000 dollar deal? How can I sell a half a million dollar deal…”
Jen Abel Nov 9, 2025 ▶ 20:55 $1M to $10M: The enterprise sales playbook with Jen Abel
McNairn: Technical founders learning to sell outperforms hiring early salespeople
“The idea of being the salesman or not is rubbish. Like it's actually even better if it's a product person or an engineering person that learns that talent, because that's where you get everything early on”
Ross McNairn Aug 14, 2025 ▶ 23:28 He grew to millions in ARR in 18 months—by fighting with his co-founders on purpose. | Ross McNai... · PMF Show
Walling: Enterprise sales reps should generate 10x their total compensation in ARR
“If they make, let's say a salesperson makes a million dollars in, in, it's obviously salary plus commission, they should be generating, I think that it's a loose tenant, 10 to one, I think, they should be generating ten million in ARR for you.”
Rob Walling Aug 12, 2025 ▶ 9:47 Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Inst...
NEON SHOW Prediction Not checkable as stated
Chopra: Roles requiring trust will rise in value because AI avoids jail
“Because someone is going to pay you a million dollars, and at least for next 10 years, that trust can only be built by humans, because you can't jail an AI, but you definitely can jail a person. So a lot of these things which require this human trust, for lack…”
Paras Chopra Jul 4, 2025 ▶ 6:49 Paras Chopra: How To Build A Successful Startup In India | Sold Wingify For $200 Million
Lundin: Founders close sales using executive authority that hired reps lack
“The founder also has one thing going for them that nobody else does. Authority. Sean, if I break this, I'll fix it. And the seller can't.”
Ken Lundin Apr 15, 2025 ▶ 2:42 75% of Sales Is Framework, 25% Is Human, and AI Knows It
Lundin: Companies cannot scale or hire sales reps without documented processes
“And then if you can't write down a process so that somebody else can follow it, that's client centric. Then you're not ready to hire a salesperson and you're not ready to scale.”
Ken Lundin Apr 15, 2025 ▶ 25:45 75% of Sales Is Framework, 25% Is Human, and AI Knows It
a16z Assertion Not checkable as stated
Modern sales reps use 20 to 30 different tools in their stack
“If you look at the modern like salesperson today, they use 20, 30 different tools as part of like their sales stack.”
Prabhav Jain Mar 20, 2025 ▶ 14:10 The Future of Digital Workers
20VC Insight
Challenger Brands Require Higher Caliber Salespeople Than Established Companies
“That's why when you are a challenger, you need a higher caliber of salesperson because you don't have the brand. As your brand gets bigger and bigger, either great salespeople become more productive or you know, you're able to get more junior or less talented …”
Carlos Delatorre Jan 24, 2025 ▶ 1:06:50 Carlos Delatorre, CRO @Harness: Why Every Sales Rep Should Do Pipeline Generation | E1251 · 20VC with Harry Stebbings
Dev tool founders should reach $1M ARR before hiring their first salesperson
“As a rule of thumb, I would wait to get to about one million AR before hiring your first salesperson.”
Nicolas Dessaigne Nov 26, 2024 ▶ 21:56 How To Start A Dev Tools Company | Startup School · Y Combinator
SAASTR Insight
Padelford: Salespeople are fundamentally part of the product itself
“There isn't the product and the salesperson. This is all the product. And so how you talk about it, how much you know about the industry, how much you know about the other customers is part of being a great sales rep.”
Loren Padelford Oct 8, 2024 ▶ 30:21 The Secrets to Selling and Scaling in Vertical SaaS with Slice's CRO
20VC Insight
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.”
Brendon Cassidy Mar 8, 2024 ▶ 29:28 Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 · 20VC with Harry Stebbings
LENNY'S PODCAST Assertion Supported
Rachitsky: Notion waited until $10M ARR to hire its first salesperson
“I think notion, I think at ten million ARRs when they hired their first salesperson.”
Lenny Rachitsky Feb 18, 2024 ▶ 11:19 Building a world-class sales org | Jason Lemkin (SaaStr)
SAASTR Insight
Startups should always hire two salespeople or SDRs simultaneously
“When you're hiring your first sales person or your first SDR, you should always hire two.”
Sam Blond Feb 9, 2024 ▶ 17:01 Bringing Product-Led and Sales-Led Growth Together For Go-To-Market Success with Zapier's CRO
20VC Insight
Kellogg: Marketers focus on correctness while salespeople navigate room politics
“Now, I think the difference between a salesperson and a marketing person is I tended to be more theoretical. What is correct? What is right? Whereas a seller is reading the room very closely. Who cares about what? Who has what interests?”
Dave Kellogg Jan 31, 2024 ▶ 3:00 Dave Kellogg: How to Forecast in 2024 & Why CaC Payback is Flawed and CAC Ratio is Better | E1110 · 20VC with Harry Stebbings
Weisbrot: Splitting sales objections into trust versus service clarifies hesitation
“So in essence, you're splitting the handling of objections between me and my business and the service. And I, and I'm curious to see how that works because I've never tried it before. I'm curious to know if you have any experience or any thoughts on that, but …”
Sean Weisbrot Dec 19, 2023 ▶ 22:49 Conviction Before Competence: Why Top Earners Defy Every Sales Profile
20VC Insight
Doug Adamic: Sales reps perform poorly without supporting teams and enablement
“A salesperson on and to themselves aren't going to sell well on average. They need to be supported by a team of people that tools them correctly, and then that works much better.”
Doug Adamic Sep 8, 2023 ▶ 54:43 Doug Adamic: Why Discounting is BS; How to Reduce Sales Cycles and Create Urgency | E1058 · 20VC with Harry Stebbings
20VC Insight
Jiménez: Curiosity and active listening are key traits of great salespeople
“One of the most important characteristics, in my opinion, with a great salesperson is being curious. It's someone who can ask a question, who can ask the next question that's connected to that first question. Really listen to the first answer, not just for the…”
Lori Jiménez Aug 2, 2023 ▶ 0:00 Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043 · 20VC with Harry Stebbings
Wickberg: Enterprise sales reps can carry 3x larger quotas upmarket
“We realized that the right type of salesperson can carry like a three times bigger quota.”
Daniel Wickberg Mar 22, 2023 ▶ 10:48 He's $14m in ARR, Here's why he IPO'd and plans to grow 30% this year
CATALYST Assertion Not checkable as stated
Popham: Most dealership salespeople earn lower commissions selling EVs
“And then for various reasons based on how commissions work, typically the salesperson on most dealerships, not all, would then get paid less.”
Carl Popham Jan 18, 2023 ▶ 2:48 Introducing: With Great Power, a show about the people building the future grid
SAASTR Insight
Hariharan: Founders should only hire sales reps after demos become boringly predictable
“You hire a salesperson when your sales call and demo calls become extremely boring and repetitive because that's when you've figured out what your go to market motion is.”
Anu Hariharan Sep 29, 2022 ▶ 18:15 5 Critical & Company-Altering Learnings from B2B Startups | Y Combinator MD Anu Hariharan
SAASTR Insight
Appleyard: Sales reps rarely leave cybersecurity once they pass one year
“In the cybersecurity industry, you often just need to spend a year just understanding the industry, and once you've learned all of that, even if you don't want to be a salesperson, you usually don't want to leave the industry.”
Amy Appleyard Dec 30, 2021 ▶ 14:32 How to Scale Outbound Sales with the CROs of Outreach, Malwarebytes, HubSpot, Seismic
SAASTR Insight
Dorsey: Involving customers early beats salespeople at explaining product execution
“The people that know the how best on your product are the customers. Get them involved way earlier, because they can speak to the how better than any salesperson will ever be able to, right?”
Kevin Dorsey Jul 28, 2021 ▶ 21:49 Kevin Dorsey, VP Sales at PatientPop Shares Cutting Edge Techniques for Building Trust in Sales
Walling: Founders must establish a sales process before hiring outside sales reps
“Because you need to have that sales Some type of sales process dialed to be able to hand it off to an outsider. You forget all the institutional knowledge that you have, you know, and all the love for your product and all the knowledge of the space and how har…”
Rob Walling Sep 17, 2020 ▶ 16:51 TinySeed Tales Season 2 | Episode 2: Moving Upmarket
NEON SHOW Insight
Gandhi: Founders should not start companies with dedicated salespeople early
“Oftentimes you don't just start a company with a salesperson because you don't just then, you don't know what, how to utilize them unless that salesperson is open to doing other things initially, right?”
Shruti Gandhi Sep 14, 2020 ▶ 22:01 Shruti Gandhi, Array Ventures on taking SaaS companies from Zero to $10 Million ARR
MAD Disclosure
Datadog hired its first salesperson at under 30 employees
“We were, I think, a bit less than 30 when we hired the first salesperson.”
Olivier Pomel Jan 22, 2020 ▶ 21:14 Fireside Chat with Olivier Pomel (Founder & CEO of Datadog) and Matt Turck (Partner at FirstMark)
Duke: Managers should fire a salesperson who closes 100 percent of sales
“And then all of a sudden you have a salesperson who's closing a hundred percent of their sales. And by the way, if you can't change that, you should fire them.”
Annie Duke Nov 19, 2018 ▶ 28:54 Annie Duke – Thinking More in Bets (Capital Allocators, EP.76)
SAASTR Insight
Stanimiroff: Sales reps often do not realize goal deficits until mid-month
“If a salesperson or the team in the example I gave you before, start slipping behind goal, and they start losing their track a little bit, it's very often the case that they don't really appreciate the gravity of their situation up until it's too late. So in m…”
Dimitri Stanimiroff Aug 14, 2018 ▶ 15:35 Sales Rep 2.0: How to Make Sales Agile with Heresy
Benson: 15-minute onboarding calls are viable for $420 annual SaaS plans
“We do reach out to even as just someone who looks like a single seat deal will at least reach out to them and ask them if they have questions about how to use the product. You know, we'll set it up for them, get them successful. That call usually takes 20 minu…”
Steve Benson Dec 8, 2017 ▶ 6:05 867 SaaS: 80% yoy Growth, Badger Maps Passes $180k MRR
SAASTR Assertion Supported
Fala: Salespeople cost 50% more in the San Francisco market
“You have to pay 50% more for a salesperson in this market.”
Alex Fala Aug 21, 2017 ▶ 21:26 Three Non Obvious Lessons Learned Selling to SMBs with Xero and Friends
20VC Insight
Cerny: Unaligned sales tools force reps to contort their process
“When the technology doesn't map onto how a salesperson would optimally want to run that conversation, it actually becomes a hindrance. The rep has to contort themselves and their sales process to the inadequate tool that they have at their disposal.”
Branko Cerny Mar 25, 2016 ▶ 4:02 Immediately's Branko Cerny on The Rise Of Bottoms Up Sales and The Importance of Branding For Enterprise SaaS Companies

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