sales team

also referred to as: sales teams

26 statements across 23 episodes · 5 bullish · 7 bearish · 23 people on the record · first statement May 27, 2021 by Byron Deeter · across every show →

Everything said about sales team, oldest first

May 27, 2021 negative
Insight
Founders Cannot Outsource Early GTM Discovery to Early Sales Hires
“And you can't outsource that to your sales team early, or you're going to lose the magic. You're going to lose the insights, and you're going to shoot the rocket off, 10 degrees off target, even if it's working.”
Byron Deeter May 27, 2021 ▶ 22:15 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
Dec 8, 2021
Insight
First sales leaders must build from first principles, not copy playbooks
“You need to bring in someone who just has more perspective and playbooks. I don't think it's about copy pasting what those people have done in the past, but it's about coming in, understanding where they're at today. And from first principles, starting to buil…”
Kyle Parrish Dec 8, 2021 ▶ 9:42 20 Sales: When To Hire Your Head of Sales/ First Reps, What To Look for in 10x Sales Candidates, How To Structure The Hiring Process, How To Onboard New Reps Efficiently, How To Set First Quotas and more with Kyle Parrish, Figma's VP Sales
Mar 9, 2022 positive
Insight
Grosser: Founders should hire sales teams earlier than they anticipate
“I think bringing in a sales team often probably should have happened earlier than founders anticipate.”
Jeanne DeWitt Grosser Mar 9, 2022 ▶ 6:05 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St
May 25, 2022 bullish
Insight
Non-developer PLG startups miss significant growth without sales teams
“Almost every other persona. Sales make sense, right? To compliment, not to say that you have to lead with sales, but sales can really help you move up and get to the larger, more strategic conversations. So I think it depends on your product. But generally spe…”
Oliver Jay May 25, 2022 ▶ 4:00 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Jun 22, 2022
Insight
Deal reviews should educate the surrounding team, not just the rep
“I think the purpose of the deal reviews is primarily for your sales team to learn what to do well and what not to do well. I think your audience for the deal review is not the person who did the deal, but all the people around.”
Zhenya Loginov Jun 22, 2022 ▶ 44:58 Mire CRO Zhenya Loginov: Hiring Tips for Sales; Why Dropbox Lost Enterprise | 20VC #900 · 20VC with Harry Stebbings
Jun 22, 2022
Insight
Building sales teams too early makes adding PLG later extremely difficult
“If your PLG motion is figured out, but the PLG, if you miss it, and if you build the sales teams too early, it's very hard to build later.”
Zhenya Loginov Jun 22, 2022 ▶ 4:16 Mire CRO Zhenya Loginov: Hiring Tips for Sales; Why Dropbox Lost Enterprise | 20VC #900 · 20VC with Harry Stebbings
Jul 27, 2022
Insight
Jordan Van Horn: Founders must explicitly document who NOT to sell to
“Also, by the way, it's really important for that founder to document who you're not trying to solve the problem for, because that's going to be a direction of how you actually focus the sales team that you go and hire.”
Jordan Van Horn Jul 27, 2022 ▶ 4:51 20VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the First Sales Hire Be a Leader or a Rep?
Jul 19, 2023
Insight
Isford: Sales teams in PLG companies require a distinct team composition
“If you decide that something like a product-led motion makes sense and that users should be able to experience your product and learn its value by being inside the product and becoming a user, then developing a sales team later on takes on a very different fla…”
Lauryn Isford Jul 19, 2023 ▶ 9:50 Lauryn Isford: Product Growth Secrets from Facebook, Airtable, BlueBottle, Dropbox & Notion | E1037 · 20VC with Harry Stebbings
Feb 21, 2024
Prediction Not checkable as stated
Williamson: Budget constraints are forcing PMs into short-term tactical work
“There are fewer engineers, fewer PMs, fewer designers. People are being asked to do more with less. I would guess the average PM probably has less time to get out of the building. And there's more focus on revenue. And if you're a product manager and you're tr…”
Scott Williamson Feb 21, 2024 ▶ 51:33 Scott Williamson: Hiring the Best Product People in Five Steps, Why the Best PMs are Writers | E1118 · 20VC with Harry Stebbings
Apr 20, 2024
Assertion Not checkable as stated
Freshworks under-hired software engineers relative to sales during its 2015 growth
“दो हजार पंद्रह में हम वास्तव में बहुत तेजी से बढ़ रहे थे और हम sales team को nuket कर रहे थे और sales का पहिया engineering के पहिये से तेज घूम रहा था. हमने जरूरत मताबिक engineers को hire नहीं किया”
Girish Mathrubootham Apr 20, 2024 ▶ 31:22 Girish Mathrubootham (HINDI): Biggest Product and Pricing Lessons from Scaling to $597M in ARR · 20VC with Harry Stebbings
Apr 24, 2024 negative
Insight
Zaparde: Verticalizing sales teams is extremely expensive and requires massive scale
“It is extremely, extremely expensive to verticalize. Your sales team and at least from other founders that are much ahead of us that I've spoken to, like it's when people do it is at a much, much, much different level of scale.”
Rujul Zaparde Apr 24, 2024 ▶ 21:07 Rujul Zaparde: Why Hiring Inexperienced People is Better | E1144 · 20VC with Harry Stebbings
May 10, 2024
Insight
Stebbings: Listening to support calls best trains sales empathy
“It is the most effective thing that I urge all founders with sales teams to hear the pains of customers. You hear, you speak about training empathy. It's probably the closest way to train empathy, just to listen to the customer support.”
Harry Stebbings May 10, 2024 ▶ 27:43 Larry Shurtz: How to Hire, Train & Retain the Best Vertical Teams | E1151 · 20VC with Harry Stebbings
May 10, 2024 negative
Insight
Shurtz: Adding sales priorities without removing old ones breaks team execution
“When you're when you're like, it's a very diminishing trait when you try and do too much, my opinion, because you flow it down and you keep adding things on. You never take anything off. Like the list just kind of keeps growing. And when the list grows, your t…”
Larry Shurtz May 10, 2024 ▶ 4:13 Larry Shurtz: How to Hire, Train & Retain the Best Vertical Teams | E1151 · 20VC with Harry Stebbings
Aug 2, 2024
Insight
Fiechtner: Structure sales teams around product-market fit, not geography
“Be extremely intelligent and design your sales team based on product market fit.”
Ben Fiechtner Aug 2, 2024 ▶ 52:46 Ben Fiechtner: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | E1185 · 20VC with Harry Stebbings
Jan 17, 2025 neutral
Assertion Supported
Monday.com has expanded its sales organization to over 1,000 people
“We built an amazing sales team, you know, going forward to today where we have more than a thousand people in our sales team, but it was not obvious back in the days.”
Eran Zinman Jan 17, 2025 ▶ 24:38 Eran Zinman, Co-Founder & Co-CEO @Monday.com: Going Upmarket, International and Multi-Product |E1247 · 20VC with Harry Stebbings
Jan 24, 2025
Insight
When Sales Teams Slump, Pause Work and Address Morale Immediately
“I think the best thing to do is just to stop. Let's all get in a room and let's talk about it. Let's talk about how we're feeling.”
Carlos Delatorre Jan 24, 2025 ▶ 47:57 Carlos Delatorre, CRO @Harness: Why Every Sales Rep Should Do Pipeline Generation | E1251 · 20VC with Harry Stebbings
Mar 7, 2025 positive
Insight
Stebbings: Hire salespeople displaced by division shutdowns over general layoffs
“I always say look for shutdowns, which is like, if you shut down a whole product division and the sales team are gone, that may not have been that they were shit. It may have been that the product didn't have product market fit.”
Harry Stebbings Mar 7, 2025 ▶ 15:51 Julian Teixeira, CRO @ 1Password: How to Hire and Train Your First Sales Hires · 20VC with Harry Stebbings
Mar 17, 2025
Insight
Rangan: Moving upmarket requires upskilling sales for complex buying committees
“When the complexity of the buying process on behalf of the customer goes from I'm making decisions, I got the budget, to I have a committee of people that now need to make the decisions, that includes IT, that includes procurement, that includes security, that…”
Yamini Rangan Mar 17, 2025 ▶ 25:55 Yamini Rangan, CEO @ HubSpot: How HubSpot Competes Against Salesforce · 20VC with Harry Stebbings
Apr 4, 2025 bearish
Prediction Not checkable as stated
Mukherjee: Future sales teams will shrink to 10-20% of current sizes
“Dramatically smaller. It could be 10 to 20% of current kind of org sizes.”
Ishan Mukherjee Apr 4, 2025 ▶ 0:04 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox
Apr 4, 2025 bearish
Prediction Not checkable as stated
Mukherjee: AI productivity will cut sales and marketing OPEX from 40% to 20%
“Instead of having large teams, you need fewer teams who hold more book, and management layers kind of compress, and then you need different kinds of leaders. And that completely changes, like, sales and marketing is 40% of your OPEX, right? Like, it could pote…”
Ishan Mukherjee Apr 4, 2025 ▶ 1:02:35 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox
May 1, 2025 bearish
Prediction Open · timeframe May 2027
Lemkin: AI will replace half of sales and customer success teams
“Half of these sales teams will be gone in two years. Half of these sales and customer success teams will be gone in two years because they're mediocre. They'll be gone. They're all going to be laid off.”
Jason Lemkin May 1, 2025 ▶ 1:26:41 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 2, 2025 neutral
Assertion Not checkable as stated
Sierra Gathers Its Remote Sales Team in Person Once a Month
“Now we do have offices that, or people that work from home that don't live in those major cities, but I bring the sales team together once a month.”
Reggie Marable May 2, 2025 ▶ 47:03 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
Jun 27, 2025 negative
Insight
Graves: First sales hires should focus on learning, not quota execution
“The earliest stage of building a sales team is not looking for Traditional coin operated reps that are going to come in and just build the sales playbook for you. The earliest stages are actually about learning.”
Kim Graves Jun 27, 2025 ▶ 20:02 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves
Aug 4, 2025 bullish
Assertion Not checkable as stated
Databricks has approximately 20 sales reps earning over $1M annually
“Now we probably have 20 guys make a million bucks in in the sales team.”
Ron Gabrisko Aug 4, 2025 ▶ 37:00 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko
Dec 12, 2025 positive
Assertion Not checkable as stated
Wiz built an internal AI sales bot used daily by every salesperson
“Marilyn is our internal go to market chat bot, and it's a multi-agent system I'built with one engineer. I've never had something I've built that had like a better ratio of impact to effort. So this is like me and one engineer as like a part-time thing for him.…”
Raz Herzberg Dec 12, 2025 ▶ 1:08:23 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg
May 23, 2026
Insight
Degnan: Sales teams in consumption models must be incentivized on usage
“I think like you have to go in and you have to then sell, like in a consumption model, you have to get usage. So like we talk about forward deployed engineers. Okay. Well, that's an ideal situation to deploy a forward deployed engineer or professional services…”
Chris Degnan May 23, 2026 ▶ 16:03 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.