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20VC Insight
Disqualify sales candidates whose only motivation is making money
“Is that the only thing that motivates you? Because if that's the only thing that motivates you, we're done here. I have nothing to discuss with you.”
Chad Peets Aug 23, 2024 ▶ 8:22 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Sales-driven customer discovery must precede product building
“That has to take place before you build the product. Otherwise you could build a product that nobody wants to buy.”
Chad Peets Aug 23, 2024 ▶ 13:33 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Assertion Not checkable as stated
Hiring pre-product CROs requires raising $10M seed rounds
“Yeah, usually you're going to need more than a couple million bucks to do this. You don't need 20, but you probably need 10.”
Chad Peets Aug 23, 2024 ▶ 15:22 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
CROs know what customers buy better than product teams
“The person that knows what the customer wants to buy is the person that's talking to the customer. It's the CRO.”
Chad Peets Aug 23, 2024 ▶ 16:39 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Assigning sales reps broad geographic territories without ICPs is disastrous
“What I never want to see is, Hey, I just hired 10 reps. I put a rep in New York, rep in Dallas. And a rep in San Francisco and Los Angeles, and I told them they can have all the accounts in those geographies. You're in deep shit.”
Chad Peets Aug 23, 2024 ▶ 19:00 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Product teams are ultimately responsible for revenue alongside sales
“They are, in fact, while not as directly responsible as sales, they're still responsible for revenue.”
Chad Peets Aug 23, 2024 ▶ 22:50 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Salespeople are predictable and driven entirely by compensation plans
“Salespeople are great because they're predictable. I can get you to do whatever I want you to do by setting up the comp plan accordingly.”
Chad Peets Aug 23, 2024 ▶ 23:22 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Opinion
CROs, not founders, should decide sales enablement hiring
“So first of all, it should be the CRO's decision, not the founders.”
Chad Peets Aug 23, 2024 ▶ 27:11 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Sales interviewers must either qualify candidates or sell the role
“If you're going to be in my interview process, you are either uniquely qualified to qualify or you are uniquely qualified to sell. If you are not one of those two things, you are not getting into the interview process.”
Chad Peets Aug 23, 2024 ▶ 33:26 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Sales reps blaming a lack of leads will not succeed
“If I ever hear that a rep says, well, why aren't you hitting your number? Well, I'm not getting any leads. You ain't going to make it. So yes, they are ultimately responsible for their own lead generation, but they should be supplemented.”
Chad Peets Aug 23, 2024 ▶ 37:32 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Opinion
Many join Databricks solely because it is perceived as hot
“Look at Databricks, right? Like Databricks is hiring lots of people. Some might argue too many people. I, we'll see how that plays out. But A lot of people are just going to Databricks because it's a hot company, or so they think.”
Chad Peets Aug 23, 2024 ▶ 45:10 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Assertion Not checkable as stated
Cold email and LinkedIn sales outbound no longer work
“Like what I'm being told, and again, I don't do it, but the feedback I get is emails, LinkedIn simply doesn't work. It just, it, there's too much of it.”
Chad Peets Aug 23, 2024 ▶ 50:25 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Gross retention measures product fit; net dollar retention measures go-to-market
“Gross retention tells me if people like my product. Like, I understand if my gross retention is 90%, I probably have a pretty good product. Right? If my gross retention slips down to 70%, I have a product problem. Net dollar retention is about expanding. So yo…”
Chad Peets Aug 23, 2024 ▶ 55:29 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Early-stage startups should accept negative-margin deals for references
“Early stage company, look, we do, you'll do negative margin deals, right? Like we're going to do this deal, but we're going to lose money on the deal. But we need the referenceable account, and we'll make up for it later.”
Chad Peets Aug 23, 2024 ▶ 1:01:34 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Peets: Great products lose money with bad salespeople
“Even if you have the best product in the world, you're still going to leave money on the table if you have shitty salespeople.”
Chad Peets May 23, 2026 ▶ 0:00 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Insight
Peets: Evaluate sales candidates by sales org quality, not company prestige
“There's great companies with very shitty sales organizations, and there's shitty companies with world-class sales organizations. So the first thing you look for is what quality of sales organization does the individual come from?”
Chad Peets May 23, 2026 ▶ 7:25 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Insight
Chad Peets: Sales managers must oversee at least three productive reps
“You never want a new manager to have less than five productive reps. You can't scale the organization from 100 to 300 and not have that. What I mean is if I have a manager, he's got five reps on his team, he or she, three of those reps should be productive, tw…”
Chad Peets May 23, 2026 ▶ 36:25 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Assertion Not publicly verifiable
Chad Peets: Snowflake expanded sales reps from 100 to 300 in one year
“I think one year we went from 100 to 300.”
Chad Peets May 23, 2026 ▶ 37:16 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Insight
Peets: Sales reps are only productive when hitting full quarterly quota
“A productive rep, if the productivity per rep is a million dollars per year, the first quarter they're productive is the first quarter you can expect them to do two fifties. So first of all, you have to, people get this definition wrong all the time. Like the …”
Chad Peets May 23, 2026 ▶ 39:13 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Insight
Peets: Sales rep ramp time cannot be shorter than the sales cycle
“You can do a good job of getting the enablement to happen within 90 days, but if your sales cycle is six months, you're still gonna have ramp time of six months.”
Chad Peets May 23, 2026 ▶ 39:32 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
20VC Insight
Peet: Top sales candidates memorize every detail of past performance metrics
“Somebody that's passionate about their career will know every single one of these details. They're proud of it. They hang their hat on it, right?”
Chad Peets Jan 9, 2026 ▶ 16:18 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Insight
Peet: Sales candidate specs for AI startups have narrowed significantly
“And so it makes it harder because I, again, I need more senior people, but I can't give up that ability and willingness to do the hard grunt work, the PG pipeline generation. So it makes it harder. The spec has gotten more narrow.”
Chad Peets Jan 9, 2026 ▶ 24:02 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Assertion Not checkable as stated
Peet: Every scaling company he worked at experienced ~25% sales attrition
“And so every scaling company that I've ever been a part of, we will model 25% attrition, and we're typically right there.”
Chad Peets Jan 9, 2026 ▶ 30:03 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Insight
Peet: Sales capacity plans must account for 6% quarterly turnover by overhiring
“Ok, so I have to, when I'm building a productivity plan or a hiring plan for a company, I have to bake into the fact that I'm going to have six percent turnover every quarter. I have to hire ahead of that turnover.”
Chad Peets Jan 9, 2026 ▶ 30:45 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Assertion Not checkable as stated
Chad Peet: Snowflake maintained sales productivity despite rapid scaling
“As you scale, you would expect productivity to come down. The only place I did not see that was Snowflake. We could not hire fast enough to bring the productivity down.”
Chad Peets Jan 9, 2026 ▶ 38:35 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Insight
Chad Peet: Quotas should be set 20% above expected sales productivity
“So, I take my productivity, expected productivity last year, let's assume it's a reasonable number, and then I tack on 20% to set the quota. I expect my average rep to sell 1.2, I don't want everybody hitting quota, so then I'll take the 1.2, tack on 20%, and …”
Chad Peets Jan 9, 2026 ▶ 38:47 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Insight
Peet: Sales reps default to account expansion because it is easier than new logos
“The usual problem is, my new logo ACV is not where I want it to be. All my reps are doing is focusing on expansion. Why? Because expansion's easier than opening a new account.”
Chad Peets Jan 9, 2026 ▶ 40:26 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Opinion
Peet: MongoDB has the best sales training of any at-scale company
“MongoDB at scale. Has the best training and development of any at-scale sales organization I've ever seen. It's a world-class place.”
Chad Peets Jan 9, 2026 ▶ 58:31 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets
20VC Disclosure
Sutter Hill Ventures Incubates 100% of Its Portfolio Companies Internally
“Everything we do, we incubate inside the four walls of Sutter Hill.”
Chad Peets Nov 7, 2025 ▶ 17:35 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Sales Rep Behavior Can Be Directed Completely via Compensation Plans
“Salespeople are great because they're predictable. I can get you to do whatever I want you to do by setting up the comp plan accordingly.”
Chad Peets Nov 7, 2025 ▶ 24:46 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
A $10K ACV Product Requires an Inside Sales Motion
“If I'm a 10 K ACV, then I'm exclusively inside sales and I better be able to keep the cost of sale low. Otherwise, to your point, I can't justify it. The unit economics don't work.”
Chad Peets Nov 7, 2025 ▶ 26:26 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Field Sales Reps Must Yield 3x Their On-Target Earnings
“It's sort of a rule of thumb. My reps should be able to generate three times their OTE. So if your OTE is 300 rough numbers, you should be able to get 900 K in productivity.”
Chad Peets Nov 7, 2025 ▶ 26:53 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Stop Hiring Sales Reps Until Core Productivity Benchmarks Are Met
“If you have a field sales organization, and you have 10 reps, and the productivity is 600 grand, you better not be hiring. You need to get that productivity, and until such time as either you get that productivity up, or at least can look at the data and see t…”
Chad Peets Nov 7, 2025 ▶ 27:06 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Enterprise Sales Rep Ramp Times Realistically Average Nine Months
“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months in enterprise.”
Chad Peets Nov 7, 2025 ▶ 27:46 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Dedicated Sales Enablement Is Needed at 30 to 40 Reps
“So at 10 reps, do you need an enablement person? Probably not. And each circumstance clearly is unique, but at 30 to 40, yeah, you better start to think about it.”
Chad Peets Nov 7, 2025 ▶ 28:38 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Assertion Not checkable as stated
Early Snowflake Accounts Expanded From $15K to $150K in Six Months
“In the early days, it was crazy. Like people would buy A 15 K land deal, and they'd expand to 150 in six months, right? So when you have product like that, that just expands on its own, you can get away with less customer success. I've not seen that since Snow…”
Chad Peets Nov 7, 2025 ▶ 29:44 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Sales Engineers Leave Struggling Startups Before Sales Reps Do
“Your SEs will start to depart before your reps. And when your SEs start to depart, the reps know that the SEs know more than the reps know about the product. Right. So you'll see SE start to depart and the reps will start to follow.”
Chad Peets Nov 7, 2025 ▶ 55:01 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
20VC Insight
Conducting 10 interviews per hire kills sales team scaling productivity
“If you're going to scale like that, you can't have 10 interviews per hire, right? It kills the productivity.”
Chad Peets Aug 23, 2024 ▶ 6:50 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Wealthy veteran sales executives rarely return to operational CRO roles
“Most of these guys are now reaching a point where they've made so much money where they may not want to go back and do this again. So you have to look for the next generation.”
Chad Peets Aug 23, 2024 ▶ 11:30 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Sales reps should collect customer data, not write marketing content
“Salespeople, as good as they are, is capturing and understanding the data. That doesn't mean they're necessarily great at creating content. So what you want them to do is capture all of the information, feed it back into product marketing and let product marke…”
Chad Peets Aug 23, 2024 ▶ 20:55 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
$10K ACV products cannot support dedicated field sales reps
“So if you look at a 10 K ACV, well, that's definitely not a field sales rep, right? If I'm a 10 K ACV that I'm exclusively inside sales and I better be able to keep the cost of sale low. Otherwise, to your point, I can't justify it. The unit economics don't wo…”
Chad Peets Aug 23, 2024 ▶ 25:00 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Sales reps must generate at least 3x their OTE in productivity
“My reps should be able to generate three times their OTE. So if your OTE is 300 rough numbers, you should be able to get 900 K in productivity.”
Chad Peets Aug 23, 2024 ▶ 25:38 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Startups should pause sales hiring until productivity targets are met
“So if you have a field sales organization and you have 10 reps and the productivity is 600 grand, you better not be hiring. You need to get that productivity, and until such time as either you get that productivity up, or at least can look at the data and see …”
Chad Peets Aug 23, 2024 ▶ 25:51 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Enterprise sales ramp times realistically trend toward nine months
“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months in enterprise.”
Chad Peets Aug 23, 2024 ▶ 26:33 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Startups need dedicated sales enablement at 30 to 40 reps
“So at 10 reps, do you need an enablement person? Probably not. And each circumstance clearly is unique, but at 30 to 40, yeah, you better start to think about it.”
Chad Peets Aug 23, 2024 ▶ 27:31 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Assertion Supported
Early Snowflake had no customer success organization
“They don't have a customer success organization at Snowflake, or at least they didn't. Maybe they've created one out, but they didn't. The feeling was everybody's in customer success.”
Chad Peets Aug 23, 2024 ▶ 28:21 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Assertion Not checkable as stated
Early Snowflake accounts expanded from $15K to $150K in six months
“Like, people would buy A 15 K land deal, and they'd expand to 150 in six months, right? So when you have product like that, that just expands on its own, you can get away with less customer success. I've not seen that since Snowflake.”
Chad Peets Aug 23, 2024 ▶ 28:42 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
20VC Insight
Startup sales reps cannot expect to love daily pipeline generation
“Having a rep that loves his day job is, is very difficult in our environment because nobody likes doing pipeline generation. It's not fun. It's a grind.”
Chad Peets Aug 23, 2024 ▶ 40:23 Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193 · 20VC with Harry Stebbings
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