Outbound Sales

topic on 7 shows · 30 statements across 29 episodes

the Y Combinator Startup Podcast Startup Acquisition Stories the Neon Show the Official SaaStr Podcast A Product Market Fit Show Top Founders 20VC

30 statements about Outbound Sales, every show

Hughes: Targeting C-level executives for product feedback drives delegated sales deals
“If you can get in like at the highest level and work down the chain that's a good start to put.”
Mark Hughes Jun 1, 2026 ▶ 26:45 He hit $1M ARR by sending 500,000 cold emails—then raised a $25M Series A in 6 days. | Mark Hughe... · PMF Show
20VC Insight
Lindquist: Outbound sales will never be dead
“Outbound will never be dead. You can't reach every single company and every single buyer with whatever marketing you're doing.”
Becca Lindquist May 2, 2026 ▶ 53:20 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
SAASTR Insight
Lemkin: AI SDRs fail unless an outbound sales playbook is proven first
“If you haven't gotten any outbound to work, Buying an AI to do it isn't, it's not going to help you. You have to prove it. Any of the agents we use, any of the dozens of agents we use, we are taking a playbook that at least works a little bit.”
Jason Lemkin Mar 18, 2026 ▶ 5:49 10 Things to Know Before You Deploy Your First AI SDR
Paffenholz: Top startup candidates do not apply to inbound job postings
“The best candidates aren't applying. They're probably already working somewhere else. You can think of this as very similar to outbound sales.”
David Paffenholz Nov 7, 2025 ▶ 8:13 The Startup Playbook for Hiring Your First Engineers and AEs · Y Combinator
NEON SHOW Disclosure
Makhija: Outbound remains the largest customer acquisition channel for Unicommerce
“Our earlier journey was a lot focused on outbound, and that still is the largest channel for us.”
Kapil Makhija Aug 29, 2025 ▶ 1:04:50 7 Myths About Selling B2B SaaS In India ft Unicommerce Founder Kapil Makhija
20VC Opinion
AI is already better at outbound sales than human representatives
“I don't know if completely replace it, but certainly I think outbound stuff, the AI is actually better at it than humans, in my opinion, because it'll also learn what works faster, right?”
Ron Gabrisko Aug 4, 2025 ▶ 54:50 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
Trevor Lee: Platform marketplace distribution outperforms outbound sales
“The benefit is when you figure out the distribution mechanism, it works significantly better than like, doing outbound sales.”
Trevor Lee May 20, 2025 ▶ 5:26 The Lean SaaS Exit: PLG, Profitability, and a Strategic Acquisition
A scalable outbound sales operation cannot function at a $29 price point
“We knew it wouldn't scale long-term, not at 29 bucks a month. Like you can't run a really effective outbound operation. That was one thing we've learned about the economics of a business.”
Forrest Zeisler May 5, 2025 ▶ 37:54 1 year in he had just 3 customers—today he’s at $100M ARR. | Forrest Zeisler, Co-Founder of Jobbe... · PMF Show
Chopra: Outbound sales models do not work for $1,000 deals
“Because the go-to-market model was so expensive, no one's going to do outbound on a thousand dollar deal, right?”
Saurav Chopra Mar 6, 2025 ▶ 31:52 He started Groupon for SMBs, grew to $36M ARR—then exited for $170M. | Saurav Chopra, Founder of ... · PMF Show
20VC Insight
Outbound Sales Models Break Down Below $50k Contract Sizes
“Certainly down to 50 K, maybe below 50 K probably, you know, starts to break down. Cause down to 50 K you know, your reps are gonna be earlier in career, and so their OTE is not as high.”
Carlos Delatorre Jan 24, 2025 ▶ 38:24 Carlos Delatorre, CRO @Harness: Why Every Sales Rep Should Do Pipeline Generation | E1251 · 20VC with Harry Stebbings
Y COMBINATOR Prediction Not checkable as stated
Conrad: Effective AI SDRs will overwhelm and destroy outbound sales
“What'll happen is it'll just destroy outbound the, as a channel, it will cease to work and cease to function because it'll just get so overwhelmed at that point.”
Parker Conrad Jan 10, 2025 ▶ 35:30 How To Build The Future: Parker Conrad · Y Combinator
20VC Opinion
Plank: People calling outbound sales dead lack experience or seek clout
“I think people that say outbound is dead are either one of two things. Like they're either engagement bathing, you know, looking for a reaction on LinkedIn or whatever that they know that there's a whole army of people out there where that's their profession a…”
Matt Plank Dec 20, 2024 ▶ 7:05 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Walker: Outbound and founder sales no longer scale companies to $100M revenue
“If you want to build a hundred million dollar revenue company, then it's going to be really hard to do that through founder sales or even just scaling outbound sales. Everyone knows that that's not going to get you there anymore. Maybe it did in 2007 when the …”
Chris Walker Jun 17, 2024 ▶ 15:14 He grew to $22M ARR in 4 years—but regrets spending so much on growth. | Chris Walker, Founder of... · PMF Show
20VC Prediction Not checkable as stated
Stebbings: AI Will Cause The Complete Destruction Of Outbound Sales
“I think AI will actually destroy outbound in many cases, because it will just create infinite supply of messages, or infinite supply of whatever channel that is, and so I think you actually see the complete removal of it.”
Harry Stebbings Apr 24, 2024 ▶ 44:50 Rujul Zaparde: Why Hiring Inexperienced People is Better | E1144 · 20VC with Harry Stebbings
20VC Insight
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…”
Sam Blond Apr 12, 2024 ▶ 56:53 Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 · 20VC with Harry Stebbings
20VC Insight
Gonto: Internal tech stack initiatives are stronger outbound triggers than industry verticals
“We realized that the initiative mattered more than the industries. So for example, if a company's upgrading the technology stack, moving from JavaScript to Java, then at that point, it actually made sense for them to think about the authentication provider.”
Martin Gontovnikas (Gonto) Feb 14, 2024 ▶ 13:04 Martin Gontovnikas (Gonto): The Biggest Mistakes Startups Make When Scaling into Enterprises | E1115 · 20VC with Harry Stebbings
20VC Insight
Kellogg: Outbound sales strategy fails on low ACV $5k productivity products
“If you're selling a 5000 dollar a year system to anybody, As a generic productivity tool, I have a lot more trouble getting excited about outdoor.”
Dave Kellogg Jan 31, 2024 ▶ 51:14 Dave Kellogg: How to Forecast in 2024 & Why CaC Payback is Flawed and CAC Ratio is Better | E1110 · 20VC with Harry Stebbings
20VC Insight
Howie Liu: Single-User Software Cannot Support Outbound Sales Economics
“If you're taking a single user product out to market it's just harder to make performance marketing work. It's harder to make, you know, you can't really make outbound sales work, right? The economics of, You know, pitching a single user who pays a single and …”
Howie Liu Aug 25, 2023 ▶ 3:03 Howie Liu: Decoding Airtable's $11B Valuation; The Impending AI Revolution in Enterprise | E1053 · 20VC with Harry Stebbings
SAASTR Insight
A 100% Win Rate Means You Are Failing At Marketing And Outbound
“When I hear that we win every deal, I just know it means you're not doing any marketing. You're not doing any marketing and you're likely not doing any outbound in sales either.”
Jason Lemkin Aug 21, 2023 ▶ 11:46 The Top 10 Worst Pieces of SaaS Advice with SaaStr Founder Jason Lemkin
20VC Opinion
Lawryk: Outbound sales requires a multi-channel approach, not just cold emails
“I don't think outbound is dead. I think outbound has just has fundamentally changed in terms of the methods that you need to use to engage prospects. And you have to take like a multi-channel approach to that.”
Zach Lawryk Feb 21, 2023 ▶ 8:18 Zach Lawryk: The Ultimate Guide to Sales Engineering | E980 · 20VC with Harry Stebbings
TOP FOUNDERS Disclosure
Gomez: 95% of Serviceform's business comes from its 20-person outbound team
“The other reason why we have too many people is because of entire business so far, I would say maybe about 95% of it is outbound sales driven. So that's where, you know, more people come in sales, and we have about 25% sales team. Actually, 20.”
Aranthe Gomez Dec 25, 2022 ▶ 8:58 How She Landed $13m Valuation with $1.8m in ARR Last Week for SMB SaaS
Olson says selling OKRs via outbound is like selling a root canal
“We don't do any outbound because selling strategy and OKRs is like selling a root canal. So we stopped doing that. It doesn't work for us.”
Erica Olson Nov 14, 2022 ▶ 9:50 How my shift from SaaS to SaaS+ moved retention from 74% to 107%
20VC Insight
Outbound sales requires distinct buyers, messaging, and larger deal sizes
“For outbound to be successful, generally speaking, you're selling to a different buyer. Probably a more senior persona. You're probably selling a different value. And so therefore you need different messaging. In terms of the sales process, absolutely, you'll …”
Oliver Jay May 25, 2022 ▶ 40:41 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
20VC Insight
Cold outbound fails without company-wide marketing and product alignment
“If what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people. It won't gonna work because your entire conversion process is designed around a different buyer, articul…”
Oliver Jay May 25, 2022 ▶ 41:31 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Latka: Outbound sales playbooks are unsustainable at $200 per month
“I mean, you can't run an outbound sales playbook at 200 bucks a month. There's not enough margin to play with the cover sales expenses.”
Nathan Latka Mar 11, 2022 ▶ 7:02 SaaS Startup Raises at $3m Valuation Helping Precious Metal Dealers Verify Buyers and Sellers
TOP FOUNDERS Disclosure
Dragunov: Batch Products currently does zero outbound sales
“We're missing a lot of key things at the moment with any kind of outbound sales, which we're currently not doing at all.”
Ivo Dragunov Mar 30, 2021 ▶ 14:29 Real Estate SaaS Did $2.2m Last Month, 140% Growth, Mostly Affiliate Sales
Bice: Pure outbound sales fails at BoomTime's current price point
“So just pure outbound sales is not going to work at this price point.”
Bill Bice May 30, 2020 ▶ 15:08 BoomTime.com: Hit $2.8m in Revenues, First 100 Customers From Linkedin
Y COMBINATOR Disclosure
Second Measure acquired its first 150 clients with zero outbound sales
“We actually haven't done any outbound sales yet, right? We have a 150 clients. Every single one of them came to us through inbound, right?”
Michael Babineau May 29, 2019 ▶ 47:24 Analyzing Billions of Transactions to Understand Consumer Behavior - Michael Babineau and Kevin Hale · Y Combinator
Halligan: Outbound sales and cold calling are dead and actively harm brands
“I think outbound is largely just dead. I don't think cold calls work at all. In fact, I think they're negative.”
Brian Halligan May 8, 2019 ▶ 18:56 HubSpot CEO and Cofounder Brian Halligan with Wufoo Cofounder Kevin Hale · Y Combinator
Macia: Outbound sales outperforms online marketing for vertical targeting and feedback
“Now we are putting more resources on, on Advant, because it's a way to be more strategic in sales, because this way we can target better with the industries where we are more strong, and the good thing here is that we get a lot of feedback, because we can actu…”
Oscar Macia May 12, 2018 ▶ 9:50 1022 How This Barcelona Sales Tool Grew 2x YoY, Raised $16m, Charging $200/Seat

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