outbound sales

12 statements across 11 episodes · 3 bullish · 3 bearish · 11 people on the record · first statement May 25, 2022 by Oliver Jay · across every show →

Everything said about outbound sales, oldest first

May 25, 2022
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
May 25, 2022
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
Feb 21, 2023 positive
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
Aug 25, 2023
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
Jan 31, 2024 bearish
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
Feb 14, 2024
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
Apr 12, 2024
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
Apr 24, 2024 bearish
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
Dec 20, 2024 negative
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
Jan 24, 2025
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
Aug 4, 2025 positive
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
May 2, 2026 bullish
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
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