small, medium-sized businesses

also referred to as: small, medium businesses · smb · smbs

16 statements across 14 episodes · 7 bullish · 1 bearish · 14 people on the record · first statement Oct 22, 2020 by Eoghan McCabe · across every show →

Everything said about small, medium-sized businesses, oldest first

Oct 22, 2020 positive
Assertion Supported
McCabe: Intercom built a $100M business selling to SMBs
“We built a hundred million dollar business with SMB.”
Eoghan McCabe Oct 22, 2020 ▶ 15:58 20VC: Intercom Founder, Eoghan McCabe on How To Deal with the Weight of Expectation, Having Your Identity Tied To Your Company, How To Be Your Authentic Self Even with Stakeholders & Why There Are No Rules
Mar 15, 2021 bullish
Prediction Not checkable as stated
Fadell: Financing SMB tech adoption represents a massive profit opportunity
“We are going to have to finance so many things, and this is where the finance industry can make a ton of money if they start looking at these small, medium-sized businesses And start looking at the technology that they could adopt if they were financed properl…”
Tony Fadell Mar 15, 2021 ▶ 39:38 20VC: Tony Fadell "The Father of The iPod" on Mentors, Self-Doubt, Vulnerability, His Relationship To Money, Why Entrepreneurs Need to Be Coachable, Why VCs Need To Be More Direct & Why The First Trillionaire Will Innovate Around Climate Change
Dec 8, 2021
Prediction Held up
Figma is preparing to launch an SMB sales segment
“And we're actually soon launching SMB”
Kyle Parrish Dec 8, 2021 ▶ 27:32 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
Jan 25, 2023
Insight
SMBs measure compliance speed while enterprise customers measure risk reduction
“So an SMB is measuring How quickly can I complete this process to prove I'm compliant? And a mid market customer is really measuring how much time can I save? How much risk can I reduce?”
Stevie Case Jan 25, 2023 ▶ 22:35 Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970 · 20VC with Harry Stebbings
Jan 25, 2023
Insight
Individual sales reps cannot simultaneously handle SMB and enterprise deals
“I think the thing that goes wrong is when You've got a team focused on one segment and you ask them to dip a toe in the water of another segment. And it's very hard for any one person to both do, you know, high velocity bottom of the market deals and also do s…”
Stevie Case Jan 25, 2023 ▶ 25:06 Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970 · 20VC with Harry Stebbings
Aug 4, 2023 positive
Insight
Sela: Driving local business growth requires moving phone buyers to digital
“And so to me, more sales for SMBs meant how do I increase the customer lifetime value of the existing customers? And the way to do that is to move them from the phone channel to the digital channel.”
Ilir Sela Aug 4, 2023 ▶ 39:31 Ilir Sela: How I Founded Slice Pizza & Became One of Macedonia’s Largest Employers | E1044 · 20VC with Harry Stebbings
Jan 24, 2024 negative
Insight
Enterprise Expansion Yields Slower Returns on Speed Than SMB
“You need some capital to go into the enterprise and you won't get that immediate love. You won't. It takes time. It doesn't have the same return on speed as the SMB or mid market will have.”
Sean Murray Jan 24, 2024 ▶ 47:05 Sean Murray: Why Discovery Today is F***** & How to Scale Into Enterprise Effectively | E1107 · 20VC with Harry Stebbings
May 17, 2024
Insight
Zhang: Content creators are SMBs and SMBs must become creators
“We believe that, you know, creators are SMBs and SMBs are creators, meaning creators are trying to make money and SMBs in order for them to be, to survive in the world today, They need to understand social media. They need to be much more digitally native. We …”
Jiaona Zhang May 17, 2024 ▶ 22:28 Jiaona Zhang: Why All Product Teams Should Have a Scorecard & How to Use It | E1154 · 20VC with Harry Stebbings
Jul 12, 2024
Insight
Roberge: SMB startups need 15%+ revenue expansion for 100%+ NRR
“Now, when you are, if you do want to make your business work in SMB, You just need a really healthy up expansion motion because I just macroeconomics because of like small business bankruptcy and budget sensitivities at, if you're doing really well, you probab…”
Mark Roberge Jul 12, 2024 ▶ 27:36 Mark Roberge: The Framework for How Startups Should Scale into the Enterprise -Stage 2 Capital|E1176 · 20VC with Harry Stebbings
Aug 21, 2024 neutral
Disclosure
Narang: Toast has higher market penetration in mid-market than SMB
“In fact, we have more market penetration within mid-market than we even do in SMB today.”
Aman Narang Aug 21, 2024 ▶ 38:40 Aman Narang: 5 Lessons Scaling Toast to $14BN Market Cap | E1192 · 20VC with Harry Stebbings
Sep 27, 2024
Assertion Supported
HubSpot study found SMBs average 250 software applications
“There was some research done by HubSpot not too long ago where SMBs had a tech stack of about 250 apps.”
Jeetu Mahtani Sep 27, 2024 ▶ 40:40 Jeetu Mahtani, Sales Leader @Hubspot: How and When to Go International and Crush It | E1207 · 20VC with Harry Stebbings
Oct 23, 2024
Insight
Selling to Fortune 100 and SMBs simultaneously will kill early startups
“If you all of a sudden are trying to go to the fortune 100, and also sell to SMBs, you're gonna fail.”
AJ Tennant Oct 23, 2024 ▶ 7:55 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Oct 23, 2024 positive
Assertion Not checkable as stated
AJ Tennant: Glean maintains a 97% to 98% gross retention rate
“And so, you know, luckily at Glean, we have like a 97, 98% GRR. The only accounts we're churning are SMBs,”
AJ Tennant Oct 23, 2024 ▶ 32:20 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Mar 17, 2025 positive
Assertion Not checkable as stated
HubSpot's early growth relied on SMB focus, single platform, and culture
“Deep conviction in SMB. Deep conviction in building a platform and crafting the platform Deep conviction in having culture as a product. Like, those are decisions that I just loved, and I completely believed in.”
Yamini Rangan Mar 17, 2025 ▶ 1:40 Yamini Rangan, CEO @ HubSpot: How HubSpot Competes Against Salesforce · 20VC with Harry Stebbings
Aug 7, 2025 bullish
Prediction Not checkable as stated
Rory O'Driscoll predicts SMBs will adopt pre-packaged AI within two years
“So over the next couple of years, it may well be, as I say, for things like phone answering, simple order dispatch, that there'll be a whole, whole bunch of pre-canned, pre-baked, This is how it works, Mr. SMB. Just turn it on, and you too can sound like a big…”
Rory O'Driscoll Aug 7, 2025 ▶ 54:19 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Feb 28, 2026 bullish
Prediction Not checkable as stated
Jerry Murdock: Small and medium businesses will adopt autonomous agents before enterprises
“I think the first companies that are going to go with this are going to be small, medium businesses, because they're the ones that, wow, one secretary makes a huge difference in their, in, in how they, you know, two, three, four person company, how they handle…”
Jerry Murdock Feb 28, 2026 ▶ 26:16 The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
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