DocuSign, every mention

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every year anyone Brendon Cassidy 11Harry Stebbings 9Josh Breinlinger 6Jason Lemkin 6Mitchell Green 3Jason Calacanis 2Jake Saper 2Fred Turner 2Des Traynor 2Byron Deeter 2

Verbatim, from the transcripts: the passages where DocuSign comes up

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We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO Jul 18, 2026 · 2 mentions

  • ▶ 53:55 Fred Turner She'll open up the DocuSign link and then click the button, and it's my signature on that agreement.
  • ▶ 1:09:39 Fred Turner So the agent opens DocuSign and clicks the sign button and it's legally binding and it has my signature on the page.

Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings Jun 6, 2026 · 1 mention

  • ▶ 16:52 unnamed speaker There's people that are vibe coding Salesforce and, and, and DocuSign and other companies.

Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings May 14, 2026 · 1 mention

Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings Apr 23, 2026 · 1 mention

  • ▶ 18:49 Rory O'Driscoll So they'll get the shareholder consent in the docusign and they'll say, thank you very much.

NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings Mar 19, 2026 · 1 mention

  • ▶ 33:38 Jason Lemkin Obviously, if you just look at Rory's investment in DocuSign, it is doing more than two million today.

Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings Feb 26, 2026 · 4 mentions

  • ▶ 6:01 unnamed speaker I was thinking about one of our own DocuSign. 3 times in the scene
  • ▶ 1:02:31 Jason Lemkin Listen, I'm not as big an expert in Figma as I am say in DocuSign, but there's a similarity between the DocuSign and the Adobe Sign and Figma, which is that the products are much more workflow oriented.

Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings Sep 18, 2025 · 1 mention

  • ▶ 1:09:08 unnamed speaker Um, I mean, knowing Rory, like, even if, even if EchoSign had just done okay, and we'd gotten up to a hundred million, just the folks that DocuSign turned down would have come and bought us for a billion bucks.

Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings Aug 7, 2025 · 1 mention

  • ▶ 45:40 unnamed speaker We did HubSpot, Box, DocuSign, and I think RingCentral.

Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings Jun 12, 2025 · 3 mentions

  • ▶ 37:55 unnamed speaker Look, if I knew DocuSign was going to compound to where it did, I would have done the round at 19 bucks a share, too.
  • ▶ 39:29 Jason Lemkin The DocuSign and even the EchoSign, AdobeSign lesson, looking back, having been there, right?
  • ▶ 51:28 unnamed speaker And that's an extreme example, but I think DocuSign wrestled with some of the similar things, right?

a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings Apr 17, 2025 · 1 mention

  • ▶ 5:27 unnamed speaker So, you know, anyone who needed a Zoom account or a DocuSign account has a DocuSign account, because they all got on COVID.

Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings Mar 26, 2025 · 3 mentions

  • ▶ 10:34 Mitchell Green There was a company called SafeSend that makes, um, it's like a verticalized version of DocuSign for tax returns. 3 times in the scene

Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings Mar 10, 2025 · 2 mentions

Mark Roberge: The Framework for How Startups Should Scale into the Enterprise -Stage 2 Capital|E1176 · 20VC with Harry Stebbings Jul 12, 2024 · 1 mention

Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 · 20VC with Harry Stebbings Apr 12, 2024 · 1 mention

  • ▶ 15:47 Sam Blond Um, if Jason had solved for hiring people from either DocuSign, which was like the direct competitor

Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 · 20VC with Harry Stebbings Mar 8, 2024 · 11 mentions

Sean Murray: Why Discovery Today is F***** & How to Scale Into Enterprise Effectively | E1107 · 20VC with Harry Stebbings Jan 24, 2024 · 1 mention

  • ▶ 38:29 Sean Murray But what I need to be able to say is you, it's like, Harry, look, I'm going to set you up with the folks at Slack, DocuSign and Snowflake, and they're going to tell you a story of how they use my product.

Brian Halligan: Leadership Lessons Scaling Hubspot to $28BN | E1103 · 20VC with Harry Stebbings Jan 15, 2024 · 1 mention

Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings Nov 15, 2023 · 1 mention

Chris Degnan: Why You Should Hire a Head of Sales Sooner Than You Think | E1080 · 20VC with Harry Stebbings Nov 10, 2023 · 2 mentions

  • ▶ 3:08 Harry Stebbings There are 6000 companies, including Zoom, Siemens, Okta, DocuSign, and many more, who depend on Outreach to power their revenue organizations.
  • ▶ 56:27 Harry Stebbings There are 6000 companies, including Zoom, Siemens, Okta, DocuSign, and many more, who depend on Outreach to power their revenue organizations.

Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043 · 20VC with Harry Stebbings Aug 2, 2023 · 1 mention

Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings Jan 13, 2023 · 1 mention

  • ▶ 2:44 Jason Lemkin And back in the days when I was competing with DocuSign, I almost wanted to jump off the roof if we couldn't be number one in categories, right?

Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960 · 20VC with Harry Stebbings Dec 15, 2022 · 1 mention

  • ▶ 10:16 Maggie Hott You know, not necessarily for next year, but for the next five years, these are going to be things like, you know, a couple little bit of our tech stack is DocuSign.

Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings Nov 30, 2022 · 2 mentions

  • ▶ 22:29 unnamed speaker You can't get it like EchoSign and DocuSign did in the early days because there's nothing else.
  • ▶ 31:42 Jason Lemkin DocuSign was a windows printer driver.

Des Traynor: How I Founded Intercom; Product Marketing Tips; Feature Creep | 20VC #907 · 20VC with Harry Stebbings Jul 18, 2022 · 1 mention

  • ▶ 51:45 Des Traynor Is you're just getting hit with like DocuSigns left, right, and center, or like due diligence things, or like, oftentimes it'll be like, hey, we have to form this other company, which is a special purpose vehicle to make this investment,…

Fabrice Grinda: The First Person to Predict the Collapse of Credit Suisse? | 20VC #886 · 20VC with Harry Stebbings May 21, 2022 · 1 mention

  • ▶ 55:41 Fabrice Grinda You cannot imagine to the extent I abhorred, which is why I auto-docu-signed, you know, documents for 15 years without ever reading them, uh, which is okay when you're deploying your own capital, but if you want to be a manager of other…

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 May 27, 2021 · 1 mention

  • ▶ 0:35 Harry Stebbings To name a few of the investments, Twilio, which we focus on today, Service Titan, HashiCorp, Canva, Intercom, DocuSign, SendGrid, the list goes on.

20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open Jul 8, 2019 · 2 mentions

  • ▶ 0:40 Harry Stebbings Byron's investments include the likes of Twilio, Intercom, SendGrid, Gainsight, Box, DocuSign, and many more incredible companies.
  • ▶ 15:45 Byron Deeter And then, uh, indirectly supporting my partner, uh, Ethan Kurzweil, who is the lead on our pager duty investment, but seeing fantastic CEOs like Jeff and Samir and Dan at DocuSign and Jen's hot and the like, the end of the day is pretty…

20VC: The Framework LPs Use To Assess Emerging Managers, What Concerns and Excites LPs in Potential Opportunities & The Current State of Seed Today with Hunter Somerville, Partner @ Greenspring Associates Jan 21, 2019 · 1 mention

  • ▶ 0:27 Harry Stebbings On the direct side, their portfolio includes the likes of Sonos, App Annie, DocuSign, and Alibaba, just to name a few.

20VC: Jason Calacanis on The 4 Questions Investors Must Ask Founders, Whether YC Have Scaled Their Process Successfully & Why Early Founder Liquidity Is Good Not Bad Aug 14, 2017 · 2 mentions

  • ▶ 28:08 Jason Calacanis Literally, like, there was one class where, like, one of the people sent me a DocuSign for a 100,000 dollars, and, like, I almost clicked on it, and I did click on it to open it, and I was like, what is this? 2 times in the scene

20VC: Why Spray & Pray Investing Is Wrong, Why Data-Informed VC Beats Data Driven VC & What To Look For When Investing In A Marketplace with Josh Breinlinger, Managing Director @ Jackson Square Ventures Apr 5, 2017 · 6 mentions

  • ▶ 20:33 Josh Breinlinger At Jackson Square Ventures, the partners here, we've invested in four unicorn companies, and three of them, Equalogic, DocuSign, and Responsys, they all had bridge rounds. 6 times in the scene

20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners Nov 28, 2016 · 1 mention

  • ▶ 0:38 Harry Stebbings Rory currently sits on the board of some incredible companies, including Bill.com, Box, Datasift, DocuSign, OneLogin, and many more incredible names.

20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight May 2, 2016 · 2 mentions

  • ▶ 19:23 Byron Deeter Whereas you contrast that with a business like Eloqua or Cornerstone on demand or DocuSign, all great, you know, unicorn businesses in our portfolio.
  • ▶ 20:18 Harry Stebbings And you mentioned some of the incredible investments there that Bessemer have made in SendGrid, in Box, in DocuSign, just, you know, picking some out of thin air there.

20 VC 034: 250 Investments, AngelList Syndicates and Microsoft with Jon Staenberg May 7, 2015 · 2 mentions

  • ▶ 0:14 Harry Stebbings John has made an incredible 250 investments in startups, including the likes of the amazing Matt Mullenwigs Automatic, StubHub, and DocuSign, just to name a few.
  • ▶ 10:39 Jon Staenberg I tend to think of myself as an early stage investor, but having said that, uh, you know, I'm in, uh, DocuSign, which I did later in Avalara,
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