Zenefits, every mention

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every year anyone Sam Blond 77Matt Plank 19Jason Lemkin 14Brendon Cassidy 3Jen Knight 1Henrique Dubugras 1Brian Murray 1Ben Braverman 1

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

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CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina Sep 9, 2026 · 3 mentions

  • ▶ 14:11 Sam Blond This is always a fun one, and I can certainly do it at Brex, Zenefits, and others.
  • ▶ 16:25 Sam Blond There's the first one, interestingly, that you highlighted it, you know, most of my career, I was at a company called Zenibits and then Brex more recently at Zenibits. 2 times in the scene

The Agents #008: Agents Are Merging, Not Multiplying. Plus, Sam Blond on Why Outbound Isn't Dead. Jul 1, 2026 · 2 mentions

  • ▶ 36:41 Jason Lemkin Zenefits, uh, was our first outbound leader in the old days at Adobe Sign, Echo Sign, partnered Founders Fund, and now founder and CEO of one of the hottest GTM startups.
  • ▶ 1:00:35 Jason Lemkin Classic Parker Conrad, old Zenefits playbook, done again, works, right?

How Windsurf Built A Billion-Dollar AI Leader and a Winning Sales Machine Mar 5, 2025 · 1 mention

  • ▶ 21:26 Sam Blond And, and, and I can sort of relate where thinking back to the organizations at, at Brex and at, at Zenefits,

Usage-Based Revenue Models: Successes & Pitfalls from Checkr COO Lindsey Scrase on CRO Confidential Jan 8, 2025 · 1 mention

  • ▶ 20:09 Sam Blond When I was at Zenefits, which we made money as a health insurance broker, and we were licensed in all 50 states.

How to Think About Product-Led Growth, Bootstrapping vs VC, and Early Exits with Jason Lemkin Dec 18, 2024 · 1 mention

  • ▶ 19:07 Jason Lemkin And they took the model, Parker, and Sam built that model at Zenefits, and then they reproduced it at Rippling.

The Future of AI and Sales in SaaS with Henry Schuck, CEO of ZoomInfo and SaaStr CEO Jason Lemkin Oct 18, 2024 · 3 mentions

  • ▶ 9:51 Jason Lemkin And he started to talk about the compound startup of how after the Zenefits experience, he wanted to build all the HR products. 3 times in the scene

The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale with Rippling CRO Matt Plank Sep 27, 2024 · 1 mention

  • ▶ 14:37 Matt Plank If you go back 10 years ago, when we were building SDR teams at benefits, it was like, yeah, spreadsheet, it wasn't even outreach, right?

Deep Dive: Easy Sales Concepts So Many Get Wrong with Sam Blond Jun 21, 2024 · 3 mentions

  • ▶ 4:54 Sam Blond The candidates that I brought in, the first hires that I brought in, were all personal network from Zenefit and other places that I had connections. 2 times in the scene
  • ▶ 18:33 Sam Blond Jason Lemkin, Parker, who on this slide, Parker was my CEO at Senefits, and several others.

Advice Every SaaS Founder Needs to Know to Scale to $100m with Sam Blond and Jason Lemkin Mar 20, 2024 · 2 mentions

From Zero to Hero: How to Dominate Outbound SaaS Sales with Rippling and Sam Blond Jan 4, 2024 · 6 mentions

  • ▶ 0:29 Sam Blond And let's see, Ashley started as an SDR at Zenefits when I was the VP of sales.
  • ▶ 5:11 Sam Blond Ashley, you joined Brex when we are about two million dollars in ARR, and I would say for a lot of businesses, if you're a software business, that maps to less ARR because Zenefits made money on interchange.
  • ▶ 36:53 unnamed speaker I remember at Zenefits at one point, I think I had, like, 35 SDRs reporting to me as a manager, and that was terrible. 4 times in the scene

CRO Confidential: The Hangover's Over: 5 Ways to Get Your SaaS Revenue Back On Track with Gong's SVP Nov 23, 2023 · 3 mentions

  • ▶ 14:13 unnamed speaker Even if like in the world of Zenefits, we were overloaded with pipeline, but the minute we started running out of pipeline, right?
  • ▶ 26:36 Sam Blond Um, so I'll frame this when I think about the two most impactful things that I have, uh, done at Brex, at Zenefits, at companies that I've been at, companies that I've sort of advised for and worked with. 2 times in the scene

The Proven Customer Acquisition Strategies Behind Toast's Record Breaking Growth with Toast's CRO Nov 3, 2023 · 1 mention

  • ▶ 30:34 Sam Blond Uh, and it's, it's one of those things that it, it's not a one size fits all where the thing that worked for Zenefits, it, it would be different from the thing that worked for Rex.

10 Things Top CROs Wish They Knew Early in Our Careers with CRO Justworks Aug 15, 2023 · 1 mention

  • ▶ 0:17 Brendon Cassidy I followed the space in the category and saying sort of JustWorks and Zenefits and others and, and watching sort of JustWorks emerge as a category winner there.

How to Grow Revenue Faster in the Second Half of 2023 with Founders Fund Jul 19, 2023 · 1 mention

  • ▶ 15:03 Sam Blond There's an example that I'll give here, a company that I'm, I'm on the board of that, uh, Founders Fund, a large investor, I'm close with Parker from Zenefits.

Why You're Unfundable Today: The Cold, Hard Truths About SaaS Part 2 with SaaStr CEO Jason Lemkin Jul 14, 2023 · 1 mention

  • ▶ 46:12 Jason Lemkin Well, look, I think there's a lot, I mean, there's a lot of, what, what most folks do wrong, almost all COs, um, I remember I actually did it with Sam and Parker in the early days of Zenefits, and then they got it, they got it right, is…

Rippling CEO Parker Conrad's Theory of the Compound Startup: Disrupting How We Think About Software Jun 27, 2023 · 4 mentions

  • ▶ 18:48 Sam Blond Um, and then you were founder and CEO at Zenefits, which was, it was more compound startup, and now you're rippling, which is sort of like the ultimate compound startup. 4 times in the scene

SaaStr CRO Confidential: Principles that Drove Wiz’s $0 to The First $100m ARR | Wiz CRO Colin Jones Jun 1, 2023 · 9 mentions

  • ▶ 5:03 Sam Blond So there are some, some similarities to what I experienced in joining Zenefits and Brexit, and there's one thing that stands out that is, um, dissimilar. 3 times in the scene
  • ▶ 13:39 Sam Blond Jason, uh, Lemkin introduced me to Parker at Zenefits when I was ready for my first VP of sales opportunity and YC 2 times in the scene
  • ▶ 20:57 Sam Blond I knew him from Zenefits. 2 times in the scene
  • ▶ 37:43 Sam Blond Um, when Zenefits was, uh, very young and immature, we had a goal of going from like 500,000 dollars in ARR to ten million in ARR in, uh, one year. 2 times in the scene

CRO Confidential: 3 Secrets For Early-Stage Startups To Acquire Customers | CoSell.io Co-Founder May 16, 2023 · 4 mentions

  • ▶ 0:58 Sam Blond And one session with Parker Conrad, uh, the CEO at Rippling, my former CEO at Zenefits, also close friend and awesome person.
  • ▶ 8:19 Sam Blond Um, as a sales leader, when I was at Rex or Zenefits, uh, or even echo sign,
  • ▶ 23:47 Brendon Cassidy I imagine you did that at Zenefits Brex, because, you know, and we use that as, as, um, armor.
  • ▶ 36:27 Brendon Cassidy then Beyond and then Brax and Zenefits, just I'm such a huge fan of yours.

SaaStr CRO Confidential: Sam Blond + Omni Founder Colin Zima on the Power of Leveraging Your Network May 9, 2023 · 2 mentions

  • ▶ 1:05 Sam Blond And, um, Parker, who is my CEO at Zenefits, now the CEO at Rippling, I came to him and said, uh, I'm investing now.
  • ▶ 5:49 Sam Blond And I really liked the analogy that I hadn't thought of before you making it, but, um, the, the, the circumstances were certainly different, but, you know, Parker sort of building Zenefits two point O, which is now rippling.

CRO Confidential: Guild Education SVP, Go To Market Strategy, Operations & Enablement Cherishma Shah Apr 5, 2023 · 4 mentions

  • ▶ 13:49 Sam Blond Lots going through my mind just around my personal experience, uh, both with Zenefits and then with Brex. 2 times in the scene
  • ▶ 34:00 Sam Blond And I remember when I went to Zenefits, this was again, back in, um, when I went to Zenefits, uh, 2 times in the scene

How The Biggest Product-Led Enterprise Company In The World Did It | Atlassian CRO Cameron Deatsch Mar 7, 2023 · 3 mentions

  • ▶ 12:59 Sam Blond I I've talked on this podcast before, um, about the other end of the spectrum, which was my experience at Zenefits when relatively early we scaled the sales team far too quickly, uh, and did have, uh, 2 times in the scene
  • ▶ 19:46 Sam Blond Uh, I've done segmentation at, um, every company that I've been at, whether it was EchoSign, Zenefits, Brex.

How To Adapt Your Sales Strategy To The Current Sales Environment | Modern Health SVP of Sales Feb 7, 2023 · 10 mentions

  • ▶ 0:29 Sam Blond Uh, we worked together, uh, at, at Zenefits, at Rainforest,
  • ▶ 12:49 Sam Blond And so, you know, at Zenefits, we were selling, uh, HR, largely HR, uh, software.
  • ▶ 18:38 Sam Blond I'll, I'll tell a story about Zenefits, uh, where Hannah, you and I both lived this, um, and then I'll, I'll try and get to the way that I determine the right size of teams, like the, the things that I use in determining 5 times in the scene
  • ▶ 24:54 Sam Blond I remember it's benefits. 3 times in the scene

CRO Confidential: Sales Recruitment and Hiring Managers With Ben Braverman Jan 27, 2023 · 8 mentions

  • ▶ 2:48 Sam Blond You with Flexport that we just talked about me with both Zenefits and Brex.
  • ▶ 7:52 Sam Blond Um, I'll, I'll talk a little bit about joining Zenefits and joining Brex. 4 times in the scene
  • ▶ 14:48 Ben Braverman But in your case, like, when you looked into what Zenefits was building, ultimately what Brex built, I mean, it was just obvious, like, these were special people building special things, endorsed by the smartest people in the world.
  • ▶ 23:09 Sam Blond Parker told me Zinovitz is going to be a hundred billion dollar company, and I believed him. 2 times in the scene

SaaStr CRO Confidential:Hiring a Great VP of Sales Today Sam Blond + Former Lattice CRO Dini Mehta Jan 3, 2023 · 2 mentions

  • ▶ 18:40 Sam Blond And, um, you know, to take again, some of these podcast guests, Zenefits alone produced 2 times in the scene

SaaStr CRO Confidential: Founders Fund Partner Sam Blond + Rippling VP Sales Matt Plank Dec 15, 2022 · 20 mentions

  • ▶ 0:10 Sam Blond Uh, I was a groomsman in his wedding, somebody that I've known for, it's probably been like 12 years at this point, uh, Matt Plank, who, uh, was first in AE with me at Echo Sign, uh, the first hire alongside Jameson, last week's podcast… 2 times in the scene
  • ▶ 2:41 Matt Plank Essentially, if we were moving somebody off of their current system to Rippling, um, in pretty much any case, we were replacing, like, an existing kind of HR and payroll system, whether that was a modern solution, like your, you know, uh,… 4 times in the scene
  • ▶ 6:00 Matt Plank And I don't think, you know, Parker, we had worked together at Zenefits for, you know, three and a half years for a lot of that time, uh, you know, you 2 times in the scene
  • ▶ 8:51 Matt Plank I mean, you know, almost every company we were emailing in the early days, just kind of given like the value prop we had was a company that was likely already using like gusto or Zenefits or like some kind of modern, you know, all in one… 2 times in the scene
  • ▶ 12:58 Matt Plank And, and it's really because it's benefits. 3 times in the scene
  • ▶ 19:12 Matt Plank We were both lucky after Zenefits to have this like incredible network of people 3 times in the scene
  • ▶ 25:17 Matt Plank Like, that's ultimately how he convinced me to come work at Rippling, because I didn't want to work at Zenefits two-dot-o either, and he convinced me, like, this is definitely not that, 4 times in the scene

SaaStr CRO Confidential: Founders Fund Partner Sam Blond + Gong VPS Jameson Yung + Jason Lemkin Dec 7, 2022 · 10 mentions

  • ▶ 0:58 Sam Blond To have him join me at Zenefits for a number of years. 2 times in the scene
  • ▶ 8:47 Sam Blond Um, and Zenefits was similar in that we were sort of creating a category as well. 4 times in the scene
  • ▶ 17:52 Sam Blond My, my, my learning from the Zenefits experience, and again, like kind of this concept of category creation, um, was, was a little, uh, was a little different. 4 times in the scene

SaaStr CRO Confidential: Founders Fund Partner Sam Blond + Divvy CRO Sterling Snow Nov 17, 2022 · 1 mention

  • ▶ 14:29 Sam Blond Um, one thing that, that has worked and that we did, both at Brex and Zinovitz and elsewhere, um, it's during discovery, um, you, you ask, are you evaluating any other solutions or just looking at us today?

SaaStr CRO Confidential: How to Raise in Late 2022 with Jason Lemkin and Sam Blond of Founders Fund Nov 1, 2022 · 3 mentions

  • ▶ 9:53 Jason Lemkin And you know, the, whatever the 400
  • ▶ 18:31 Sam Blond Um, so my, my background, I joined Echosign with you, um, Zenefits and then Brex all around, like between 10 and 20 employees, uh, and relatively little revenue. 2 times in the scene

CRO Confidential: Sales Comp, Quotas & Recruiting with Jason Lemkin and Sam Blond of Founders Fund Oct 27, 2022 · 3 mentions

Live from SaaStr Annual 2022: AMA with SaaStr's CEO Sep 16, 2022 · 1 mention

  • ▶ 6:42 Jason Lemkin I think in March, he did a great, and go watch it on YouTube, he did a great presentation on how to set sales goals for his team, and someone who's been CRO of Brex from like, I think, maybe 10th employee, so first sale, then he did it at…

Product-Led Growth: Panacea or Boondoggle? | AgentSync Co-Founder/CTO + OpenPhone Co-founder Mar 15, 2022 · 2 mentions

  • ▶ 4:44 Jen Knight Uh, so Niji had a lot of connections in the space from his time at Zenefit, so he went through that rollercoaster a little bit, uh, with Brian's familiar with.
  • ▶ 7:17 Brian Murray So, so AgentSync, um, the story with Kraft and our partnership with AgentSync, most of us, many of us at Kraft worked at Zenefit, so we, we knew Niji and, and the founding story and the problem they were solving.

The Future of Sales Post-Covid with Brex's CRO, Sam Blond Mar 18, 2021 · 4 mentions

  • ▶ 0:03 Jason Lemkin I am here with one of our good friends and my good friends, for me, since almost inception in Sastr, and for you guys since the earliest days of Sastr, Sam Blond, um, now Chief Sales Officer at Brex, uh, one of the great innovators in, in…
  • ▶ 3:32 Jason Lemkin Are you going to go back to, to, to floors of endless AEs and SDRs like in the Zenefits and others days? 2 times in the scene
  • ▶ 36:32 Sam Blond Whether it was at Brex or at Zenefits or, or I'm sure you remember at EchoSign just by being able to pull people into two rooms and have those ad hoc.

How to Hire a Great First VP of Sales Nov 5, 2020 · 1 mention

Lessons From a Second-Time Founder: How Brex Went From 0 - $1B in Under 2 Years Apr 22, 2019 · 1 mention

  • ▶ 19:32 Henrique Dubugras So, you know, you're gonna have a little bit of a counter advice that is a little bit against what people say, so one thing that worked really well for us is bringing executives really early on, um, but the type of executives that we…
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