The B2B SaaS VP Sales Journey - with Brendon Cassidy, Founder and CEO CoSell

**Ray Rike** (0:00)
Hello, I'm Ray Reich, founder and CEO of RevOp Squared, and your host of the Metrics that Measure Up podcast. We talked to a wide variety of B2B, SaaS, and Cloud thought leaders, executives, investors, and people just like you to discuss the metrics and benchmarks they use to make metrics and form decisions. Now on to today's show. Welcome to today's episode of the Metrics that Measure Up podcast. Today, we're joined by Brendon Cassidy, founder and CEO of cosell.io, and multiple-time head of sales at great Silicon Valley companies. Today, we'll be covering three main topic areas with Brendon. First, the metrics that matter to a B2B SaaS or Cloud VP of sales at each stage of the early part of the journey. Second, field sales versus inside sales versus partner sales. Which are most relevant? Why and how do you execute it? And third, the value to paying it back and paying it forward. Brendon, please take a moment to give a brief background overview of your journey to becoming a guest on the Metrics Measure Up podcast.

**Brendon Cassidy** (1:19)
Yeah, Ray, I appreciate it. Thanks for inviting me on. I'm happy to spend some time with your community here. As you said, I'm the founder and CEO of a company called CoSell.
That's trying to help drive and create a platform around referral selling and warm introductions for sales, sales organizations and revenue generation. Been at this a while, so most of my career sort of on the startup side, I was an early employee at LinkedIn. Depending on who you ask, somewhere in the first 30 employees, really like first hire and make the go to market side. So it really kind of built the sales organization at LinkedIn back many, many years ago. I guess in our world, it's like 2005, 2006, which was a great experience to be involved in, obviously at what became a great company and to be sort of involved in the room when some pretty big strategic decisions were made, was a great experience in my career and something that I certainly leaned on many times. After that, I was the VP of Sales for a company called EchoSign, grew quite a bit of growth there and we were fired by Adobe in 2011, and then spent almost three years at Adobe post-acquisition. And then more recently, I was the fifth employee, VP of Worldwide Sales for a company called Talkdesk, which is in the burgeoning support cloud. And they actually just recently got about a $10 billion valuation, which is pretty exciting. And then it was also founding advisor for a company called Dong, which is just got a $7 billion valuation and I helped. Literally was in the basement with their founders, started bringing their first 50 customers on. So yeah, that's who I am.

**Ray Rike** (2:51)
What a great ride that you have and it's interesting. previously, I hosted one of the co-founders of LinkedIn on the podcast, Constantine Gerica. And one of the things I love that he's shown is when you guys would take pictures of yourselves with holding up 1 million members, 5 million members, or 10 million members. And now what? Is it like 600 to 700 million members?

**Brendon Cassidy** (3:12)
Yeah. So it's certainly north of 500 million. I guess you could say on a path to a billion probably. And obviously part of Microsoft. I mean, what a great acquisition for Microsoft. Certainly, I think LinkedIn's revenue, I can't remember what their revenue was most recently, but it was pretty impressive.

**Ray Rike** (3:28)
Just read a report that it might be worth like, gee whiz, 8 to 12 times more than it was when Microsoft bought it. But let's look at your experience, Brendon, because I think our living audience would really benefit from your early stage experience at highly successful companies. And the first question I have for you is, are there some common sales leader challenges that you've seen at the major inflection points of an early B2B technology company? What are those challenges that you think ahead of sales, ahead of revenues to be prepared for?

**Brendon Cassidy** (4:03)
Yeah. I mean, there's definitely commonalities amongst all the companies I've sort of worked full time for, and then I've advised or consulted for probably 40 others at varying points. So it's actually a pretty broad sample size.
And some of it's not even like directly related to what you would typically think a VP of sales would be responsible for, which is sort of, I think one of the things, sort of unknown factors unless you've been at that stage in a startup, you're going to have your hands in a lot of things. And I actually was talking about this with somebody recently. One of the most common themes I've seen in my career and amongst even fairly successful startups is the team has a really hard time describing exactly what problem they're solving and why. And I think you go to like even back to LinkedIn. LinkedIn obviously was, when I joined, really just a pure consumer internet company, right? And so it was, okay, what are we going to sell? And what is the problem that we're solving? What is the market that we're entering into? How are we going to transform that? And obviously in that world, it was, you know, the monsters and hot jobs and career builders were considered to be sort of the status quo and sort of what everyone called the recruitment tech cloud. And so, yeah, but like at every stage, really being very, very clear about being able to talk about, hey, this is who we are. This is why we exist. This is the problem that we solve. This is why we're incredibly passionate about solving it. People have a really, really hard time conveying what that is. If you can't communicate what that is at like a founder level, then you can't sell it. And so that's really like one of the things with, you know, I would say 80% of the companies have been involved in on some capacity was really like, hey, let's just, let's have a very clear black and white possible to misinterpret what we're doing, what problem we're trying to solve, and how we're trying to solve it. Because if you can't do that, if you can't describe why you're doing it, I don't know why you could be able to describe why somebody should buy it. So that would be one for sure.