Inside The Pipeline: B2B Sales and GTM
00:00:10 · Tris Tusa
[00:00:10] S0: Welcome back to another episode of Inside The Pipeline. I'm Tris Tusa, and this is the show where we talk to sales leaders about what is actually working right now. My guest today is Nick Casale, VP of sales at AirOps. Nick's path is one a lot of people working in sales will recognize. He started out cold calling at Talkdesk in San Francisco, then went and joined Sendoso as one of its first sales hires. He ended up leading its mid market and enterprise teams through to its series c before leaving to start his own company. However, he found out he preferred scaling businesses to building them from zero and landed at AirOps, which at the end of twenty twenty five raised a 40,000,000 Series B led by Greylock. What does AirOps do? AirOps sells software that helps brands stay visible as search moves to AI engines. It used to be that people would focus on search engine optimization for things like Google, but now that's changed given that people look for information so much more in things like ChatGPT or Claude. AirOps calls this content engineering, and you'll hear more about this in our episode with Nick coming up right now. Welcome to Inside The Pipeline episode 23 here in New York with Nick Casale, who is the VP of sales at AirOps. Nick, thanks for having me in your in your office. We're sitting in a nice sort of content studio here with very sophisticated equipment. And really looking forward to talking to you today about the growth of AirOps, about SEO, GEO, and how you're taking this nascent industry, this nascent product to market right now. The question I always like to ask people at the start is, what was it about sales that that drew you in? Is it is it part of your character? Is it something else? Maybe you talk me a bit about the motivations.
00:02:07 · Nick Casale, Tris Tusa
[00:02:07] S1: I... So I always joke. I got into startups actually before I got into sales. Mhmm. Funny enough. I think I I probably always had sort of an inkling that I could do sales, but I was very much the kid in college that had no clue what I wanted to do. Mhmm. And at least when I was in school, no one would sort of tap you on the shoulder and say, did you know you can go work at, like, 10 person companies or 20 person companies? It was sort of on campus. It's either, you know, consulting or finance. I think Oracle was the only sales job, and that didn't resonate with me. No. But I did a startup competition at at Boston College, and the long story short is basically my roommate and I won that and had a lot of fun sort of accidentally learning all about startups and fundraising and pitches and what... It it was very much so, hindsight, a joke of a dorm room start up. We we obviously thought it was [00:02:58] S0: What was the start up? [00:02:59] S1: So it was... I... It's still a good idea, truthfully, but the the concept was basically, how do you apply to college in in The UK? Is there like an application? [00:03:07] S0: Yeah. It's a... It's an application. I think you talk to them about your exam results Yep. And submit like a personal statement, which is usually page long, and you try and put like everything about your life and your motivations into that one page.
00:03:07 · Tris Tusa, Nick Casale
[00:03:07] S0: Yeah. It's a... It's an application. I think you talk to them about your exam results Yep. And submit like a personal statement, which is usually page long, and you try and put like everything about your life and your motivations into that one page. [00:03:20] S1: Well, see, in America, we envision in The UK that it's like Hogwarts and you guys just get sorted. Here, it's this sort of very archaic one pager. Yeah. Right? It's called the common app. Okay. And it's like you fill out bubbles and then you submit your scores, and it's very flat is a sort of summary. It's a very flat representation of who you are. And this was around the time LinkedIn was really, you know, get... Starting to get popular, and, obviously, we all had Facebooks at the time. And so the concept was, you know, why don't you apply to college on a very sort of digital resume that would really, you know, showcase who you are as a person and not be this sort of one dimensional paper. And then colleges could market to students on the site, and students could communicate with counselors. And it was a... It was in theory a good idea, but I learned the hard way why education is the worst customer. [00:04:06] S0: I feel like you... What? When were you at university? How many years ago was that? [00:04:10] S1: This was 2013. So
00:04:10 · Nick Casale, Tris Tusa
[00:04:10] S1: This was 2013. So [00:04:12] S0: you're probably like ten years too early. I I feel like Jack and Jill... Do know Jack and Jill? Yeah. Yeah. I feel like they're basically doing that for for hiring. Yeah. In terms of just like, let's ditch the CV. Let's talk about actually who you are and what you wanna do. [00:04:24] S1: Yeah. I think if we had picked any customer other than universities, we we might have been onto something. Their their lack of innovation is is I think a little self imposed. [00:04:32] S0: And so Boston College through to... I think you did an internship at Dell?
00:04:32 · Tris Tusa, Nick Casale
[00:04:32] S0: And so Boston College through to... I think you did an internship at Dell? [00:04:37] S1: I did. That was that was a very unserious internship. Once again, I I owed all to Boston College and and frankly my mom because she met a kid who was two years old and made BC. The year I was sort of graduating and I I had... I knew at that point I wanted to go to sales. That was what I realized I loved most about the startup thing was sort of pitching and and selling the idea. Mhmm. And I interviewed a bunch of school... Bunch of companies in Boston, but I kinda had a conversation with a couple people who basically said, if you're gonna do this, go to San Francisco. Yeah. This is obviously, you know, twelve years ago, whatever. And it was great advice. And my mom met a BC kid who was two years older than me at a BC event, and his name is Frank Gold, and he's still a close friend. And he said, if you're gonna come out to SF, interview with with me at at Talkdesk. He was an AE there. Yeah. And every every role I've had, that role and every role since has been the result of people I've met before or during that job. [00:05:32] S0: What were the main things that you learned while working at Talkdesk? [00:05:36] S1: I learned... I mean, I I really learned every... Everything I know now about sales is is very much so built on the foundation of of what I learned at Talkdesk. And I think, you know, obviously, so much has changed, but I think a lot of it gets very... One, I think a lot of what sort of is old is new again. Right? [00:05:56] S0: Like Cold cooling.
00:05:56 · Tris Tusa, Nick Casale
[00:05:56] S0: Like Cold cooling. [00:05:57] S1: Phone is back. Yeah. Everyone's like phone is back. Gifting. I laugh I laugh so hard now every time someone brings up gifting direct mail. That was Sendoso obviously after after Talkdesk. Right? But you do start to realize, like, things things... Everything is cyclical. Everything starts to repeat. I think at Talkdesk, there's so much that has come back that we were doing at the time. [00:06:16] S0: Mhmm. [00:06:17] S1: And there's so much that just is is the immovable reality of of good sales foundation. [00:06:25] S0: How how different was your day to day... Obviously, you're in a leadership role now, but how different was the sales job day to day back then to to how it is now? [00:06:34] S1: I mean, I think it was... This was before... It's... Kinda like what what was what was old is is new. This was like before LinkedIn got around to blocking old school scrapers. Okay. So we would just we would just scrape and blast. Email works back then, actually. That's probably a big difference. But I think there was probably a bit in the middle where you had to do things the old fashioned way, but we were early to scraping and blasting, and that worked like a charm. And I think I think now everyone is still scraping and blasting, but I think that it's probably diminishing returns. [00:07:06] S0: And and so you then move from from Talkdesk to Sendoso. I think you're one of the earliest sales hires there. What was it that made you take that leap to Sendoso?