Inside The Pipeline: B2B Sales and GTM
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?
00:07:06 · Tris Tusa, Nick Casale
[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? [00:07:18] S1: So the the guy, Chris Rudigrap, who started Sendoso started it at Talkdesk as an AE with me. I was actually his SDR, and then we were AEs together. And I could just never figure out how Chris got so many more meetings than everyone else. And he would, I mean, he would, like, feed me lists and be like, hey. Yeah. Here's, you know, here's more leads you can you can get. [00:07:36] S0: Yeah. Yeah. Yeah. [00:07:37] S1: And get him all these meetings and then made us both look good. But come to find out, he had he had basically hired, you know, hired a guy to build a plug in to Salesforce so he could type up a note, and it would get sent somewhere and someone would write the note and ship it on his behalf. And that was the the sort of [00:07:55] S0: What what sort of Sendoso. What what sort of response rates were you guys getting [00:08:00] S1: off this? Oh, I can't remember. I mean, the early days, it was like, if you would get... If you got a box to someone's office Mhmm. It was like 50 it was like 50% or higher. Right? Like, we would... The play was was, like, send a box of cookies or a box of cupcakes to someone's office, something that they have to, like, share. [00:08:20] S0: Yeah. Because if use
00:08:20 · Tris Tusa, Nick Casale
[00:08:20] S0: Yeah. Because if use [00:08:21] S1: a bottle of wine or, like, a letter, there's no guarantee that more than just them are gonna see it. Yeah. You know, but if you send the cookies Okay. This is the art of the deal, cookies. K. The cookies end up on the counter. Right? And then everyone's like, oh, and you could put your logo on it Yeah. If you really wanted to, you know. [00:08:39] S0: What what were some other of the popular GIFs that you guys were sent? I mean, you must be literally the master. You must know what [00:08:46] S1: your traits. Yeah. We we joke that one of my one of my my best days from there is is now on the team here, and he still does this. But he's like, hey. Would you... He just puts in the email, he's like, do you want cupcakes or steaks or whiskey? [00:09:01] S0: He's doing steaks? Steaks. [00:09:03] S1: No way. Cupcakes, steaks, or whiskey. [00:09:04] S0: Yeah. So so that goes through a butcher who's then... [00:09:08] S1: No. It's like it's like Crowd Cow. I don't know what you guys have in The UK, but there's websites that do the, you know, the professional vac sealed. [00:09:14] S0: Okay. [00:09:15] S1: Yeah. It's a real... [00:09:15] S0: God, it's it's a business. It's a business. That's some serious alpha for the listeners there.
00:09:15 · Tris Tusa, Nick Casale
[00:09:15] S0: God, it's it's a business. It's a business. That's some serious alpha for the listeners there. [00:09:19] S1: But I will say, I think nowadays you can be much more clever, and I think you can send thought leadership content. You know? You can you can still have sort of an offer. Like, you can have a nice thing with it. Mhmm. But I think you can get more... I think you can be a little bit more more clever now. [00:09:34] S0: Mhmm. [00:09:34] S1: There's ways to personalize it with with AI and whatnot. Yeah. And and what were some [00:09:38] S0: of your numbers when you were working at at Sendoso? Because I know that that business grew rapidly Mhmm. Whilst you were there. Maybe you could talk about some of the highlights in terms of the deals that you that you won and the the logos that you brought on board?
00:09:38 · Tris Tusa, Nick Casale
[00:09:38] S0: of your numbers when you were working at at Sendoso? Because I know that that business grew rapidly Mhmm. Whilst you were there. Maybe you could talk about some of the highlights in terms of the deals that you that you won and the the logos that you brought on board? [00:09:51] S1: You know, it's... I'll I'll... Like, yes, you know, going... I remember going on-site at at, like, Google, and that felt like a big moment in the career and and in the business. There... There's these... There's moments for sure. But the cliche that I always that I always kind of remind my team now as we're on this incredible journey is, like, the numbers and the accolades really, really do fade. Right? And it's like there's deals that I remember so vividly because, like, if I if I if I pull the thread, it's just still there because you just... I don't think you lose it when you're that invested in something. But it's not the first thing that comes to mind when I, like, remember back on that on that phase. It's really, like, it's the people and it's the relationships. And I think that's what I always remind young sellers is, like, when you're... Really, I would I would tell anyone this. But I think, like, when you're evaluating an opportunity, I think people over index aggressively on the numbers. [00:10:50] S0: Really? [00:10:50] S1: You know, it's like it has to have the measurables, but every place... Every every job I've taken, the deal... Like if you were like, oh, what's your ACV? What's your win rate? Like, they sucked always. [00:11:03] S0: Yeah.