June 13, 2024

Between Two Hires with Special Guest Greg Costigan

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Episode Highlights

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Episode 6 of Between Two Hires (The Subtle Art of Not F#*cking Up Your Team) is here!

In this episode, Tom Wilkinson is joined by Greg Costigan who has hired over 35 salespeople (BDRs, AEs, Ops, Enablement, and Managers) at companies like Zuora, Zenefits, and Box. 

Together, they discuss the importance of leadership’s personal brand for recruiting, the ABR (Always Be Recruiting) mindset, whether sales is science vs. art, and mistakes to avoid when hiring salespeople.

These are sales hiring tips you won’t want to miss out on if you’re hiring salespeople now or in the future. Watch the full episode now!

Episode Transcript

Mr. Greg Costigan, how the devil are you? Good to see you. Well, look- hey, thanks for joining, mate. I’m keen to get into your mind a little bit here. And I know there’s some good stories behind some of this stuff.

So we’ll get straight into it. I love it. Let’s do it. Let’s talk numbers to begin with. So I know in various capacities, you’ve done a good amount of hiring. So what are your numbers? How many people have you hired across the course of your career? Yeah, that’s good. Just in prep for this, like I think it’s about 30-35 total. So I’ve hired AEs, mid market, enterprise, SMB. I’ve hired sales managers in the closing role. I’ve hired BDRs, I’ve hired BDR manager, I’ve hired sales ops and I’ve hired enablement. It’s about 35 total. A lot of it was at Hone, my last role. Love it at Hone, but starting off early at Box, you’ve been at Zuora, Zenefits. Some of these behemoths in the space.

Well, I mean like- okay so my experience in the interview process either as a candidate, yeah of course. Like when I was at Box I was early stage I was an IC, had Zora as an IC as well and Zenefits I was an IC. But Zenefits is really good about including folks. Like I was in the enterprise team in the process.

So I would be on an interview probably once a week. And then, you know, I went to an early stage company called LearnUp, I was director of sales there. We were small, but we did some interviewing. And then when I was at Mind Gym, I did some interviewing. But yeah, early days was Box, Zora, Zenefits. And those were, those were fun, fun times.

And companies that hired well, as well. So you’ve been there and you’ve seen it. So moving into that, what about some of the, I guess, some surprises along the way? Maybe some stories about the best or worst hiring surprises you’ve had. It’s so funny because you were on the webinar that I did like a couple weeks ago where it’s like sales is an art or a science, right?

And I was like, I was doubling and tripling down on like sales is a science, sales is a science. And salespeople aren’t born, you know, they can be aspects of it, but they have to be trained. It’s funny. It’s just, when you asked me this question, there’s one person that I thought of that I swear she was born like a salesperson. To quote like Tommy boy, she could sell a ketchup Popsicle to a woman in white gloves. She was just like a born salesperson.

And when we were going through the process, Tom, I’m telling you, it was so unconventional in her answers and the way that she approached it. But the energy was so infectious and the positivity was so infectious. And we got to references, all of her references were like, I don’t know how she does it, but do not doubt that she’s going to do it.

We took a little bit of a chance on her and we hired her and she was like one of the top reps I’ve ever worked with. So we’re talking about Annalise. I’m talking about Annalise. Yeah. I mean, she is unconventional in her ways, but like an elite performer in so many ways. So kudos to her. Yeah.

So it’s interesting then. There’s maybe a deficit sometimes on individual’s ability to interview, yet, in the role they can come through swinging and be top performers. It’s tough, right? It’s tough because you want to be scientific and you want to evaluate it and you don’t want to go off of gut feel like I think those days are gone. But you need like this tenacious work rate in sales and you have to be gritty and you have to improve by one percent like every day.

And those are certain things that, I don’t know, only exist in a rare bit of people. So there was some things that were unconventional in Annalise’s process, but you could tell like that fire was there. So yeah, we took a chance and it worked out. Worked out well.

Conversely, have there been individuals that you were bullish on, said all the right things, did all the right things, and they didn’t

end up delivering? Won’t name names or anything, but I think Jason Lemkin talks a lot about this. But I’ve worked, Tom, you know I’ve worked for startups mostly. Seed A, Series B companies, certainly as a leadership role. I think it’s very hard, honestly, to take big co person and put them in an early stage startup, right?

Even if they have the industry experience. Even if they were like in a division of a big company, where they hustled, but then came over to the the startup. Like the infrastructure doesn’t exist. And I’ve been burnt more than once- not again, I won’t be. But we need the Navy seals, I think in some of these early stages.

And it’s not time for infantry yet. And I think I’ve made that mistake a couple of times thinking big company was going to solve it. Just doesn’t. Yeah.

On the recruiting front, is there a secret weapon that you use to source top talent? Yeah, I went to this guy Robbie Allen that I used to work with at Zenefits talks about. He’s got this famous like quote from Nick Saban.

It says, I got right here that, “Leaders of the most talented teams commit 20 percent of their time, even when doing their job to recruiting at all times”. I think that’s the one that sticks with me. So I don’t know if it’s like a secret weapon. But if you’re building a team, even if you’re not necessarily hiring at that moment in time, like you need a personal brand as a leader, forget about the company, like you need your own brand as a leader.

And you have to be thinking about your bench and your relationships. So I mean, my secret weapon, I guess would be to have genuine like authentic relationships that can, you know, follow you potentially at different organizations. I think you got to be really intentional about that when you’re in leadership, especially in sales.

Yeah. And a good sign for many sales leader that individuals that they’ve worked with in the past follow them into their next endeavors. I think so. I think so. 20%? Maybe even- that’s a base level, even. You think it’s higher? Yeah. I think that you need to be eternally recruiting and whether those people are getting hired next week, next month, next year, that’s fine.

You’ve got to be doing it and it doesn’t ever stop. It just doesn’t. Yeah, it’s a good point. I think like the authentic connections, you know. The understanding of folks and like shortening the cycle, like the time from meeting someone to hiring them is going to be a timeframe. If you can have some good long standing ally relationships, you can sort of

be a little quicker when it comes to the actual recruitment phase, if you have those relationships, you know. Yeah, very much.

Talking of interview moments now, weirdest or strangest interview moment you’ve experienced? It’s funny. We were talking about this in the prep. I’ll give you one as a candidate.

How about that, right? So a long time ago, I interviewed with Sam Blahn for enterprise sales at Zenefits. This is early days. And I was bullish on Zenefits. Of course, it’s hard not to be. And my final step was an on site with Parker, right? And again, this is like early days. And I actually thought, you know, in the process, usually you go on site, you meet,

and then you go away and there’s like a written offer. There’s like a back and forth after that and all that. I remember like the interview was over and I went to get up and walk out and Parker closed me on the spot and he like shook his hand out. He’s like, “Do I have a verbal agreement that like, you’re going to move forward

like with this?” And I was like, holy shoot. Like, is this happening? And I mean, I was going to go with yes anyway. But I mean, talk about a closer and he’s got a presence and an aura about him, right. So like when he did that to me, I was all in. I shook his hand and gave him the verbal right then and there. Pushed me a little outside my comfort zone

and I respect it. So I don’t know if it was the weirdest, but it was great. So I love it. I love it. Yeah. Nothing worse than days on end waiting to hear a decision on these things when both parties know it’s the thing. What’s the point in wasting time on it? Get into bed. Do it. He was a closer man. I mean, he was a closer and he got it done,

so I was there. Very cool. What about questions that you like to ask?

Is there a secret or unconventional interview question or tactic that you employ? We talked about this in the prep too. I mean, I like to do- look, I think a big part of sales is, are you an elite performer or are you competitive or do you desire for excellence?

So a question that I like to ask is just, let’s take 60 seconds and talk to me through something that you’re exceptional at. And how did you get there? And it can be anything, right? And I’ve had a range of answers. I have people talk about like their golf swing or cooking or, you know, anything. But if you just sort of open it up and you got to give some time and space in the interview for it.

But what’s something that you’re elite at, exceptional at, and you’ll see how people think, how they like get better at something. You’ll see that passion come out. And if you don’t, I think that’s a red flag. And if you do, you know, a big part of sales is going to be like learning the product and learning the company anyway.

So it sort of tells me that like, hey, if I can enable this person and then they’re going to be great if they answer that question well. So I like that question around take 60 seconds and tell me something that you’re exceptional at. I love it. I love it. Yeah.

What about wisdom on the hiring, things that you wish you’d known earlier?

Man, Tom, it’s the same as my one before. It’s the bench. It’s the bench, personal brand always be recruiting like ABR. Always be recruiting. And again, I think it has to be like genuine and authentic. I guess I always thought early in career that the company brand or the department brand or something like that would be enough to get really high quality candidates to join a company.

But it’s, it really, a lot of it is the leader, right? So I need to be like super intentional on who I am. What are my beliefs? What am I going to bring to that person that I’m going to bring on board? I think it’s just always having a presence. And always be connecting with like really high quality folk.

You could have always done that more in the career and eager to do it more now to build that base, you know. Very much. I couldn’t agree more. I think it’s a great piece of advice and one that I think we look at these things in cycles. It’s sort of the cyclical nature of, we know that we need this role.

Maybe we know when we need it. And then it’s ongoing. It’s this next hiring round and this next hiring round. But the reality is you need to be talking to great people regularly, whether you’re going to hire them or not. I think it shows, you know, something about any sales leader at that level should be doing that.

Make it part of your day, right? It doesn’t- just make it 20 minutes, a half hour of your day to connect with folks on LinkedIn. Don’t see it as like this admin exercise, see it as actual, like a function of the job, especially in a leadership role. It’s a function of the job.

That’d be my learning. Yeah. Very good. Well, I wanted to kind of close things off with a bit of better understanding and for those that are going to watch this, what are you working on at the moment? And who should sort of reach out to you if they need to? Tom, I think I speak founder well. My experience is early stage, Go-To-Market teams.

I’ve worked with founders in the seed and A stage directly. I’ve built teams in the B stage myself. I’m currently doing a fractional role for one client and advisory for another. I have my own Go-To-Market consulting practice. You can find it on LinkedIn, Greg Costigan, but I’d be eager to work with folks on their Go-To-Market strategies,

consulting, or I like to actually roll my sleeves up and do some of the work as a fractional person themselves. So you can find me on LinkedIn and I’ll tell you more. Very good. And aside our experience working with you through the period of time at Hone was remarkable. We loved every minute of it and so did the individuals that ended up working with you. So strong advocate of Greg Costigan. I got to give you a shout out too. I mean, Tom, you were like the huge source of our talent pipeline. You know that, right? So for folks watching, like we hired and grew because of you all. So like I am a big advocate of you and I appreciate you honestly, for everything you helped with.

Thank you for saying that. Appreciate it, Greg. Well, many thanks for today. Looking forward to the next time. Appreciate it. Thanks. Bye!

Episode 7
Episode 7 of @Between Two Hires (The Subtle Art of Not F#*cking Up Your Team) is LIVE right now. Join David Cook and...

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