June 3, 2025

Between Two Hires with Special Guest Erin Bates

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Episode Highlights

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What do 400 hires, one dirty t-shirt, and an SDR turned AE all have in common?

They’re part of the wild and insightful hiring journey Erin Bates shares in this can’t-miss episode of Between Two Hires.

Tom Wilkinson digs into Erin’s biggest hiring lessons from 15+ years scaling elite sales teams:

  • How to spot interview B.S. and ask level 2 questions
  • Why a “soft yes” is really a no, and how to avoid the wrong hires
  • What it takes to hire fast while keeping quality high in hypergrowth environments
  • The red flags she won’t overlook again

Erin keeps it real, from hilarious interview moments to hard-earned leadership wisdom.

If you’re building a sales org, this one is essential listening.

Episode Transcript

[00:00:09] Erin Bates, it’s good to see you, my friend. How are you? Great to see you, Tom. I am doing great. How have you been? Very good. Very good. Yeah, happy days. It’s been cool to watch your career over the last, because we were just talking about how long we’ve known each other and sort of seeing this last decade just fly by. But also to see kind of the growth that you’ve experienced personally and within the companies that you’ve joined.

[00:00:35] Good ones, of course. It’s been really wonderful to watch that rise. That’s great. Yeah, it’s been a wild ride in the last decade for sure. Lots of- lots of great companies, lots of change, lots of market conditions change too. So it’s definitely had the industry and the markets have their ups and downs.

[00:00:51] But it’s been a really fun, wild ride with some great companies and, you know, really, thank you for having me- having me today. Yeah, of course. And side note for our viewers, [00:01:00] I don’t know if they care for this or not, or if it’s just sort of divulging personal work that we’ve done together in the past.

[00:01:06] I did place Austin, your husband, many, many moons ago. That was a good one for me. Yeah, it kicked off a really wonderful and amazing career for him placing him at open DNS so many, so many years ago. And I don’t think that he’d be where he was, if it wasn’t for you placing him there. So, thank you.

[00:01:25] It’s been great. He says hi, by the way. Nice, nice. Hi from me. So we’ll get straight into it. I wanted to just start off with getting some context on how many hires you’ve been a part of over the course of your career. Yeah. Yeah, I was- it’s hard to say. I’ve been in leadership for about 15 years, and even before then, been a big part of hiring panels and really helping to hire folks.

[00:01:49] Hiring is one of my passions. Really hiring successful reps and top talent. I think if I could go back around the different roles that I’ve had, I’d say I’ve probably hired 300 to [00:02:00] 400 new hires into the companies I’ve had over the last 15 years. And this is across, you know, SDRs, account executives, customer success reps, solution reps, enablement, rev ops. Probably about three to 400 folks.

[00:02:13] And that doesn’t include promotions. If you also think about internal promotions that we’ve been a part of, it’s probably another 150 to 200 in there. So it’s been a lot. Thinking about the numbers, it’s surprisingly large. But it’s been a great opportunity and bringing in and building really amazing teams from the ground up.

[00:02:31] Yeah. And speaking of building amazing teams, maybe more specifically on the hiring side, I think with those kind of numbers, there have to have been some interesting surprises maybe along the way. And I was curious to try and get your best and worst hiring surprise if we could. Oh yeah.

[00:02:51] Oh, there’s probably too many to count. I’ll start with the best and I’ll kinda end with the worst. But I think the best one was really making the wrong decision about a [00:03:00] hire. It was a surprisingly best surprise here. This is when I was working at Checker and we were building out a sales development team, which was something new that we haven’t had before.

[00:03:09] And I think we made a couple hires and we were interviewing somebody that was coming in from a different industry, like outside of our typical persona that we like to sell into or even just a type of solution. I think they were in ad tech and we were selling more of like a SaaS solution.

[00:03:27] So we decided to bring him on board as an SDR, back where he was an AE at his current company. Brought him on as an SDR, and within the first week, I went, “Oh, I made a really big mistake”, a surprisingly good mistake. And realizing that he really should have gotten brought on as an account executive.

[00:03:44] And so I think within the next month I promoted him to back to AE where he rightfully deserved. And he worked with me at that company and we’re still really close. He moved on into leadership and had been a really great role model. So that was a really great learning, in terms of a great surprise

[00:03:58] that I had and just really [00:04:00] making sure, again, I hire the right person for the right role. And I think some, I don’t have like a specific one one from a worst surprise. I mean, I do have some that I probably won’t share, but a lot of them are just surprises of people embellishing on their resume.

[00:04:14] But especially there was one candidate that we ended up hiring that straight lied about the role that they had before and needless to say, integrity and trust is very important when you hire a team. And so just the importance for candidates, not to lie on their resume, but also the importance to really back channel.

[00:04:32] That was earlier on in my career, when we made that mistake. And I don’t hire somebody without having at least one back channel from somebody else that, that I know or somebody in my network. Because you always just- people can lie on resumes and can be really good at, really good at lying or just embellishing what they’re doing.

[00:04:48] So it’s just so important to be able to cut through all that. There’s a couple of good examples. And we’re talking about salespeople here. So, you know, by all rights they should be quite good at talking about themselves and their [00:05:00] performance and their past. So, I think that leads us nicely into our next question, which would be in hiring those reps, you’ve probably been able to create a pretty good bullshit detector.

[00:05:12] How to spot a true performer from someone that’s just really good at interviewing, like you said. How do you do that? Yeah, it’s definitely been some learnings. I think early on, making some poor hires because of just not having a good understanding of like the role that you’re hiring for and what your needs are.

[00:05:31] But then also taking people for like what they’re saying without kind of looking under the hood or asking level two, level three questions. I look at hiring just like I would selling into a prospect or renewing a customer, is that you really have to do like deeper discovery. And so a big part of this is not just asking a question, saying, cool, and moving on.

[00:05:53] Be like, tell me more about that. And so asking behavioral questions is so important because it’s not, how would you do [00:06:00] it, but how have you done it in the past? And then making sure you always ask one or two follow-up questions based off of something that they said is really great. I’ll also ask the same question sometimes in different ways, either during that process or sometimes later on to be able to sniff that out.

[00:06:18] I had a great example of a candidate in the first call and he goes, “I am a top, the number one rep of the company. I’ve been the number one rep for the past few quarters”. I’m like, “Oh that’s amazing. Congrats. Like, that’s really something to be proud of and accomplished”. And towards the end of the interview I said, “Oh, okay, great.

[00:06:34] So how many people are currently sales reps on the team?”. And he goes “Two”. So making it like a really big thing about how important it is and how big of an accomplishment it is being the best top performer and the second person had just been hired the quarter before. So stuff like that.

[00:06:52] ’cause again, trust and integrity I mentioned are so important. And just like knowing the core values that you’re trying to bring on board. It’s really easy again for people to, [00:07:00] to frame it up in a certain way. But being able to ask like an additional question or ask it a different way, you can sometimes really sniff out some of, some of that bs.

[00:07:08] So, I have a lot of different tips and examples about how to do that. But it is really important because, a bad hire can really be the reason you don’t hit your numbers because you have to unfortunately rehire that person or you bring someone on that you have to really level up their skill development.

[00:07:23] So it can be really, really tough, especially if they’re really bad for the culture of the team as well. And so nothing surface level looking to go a few layers deep with the same lines of questioning, just to see how the candidate responds to that. I love that. Also, I think you talked about the back channels earlier on.

[00:07:41] Mm-hmm. And so those worth their weight in gold because it seems references alone don’t really do you know what they are intended to do. So those back channels all important for getting a maybe a unbiased or a true review of someone’s performance. Yeah. People will spill the tea if they don’t know that they’re the ones that are [00:08:00] getting a brought up for- if they know that somebody’s asking me to be a reference, it’s a whole lot harder than I know that they’re never, this isn’t going to go back to them.

[00:08:07] So you really get the cut through all the BS and get through the real stuff. So having hired in the hundreds, there must have been a few, maybe standout moments. I think interviewing alone is a interesting sort of concept. It puts people in a, maybe a sort of a high pressure environment, if you will.

[00:08:26] Quite a lot on the line. Weirdest interview moment you’ve experienced, if you can. Oh gosh. Weirdest interview moment. I think there was, this was back when we were all in person again. I know a lot of our people are hybrid and we do a lot of Zoom calls. But this was earlier on back when you would come in for an interview and we would like fly people out.

[00:08:48] And I had somebody show up in flip flops and a t-shirt and jeans to their interview. And the role definitely wasn’t something like that. And we weren’t fancy, but you know, you typically dress like business [00:09:00] casual at the company. Jeans are fine, but when you pair it with a semi dirty tee and some sandals. Some like rainbow sandals, it doesn’t really show like how could you present.

[00:09:09] It was an in-person role of like doing a lot of traveling, front of customers. And so I think that was one of the first things is, it didn’t lead to a good interview. I think that the way that they showed up dressed also kind of went through with the rest of their kind of casual attitude too through it.

[00:09:25] So that was one of the really weird moments. And then I also had a very weird moment where, again, this is in person. I’m very honest and transparent when people ask me for feedback, and I will tell people sometimes, like if it’s not a right fit out of the gates. And so that was an example where we did that and that person actually like went to the bathroom and wouldn’t leave.

[00:09:43] And we had to have security come and take them out because they wanted the job so bad. So that, that was a very strange moment as well. It definitely gave some weird vibes. But you get some strange reactions sometimes one way or the other.

[00:09:57] I haven’t, that’s a new one for me. I have not heard [00:10:00] that one. Well at least it shows quite a high level of dedication if nothing else. Exactly. He’s like, “I really want this job”. Oh my God. You’ve worked at some hyperscale companies, name brands. These are, you know, companies that have done exceptionally well and also grown really fast.

[00:10:20] How do you hire quickly but keep the quality of your hires? Let’s see, in one year we were growing- this is a company that I worked at previously. We were growing from eight people to 80 people in the span of one year, across even just two different roles on that team. And

[00:10:36] our numbers supported, if you miss a hire, you’re late on your hiring dates. Like we are always catching up to that number. And it’s really important to meet your hiring goals so that way you’re hitting our financial plan, right? But hiring a bad person could be just probably worse than missing a hiring goal.

[00:10:53] And so I think one of the big things that I learned is the past of bringing in a couple people that you wanted to hit a [00:11:00] hiring goal so bad that you hired a B player that you knew as a B player, and that was always a mistake. And so I think that even when you think you’re bringing on an A player and hiring an A player, sometimes they turn out to be B players. Probably not C or D players, thankfully.

[00:11:15] But I think don’t just hire people for the sake of hitting hiring goals. If you’re not getting the quality of candidates that you need to hit your hiring goals, you need to either put more resources in. So one of the things we do is I have all my leaders source at least five candidates per week themselves on top of our internal recruiters.

[00:11:34] Sometimes if we need an external recruiter, we’ll bring external recruiters on for just more difficult roles. And so just making sure that you’re really putting the effort in to get more candidates and doing more touches and outreach. And that’s the reason why, so you still hire a really high quality candidate.

[00:11:50] That would be the first thing that I would say is like, don’t make that mistake of just hitting a hiring goal. Some of the big ones I’ll say is know what you’re looking for. Like we are hiring a [00:12:00] strategic and account executive. What does that mean? Are they selling into a billion plus revenue companies?

[00:12:07] Are they selling 10,000 plus employee size companies? Okay, great. So what is the experience that we need to, for them to be able to be a fit in this role? What are the core competencies that we need? So that would be technical experience, that would be soft skills as well. And of course, like hiring to culture.

[00:12:25] The first interview, if they don’t hit your experience, you have to walk away. Like there’s too much at stake and everybody is way too busy to have a mediocre candidate make it to the end just to say no. So if you know you’re on the fence, you know you’re going to say no, just say no. And that’s the big one.

[00:12:42] So know exactly what you’re looking for and hire exactly to that. If you have a great candidate that’s not a fit, maybe they’re better in a CSM role or they’re better as a SMB AE, just keep them warm and bring them back in the funnel if you don’t have a, an opportunity for them. But don’t try to fit a [00:13:00] square peg in a round hole.

[00:13:01] So I think that’s one of the big ones, is just know what that you’re hiring for and just make sure that you hire for that, that person. And the last one I’ll say is just like always, hiring candidates that may not necessarily be the perfect fit. I always say if they have 70% of the qualities that you’re looking for, hire that person.

[00:13:18] If somebody has a hundred percent of what you’re looking for, they’re probably interviewing for the wrong role, and there’s something, there’s something up, right. So you want people to be hungry. You want people to know that they’re not quite a fit, but they’re a pretty good fit. And then just make sure that you have strong enablement and strong leadership to be able to fill that gap of that 30% that they don’t have.

[00:13:38] So I think that’s also like high potential people to me, are more important than like very skilled people in a lot of ways because they’ll come in really hungry. And then if you can coach and enable them, those are always the best, the best folks. I love those examples. Thank you. Sort of to round things out, most important piece of wisdom on hiring,

[00:13:58] that you wish you’d known [00:14:00] earlier? I actually touched on it just before, but I’ve wasted a lot of minutes of my life, a lot of time of my life, keeping progressing candidates that I’ve been on a fence on, and not just making the hard decision, right? Like there’s really good people out there and there’s really good humans out there, but it’s okay for them also not to be a good fit for the role.

[00:14:18] And sometimes I think we want to hire, because we’re talking to someone that we’re connecting with, they pass the beer test and you would go and have a drink with them for happy hour, but they’re not a good fit. And then at the end of the day, either you have an executive that comes over and goes, what are you doing?

[00:14:33] Like, we’re not going to hire this person. And now you’ve wasted a lot of people’s time and cycles, or maybe you just ultimately say no. So to me, I always say a soft yes is a no. So, if you are looking and you see a bunch of soft yes’es or a bunch of maybes, you need to have- I’d rather have three people be a passionate yes

[00:14:52] and two people be a no. And there’s obviously something there as long as there’s no red flags in the no’s. But I’d rather have [00:15:00] that than five soft yes’es because usually if you have a bunch of soft yes’es, that person is not going to be a top performer and they’re not going to really like take you to that next level.

[00:15:09] So hiring a force multiplier that really like raises all the tides so other people can learn. They do something new. They bring a new element to your team that you don’t have today. That is so important. So you really want people to be passionate about the hires you have. So if you’re on the fence or you’re a maybe or a, oh, I’ll just move them forward.

[00:15:28] It’s probably a no, but let’s just give them another chance. Just say no. It’ll save you a lot of time. Like we’re all, like I mentioned, we’re all way too busy in life right now to spend time on candidates that won’t be a fit. So just knowing when to walk away really early on, I think is really important.

[00:15:43] That’s another good one. Just say no, I like it. Say no. Just say no. Erin, well then just to kind of finish, are you hiring right now and who should be reaching out to you and just to the audience and anyone else that might be listening. Knowing Erin firsthand for many years, people that have worked under [00:16:00] you have had phenomenal careers, done extremely well for themselves.

[00:16:04] Are you hiring and who would you like to sort of reach out to or have reached out to you if they’re interested? Yes, we are hiring. We’re always hiring, but yeah, we definitely are. We’re looking for- hiring across all different roles. We’re hiring for account executives. We’re looking at both an enterprise account executive, an expansion AE on the enterprise side.

[00:16:24] We’re looking at customer success managers. Next week we’re launching a couple open roles for an SDR team. And we’re looking across a couple different, other roles across the business, even outside of revenue. And so, definitely looking for people that have large enterprise experience, people that have experience managing customers, but in a very, like revenue focused

[00:16:46] mindset is they do own renewals and some expansions as well on the CSM side. That’s how our org is set up. And then, yeah, if you know of any great SDRs, it’s actually the first SDRs that we’ll be having on the team. We have some BD roles today that do something a [00:17:00] little bit different.

[00:17:00] So this will be, we’re actually kicking back off the SDR role. So any good ones, send my way. Erin, I know a lot of these topics close to your heart on hiring. Thank you for the wisdom, the knowledge. Very much appreciate it. Thank you so much. Thank you, Tom. Really appreciate you having me on.

[00:17:16]

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