Between Two Hires with Special Guest Ruairi Wiepking

Ruairi, how’s it going? Good to see you, mate. Good to see you. Thanks for spending some time. It’s good to be here. I’m excited to be on the podcast. Excited to have you on. And we have a pretty long standing relationship at this point, both from a sort of client and candidate perspective. So it’s been amazing to chart your career and sort of see where you’ve got to over the years, it’s been fantastic actually. But you know, for those that aren’t familiar with you, I’d love to just get a brief overview of how you’ve kind of got to where you are along the way.

Yeah. Well, I owe pretty much everything to you. You got me my first what I would say, real sales gig, as an account executive at Rainforest QA. And yeah. I mean, prior to that, I was like working at a couple of startups and they were awesome. I learned a ton, but in terms of like a repeatable sales culture, I had some friends that moved on from

an early startup gig walk, and I was like, “Oh, man, these guys are making like real good money”. And so I remember getting in touch with you and you looping me into Rainforest, and it was literally the best thing that ever happened to me. I learned a ton. I got promoted a bunch, two times in the three years I was there. Went from IC to second line leader,

which was fantastic and just met some awesome people. I built a pretty special network and then went to Segment, moved to your neck of the woods. I was in UKI, so I was in Dublin where I am now. And then spent a lot of time in London going from IC into a second or first line leader there as well.

And then moved back to the States, so. Yeah, and all along you and I have kept in touch. I’ve referred candidates your way. I consistently say you’re the best recruiter. You and Megan, who I worked with from your agency back in the day, just fantastic partners. So yeah, man, it’s that’s how I got here.

I’m super excited and now leading a U.S. Sales for Monte Carlo. So I’ve been here about three years. Yeah. And it’s just been phenomenal to see your rise and rise. It’s just- I don’t know, man, sometimes it doesn’t feel like that. It certainly looks like that, but you’re a humble guy. So let’s get into it just to kind of speak to the numbers.

Yeah. How many have you hired now at this point? So I saw your question and I think it’s probably- at first, I was like it’s probably 30 or 40. But I actually went and did the math and it’s well over 100. Both for my team, my teams, and peripheral roles. I mean, if you count folks that aren’t directly working for me, I’d say it’s closer to 200.

And then yeah, directly under me at any point in time. Yeah, I mean, I’m always hiring. That’s the big thing I learned at Segment. So always, always be extending your network, building your bench. And yeah, so probably over a hundred. Well, a hundred plus sort of notches now. That’s an impressive number in itself.

That’s a slow week for you, Tom. I don’t know about that. But within that, there must be some good stories along the way. So what I’m looking for are sort of the best and worst hiring surprises. Yeah. So best was a guy who I work with now. I can’t say it was a surprise, but I hired him at a previous role too.

And he was like the number one performer by like a hundred percent as an SDR. And it was an internal promotion set up. And I say this, Alex, if you’re listening, you’re a bit of a bull in a China shop, man. I was just like, this guy’s like killing the leaderboard, but I just don’t know if he’s going to be a good AE.

And I remember there was another guy interviewing who I really liked and ended up promoting later, that I really wanted to promote because I’m like, this guy’s got more polish. I think he’s just better. But Sam blonde, who was the CRO at Rainforest at the time, and then went on to Brex and is recently at founder’s fund told me, he’s like, dude- in a much more blunt and direct way he’s like, “Look at the leaderboards, as long as there’s not like a major culture issue or anything like that.

If this person is like that far ahead, you should promote that person, right? Versus the one that you think maybe has the softer skills”. And I’ve always adhered to that. And so this guy came in, I was like, I just don’t know. Doesn’t know shit about QA. Was a firefighter a year and a half ago. And he came in and regularly was doing like 40 to 50 percent of my team’s number month over month, quarter over quarter. And he went on to have like an amazing run at gong shortly after Rainforest. He was one of the first AEs there. Took them basically from single digit to high triple digits in millions.

So I would say in a lot of ways I wasn’t surprised, but I was surprised at like how obvious the decision was when I got the feedback from Sam. Like, “Hey, this is how I think about stuff” and it really made a ton of sense. So I’ve always tried to adhere to that when I’m hiring and when I’m giving hiring guidance.

So I’ve had conversations with our SDR leadership here around who we should promote, things like that. The SDRs, they come to me and say, “Hey, what do I do to get a sales role at Monte Carlo?” And I’m like, be the best at beating your number because there’s like a mindset of whatever the target is, if you take no excuses and you just go for it, those people learn that muscle of beating their targets.

And so I’d say that’s the biggest, it sounds so stupid saying it out loud, but I think that’s like the biggest surprise of like, oh, it’s that simple. The flip side was, and this is not like a negative thing. The worst surprise was I’d hired a guy, he was 3 months in. He was doing really well. Came from Salesforce.

This was that Segment. And I went on vacation and he dropped a bomb on me in our 1 on 1. Literally three months in that he was just ready to like quit, not ready to quit. He did quit and he was going to go be a pilot. Like just completely pivoted. And that was tough because sales leaders, if you’re listening, you know how it goes. You got to carry their number.

And I unfortunately had another guy who was struggling with just like the day to day mental grind of the job who quit literally like two hours later on me. And both of those guys started on the same day. And so I’ll always remember that. I’m super like you know, supportive of people going off and doing what they want to do, because sales, you got to be all in.

But yeah. That was one, one day where I was just like, man, I did not expect that. Very rarely am I surprised when someone bounces, but when- Hunter, if you’re listening, I hope you’re enjoying being a pilot because I loved that decision, but it definitely was hard to backfill you. So yeah, that was probably the one that caught me off guard the most.

Yeah. Some great examples. Just moving into your methodology or sort of secret to recruiting. So sourcing of talent, what’s it look like? So I think that the biggest thing is honesty during the recruiting process. So like kind of under sell, and I learned this from my boss, Jordan. You don’t want someone coming in and feeling like that sort of the wall was pulled over their eyes in terms of what to expect.

And I think in this day and age of salespeople, people get like the market’s tough. If you’re out there making, you know, seven figures or high six figures, you’re probably not leaving. And those companies are few and far between. So I think if you are honest about the challenges, people really gravitate towards that.

So some of the best folks I’ve hired, I’ve been like, dude, in the first six months you’ll be lucky to make your OTE, you know, because I don’t want to come in and tell them, “Hey, you’re guaranteed 300%”. Because if you’re guaranteed 300%, that company is going to grow. They’re going to triple dilute the sales team in six months.

And, you know, you’re going to be back at square one. So I try and especially working at a startup, I try and showcase the opportunity, but I’m also very realistic about like look, there’s- like Monte Carlo, we just hired a new CRO who I’m super excited about. Not just saying that if you’re listening, Tim. Welcome to the team.

But you know, I was like, look, we’re in the process of evaluating sort of new leadership to come in. And that’s something like I would want to know about. That creates a bad taste in my mouth. I’m sure you’ve had moments in the past where a candidate comes in and a change happens. And you’re always very transparent with folks about what the opportunity is, what the downside is.

And you always put the best candidate interest in sort of in your mind. And I was trying to take that, right? Like, “Hey, look, here’s what’s going on here. This is what our best reps are doing. Here’s an example profile of who hasn’t been successful”. And then, you know, let them make the decision for themselves.

You never want to seem too desperate either. And then the last thing I think that maybe it’s a little bit different is for the candidates I really want to bring in, I’m definitely like a very strong advocate for. And I’ll call them up and text them and be like, look, if you have other questions, you know, outside of like a recruiting context, just call me or text me anytime. Because that’s who I am as a leader as well.

Like I’m definitely not- maybe to my detriment at times, like a rule by fear type. I really feel that if I bend over backwards for reps, they’ll bend over backwards for me. And then what I will say is like, I’m quick to move the ones who don’t, out of the business. But I definitely don’t endorse like a fear based style of leadership.

And so when folks are asking me questions off the cuff or like texting me, I’m always responsive and I try and be really sort of positive and engaging and friendly because I think one, you’re the sort of the tip of the spear for the company from a recruiting standpoint. And two, like the world of sales has changed and the demographics and that the folks that are getting into this role are very different from what they were maybe 20 or 30 years ago.

And so I think a lot of folks really want to know that a sales manager is someone that they can relate to and almost kind of be like a half therapist at times, which sucks, but it’s a hard job. I had an old CRO that used to say like “Look, you know, you gotta learn, earn, and grow”. But he’d also say on the flip side, internally, very few of us are in this just for fun, right?

You want to make money and you want to grow your career. And so I always keep that in mind. It’s like you have to have a balance of both. And you have to communicate that to the candidates for sure. Very good. So lots of interviews across the years. Yeah. What I’m looking for is maybe some standout moments or the weirdest interview experience that you’ve had.

Let’s see. Weirdest interview. Oh yeah. Jeff Garcia, I love you. Jeff, I came in after him at Monte Carlo. Jeff’s no longer at Monte Carlo. My first interaction with Jeff, my boss, Jordan, was like hey, I want you to go talk to Jeff. Jeff was like the top ever rep at Looker. And he was. Like it was evident when you work with him.

This guy is talented. And I was coming in, like coming from mid market leadership at Segment, which was sort of like the equivalent of Monte Carlo’s enterprise. And Jeff was working like Walmart at Looker, right. Again, I speak candidly cause I still talk to Jeff. And I remember Jeff saying to me, he’s like look, we’re maybe 10 minutes into the call and Jeff is so direct.

He’s like, look, I don’t know how to say this and I don’t want you to take offense to it but I’m kind of used to being managed by like old silverbacks, you know? And I was like, what do you mean old silverbacks? You know, I got some grays. You can’t really see him right now because I just got a haircut but it was kind of intimidating because I’m sitting there and like this is the guy that partially led Looker to the promised land,

right. And, now I say that, and there was obviously a ton of success stories at Looker, but Jeff is a great guy and a straight shooter. And I quickly realized like coming in, that was just his personality. I don’t think he meant anything by it but it was one of those things where, candidly for me, because I always have imposter syndrome as a leader.

I was like, oh, my God. Does this guy like, see through me? Am a fraud? Is he going to- but we actually had a great relationship. I kind of at times maybe you know, I wanted him to know that I definitely had his back because I just believe in him as a person and he’s a great dude and a real high caliber seller as well.

But yeah. That was one of those moments where I was, like, I was getting interviewed a little bit and I was like, man, this guy doesn’t think I’m good enough. But Jeff, if you’re out there, I really appreciated working with you. You’re awesome. Turn the tables on you a bit there. But- oh yeah, totally.

And you see that, you know. I see it even still with candidates and with with reps and QBRs sometimes. They’ll start grilling you and you’re like, whoa, wait, what? Hold on. . Wait a second. So, yeah. So let’s go into your maybe interview styles. Do you have a secret or unconventional tactic that you like to use?

So I’m really like, there’s not like a secret. I think like anything else, one, you got to be really consistent with recruiting. So, if you’re in a high turnover sales environment, or just a high growth sales environment, like 50 percent of your job is recruiting. And I learned that at Segment. I remember when I was first interviewing, getting promoted to being a leader at Segment,

I’d done well as an AE and I’m interviewing at the time. And my boss, Jerry Tracy, who led in the effort for Segment said like, “How much of your time do you think you should be recruiting?” And I was like, I don’t know, like five- 5%? And Jerry’s like 50%. And to me, that was like mind blowing.

And I didn’t realize it until I really got into it. But now, I’ll get into like the questions I asked, but the reason was it’s just like, if you have good people on board, your job as a sales leader becomes really easy. So a couple of things. I talked about my “secret weapon” for like attracting talent and being honest with them.

But I think the things I look for in a candidate, first and foremost, can they identify patterns, right? So I’m a big believer in medpick and command the message. But can they identify patterns and then qualify against that framework? So that’s really critical. I think the second thing that I see a lot of hesitancy around is how does someone feel about going high early.

Now look, if you’re in a PLG sales motion and you know, you’re selling $90 deals a month or something, you don’t need to go high, right? Just someone signs up on a credit card. But what my experience has been is for enterprise sales, when you’re selling half million ACV or quarter million or a seven figure deal, the big head honchos know about those deals early.

They know about what’s going on. And if I hear reps that don’t like that, or like, hey, I need to build up a little bit more. I mean, look, there’s always a time and a place, but often that’s just an excuse for not wanting to burn someone as a champion. But in reality, all it is, is a test as to whether they are a champion or not.

So I really, the second thing I look for is do they want to go high and do they have any sort of aversion or allergy to going high. And then the last thing, which might sound a bit like a profiling exercise, but it’s truly not, is putting someone in front of a CEO. Right. The question I ask myself, and this was guidance I received,

so this is not like original. But you ask yourself, like, hey, what I put this person- feel comfortable putting them in front of the CEO of you know, American Airlines or X company, right? If you’re going and transacting a 7 figure deal or high 6 figure deal, the odds are you’re going to be putting that person there. And it’s not about like presentation skills or appearances or anything like that.

It’s how competent and how confident, how does this person carry themselves? Do they follow up? Do they prepare? All those kinds of things. That comes across very evident in interviews. For example, Alex Lin, who I told you is like one of the best sales reps I’ve worked with, works with me now at Monte Carlo.

I have probably 8,000 text messages 24/7 throughout the day from Alex asking me questions, doing follow up, eliminating any doubt that I might not hire him. I’m like, dude, like I’m going to hire you. But that sort of due diligence and follow up is something that’s indicative to me of

okay, this person is someone I want to put in front of a leader and I trust. And recently I was at a dinner with the CRO of Snowflake. I did not belong in the same room as those people, but I was very flattered to get tagged in for my CEO who is going out on mat leave. And I remember him saying he had a conversation with Frank Slootman and he was like, Chris, if there’s ever a doubt, there’s no doubt.

Meaning, if you ever have a doubt about someone, there’s a good chance that- not even a good chance, there’s a 100 percent chance that that person’s probably not a fit either for your org or for your company or for your team, right. And so I actually really liked that and that’s something in the back of my head.

So I feel very confident about that org and the team that I have here. There’s no doubts. I feel like I have the right people on the bus. And so I encourage sales managers that I talk to and other folks that are hiring, look, if you have second thoughts about someone, don’t take the leap, right?

There’s always going to be another candidate. Very good. So let’s round it out with the most important piece of wisdom on hiring that you wish you’d known earlier. Yeah. It goes back to kind of what I learned a little bit about Segment. But I think a little anecdote from my father in law, Max Kramer, sums it up best.

So Max has done a lot of sales in his career and the topic he was talking to me about had nothing to do with sales and fairness, but he knows his way around the business and his son, my brother in law leads global sales for Looker as well. So there’s a lot of sales DNA in that family.

And Max was telling me this story about, I don’t know if it was him, cause he used to coach basketball or his buddy or a book he read. So forgive me if I, you know, am botching that. But he’s talking to John Wooden who’s the famed coach of UCLA basketball, right? They won like a hundred games in a row, several national championships, like amazing story.

And he’s basically saying like, look, these guys are running a full court press on my team. If you don’t follow sports, all it means is you basically have a defense that’s set up across the court and going playing man on every single player on the team. And the team couldn’t even advance the ball past the half.

And the guy who’s coaching the team goes to, whether it’s my father in law or whoever, goes to Wooden and he says like, “Hey, how do you coach around that? Usually there’s like an outlet and you get a skilled dribbler that can run up” whatever. And Wooden just said get better players. Right?

And I think like the message there, which is like, look, Sometimes you can’t out coach your way out of not having the right people on the bus. And so I think that applies a lot to sales recruiting. As a sales manager, you can level up your B players. You can manage out your C players.

The difference between like your star performers and even your a minus or B plus players is night and day. It might be three to four X performance. And so, if you can get a team of 90% A players, which never happens, but like it can- your job becomes, you know, it’s like you might as well be retired.

Right? I mean, I say that in jest. But that has always stuck with me that little story. And I think it, it didn’t really sink into me until I started working at Segment and realizing, okay, the people that I have to invest a ton of time in, that’s actually sucking me away from working a deal that might be high six figure TCV instead of trying to help this person close a 20k deal or close a door.

And so that’s where I really shifted in my career because I came from being a teacher. And so I was like, I just want to help everyone. I want to elevate everyone. And ultimately, you can’t do that all the time as much as that’s my natural instinct. And so if you get the people that are like good workers, good teammates, autonomous and have done it or have the appetite to do it.

I got a guy on my team who’s one of our best performers and he was an SDR 9 months ago, but he just has that drive. Those are the folks like you spend your time with and I just didn’t realize that early in my career because I thought I could make everyone a you know, an A minus player. But I’m like, look, I’d rather have three superstars and maybe one or two B players and coach those guys.

But yeah. I would say that’s probably the biggest thing. Yeah. Ruairi, you’re a legend. It’s likewise. But evident that you care, you care deeply. And I think, you know, anyone that I’ve known that’s worked alongside you, beneath you, above you, the theme is consistently the same. And so, anyone would be fortunate in my network to partner with yourself in the future, you know, reach out to Ruairi when they’re looking to hire again, because- yeah, absolutely.

Tom, thanks for having me, man. This was super fun. This was great. Thanks Ruairi.