INSIDE Inside Sales – Ep 109: You’re Hired!

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There is a lot more to being hired for an SDR role than just submitting applications and hoping for the best. You need to stand out!

This week on INSIDE Inside Sales, Darryl welcomes Vendition’s Head of Partnerships and sales hiring rockstar, Brian Smith. Darryl gets Brian to share his insights and opinions as to what makes an SDR candidate stand out from among the crowd, as well as what hiring managers are prioritizing these days. They share extremely valuable tips such as how you need to be a storyteller, the importance of finding a sponsor, and how to maintain the right attitude to navigate the hills and valleys of sales. Learn how to avoid your CV landing on the “No” pile of applicants on this episode of INSIDE Inside Sales!

'' I'm looking for someone that considers themselves the comeback kid.'' 🎧 Listen as @iammrsmith__ shares his expertise on both how to hire new #SDRs and how to land your next gig as a sales rep. #HiringTips Click To Tweet





Host: Darryl PraillVanillaSoft

Guest: Brian Smith, Vendition


Darryl Praill: All right, my friends how are you doing today? Oh my goodness, my goodness I’m feeling good. I’m feeling good. Which is interesting because I personally have been going through some seriously stressful times as I juggle all that I do in my job. It is crazy. How about you? You going through some stressful times? I mean, all of 2020 has been stressful times. Has it not? Oh, crazy. Who saw this one coming? Here are you into months, months and months and months after this whole process started. And we’re still talking about it. My friend this is nuts. Anyway, I’ve missed you, I’ve missed you. It’s been like a week. It feels like more. You know I was thinking about what I want to talk about this week and I kind of had in my head that it may be time to do a little more sharing. Now I know you’re sitting with yourself going, Praill all you freaking do is share.

Darryl Praill: Like you’re the king of share. Like you overshare. I really don’t wanna hear more about your schtick. I don’t wanna hear about your wife. I don’t wanna hear about the challenges you have. I don’t wanna hear about how you used to sell photocopiers door-to-door. I’ve heard it, man. I’ve heard it. I’m tired of it. I get it, I get it. Lemme give you a different share this time, okay? So over the past few months, many of you know my role has changed. Once upon a time, I was the Chief Marketing Officer here at VanillaSoft but you know in the last few months I’ve become the Chief Revenue Officer here. And that’s caused, you know that had hardship. Now you would think yourself, hardship? Where’s the hardship? That’s pretty exciting, man.

Darryl Praill: You’ve become the CRO. Like that’s the pinnacle and no less you did it from the marketing side and you would be right. And that is exciting. And I am glad that I have been blessed and fortunate enough to have that experience. But the hardship comes not when you’re given the job, the hardship comes when you have to actually execute. We all know that, right? We all know from personal experience the hard times that we have to execute. So, you know, looking back I can share some of the things that I did. And in my first 30 days on the job what I had to do was I had to assess what I had. So I had kind of a 30-60-90 day plan if you haven’t heard me talk before. The first 30 days is gonna be assess, situation assessment, and make some decisions so I can move forward.

Darryl Praill: The next 30 days is gonna be, you know, rip and replace and look at all the cadences, all the email, all the messages, all the scripts, all the other value props, who’s our ICP, what’s our USP, who’s our personas you know and just overall everything. And then the final 30 days was gonna be the massive training of rollout of all the staff to make sure they could adopt and adapt to execute. So 30-60-90, that was the plan. I had it blessed by the management team and everything else. But you know in many regards the hardest part was the first 30 days. And you’re trying to understand what it is you’ve inherited. So whether or not I mean, I’m looking at people. Now I’ve known them, they were in my company before, but now I’m critically analyzing them and like do you have the skills?

Darryl Praill: Do you know how to sell? Do you know how to sell? Do you know how to open a question? Do you know how to ask an open-ended question? Do you know how to ask a closed-ended question? Do you know how to handle objections? Do you know how to do discovery? Do you know how to do a challenger sale? Do you know how to do consultative selling? Do you know how to actually map your account? Who’s the economic buyer, who’s the technical buyer? Who’s the veto, who’s the champion, et cetera. You know, do you have a sales methodology in mind? Is it Medtech? Is it something else? You know, what are you doing? You know, can you grow the size of a deal? How do you handle competition? You know, are you relational? Or what are you, you know? Can you know how to ask the hard questions?

Darryl Praill: So when you do all that, you’re doing this you don’t understand, okay I don’t expect you to have all the answers. So what do you need? Oh, you need more sales skills. Maybe you need sales skills on starting a conversation. Maybe you need sales skills on closing a deal, right? But then you do this matrix score, there’s those sales skills are under one axis on the matrix. But the other axis in the matrix is product skills. Do you know what our product physically does? And you know, many of our reps did not have a good understanding of that. So we had to bring in sales training, we partnered with some of the industry’s best sales leaders, including Mark Hunter to help us with some of the sales skills and others.

Darryl Praill: We partnered with our own in-house corporate trainers to bring this in. We built a sales enablement crew, an entire team. We hired solution engineers to offload some of the technical burdens that the account executives and the SDRs were facing so that we had a bigger team. I mean, this was overwhelming cats, lemme tell ya. And every step along the way there all I was doing was saying, “Does this person have what they need? And will they help me achieve my corporate goal?” Because I’m at the pinnacle but I can fall off this mountain really, really fast and the next person to come in and I know that.

Darryl Praill: So, at the same time I’m having this conversation with my people, I know that they’re looking at me and between you and I, many of them are shitting bricks because it’s like, oh my gosh, a new sheriff in town. What if he doesn’t like me? What if he actually decides to let me go? What if he decides I’m not part of “NewCo”? You know, what if I just don’t fit what he’s looking for? What if that one time I told him he was an idiot he remembers that and kicks my ass out of here, you know. And then I’ve got other people from outside the organization saying, hey okay congrats you’ve been looking for new people you should check me out I’m the best thing ever. So it’s overwhelming.

Inside Inside Sales Podcast

Welcome Brian Smith

Darryl Praill: So what do I do? What do I do to make sure that I put my SDRs, you know, at ease, I give them comfort, I relieve their anxiety so they can perform and not get distracted? But what do I do to make sure I’ve got the right team, the right skill sets? Well, that’s a golden question let me tell ya. And I decided that I needed to bring an expert in to help us with that conversation. Somebody who understands all sides of this staffing equation. So sit back and relax. You’re gonna like today’s conversation.

Darryl Praill: I’m not gonna teach you how to sell a damn thing. I’m gonna teach you how to be a better employee or how to get yourself the right job. Or if you’re a leader, if you have a team we’re gonna talk a little bit of shop for you too. Something for everybody. Who am I doing this with? I’m glad you asked. I thought you’d never ask. It is a repeat performance. I am so pleased to welcome back my good friend, Brian Smith. Brian, baby, how you doing, sir? It’s been a long time since you’ve been on the show. Welcome back! What is up?

Brian Smith: Yeah man, I’m so glad to be back, man. It’s been cool to watch this thing grow. Super honored to do it. You would even have me on at early days, I’m sure I probably butchered it, so sorry about that. Give a little bit of redemption here, but yeah man beautiful life having some success in the career, and just excited to share my story, man.

Darryl Praill: Now, when we last met up with Brian, if you don’t recall go back and listen to the episode it was fantastic. He was really honest and transparent, you know, living the life of an AE and he had a little girl who was new, and we were just talking in the green room before we went live. And that’s not the case anymore. You don’t just have, you know, one little girl anymore do you, Brian? You’ve got, I understand you might have another addition on the way, is that the case?

Brian Smith: Yeah, I can’t figure it out, if this is considered one and a half right now, you mentioned jumping on just like I have to. That’s a lot of stress in itself, right? So one and a half.

Darryl Praill: One and a half soon to be two. Well, congratulations. That is so exciting. And you’re living the life. I love it. All right, so Brian let’s get some context out of here. You’re with Vendition and you run partnerships there. But I love when I talk to you like your title is like Partners or Partnerships, what have you. You know like, dude, that’s just a fancy word for an AE, I am a full-cycle rep. So you do the SDR role. You do the AE role, you do the whole enchilada. For those who don’t know about Vendition, alright cause I think it’s contextual to today’s conversation. Can you kind of just give us a little blurb on what Vendition is all about?

Brian Smith: Yeah, I’d love to. Ultimately, man, we want to be that educational resource for SDRs. We really want to change how companies partake in hiring SDRs. What does it look like? What does an SDR really need to know? What type of information should they have before they get their first gig? You know, new congratulations on your new CRO role, we can easily look at your resume and see that, hey this guy probably can fit the bill. With an SDR, typically because it’s considered “entry-level role”, a lot of times we can look at a resume and see if they can fit the bill. And so that’s where we come in to fill that gap in between that person who wants to get into the SDR role and also helping our partners feel comfortable in that person’s background. So changing the game of how we hire, so the development like is how I like to say it.

Darryl Praill: All right, so you’re all about you know, the hiring and the development of SDRs specifically. So based on that I thought you were the right guy to have this conversation. So if it’s okay with you, I’m gonna go back in time to months ago when I was starting my CRO gig. And I wanna drill down some questions on you that I think my audience would get a kick out of. And by the way, folks you haven’t done it yet. You know what I always say but it’s never more true with Brian Smith. Get on LinkedIn and follow him. He’s great, I just love watching him. And you know this guy, he hangs out with the who’s who. I believe you were on a bus not too long ago, Brian, would that be a fair statement? For those who don’t know maybe you can give them a little background on that little adventure you took.

Brian Smith: Yeah man, it’s crazy. I think if anything, you gotta surround yourself with good people, honest people. That’s why I’m having this conversation with Darryl. Good, honest, good person. And I was having dinner one night with a couple of people, Scott Barker, Becc Holland, and Josh Braun. And you know I heard about the flip of the script for and Becc as the group salesperson that she is, not just a leader, a great salesperson she is. She convinced me to convince my family to get on a bus with like a 12-hour notice, basically cross-country and across to Denver on a sales tour and I learned a lot. It was pretty fun. And I’d love to do it again.

Darryl Praill: All right, so I told you this cat hangs out with the coolest, smartest people going so there you go. So that’s his pedigree. You lived your life and he’s part of the cool kids club. I wanna be him when I grow up.

Hiring sales reps

Darryl Praill: All right, so you’ve been on kind of all sides of the desk here. You being that SDR, you’re a full-cycle AE, but now you’re also sourcing AE’s. You’re helping build a team. I got lots of questions. I’m trying to, where do we wanna start here? Let’s start with this. If you’re building a team today, you’re a sales leader, SDR leader. You know, based on what you’ve seen now what makes it good team? What makes a less than good team?

Darryl Praill: What are some of the tips you can give to these sales leaders that they should be looking for in SDR candidates? And especially focusing on some of the things that they might not have thought of. And now for the SDRs who are not the team leader, so here’s the SDRs, listen to what they’re saying because hiring managers who look for these things that Brian’s gonna share are the people that you wanna work for. That’s where you believe you should be listening. But again, I’m building a team out. Brian, what are some of the things that I should be considering as I’m building my team up, in talent and skill, and people?

Brian Smith: Yeah, for sure. I think there’s a couple things you should be looking for but let me give some context. I think the notion right now is to figure out things like is a person hungry? Are they money motivated, right? To me, all of those things can come crashing down pretty quickly. I think you should be looking for a person that can be a great storyteller. I don’t know if we’re trying to figure out in interviews if a person who tell a good story, if they can provide value in sharing the time where they can back up the information to give them with research and then tie it to the current lead for the employer or interviewer. So I think we do look for people who are creative and are storytellers. And there are some ways that you can do that in an interview.

Darryl Praill: So on the storytelling point, it’s actually kind of interesting because of those who are regular listeners you may recall those who just joined the podcast recently, you should know that a few months back we had a wonderful episode focused explicitly on the art of telling a story and how it makes a dramatic difference. Think about even what we’re doing here in today’s conversation, right? We’re telling a story about Brian’s journey, Brian’s family, life, and how his own career has changed. How he just hopped on a bus. All that makes you relational. It makes you relatable. And you just wanna hear more from the individual.

Darryl Praill: So storytelling is a great way to both establish a rapport but it’s also a fantastic way to speak to pains or issues or obstacles or challenges that your prospects may be facing. And how other clients whom you’ve helped tackle the problem.

We all like a good story. We all like something that has, you know, a lesson to learn. Maybe there’s a moral. Maybe there’s a happy ending. Maybe there’s not. But even when there’s not a happy ending, there’s still lessons learned. So storytelling makes it far more real than simply saying yes, we can do that, no we can’t. Yes, that will happen, no this won’t. That’s just kind of black and white if the conversation is stilted and it stops.

Darryl Praill: Storytelling keeps them hooked, keeps them engaged, keeps them leaning forward, keeps them actively listening. And that’s what you want. You want them actively listening. You don’t want them tuning you out. All right, that’s my first question. We’re gonna take a break. We’re gonna go to commercial. We’ll be back shortly, don’t go anywhere. Brian Smith and I are gonna carry the conversation on about all things that you need to know if you’re an SDR or a hiring manager when it comes to what you should have in skills and talents and resources. Stay tuned, we’ll be right back.

The importance of diversity

Darryl Praill: Okay so we’re back. So that’s for building your team. What are the questions you didn’t hit on? You talked about storytelling, for example, is one of the aspects you made. If I’m a leader, where does diversity come into the composition of my team? Will it be diversity of ethnicities or diversity of skill sets or whatever but diversity where does that come in, in your opinion?

Brian Smith: Yeah, that’s a great question. I think it should come in number one in all facets. It should be ethnicity. It should be background. It should be skill. And here’s why: While the sales, the sales role is typically a lone wolf, right? Performance-based role. At the end of the day, your team’s gonna rely on each other. And there’s nothing worse than having a team that all has the same type of skill, same type of background experience cause they can’t teach you, typically they can’t teach anything new to each other, right? If I’ve got a background in professional services and I get hired with a guy who’s done SAS software his entire life, we’ve got different experiences that we’re gonna teach each other.

Brian Smith: And then from a race and cultural perspective, there’s some different ways. We’re just talking about storytelling, right? The way I communicate storytelling is probably different than a person who had a different background or grew up in a different culture than I have. And so I think when you hire those first candidates and have that diverse team it only helps communicate your value, your product, your service better, right? You’re gonna be reaching out to people who are different, have different backgrounds, right? Not everybody came from sales, not everybody came from marketing. So when you have that different skill level and that different background, I think it helps elevate your team.

Darryl Praill: Do you see people being intentional these days about diversity? When you look at other your clients or your prospects, you see that coming up in a mandate. So for example, when I took on the role of CRO, I knew I was gonna need a head of marketing. I knew I was gonna need a head of sales and I knew it was gonna need some additional bodies. And I started talking to my network, I started saying, “You know I have this stereotype composition. I would really like to be exposed to other people with other skill sets, other backgrounds, other cultures to round out my team and make us a better team.”

Darryl Praill: And when I asked that, you know not once I get somebody saying, really Praill you’re not just looking for the best person for the job? In other words, it was understood by at least my circle that, you know, sometimes it’s not the best person just on paper and skill set. Sometimes it’s those intangibles they bring to the table. It gives you different points of view, different perspectives that make you as a team a whole stronger and better, better able to compete. I was thrilled to get, that feedback but are you hearing people ask and inquire about that?

Brian Smith: Yes and no. Yes, I think it’s becoming a conversation. No, from the aspect, I think people are trying to figure out how to do it. I think we’re in a place where people aren’t sure how to do it. So yes, I think the conversation is happening which is important. But now just with anything right we’ve gotta practice it. You know it’s kind of a tangent but we’ve gotta rewrite the way our job descriptions look, right? Our job descriptions are written to attract a certain type of candidate and that may not be a diverse category or a profile.

Be the comeback kid

Darryl Praill: All right, I’ve gotta ask you a question cause you, you have been on both sides of the equation and now you’re actively out there recruiting and evaluating talent. What do you, Brian Smith look for in an SDR candidate?

Brian Smith: That’s such a great question. I’m looking for someone that considers themselves the comeback kid. And what I mean by that is someone that has been knocked on their butt. Someone that has been beaten up but has found a way to get back to the winning, talking about myself, right? Like from my own personal experience, the SDR, the sales world is a grind. I’m gonna go out on record to say you can’t consistently win. There’s just some odds. It’s hills and valleys. So I need to be able to find that person that is a comeback kid. And they have to again, be able to tell a story to where we’re continually rebounded but not only rebounded but learned and can share how they did it, right? Cause that goes back into selling their product, selling value. Don’t tell me that you found a way to find success but how did you do it, give me the formula as my guide more than any of them say.

Darryl Praill: So I really liked this concept of the comeback kid. And let me, I’m gonna explore this a little bit just so the audience really understands what we’re talking about here. So here’s the one thing you need to know right away guys. You’re not gonna win every deal, right? You’re not. There’s gonna be deals that you do everything textbook perfect. In the end, they’re gonna make some decision and you go what did I miss? And you’re gonna be upset, you’re gonna be angry with the prospect, you’re gonna feel misled. You’re gonna be bitter. You’re gonna talk to your boss. You know that they’re gonna be probing you. What did you miss? What did you consider? And the comeback kid mentality says when that happens when you’re either you know lose a deal you thought you had.

Darryl Praill: When you’re in a slump because we all get in slumps. I had a conversation with Martin MacArthur about this not too long ago about you always get in a slump. Ryan Reisert with the same concept. The comeback kid perseveres, learns, and bounces back up with new tactics, new skills, new optimism but also has the ability to put that loss behind them. Or maybe not fully behind them, but says, no problem, I’m gonna live to fight another day. And I’m gonna stay on top of that account. I’m gonna circle back in three months or six months, or a year when they realize they made a mistake or they realize they should have gone with me. And then I’m gonna actually get the deal done.

Darryl Praill: So maybe it’s not today but maybe that it’s not, you know, not forever. It’s just a period of time. So the comeback kid is what resiliency and perseverance, that’s what that really is. It’s a character trait. Now, Brian, you said, you know maybe you might be manifesting yourself a little bit here. You’ve got some comeback stories too. So just so the audience doesn’t feel like, you know you’re this rockstar hanging out with Becc and you know and Barker and crew on a wonderful bus as you go cross country. Talk to us about some of the hardship that you, you endured maybe it wasn’t you know, I’m assuming it was unexpected and how you overcame or what lessons you learned from it.

Brian Smith: Yeah I think it’s definitely common in my career, man, when I had been at the highest high and lowest lows. You know it all goes back into how you interview, what are you looking for, to finding those things, what you want in your career? Cause if you don’t do that, you’re gonna accept anything. And I’ve worked with some great companies and great leaders but again, things will not always play out how you want to. Last year, I went through two different companies within a span of seven months, six months I believe six or seven months lost both of those jobs. Why I lost those jobs?

Brian Smith: I don’t know if those are important as sharing the journey of figuring out what happened and utilizing what happened to teach other people to not make the same mistakes. At both of those two companies I did great things, large deals, quickest deal in the company history and it still didn’t work out. And so that’s what we talk about those values. Those values will come and sometimes it’s out of your control. And so figuring out what you did, sharing how you did it, how you pulled yourself up I guess from your bootstraps and continued on. I think if you can teach that to other people and how you did that, that’s true success.

Darryl Praill: Lemme ask the question here. So those SDRs out there exactly in your situation you said last year, you know those two gigs for whatever reasons didn’t work out so you had to dust yourself off and get up and look for the next gig and you have a blast and doing kick-ass results at Vendition. Which always just goes to show you, sometimes it’s not you. Sometimes it’s a fit thing, right? So, but hey guys, I’ve been the exact same boat. I always like to say every second job is a home run, even though I have to think when I pick every job that I take it’s a home run. I have done my due diligence yet despite doing all my due diligence in my career every second job has been the one I enjoy, which means I have a second job. So I’m 50/50. There you go.

Preparing for an interview

Darryl Praill: As a candidate, so we’re out there, maybe they’re impacted by COVID, looking for the next gig, they got furloughed, they’re not happy where they are, they’re looking for the upgrade. As a candidate, you know, what goes on in their mind? What do they wish they knew so that they could be prepared to give their best foot forward, their best presentation of them as a person? What secrets do they need to research to best prepare for that interview?

Brian Smith: Great question. Couple of different things. And this may not be a traditional answer you expect but I gotta give credit where credit to Robert Jefferson just shared this with me. And I’ve been going about like the completely wrong way. One, your resume needs to be able to tell a story but leave out enough information for the person to say, hmm, I wanna see more. I wanna hear more about this experience. You shared a little bit with me but it’s enough to where they want to poke holes in it to really get down to the truth. The second thing, we’ve gotta get out of this heroic mindset of salespeople that it’s all on us.

Brian Smith: My success is due solely to my performance. I’m raising my hand telling you right now, that’s not true. I’ve seen it. I’ve done great at companies and still didn’t work out. You need to find and again, kudos to Robert for sharing this with me and helping me realize this, but you’ve got to find a sponsor. Not just a mentor, but a sponsor. Somebody that’s willing to put their brand on the line for you. Somebody that’s willing to say, hey I know he’s gonna succeed and I’m gonna be that person that helps him or her reach to that point. We gotta find sponsors. So if you’re trying to find a great job and trying to get to the next best gig by yourself and only on your resume and past success alone, I think, not that it’s impossible. I think it would take you longer.

Darryl Praill: Okay, what one thing should an SDR… There can only do one thing, talked about a resume. Talk about, you know the interview a little bit here. We really haven’t talked about LinkedIn but that’s okay. What one thing should an SDR absolutely make sure is buttoned-down and kick-ass for them to not immediately end up in the ”no” pile when you’re looking for the next job.

Brian Smith: Great question. Lemme think about that for a second, just a minute. In order for you to not to end up in the ”no” pile, the number one thing you need to do is truthfully build a use case around the product that you’re attempting to sell or the company you’re attempting to work for, build a use case, put together a presentation. Again, that shows a couple of different things that you look for in an SDR, right? That may not show up on a resume creativity, storytelling, value.

Darryl Praill: Nobody does that guys. And I’m telling you as a hiring manager, nobody does that. If you did that to me and I am not saying you’re getting a job but you’re not gonna be in the ”no” pile. I’m gonna go holy shit. Assuming it’s well thought out, it’s logical. I need to know more about this person and how they think, they went that extra mile. What will they do for a prospect to get the deal? That’s how I think. So that would be game-changing.

Darryl Praill: Biggest mistake or biggest missed opportunity hiring managers make in the hiring process when it comes to evaluating candidates?

Brian Smith: Yeah, that’s a great question. I’ll go back to I think the biggest mistake we make in the hiring process is on the front end. I’m gonna try to give some context. I think the way you truly wanna deal is by fantastic prospecting. I always say I know pretty much if I’m gonna win the deal based on my prospecting efforts. It starts with the prospect. And in the same way, the hiring managers are making is on the front end with what they’re asking for in a candidate. I think what we’re asking for in a candidate nine times out of 10 in the job description is not what we ended up hiring. And if we’re truthful with ourselves we can see that with the missed quota and the turnover rate and et cetera, et cetera, it goes on and on. So I think the mistake we’re making as hiring managers is in the beginning.

Darryl Praill: Last question. One question that an SDR candidate should always ask a hiring manager is?

Brian Smith: One thing they should always ask is let’s say I have this job, we’re out having our favorite drink. We’re toasting to my success. What three things are we toasting to?

Darryl Praill: Damn, I’ve not heard that one before. I’ve used variations of that one but yours is distinctly different. I would look at how do you measure success? But you are saying what are the three things we’re toasting? And it’s just a different question because you’re putting it, you’re actually putting them in a scene. We’re out toasting changes the tone, changes the language. Love it. My friends, Brian Smith, right here. I told you he was a rockstar. There’s a reason he’s back. Check him out, check out Vendition, follow him on LinkedIn.

Darryl Praill: He is a must listen kind of guy. He hangs out with cool people. He goes cross countries in buses. And by the way, I did not get that invite so it tells you he’s just way more cooler than me. This wraps up another week my friends. Another week is in the books we did it. I missed you. I love talking to you. Hopefully, you love talking to me, but more than anything I hope you got a little bit out of this to be 1% better. If you liked today’s show there’s plenty more back at My name is Darryl Praill. I’ll talk to you soon. You take care. Bye-bye.