It’s the 5th episode of Meaningful Conversations with Revenue Leaders – No fluff. Meaningful conversations only.

Doing the job before you have it helps you land on your dream position.

Helping the team hit the quota rather than reaching your own numbers helps you lead a successful team.

And making sure everything is simple and repeatable helps you scale your team stronger.

This time, joining us is Matthew Roberts from He has more than 6 years of sales expertise under his belt and has built, managed, and inspired world-class sales teams.

Let’s join his journey and find out how to grow within the sales profession, build positive team culture, and scale a team that wins together.

Here are some highlights from today’s episode:

Highlight 1: How did you transition from being a peer to being a manager?

I think a big part of it is to do the job before you have it.

I started by hitting my numbers as an SDR and trying to be proactive and develop new ways of working.

Once I found something that was working, I shared it with others and helped them as much as I could. Then I found out that it felt so much better to have other people hit their numbers than just hitting your numbers on your own.

With this idea in mind, I started to take on new tasks. Things like:

I want to be involved in the interview process. I want to interview people. I want to help hire people. There’s a new hire. I want to help train them and onboard them.

I did these tasks all before I became the team lead or the manager.

To sum up, I think it’s about:

  1. Painting the big picture. When the time does come, you‘ll move into that role naturally – rather than other people taking directions for you.
  2. Doing the job before you have it, you’re building validation and legitimacy for everyone around you, above you, next to you.

Highlight 2: How do you create a culture of help within your team?

In the past, there were stereotypes like: salespeople are self-centered and only care about their own goals.

At the same time, salespeople are competitive, for sure – the same way sports are.

But we’re a team. So if you’re just caring about yourself, your team is probably going to lose. If you hit your quota every month but the team’s quota is never reached, you’re losing.

When there’s collaboration and trust, we’re probably going to do better as individuals and as a team.

We create an environment where everyone shares what’s working and what’s not. In the start-up world, if the team’s doing better, especially in sales, the company’s going to be doing better.

Highlight 3: When you hire for an SDR team, what are you looking for?

What we try to look for like what we did at Chili Piper and what I’m trying to do again is:

  • Find people who are always bringing positive, good energy. Things change all the time. Most people are going to a start-up for a reason, and that’s because it’s flexible and changing and you’re pivoting.
  • You have to be really comfortable with the unknown and understand that things could change. It’s not month-to-month or quarter-by-quarter. It could be week-to-week or even day-to-day.
  • On top of that, it is about being super proactive and taking ownership of things they’re doing. You want the people who are like: I’m here to do something special. I’m here to take on projects and crush them and absolutely own them from start to finish.

Highlight 4: How do you scale an SDR team?

The more simple you make it, the more successful you’re going to be.

  • Make sure your hiring is down. You need to have a process that is specific, repeatable, and scalable. It should not be something that takes too many resources or too much of your time.
  • Make sure your onboarding is super tight. Make sure your onboarding material is up-to-date. The more complex and confusing things are, the harder they become scalable.
  • Have a workflow/process that is repeatable. It’s not something that you need a rocket scientist to figure out. I’d tell everyone it’s going to take some time to learn the workflow, to learn our tech stack, to learn the space. But at the same time, you can get a little better each and every day.
  • Make sure you have the resources to hit their numbers. If people aren’t hitting their numbers and things aren’t happening, the morale is going to be trash too.

Want to check the uncut full text? Here's your transcript.

Jan: We’re just going to record. What are the things you would like to speak about? Is there anything where you’re like hey, I would like to – this is something I was speaking about? It’s early in the morning for you, like aAlter new condo stop loaded so I’m already more hyped than you are, which is okay.

Matthew: I got my espresso over here. No, nothing specifically. I’m down to answer – like you said, if you have some questions or things written down, dive into them. There’s nothing going on in my brain that’s specifically I need to get this out to the world right now.

Jan: No, that’s great. I think the first one that – I actually spoke to a friend, Emilios, and he asked How do you create a winning BDR culture? That’s a big question but what are the key pillars for you because you’ve done it at Chili Piper. You’ve going to do it again now. What are you looking at building this culture from the ground, from being the first rep or the starting reps? What do you look at to start this?

Matthew: Yeah, that’s a good question. I think it’s super obviously relevant right now for me because I’m going to try to do it again and hopefully, like you said, I am successful with it. Especially in the beginning when things are new and the team is very small, everyone knows your most crucial hires are probably the ones in the very beginning. If I’m a CEO and I’m building out a company, if I hire poorly in the very beginning, everything’s probably going to fall apart or at least set you back a good chunk. It’s the same thing for the SDR team when you’re building that out. Those first few hires are absolutely critical.

What are you looking for in the first few hires is very important to make sure you nail them. Obviously, you want to do that forever going forward, but the real world means you’re going to mis-hire, for sure. Every once in a while, it just happens. What we try to look for like what we did at Chili Piper and what I’m trying to do again is find people who are, one, always bringing positive, good energy because as you know or as anyone in a start-up who’s worked in a start-up, things change all the time and things – they’re never – if you want to go work for a large Yelp or something like that where it’s like here, we’re going to teach you one way to do something and you’re going to do that over and over until you become an AE, that’s fine. Most people are going to a start-up for a reason, and that’s because it’s flexible and changing and you’re pivoting.

You have to be really comfortable with the unknown and understand that things could change and it’s not month-to-month or quarter by quarter. It could be week-to-week; it could be day-to-day. You have to find people that are going to just constantly have that good energy. and be like, whatever. It is what it is. I’m going with the flow and not get set back because again, in the start-up world, if you’re hung up on something for a day or a week, that’s going to screw up everything. The people who can see a change and be like, whatever, okay, I’m going for the next and put their head forward and be excited to do it, I think that’s crucial.

On top of that, and it flows right into it, is just being super proactive and taking ownership of whatever it is they’re doing. Again, there’s a lot of companies out there that are large and you can really feel just like a number. Some people want to feel like a number. They don’t want all the weight on their shoulders, and they’re like, okay, just give me a task and I’ll do it. That’s not what you’re looking for in building that first few hires in the culture. You want the people who are like, I’m here to do something special. I’m here to take on projects and crush them and absolutely own them from start to finish. Again on the proactive side, think of things. You get to use your brain and you get to be somebody like an individual and you get to have a voice. I think that’s why a lot of people do enjoy working for smaller companies. You really feel that. The people who are bringing good energy, are excited, are going to be proactive, they’re going to see problems and fix them. Then when they do get any sort of project, they’re going to own it from start to finish.

Those are the really big pillars that you’re looking for in those first few hires. It’s really hard to get that out of them in an interview process but again, when you are starting to build out a team, you probably had the luxury of you don’t have to hire this number of SDRs by this date. It’s let’s find people that really embody what we’re looking for until you can really take your time and suss them out and see if they check all these boxes. Then you’ll get some rock stars, hopefully, that comes on board and they’ll crush it for you in the beginning. I always said, too – I told them this. I think a lot of my success at Chili Piper came from being able to hire two absolute studs in the very beginning. I hired Tyler and then Jay, and they both came on and owned everything from day one and went above and beyond on every project, and month over month just had really good energy and were excited. If that wasn’t the case, we would’ve moved probably a lot slower or things wouldn’t have grown as fast. I got very lucky with them. Trying to repeat it, I’m going to be looking for people who have that same passion and energy and ownership and excitement. Only good things can happen from there.

Jan: Yeah, what an answer. It’s so true, right? In the start-up world, everything is about agility. Everything is changing on a daily basis. The MQL criteria will change overnight. You have to adapt. A lot of people embrace it or break it and have to move forward. Yeah, that’s so true, and then passion. You have to enjoy it while you’re having fun. Yeah, that’s great, man. I can resemble a lot of that.

If we maybe flip that question because I want to dig a bit more because it’s such an important question. It’s about having the right people at the right seats in the right bus. Maybe you have some mistakes.

What are your hiring mistakes that you made? This is something I won’t make again, or I’m not looking at because we always speak about the things we look at, but what are we not looking at?

Matt; Yeah, that’s a really good question. I’ve always said – it’s funny because I’ve never been in recruiting but I feel like we did a lot of hiring at Chili Piper, so I understand a little bit of it, not an expert and I wouldn’t even come close to being that. If you could figure out how to never miss on a hire, you’d probably be a billionaire because it’s such a hard thing to do. I think that’s why you – questions are super important, for sure, just who’s asking them and how they’re asking them, but I think more than that, there’s also – the thing I’d say you’re not looking for is there’s a lot of people who can interview really well Then they get to the job and they just don’t really do it. I think obviously social skills are really important in an SDR role because you’re probably going to be talking to people on the pone or emailing, whatever. You have to have just the basics there. We did a lot of assessments, whether it was an email assessment, a cold email, just give them a few things. Going to see one, what’s their written communication look like? Do they form things? Are they creative? Are they thinking outside the box? Where are they there?

On top of that, it also gives them a project because going back to the ownership part, you can interview really well and show up and be lazy. It’s super hard to get out is this person someone who’s going to grind and are they going to give it their all every single say, which you need to do as an SDR, and it’s exhausting, for sure. No one’s saying it’s an easy job and you can give it 50% and hit your quota every day. That’s just not how it works. Anything you can do to try to find out what – is this person going to give it their all? Are they going to go above and beyond? Are they going to put in the work? Are they excited to do it? Are they motivated to do it? Are they someone who is always going to go above and beyond in projects? We would give email assessments. We would do a good amount of cold call training.

The other part of that is how do they take feedback. Because that’s another thing going into having that good mental space every single day. If you’re giving someone feedback in a cold call or a mock role-play and they’re not really accepting it, you can assess in the next interview step if they’re doing the cold call again because you see the notes. I interviewed someone. Hey, I gave them this feedback. They said okay, whatever, and then the next step they’re interviewing with someone, do a cold call again, and they make those same mistakes. They don’t receive that feedback very well. Okay, maybe this person is someone who doesn’t want feedback. They’re just like, I’m going to do it the way I’m going to do it and I’m not looking to be coached or anything. It’s very small things that you have to find.

Anything that can get them – that you can see what is their work ethic, are they gritty? Are they going to give 110% every day? Then also, the lip service part where it’s like maybe this is someone who just interviews really well and they come on board and don’t really do the job but they can have a conversation and you like them. That’s another really big tough thing, liking somebody and hiring them. Oh, I get along with this person and it’s a culture fit. They maybe are super friendly, too. Oh, this may be a great hire, and then they come on board and it’s just not. I think you also have to get past this might be a really great person and they seem friendly and everything but it still isn’t a right fit.

On the other side of that, not to loop Tyler back in again, but I remember we also used to do a video step in the beginning. It’d be why do you want to work here, what are three characteristics of a really good SDR? We used to do that and they’d submit a video. I remember watching these videos and I didn’t like it. I was like, “I don’t like this guy. Something’s weird with him.” But his resume looked pretty good, and I was just like, okay. I think it was a slow week, so I was like, I’ll just talk with him anyways. Again, it ended up being fantastic. There’s a lot of things I think you can try to tweak and figure out but again, if you can answer the question or figure out the problem of never making a mistake hire, you’re going to have the best recruiting firm of all time or if you’re internal, you’re going to make that whole organization explode with talent.

I’d say the hardest parts are figuring out is this person just really good with people and that’s it and they don’t want to put in the hard work? On top of that, you don’t have to hire people you always necessarily like off the bat because just because – I mean, not to say hire people you don’t like but you don’t have to be best friends with every single person on your team. You’re just looking for people who can do the job really well and want to do the job really well.

I don’t know if that totally answers the question but hopefully.

Jan: I think it’s so true. It’s a lot of examples. I think you don’t have to really be friends with them. You have to think what’s best for the company, putting them in real environments. Having a mock call tells a lot. It gives an objection How would they handle that objection? Instead of I can handle objections, actually put them into cold water. I think this is a great segue into another part that really interested me about your steps. You went from senior SDR to manager, right, or team lead? How did you transition into being a peer to what’s being a superior, even though you are not – you’re leading by example. You don’t want to have this power shift, but technically you have it. How do you move from that and how did you handle that transition, so to say?

Matthew: Yeah, no, and that’s another really cool topic. I think it’s really interesting. I remember Michael Tussaud – I think he gave a talk on it, but I know a lot of people have asked that question. I know there probably are blogs, articles, podcasts, and stuff that dives super deep into that specifically. I think a big part of it and something we’d always say is do the job before you have it. you’re making it obvious to obviously the higher ups for sure that are going to be the ones moving you in that right direction, but you’re also making it obvious, hopefully, to the people around you.

When I joined Chili Piper, there were two other SDRs. We were all peers, so we worked together for X amount of months. If it was something where I was just hitting my numbers and staying in the dark, in the shadows, they’re like hey, you’re a good rep. Let’s have you be the team leader, the manager, that would be something where I think the other SDRs would be like, I don’t know this person. They’re not – what are they going to do for me versus what I was able to do – and again, this is because I found my passion in it. I started hitting my numbers; I was doing well. I realized there was places that we could improve, so I started again, try to be proactive and change things and add something here. Then hey, this is working, so I share that with the other people and help them as much as I could. Then I found oh, wow, it feels so much better to have other people hit their numbers that you can help than just hitting your numbers on your own.

As competitive as I would say that I am and as much as I like to succeed, hitting my numbers is cool but it’s so much better to help other people hit theirs. Based on just doing that for I think a few months and then starting to be like cool, hey, I want to be involved in the interview process. I want to interview people. Cool, I want to help hire people. Oh, there’s a new hire. I want to help train them and onboard them – all before you become the team lead or the manager. I think it just, again, paints that big picture. When that time does come that you move into that role, rather than the other people that’ve been your colleagues being like, I’m not going to take direction from you, it’s like hmm, that makes sense. I get it. it’s not something that I have any problems with. They’ve been doing this already for a few months or whatever the time frame is. You’re making it a no-brainer for the managers above you and directors and CEO, but the people that are there with you are like yeah, this person is putting in the extra work and they’re being helpful, so it’s not a big surprise.

Then again, at the end of the day, if they don’t want to buy into that, that’s almost on them. Hey, I’m here to help everybody. I’m on your team. I want to make sure you’re doing better. If they’re like well, you used to be my colleague and now you’re my manager, okay. I’m still the same person. I’m still here to try to help you. It’s just I have a different title. That’s it. Obviously, it can totally backfire. I think there are the people out there who get that role and they immediately start barking orders at people. Hopefully no one does that, but I think it’s just the way you approach it. Again, doing the job before you have it, you’re building validation and legitimacy for everyone around you, above you, next to you. It’s a very interesting topic, for sure, because it can be done very poorly. It can be done very well. At the end of the day, it’s going to continue to happen and people are hopefully excited for you and understand why that decision was made.

Jan: That’s great. You have to tell me when you have a hard stop, right? I don’t want to –

Matthew: Yeah, I have five or six more minutes, so you’re good.

Jan: Then we have to run. We got the peer question. We got the recruit.

Matthew: Yeah, that’s a great question. I think there’s a lot of really, really good resources out there. At the same time, it’s one of those things where I think the more simple you make it, the more successful you’re going to be. If you try to make it really complicated, there are a lot of pieces in there and a lot of gears that could possibly break or something goes wrong. The more simple it is, probably the better off you are.

How do you scale? Make sure your hiring is down. Again, you can be much pickier in the early days when you’re not trying to hit X by X date. You still need to have a very specific process that is repreatable. It’s scalable. It’s not something that’s going to take too many resources or too much of your time. Get that down. Cool, I know how to hire people. We’re going to be extra picky right now, but we have something that – say we need to crank this up and start hiring a specific number. We can do it with our current process.

Next, make sure you have your workflow down and it’s very efficient. Everyone that’s on board can pick it up quickly, which I’m going to also tie in with your onboarding. Make sure your onboarding is super tight. The other thing about onboarding, though: that’s something that’s always living and breathing and need to be updated constantly, whether back to, again, just pivoting and changing all the time as a start-up – things change all the time. You got to make sure your onboarding material is up-to-date. As tight as that can be and the more simple – the more complex and confusing you make things, that’s not scalable, and that’s not something you want to have other new hires to experience, so make sure that’s super tight.

Then you have, again, a workflow or a process that is repeatable and it’s not something that you need a rocket scientist to figure out. I used to make the joke – it sounds really messed up, maybe, but I used to always say when people – I’d tell everyone it’s going to take some time to learn the workflow, to learn our tech stack, learn the space, but at the same time, get a little better each and every day. That’s all that really matters when you’re onboarding. I would say the job, once you have it down, it’s not super difficult. I was like, my 10-year-old niece I could probably get her to figure out how to do the job. Other than cold calling someone and being like, are you a 10-year-old little girl, I think she could book some meetings. I would say just keep it as simple as possible and straightforward as possible so that a 10-year-old can come in and be like okay, I can do this job. Make it very, very simple and not some bizarre science equation every day.

Then once that’s done, make sure you have obviously the resources to hit their numbers. The reason I say that is if you aren’t paying attention to what the quota is, or the goal, or whatever it is you want to call it, and how many – their target addressable market and what accounts they’re working on and all that, if it’s not an attainable goal, it’s going to be a total massive scale. You’re only going to get bigger and it’s only going to get more difficult for people. If people aren’t hitting their numbers and things aren’t happening, I think that’s just an immediate spiral down of not just we’re not hitting our numbers but the morale’s going to be trash until you need – when you’re looking at scaling something, you need to make sure it’s something where the morale’s going to be high. People are happy to be there; people are hitting their numbers They’re celebrating; they’re having a good time. If that’s not there, it’s going to crash.

To wrap it up, get hiring down. Get the onboarding down. Make sure that the process is repeatable and simple. Then make sure that your numbers all add up to the bigger picture to make sense. That way, people are succeeding in their role and having fun while doing it. Then the cycle can repeat because they’re going to tell their friends; they’re going to tell their people. They’re going to come in, and apply, and hopefully be great SDRs.

Jan: That’s perfect. I’m so happy this is recorded so I can play it and just – I could not have written down all of that, so that’s brilliant. Do we have time for one last question or do you have to run?

Matthew: Yes, no, let’s do one last question and then I’m going to go back to getting my bachelor’s degree in finance, which is what I feel like I’m doing right now.

Jan: In finance, though, oh, no. This has been fantastic for me. The last question that I spoke to Ashley about is for you, One of the key pillars is creating the culture of help, right? We’re here to help out each other. Why do you think that is so important, and how do you create that within the team because it’s very competitive?

Matthew: Yeah, I love that. I think the way that I – I know that in the past, there was always that conversation about sales, super competitive It’s like oh, salespeople are self-centered and they only care about their goals and things like that. At the same time, sales is competitive, for sure, the same way sports are. We’re a team, and so if you’re just caring about yourself, your team is probably going to lose. If your team cares about each other and is helping each other, the team is going to win. A team is what matters. We’d always say if you hit your quota every month but the team’s quota is never reached and the company’s numbers aren’t reached, you’re losing. It’s the same thing as in basketball. If you score 60 points but your team loses, you still lost. I don’t really care how well you did as an individual. If you score 60 points and the team crushes the other team and it wins, amazing. That’s awesome. It’s a team sport. When there’s collaboration and trust and you care about each other, I think you’re going to do much better in general just in life. If I trust you, we’re immediately going to work better together. If we work better together, we’re probably going to do better as individuals and as a team.

The more collaborative that things are and the more people are helping each other, I think it’s just also again creates that avalanche of everyone saying well, this is how you do well in this role is you help each other and you’re collaborative and you share what’s working, what’s not. Again, it’s because of – back to the start-up world, or just anything in general, if you’re helping each other, the team is going to be doing better. If the team’s doing better, especially in sales, the company’s going to be doing better. It’s the rising tide lifts all ships. Do you want to be a good A player on a D team and you’re not helping anyone and you’re not sharing what’s working and stuff? That’s not really going to get you anywhere.

What’s going to get you somewhere, even if you’re an average player on a really good team, is then other people are going to take notice of you. You’re going to be seen whether it’s for a new job opportunity or you’re going to be part of a really good company that’s crushing it. I think as people understand the big picture of this is a team sport and the more collaborative we are, we’re going to win together, it just helps every single person. What we’d always say is we want people who are absolute team players. If you’re crushing it on your own, of course, that’s fantastic. If you’re hiding all your secrets, and you’re not sharing things, and you’re not easy to work with and you’re a jerk or something, we don’t need that. I don’t care how good you are. You could be hitting your quota every single month over and over but if no one wants to work with you and you’re not helping out, you’re actually hurting the team. I think it goes back into the morale and just culture in general. We’re working 40-plus, 50, 60 hours a week, whatever, and humans are working a good chunk of their life. If you’re not enjoying the people that you’re working with or enjoying your job, that’s awful. That’s a terrible place to be. You’re going to be putting in so much time and energy and your emotions, so be somewhere you really want to be and where you’re excited.

Again, if it’s a team, fun, collaborative environment, hopefully, that makes you feel a little bit more like you belong there and want to be there versus everyone doing their own thing and no one’s helpful with one another. I think it’s absolutely crucial to have collaboration and have it looked at as we’re all here trying to get X company where it needs to go, so anything we can do to help one another is critical to the success there.

Jan: Mic drop. I’m just thinking poor Kyle. He has to say something smarter than you.

Matthew: Dude, Kyle’s a genius. I love Kyle. He’s going to come in and basically what I sounded like in eighth grade and he’ll put it into a college-level crash course or something. I learned so much from him, for sure, and I know you took all the email – you dressed it up. There was bits and pieces of all the people all over LinkedIn. They all got it down, and I’m really excited to listen to what they have to say. Also, once you have a conversation with him and hopefully I can connect you with other people, this will be a really cool spot to come and learn a bunch of knowledge. It’s another great piece of content.

Jan: Yeah, so definitely, Matt, what I’ve been thinking about – I don’t know. We have to see where it goes. The most important thing that you do, speed to innovation. Speed matters more than thinking about it, so I just keep on doing it and see where it goes. That’s the fun thing. If you are ever speaking to one other team this morning from Foto, the company that I recommended Chili Piper to get in, you could do the – there’s no content for outbound team leads, nothing, especially [0:26:10], blank space. We are thinking about maybe writing a blog together or something and see where it goes. If you’re up for that – I know you’re super busy, you can call it the outbound pross or whatever and you could do that and bring your people in. We’ll see. I’ll keep you in the loop next week.

Matthew: Please do, yeah.

Jan: Actually next week, I’m one week on vacation. I take one week off.

Matthew: Oh, yeah, get your vacation.

Jan: The week after, I would love to speak to you.

Matthew: Yeah, that’ll probably work out better for me because I’ll be deep in this onboarding stuff this week and next week as well. Just let me know when you’re back and happy to hop on with you whenever you’re on. Appreciate you reaching out and getting this set up and excited for the future.

Jan: You’re a long-time on my list but I needed to build up a good reputation before I asked you.

Matthew: No, you don’t. You have the greatest –

Jan: Like [Akaylee], I have Lauren from [0:27:19], Ashlay, Kyle, and then we’ll see.

Matthew: Perfect. I’ll look around. Let me know if there’s anyone that I can introduce you to if possible and if someone comes to mind on my side, I’ll shoot them over to you.

Jan: Thank you. That is what I always ask who would be interested to speak. You follow great people. Let me know. It’s just fantastic to speak to interesting people.

Matthew: Absolutely, yeah, I’ll put my hat on and start thinking about it. Again, if you notice anyone, reach out, let me know, and I’ll get you set up with them.

Jan: Thanks, Matt. Alright, I’ll let you go to finance. It’s the best call I had so far and honestly, no, I had another interview and it was like, meh. It was hard to focus. You have those and it’s still great that they speak about their stuff. They still [0:28:14] great but I was just like, yeah.

Matthew: Absolutely. Hopefully someone finds it helpful.

Jan: Definitely. We get everything from Upwork, so it’s 24 hours is the production time. Just need to translate it and this will end up in – we have a lot of snippets, and I will send them to you and you can use them as well if you want, of course.

Matthew: Love it. Of course, yeah.

Jan: You just get the content and can do whatever you want with it.

Matthew: Perfect Appreciate it. thank you. I’ll chat with you. Enjoy your week off and stay in touch, as always.

Jan: You, too, man. Thank you, Matt. Bye.

Matthew: Thank you. Bye.

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