Sales prospecting is tough: Matthew Roberts on how to cultivate the winning traits

Sales prospecting today is a tough job. You need to connect more, convince more, and ultimately, sell more.  

Join Matthew Roberts, who leads on sales development at Mosaic Tech, as he reveales his holy grail for winning as an SDR.  

Hint hint: It has a lot to do with grit, coachability and creativity.


Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Hi, everyone. Welcome to another episode of “On the Flip Side” with Wingman. I'm Kushal. And today's episode is going to be all about sales development, how SDRs can level up and life beyond sales. And that's why I'm so excited to introduce our guest for today, I'm joined by someone who's made a career out of sales development, worked at some top notch sales, tech companies and currently leads on sales development at Mosaic Tech. Matt, welcome to the show. Excited to have you here on the show.

Matthew Roberts: Thank you for having me, Kushal. I'm really excited to be chatting with everyone as well. 

Kushal: So just to start off, I'd love to understand from you how has sales development really changed sort of evolved over the past few years, and especially given how the world scenario has been in the past one or two years? 

Matthew Roberts: Yeah. So I think, you know, high level like how's the change of last few years, when I first started my time in sales development with my case, which was a company that used to be on by AppFolio, they recently were actually just sold to another company, but it was very much heavy on like, you know, the webinar leads, the on inbound demo requests. And we always talked about doing a lot of the outbound type work with, you know, cold calling and writing cold email scripts. And we weren't really allowed to do that. So it was just tons of webinar follow up, tons of HTML, SQL and on lead requests, things like that. And so that's sort of in my head, you know, what I thought of as like the SDR role, I did that for a few months or a little under a year and then moved over to the account executive role. By the time that I came back to sales development, it had been four years or so. So a lot had changed, for sure. And I started Chili Piper as one of their three SDRS at the time, and it was the exact opposite. And the reason I wanted to go to Chili Piper was they really took a lot of that manual work out of that role that I had done, you know, three or four years earlier, which was following up on these inbound leads, and, you know, people that are showing interest from your demo request page, and it was strictly outbound. So it was exactly what I had, you know, thought of a sales development role in the past and was really excited about that opportunity. 

And so just, you know, right then and there, I think I got to notice many changes. And again, I had a big kind of break in between, there's about three or four years where I wasn't involved in tech sales specifically. And so during that time, another thing that was very different was like LinkedIn, and content and all that around sales development and specifically. I was really fortunate when I joined Chili Piper. Michael Tusa was there, who was you know, maybe you call a thought leader on LinkedIn, and had a lot of experience and learnings and teachings and experience that they could share with us. And because of that, I think I was able to sort of like fast track those last few years that I was in sales development, and catch up on you know, what was going on, whether it was books, to be read webinars to watch, people to follow on LinkedIn, again, there was just so much more content around like sales development, and how to have a cold call and how to prospect smarter and build lists better and faster, and be more efficient with your time exactly. Yeah, now totally. 

And based on that, again, like I was able to add just flourish from Michael's teachings, and from everything else that was out there. And you can really be a sponge, you know, and just absorb everything that's out there and put it into practice, which is really fun. I'd say like, to me that was like, the biggest thing that I saw change or the last few years is just the amount of stuff that was there to help self-development. And I think a lot of people you know, in the past, you used to just stay internal, in your organization to get what you need to know to do the role nowadays, that's not true. I think that even the best ones are the people who are out there looking for best practices everywhere, whether it's, you know, outside their industry, even you can take a lot of things and kind of apply it to your industry, but there's just a ton of content. It's like just the number one thing as far as recently, you know, obviously COVID changed a lot of the sales world I can tie it sort of back into Chili Piper again, I joined Chili Piper, which is a fully remote company before COVID. Again, tying it all the way back to my case before that we used to always you know, go to lunch and talk about man, why did I have to go back to work I already did everything you need to do we followed up with all your leads, you know, called those people six times they hate you, they don't want to like pick up or what do I have to go back for like four hours for and so when I had the opportunity to work remotely, I saw how much more efficient you could be with your time and really plan your day, the way that it kind of works best for you. Like for me specifically, I was much more of a night owl, I always had been and so I would do a lot of my prospecting like late at night and wake up in the morning you know, respond to emails, make calls in the middle of the day, I sort of had free time where I could go to the grocery store, I could go grab like a long lunch with somebody because I knew that I was going to come back later and have that like prospecting so I think it really allowed me to like own my day and sort of have you know time management skills for sure, but like something that works a little bit better. 

For me, I felt more productive. And so I was really excited at the opportunity that I was able to work remotely in a sales role. I know a lot of people also said like sales is one of the things that you couldn't really do remotely because you have to have everyone together. And no doubt, it does help to like hear people talk and talk tracks and you know, swing around, and ask someone a question when you're on a call or write an email. But I still think again, like if you're a motivated person who is excited about, you know, just opportunities in general, like, and you’re going to be okay. And it really allows you to kind of control that day. And so I saw, you know, firsthand how well it could work as a remote sales team or organization. 

And then, you know, COVID comes along, the whole world changes. And I think a lot of other companies saw that, like, yeah, you can still be productive in a remote environment as a sales team as well. So how has it changed? I think it's made people much more collaborative and communicative, I think you have to, because you're not right there next to each other. So when something's working, you're really kind of, you know, siloed, if you're not responding to slack, or calling people up on Zoom, or chatting with them. So I think, it's made people share a lot more, which again, is more collaborative, and a better teamwork sort of environment. And again, Excel is also one of those very easy things to kind of pigeonhole into. Like, it's all just about individual, you know, numbers, and no one really helps each other. But I think COVID has kind of changed out a little bit more. So just some of the few things I've noticed and I feel like I've been rambling.

Kushal: It's a good thing. It sounds like technology is probably, you know, you're probably a fan of technology, right, because you work with tech companies. And because like you said, sales has become so much online today. What is maybe your favorite sales tech stack, you know, when your targets for communicating externally or internally?

Matthew Roberts: Yeah. So, again, I think I've been really fortunate like both… that the most recent organizations I've been with, they've had a very strong tech stack. And so you know, obviously some sort of CRM, I'm pretty good with Salesforce, because I've used it for long enough, but I know like, you know, there's plenty of CRMs out there that are great. And then the sales engagement tools, that's also something that's completely different from when I was first starting, in my case, if we didn't have anything, we send things out of Gmail, have a lot of templates that you shoot over. So like having, you know, a Salesloft, or an Outreach is like a total game changer, for sure, just again, allows you to really track everything so much easier. Efficiency is kind of like the name of the game when you're doing sales. And this is like everything that you could need, and more. 

So you can really like nerd out and dive as deep as you want to into making it's automation or looking at your reporting just to see how like certain you know, emails or are working in what's successful, what's not. I think a lot of sales development is also about like testing things out. And very similar to like marketing or your you should always be like AB testing, making sure you're doing the best possible work that you can see if there's some sort of sales engagement tool. I think another really useful one obviously, is thing you mentioned, like communication tools, having slack and zoom, and I'm one of those people that like grew up, we just talked about my phone being gone. So this is sort of a pain, but I was always texting. So like texting aim, if people remember like the aim chat. And so Slack for me, like I'm living on Slack constantly, whether it's just like chatting with someone about their weekend or, you know, purely work stuff. So Slack for me is like crucial. 

Zoom is obviously great, because it gives a little bit of that human element but at the same time and zoom fatigue is super real. I've had you know, the weeks in a month where you're on Zoom like six, seven hours every single day. And the last thing you want is zoom but still has its time in place a few other tools like ZoomInfo, Lead IQ Merge, Testing Apollo right now Solutia a lot of this stuff, again, kind of going back to like our founding and working in those cold leads, like it would be probably impossible to be successful. And again, like optimize your day to day if you didn't have those sorts of tools and then to be honest, like you know, your product and, and the gongs and the things that kind of do kind of pull you back again to that sales floor. Because to the point that we talked about, like I think the biggest thing that you miss outside of just like human connection by being in an office, is that like sales floor hearing what like people are saying, I remember, you know, some of the best things that that we said at my case, were just things that you'd hear someone else say over and over and over. And you could get that down, like, oh, wow, that works really well. And you could sort of like tell based off of their sort of cadence in their conversations, like when they're going to pitch or when they're going to close or when they're going to do something just because they had that like repetition. And so the tools that allow that to happen again. So in a remote environment, those are key.

Kushal: So I guess, technology, like you said is really key to how sales development happens. And you know, it's an important part of the picture. But beyond just the tools, right, what do you think are really the fundamental skills that someone needs to master really in order to create and sales development? 

Matthew Roberts: Yeah, I hear your question. We used to do like a three question video actually Piper about like, you know, what makes a successful SDR and you'd hear all sorts of things, but the ones that sort of always stick to me and what I would agree with and they're pretty… the first one being like the most basic of grit. And I always say like it. It's brought up all the time because it's true, whether you want to call it like persistence and greater tenacity like this SDR role specifically, you're not going to be very successful. If you're not somebody who's just gonna, like, you know, go, go, go, go, there's a lot of activity that you need to do. There's a lot of rejection of course. And so the people who are just gonna push through it and keep going, like they're going to be more successful at the end of the day, by far absolutely, right. Like, it's anything that you're doing a lot of people who want just kind of give up when things get tough. And then there's other people that say, like, whatever it is what it is, and I'm gonna, you know, just kind of go with the flow and keep going. 

Kushal: So people give up, and then there's SDRs.

Matthew Roberts: Exactly, maybe that's been like, the other part being like, you talk about, you know, sequences or cadences and, and it's not just emails, it's not just phone calls, it's not just LinkedIn, it's a mix of all three. And the persistence, part of that being like, you can't just hone in and hope that one is going to overpower for the others, because you're trying to find like, what channel that person communicates on and, you know, people are different. And so some people are, like me, like, I'm not going to pick up a ton of cold calls. But if it's a good, you know, email or LinkedIn message, I'll respond. Whereas there's people on the opposite side of the spectrum that immediately delete any email, they don't know, they're not connecting with the person that they'd never heard their name, but they get a random phone call, and they'll pick it up. So you're not doing all three of these, you know, like multithread or you know, even hitting people up on Twitter or sending them some sort of message, like, in the mail, you just need to find where they communicate. And so doing that, like persistently, like, that's also, you know, crucial to being successful. 

The other one, that's also, you know, talked about a lot, a lot of times the SDR role is like pretty green, and you get young people who are new to the space. So like, they have to be, you know, curious, and they have to take feedback well, and be coachable. That's the only way they're gonna get better. And if they're, you know, someone who's very stubborn, and just trying to do it their way like, that's not gonna work out very well, at the end of the day. So, yeah, whether they are Constant Learner, it's also extremely important. And the last one that I'd say now, and this goes into, like, what we've noticed, changing, and again, that goes into, like the content stuff, and being like creative, because you're not only reaching out a lot, and dealing with a lot of rejection, but you're also trying to just break through the noise. And there's a lot of noise out there, and people are getting blasted with a lot of messaging. And so if you're someone who's sort of creative or thinks outside the box, or has fun with it, like, I think you're always gonna do a little bit better. So I guess I'd tie it together, I'd say, you know, like grit, coachability, and creativity, I'd say those are the three that come to mind today.

Kushal: Got it. The Holy Grail. Nice. I've also heard talk of how SDRs are actually more suited to sit within marketing than in sales lately. I'm wondering, what is your take on this?

Matthew Roberts: So that's a great question as well, I've actually done multiple sides, multiple times. So I've reported to marketing two or three times, reported to sales two or three times. I don't feel strongly one way or the other. I think it's all dependent on the organization, the way it's being run, what the actual focus of the SDR or is whether it's, you know, purely just pipeline, if it's a mix of pipeline and brand building, like, I don't know, there's a lot of different things I think you can take with the role. I personally, like I said, just depends on what the leadership team wants to do. And if it's, you know, run well, it's gonna be run well, but I also do think, you know, I think there's more on the sales side. But yeah, I'm completely in the middle, I'm lukewarm on taking one side or the other.

Kushal: Got it. What do you think things sometimes break ss someone who kind of works right in the middle, right, between marketing sales somewhere there. What do you think is the thing that really breaks the most between marketing and sales and all these customers?

Matthew Roberts: So what's the question again?

Kushal: So what do you think really breaks? Like, you know, is where do things go wrong for instance, in so many cases, between marketing and sales, what is that friction point?

Matthew Roberts: I'd say, again, it always ties back to communication. I've seen a lot of marketing sales teams work really well together. And those are the ones that make that like overly communicated regularly met, collaboration was high. And you sort of see like, the whole big picture, again, it's not the like us versus them, or, you know, like, reporting metrics and saying, like, well, marketing is doing this and sales is doing that someone has to pick it up and, and kind of battling them together, but instead pulling everyone together and saying, you know, we're all rowing in the same direction, and sort of building that like higher, you know, higher level reasoning. So communication is key there.

Kushal: I guess a lot of times would actually then come down to the company culture, right. How's the company sort of set that in terms of responsibilities or you know, what, how everyone's supposed to be working together?

Matthew Roberts: Yes, absolutely. I think that's really key. Having just like, a common theme across the board of collaboration or teamwork is going to make like every department work better for sure. But the point of your question, like I've seen multiple times where they're battling, right, and it's always head to head and the department heads are not getting I think that's the other thing is if you can see the like leadership above getting along really well. I think it just kind of trickles down to the rest of the team. So if like the sales leader and the marketing leader don't connect and they're not, you know, communicative, and they are sort of feeding into this like us versus them mentality, then it's just gonna be a mess throughout. But if they're both, you know, close, and they're working closely together and sharing kind of what's on each other's plates constantly and, and running campaigns together, I think, you know, for instance, we had like a marketing sales sync in like few hours, super helpful. It's you know, what's marketing up to what sales up to? How can sales help marketing? How can marketing help sales, these are the kinds of things that, you know, the more conversations you have done again, or everyone rowing in the same direction, rather than us just spinning in circles, like, that's how you build like a good culture and, you know, cohesive environment for the two teams to start to exist and work with each other.

Kushal: So just to kind of switch tracks a bit and actually rewind a bit as well. You've studied film and media as well. So how did the switch sort of go and hasn't really been anything that you've been able to carry on into your work, you talked about creativity earlier.

Matthew Roberts: Yeah. So that's a really good point. So that was, I remember, I went to school, I was gonna study history, I saw everyone lining up for a film and media like course, and said, like, I love movies, and I always loved sort of like screenwriting and, you know, writing creating stories. So I hopped in. And then that's sort of just where I led. And I went, actually, to LA for about a year after work in the film industry and loved it loved all the people who didn't really like LA a whole lot and didn't like sitting in traffic, and just, you know, not my realm. And so, I came back to where I went to school at UC Santa Barbara, and all my friends had just graduated, and they were going into tech roles. And there's a few cool startups in the area. And, you know, I came back for a little bit and was just pouring wine because I had, you know, serving and bartending experience and sort of like, what they what they are up to, and wanting something different. And so they got me an interview, and I, you know, kind of all fell in place in there. 

So, I'd say to how does like the film and media sort of work still in this world? Exactly. Because you said I think creativity, like thinking outside the box messaging. I mean, there are a lot of the courses that I took were like theory based, so it wasn't as much, you know, it wasn't like UCLA or USC or making movies the whole time. It was a lot of you're watching things and digesting them, whether it's like advertisement. So there's a lot on like the media side, I think that helped just, you know, from the sales perspective, as well, as you know, writing like I was writing a ton, how is the role changed a lot, like, you know, LinkedIn and cold emails. Cold calling still, obviously is very large. But there's a lot of like, written communication and stuff these days, and also videos as well, right. And that's how you have like, your video cards and your looms. And so I think just kind of holistically, it was a lot of just theory and thinking and how do you capture people's attention? How can you stand out? How can you do different things? And so I'd say that ties into it a little bit, until that same point, like when I see someone who has an English degree, or some sort of thing, or I know, they've been writing a lot, like, I'm always a little bit more excited, because I'm like, oh, they're probably going to write killer, like cold emails, or at least I, you know, be able to form impactful sentences and paragraphs and know how to, like, tell a story.

Kushal: Got it. Yeah, I guess, sales is ultimately about telling the right story, right. And kind of hooking people then I guess, kind of staying, you know, updated on what's happening in terms of film and culture is probably one of the best ways to stay creative as well. And I think that's true for marketing, content, sales really, I think, for anyone who wants to stay interesting, and know how to grab attention at the end of movie. So Matthew, you’re also the founder of Pear, could you tell us a little bit more about this?

Matthew Roberts: Yeah. So that's a project that my friend and I started. We went traveling together, we went to Europe for about three months, came back wanted to create something, again, the creativity part, whether it was like as a book or a movie or something, and we went to a good friend's graduation, college graduation. And it was a little bit later for them to graduate. And my friend that I was traveling with his mom brought over a few like little positive prompts for all of us respond to because she used to do them, but with my friend when he was a child, and we pass them around, and there was, you know, age range from, like, 14 to 70 years old, and everyone got a little card, and they said things like, you know, something that I appreciate about the person on my right is blank, like one thing that makes this moment priceless, is playing something I'm looking forward to in, you know, the next month or so is like, we just sort of had this really, really powerful conversation. And a lot of people opened up and again, it was just some of us are strangers, some of us were very different age range, but everyone like, kind of got together and shared this really cool moment. So we looked at each other, like, well, maybe this is what we should be creating, because we hadn't met so many amazing people while traveling. And you know, sometimes you just need them for an hour or two. And you feel like you get their life story. And there's like really cool moments ever shared. So we decided to make a set of cards, essentially, we thought it would be like a, like a, you know, a family game or something for people to have like with their wine or something. And so it stands for positive engagement and response. And the whole thing is like, you know, you're just learning about each other and you're having conversations and they're all positive hopefully, if not, like that's fine too, but you're just sharing real moments. 

And so then when you did a Kickstarter, we raised $20,000 felt, you know, 5000 cents and then again, we thought I'd just be a fun little game and a lot of our teacher friends and therapists and things like that reached out and said, like, wow, I'd love to have this for my classroom or, you know, to, to use this with clients. And also a lot of like family members want to use it their children because they're sick of, you know, their kids giving the one word answers like how's your day, that's it. So we started selling sets there. And then we got really involved in like the mental health community, which is great and got to do some really cool things like go to prison and do it with inmates. He did a mental health awareness game with the WNBA, the LA sparks went down for that. And, yeah, had a lot of really fun opportunities that were presented. And then we got very involved in like the classroom, and then and then COVID hit and so then that kind of backed out. And now it's something that sadly has been like on the side burner for a little too long. But there's still you know, sets to be sold. And we still have them around the house. And we'll see if it comes back up. 

Kushal: Have you ever tried, you know, these cards with Salesforce with sales teams?

Matthew Roberts: I've done it for like team building stuff before because exactly, that's the whole point is just like you break down your barriers, and you just get to know each other. And to your like, point there. I think people work well together better when they understand each other, you don't really know that person might not be as collaborative as if you feel like you do know them, because you shared some sort of experience together. So yeah, I've done it for team building before, I used to also ask a few of the questions in there during interviews that were just more like personal just to kind of see like, what their response would be. Sometimes people would, you know, really open up and sometimes is very just kind of canned. Like that was fun. Outside of that. I haven't kind of weed that into the sales world that much.

Kushal: Got it. I think, Matthew, this is probably one of my last questions for you. And, yeah, it kind of makes sense, given what you've just shared, what is really the number one impact that you want to drive in the world? 

Matthew Roberts: I'll say, yeah, you tie that to pair for sure. And it was just, you know, to create a more positive communicative environment for everybody, whether that's in there, you know, work life or their personal life, but just, you know, letting everyone know that there's a lot of support out there for people might want to create things. And we talked about all the time, especially when people are starting up companies is it's not many people out there are really trying to be helpful. And I think a lot of people just don't think to ask, but there's a lot of people out there that want to help. So, I guess, just letting everyone know that and also being one of those people that hopefully can help others advance in their personal or career and say, you know, most exciting thing for me and what I love the most about being in sales development, like leadership is like seeing people you know, gradually get better each and every day and then move on to the next thing like that's my, like, I'd rather see someone get promoted and do really well then, you know, sort of anything else in this role. Like that's what really gets me going.

Kushal: Got it. Thanks so much, Matt. I think this has been an amazing conversation. I know we could go on and on. But yeah, I guess we'll cap it for now. Thanks so much for taking the time for this. 

Matthew Roberts: Yeah, absolutely, Kushal. I appreciate you getting this on the calendar and I'm really excited to see how it ends up.

Sales prospecting is tough: Matthew on how to cultivate the winning traits

Sales prospecting is tough | On The Flip Side Teasers

Sales prospecting today is a tough job. You need to connect more, convince more, and ultimately, sell more.  

Join Matthew Roberts, who leads on sales development at Mosaic Tech, as he reveales his holy grail for winning as an SDR.  

Hint hint: It has a lot to do with grit, coachability and creativity.


Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Hi, everyone. Welcome to another episode of “On the Flip Side” with Wingman. I'm Kushal. And today's episode is going to be all about sales development, how SDRs can level up and life beyond sales. And that's why I'm so excited to introduce our guest for today, I'm joined by someone who's made a career out of sales development, worked at some top notch sales, tech companies and currently leads on sales development at Mosaic Tech. Matt, welcome to the show. Excited to have you here on the show.

Matthew Roberts: Thank you for having me, Kushal. I'm really excited to be chatting with everyone as well. 

Kushal: So just to start off, I'd love to understand from you how has sales development really changed sort of evolved over the past few years, and especially given how the world scenario has been in the past one or two years? 

Matthew Roberts: Yeah. So I think, you know, high level like how's the change of last few years, when I first started my time in sales development with my case, which was a company that used to be on by AppFolio, they recently were actually just sold to another company, but it was very much heavy on like, you know, the webinar leads, the on inbound demo requests. And we always talked about doing a lot of the outbound type work with, you know, cold calling and writing cold email scripts. And we weren't really allowed to do that. So it was just tons of webinar follow up, tons of HTML, SQL and on lead requests, things like that. And so that's sort of in my head, you know, what I thought of as like the SDR role, I did that for a few months or a little under a year and then moved over to the account executive role. By the time that I came back to sales development, it had been four years or so. So a lot had changed, for sure. And I started Chili Piper as one of their three SDRS at the time, and it was the exact opposite. And the reason I wanted to go to Chili Piper was they really took a lot of that manual work out of that role that I had done, you know, three or four years earlier, which was following up on these inbound leads, and, you know, people that are showing interest from your demo request page, and it was strictly outbound. So it was exactly what I had, you know, thought of a sales development role in the past and was really excited about that opportunity. 

And so just, you know, right then and there, I think I got to notice many changes. And again, I had a big kind of break in between, there's about three or four years where I wasn't involved in tech sales specifically. And so during that time, another thing that was very different was like LinkedIn, and content and all that around sales development and specifically. I was really fortunate when I joined Chili Piper. Michael Tusa was there, who was you know, maybe you call a thought leader on LinkedIn, and had a lot of experience and learnings and teachings and experience that they could share with us. And because of that, I think I was able to sort of like fast track those last few years that I was in sales development, and catch up on you know, what was going on, whether it was books, to be read webinars to watch, people to follow on LinkedIn, again, there was just so much more content around like sales development, and how to have a cold call and how to prospect smarter and build lists better and faster, and be more efficient with your time exactly. Yeah, now totally. 

And based on that, again, like I was able to add just flourish from Michael's teachings, and from everything else that was out there. And you can really be a sponge, you know, and just absorb everything that's out there and put it into practice, which is really fun. I'd say like, to me that was like, the biggest thing that I saw change or the last few years is just the amount of stuff that was there to help self-development. And I think a lot of people you know, in the past, you used to just stay internal, in your organization to get what you need to know to do the role nowadays, that's not true. I think that even the best ones are the people who are out there looking for best practices everywhere, whether it's, you know, outside their industry, even you can take a lot of things and kind of apply it to your industry, but there's just a ton of content. It's like just the number one thing as far as recently, you know, obviously COVID changed a lot of the sales world I can tie it sort of back into Chili Piper again, I joined Chili Piper, which is a fully remote company before COVID. Again, tying it all the way back to my case before that we used to always you know, go to lunch and talk about man, why did I have to go back to work I already did everything you need to do we followed up with all your leads, you know, called those people six times they hate you, they don't want to like pick up or what do I have to go back for like four hours for and so when I had the opportunity to work remotely, I saw how much more efficient you could be with your time and really plan your day, the way that it kind of works best for you. Like for me specifically, I was much more of a night owl, I always had been and so I would do a lot of my prospecting like late at night and wake up in the morning you know, respond to emails, make calls in the middle of the day, I sort of had free time where I could go to the grocery store, I could go grab like a long lunch with somebody because I knew that I was going to come back later and have that like prospecting so I think it really allowed me to like own my day and sort of have you know time management skills for sure, but like something that works a little bit better. 

For me, I felt more productive. And so I was really excited at the opportunity that I was able to work remotely in a sales role. I know a lot of people also said like sales is one of the things that you couldn't really do remotely because you have to have everyone together. And no doubt, it does help to like hear people talk and talk tracks and you know, swing around, and ask someone a question when you're on a call or write an email. But I still think again, like if you're a motivated person who is excited about, you know, just opportunities in general, like, and you’re going to be okay. And it really allows you to kind of control that day. And so I saw, you know, firsthand how well it could work as a remote sales team or organization. 

And then, you know, COVID comes along, the whole world changes. And I think a lot of other companies saw that, like, yeah, you can still be productive in a remote environment as a sales team as well. So how has it changed? I think it's made people much more collaborative and communicative, I think you have to, because you're not right there next to each other. So when something's working, you're really kind of, you know, siloed, if you're not responding to slack, or calling people up on Zoom, or chatting with them. So I think, it's made people share a lot more, which again, is more collaborative, and a better teamwork sort of environment. And again, Excel is also one of those very easy things to kind of pigeonhole into. Like, it's all just about individual, you know, numbers, and no one really helps each other. But I think COVID has kind of changed out a little bit more. So just some of the few things I've noticed and I feel like I've been rambling.

Kushal: It's a good thing. It sounds like technology is probably, you know, you're probably a fan of technology, right, because you work with tech companies. And because like you said, sales has become so much online today. What is maybe your favorite sales tech stack, you know, when your targets for communicating externally or internally?

Matthew Roberts: Yeah. So, again, I think I've been really fortunate like both… that the most recent organizations I've been with, they've had a very strong tech stack. And so you know, obviously some sort of CRM, I'm pretty good with Salesforce, because I've used it for long enough, but I know like, you know, there's plenty of CRMs out there that are great. And then the sales engagement tools, that's also something that's completely different from when I was first starting, in my case, if we didn't have anything, we send things out of Gmail, have a lot of templates that you shoot over. So like having, you know, a Salesloft, or an Outreach is like a total game changer, for sure, just again, allows you to really track everything so much easier. Efficiency is kind of like the name of the game when you're doing sales. And this is like everything that you could need, and more. 

So you can really like nerd out and dive as deep as you want to into making it's automation or looking at your reporting just to see how like certain you know, emails or are working in what's successful, what's not. I think a lot of sales development is also about like testing things out. And very similar to like marketing or your you should always be like AB testing, making sure you're doing the best possible work that you can see if there's some sort of sales engagement tool. I think another really useful one obviously, is thing you mentioned, like communication tools, having slack and zoom, and I'm one of those people that like grew up, we just talked about my phone being gone. So this is sort of a pain, but I was always texting. So like texting aim, if people remember like the aim chat. And so Slack for me, like I'm living on Slack constantly, whether it's just like chatting with someone about their weekend or, you know, purely work stuff. So Slack for me is like crucial. 

Zoom is obviously great, because it gives a little bit of that human element but at the same time and zoom fatigue is super real. I've had you know, the weeks in a month where you're on Zoom like six, seven hours every single day. And the last thing you want is zoom but still has its time in place a few other tools like ZoomInfo, Lead IQ Merge, Testing Apollo right now Solutia a lot of this stuff, again, kind of going back to like our founding and working in those cold leads, like it would be probably impossible to be successful. And again, like optimize your day to day if you didn't have those sorts of tools and then to be honest, like you know, your product and, and the gongs and the things that kind of do kind of pull you back again to that sales floor. Because to the point that we talked about, like I think the biggest thing that you miss outside of just like human connection by being in an office, is that like sales floor hearing what like people are saying, I remember, you know, some of the best things that that we said at my case, were just things that you'd hear someone else say over and over and over. And you could get that down, like, oh, wow, that works really well. And you could sort of like tell based off of their sort of cadence in their conversations, like when they're going to pitch or when they're going to close or when they're going to do something just because they had that like repetition. And so the tools that allow that to happen again. So in a remote environment, those are key.

Kushal: So I guess, technology, like you said is really key to how sales development happens. And you know, it's an important part of the picture. But beyond just the tools, right, what do you think are really the fundamental skills that someone needs to master really in order to create and sales development? 

Matthew Roberts: Yeah, I hear your question. We used to do like a three question video actually Piper about like, you know, what makes a successful SDR and you'd hear all sorts of things, but the ones that sort of always stick to me and what I would agree with and they're pretty… the first one being like the most basic of grit. And I always say like it. It's brought up all the time because it's true, whether you want to call it like persistence and greater tenacity like this SDR role specifically, you're not going to be very successful. If you're not somebody who's just gonna, like, you know, go, go, go, go, there's a lot of activity that you need to do. There's a lot of rejection of course. And so the people who are just gonna push through it and keep going, like they're going to be more successful at the end of the day, by far absolutely, right. Like, it's anything that you're doing a lot of people who want just kind of give up when things get tough. And then there's other people that say, like, whatever it is what it is, and I'm gonna, you know, just kind of go with the flow and keep going. 

Kushal: So people give up, and then there's SDRs.

Matthew Roberts: Exactly, maybe that's been like, the other part being like, you talk about, you know, sequences or cadences and, and it's not just emails, it's not just phone calls, it's not just LinkedIn, it's a mix of all three. And the persistence, part of that being like, you can't just hone in and hope that one is going to overpower for the others, because you're trying to find like, what channel that person communicates on and, you know, people are different. And so some people are, like me, like, I'm not going to pick up a ton of cold calls. But if it's a good, you know, email or LinkedIn message, I'll respond. Whereas there's people on the opposite side of the spectrum that immediately delete any email, they don't know, they're not connecting with the person that they'd never heard their name, but they get a random phone call, and they'll pick it up. So you're not doing all three of these, you know, like multithread or you know, even hitting people up on Twitter or sending them some sort of message, like, in the mail, you just need to find where they communicate. And so doing that, like persistently, like, that's also, you know, crucial to being successful. 

The other one, that's also, you know, talked about a lot, a lot of times the SDR role is like pretty green, and you get young people who are new to the space. So like, they have to be, you know, curious, and they have to take feedback well, and be coachable. That's the only way they're gonna get better. And if they're, you know, someone who's very stubborn, and just trying to do it their way like, that's not gonna work out very well, at the end of the day. So, yeah, whether they are Constant Learner, it's also extremely important. And the last one that I'd say now, and this goes into, like, what we've noticed, changing, and again, that goes into, like the content stuff, and being like creative, because you're not only reaching out a lot, and dealing with a lot of rejection, but you're also trying to just break through the noise. And there's a lot of noise out there, and people are getting blasted with a lot of messaging. And so if you're someone who's sort of creative or thinks outside the box, or has fun with it, like, I think you're always gonna do a little bit better. So I guess I'd tie it together, I'd say, you know, like grit, coachability, and creativity, I'd say those are the three that come to mind today.

Kushal: Got it. The Holy Grail. Nice. I've also heard talk of how SDRs are actually more suited to sit within marketing than in sales lately. I'm wondering, what is your take on this?

Matthew Roberts: So that's a great question as well, I've actually done multiple sides, multiple times. So I've reported to marketing two or three times, reported to sales two or three times. I don't feel strongly one way or the other. I think it's all dependent on the organization, the way it's being run, what the actual focus of the SDR or is whether it's, you know, purely just pipeline, if it's a mix of pipeline and brand building, like, I don't know, there's a lot of different things I think you can take with the role. I personally, like I said, just depends on what the leadership team wants to do. And if it's, you know, run well, it's gonna be run well, but I also do think, you know, I think there's more on the sales side. But yeah, I'm completely in the middle, I'm lukewarm on taking one side or the other.

Kushal: Got it. What do you think things sometimes break ss someone who kind of works right in the middle, right, between marketing sales somewhere there. What do you think is the thing that really breaks the most between marketing and sales and all these customers?

Matthew Roberts: So what's the question again?

Kushal: So what do you think really breaks? Like, you know, is where do things go wrong for instance, in so many cases, between marketing and sales, what is that friction point?

Matthew Roberts: I'd say, again, it always ties back to communication. I've seen a lot of marketing sales teams work really well together. And those are the ones that make that like overly communicated regularly met, collaboration was high. And you sort of see like, the whole big picture, again, it's not the like us versus them, or, you know, like, reporting metrics and saying, like, well, marketing is doing this and sales is doing that someone has to pick it up and, and kind of battling them together, but instead pulling everyone together and saying, you know, we're all rowing in the same direction, and sort of building that like higher, you know, higher level reasoning. So communication is key there.

Kushal: I guess a lot of times would actually then come down to the company culture, right. How's the company sort of set that in terms of responsibilities or you know, what, how everyone's supposed to be working together?

Matthew Roberts: Yes, absolutely. I think that's really key. Having just like, a common theme across the board of collaboration or teamwork is going to make like every department work better for sure. But the point of your question, like I've seen multiple times where they're battling, right, and it's always head to head and the department heads are not getting I think that's the other thing is if you can see the like leadership above getting along really well. I think it just kind of trickles down to the rest of the team. So if like the sales leader and the marketing leader don't connect and they're not, you know, communicative, and they are sort of feeding into this like us versus them mentality, then it's just gonna be a mess throughout. But if they're both, you know, close, and they're working closely together and sharing kind of what's on each other's plates constantly and, and running campaigns together, I think, you know, for instance, we had like a marketing sales sync in like few hours, super helpful. It's you know, what's marketing up to what sales up to? How can sales help marketing? How can marketing help sales, these are the kinds of things that, you know, the more conversations you have done again, or everyone rowing in the same direction, rather than us just spinning in circles, like, that's how you build like a good culture and, you know, cohesive environment for the two teams to start to exist and work with each other.

Kushal: So just to kind of switch tracks a bit and actually rewind a bit as well. You've studied film and media as well. So how did the switch sort of go and hasn't really been anything that you've been able to carry on into your work, you talked about creativity earlier.

Matthew Roberts: Yeah. So that's a really good point. So that was, I remember, I went to school, I was gonna study history, I saw everyone lining up for a film and media like course, and said, like, I love movies, and I always loved sort of like screenwriting and, you know, writing creating stories. So I hopped in. And then that's sort of just where I led. And I went, actually, to LA for about a year after work in the film industry and loved it loved all the people who didn't really like LA a whole lot and didn't like sitting in traffic, and just, you know, not my realm. And so, I came back to where I went to school at UC Santa Barbara, and all my friends had just graduated, and they were going into tech roles. And there's a few cool startups in the area. And, you know, I came back for a little bit and was just pouring wine because I had, you know, serving and bartending experience and sort of like, what they what they are up to, and wanting something different. And so they got me an interview, and I, you know, kind of all fell in place in there. 

So, I'd say to how does like the film and media sort of work still in this world? Exactly. Because you said I think creativity, like thinking outside the box messaging. I mean, there are a lot of the courses that I took were like theory based, so it wasn't as much, you know, it wasn't like UCLA or USC or making movies the whole time. It was a lot of you're watching things and digesting them, whether it's like advertisement. So there's a lot on like the media side, I think that helped just, you know, from the sales perspective, as well, as you know, writing like I was writing a ton, how is the role changed a lot, like, you know, LinkedIn and cold emails. Cold calling still, obviously is very large. But there's a lot of like, written communication and stuff these days, and also videos as well, right. And that's how you have like, your video cards and your looms. And so I think just kind of holistically, it was a lot of just theory and thinking and how do you capture people's attention? How can you stand out? How can you do different things? And so I'd say that ties into it a little bit, until that same point, like when I see someone who has an English degree, or some sort of thing, or I know, they've been writing a lot, like, I'm always a little bit more excited, because I'm like, oh, they're probably going to write killer, like cold emails, or at least I, you know, be able to form impactful sentences and paragraphs and know how to, like, tell a story.

Kushal: Got it. Yeah, I guess, sales is ultimately about telling the right story, right. And kind of hooking people then I guess, kind of staying, you know, updated on what's happening in terms of film and culture is probably one of the best ways to stay creative as well. And I think that's true for marketing, content, sales really, I think, for anyone who wants to stay interesting, and know how to grab attention at the end of movie. So Matthew, you’re also the founder of Pear, could you tell us a little bit more about this?

Matthew Roberts: Yeah. So that's a project that my friend and I started. We went traveling together, we went to Europe for about three months, came back wanted to create something, again, the creativity part, whether it was like as a book or a movie or something, and we went to a good friend's graduation, college graduation. And it was a little bit later for them to graduate. And my friend that I was traveling with his mom brought over a few like little positive prompts for all of us respond to because she used to do them, but with my friend when he was a child, and we pass them around, and there was, you know, age range from, like, 14 to 70 years old, and everyone got a little card, and they said things like, you know, something that I appreciate about the person on my right is blank, like one thing that makes this moment priceless, is playing something I'm looking forward to in, you know, the next month or so is like, we just sort of had this really, really powerful conversation. And a lot of people opened up and again, it was just some of us are strangers, some of us were very different age range, but everyone like, kind of got together and shared this really cool moment. So we looked at each other, like, well, maybe this is what we should be creating, because we hadn't met so many amazing people while traveling. And you know, sometimes you just need them for an hour or two. And you feel like you get their life story. And there's like really cool moments ever shared. So we decided to make a set of cards, essentially, we thought it would be like a, like a, you know, a family game or something for people to have like with their wine or something. And so it stands for positive engagement and response. And the whole thing is like, you know, you're just learning about each other and you're having conversations and they're all positive hopefully, if not, like that's fine too, but you're just sharing real moments. 

And so then when you did a Kickstarter, we raised $20,000 felt, you know, 5000 cents and then again, we thought I'd just be a fun little game and a lot of our teacher friends and therapists and things like that reached out and said, like, wow, I'd love to have this for my classroom or, you know, to, to use this with clients. And also a lot of like family members want to use it their children because they're sick of, you know, their kids giving the one word answers like how's your day, that's it. So we started selling sets there. And then we got really involved in like the mental health community, which is great and got to do some really cool things like go to prison and do it with inmates. He did a mental health awareness game with the WNBA, the LA sparks went down for that. And, yeah, had a lot of really fun opportunities that were presented. And then we got very involved in like the classroom, and then and then COVID hit and so then that kind of backed out. And now it's something that sadly has been like on the side burner for a little too long. But there's still you know, sets to be sold. And we still have them around the house. And we'll see if it comes back up. 

Kushal: Have you ever tried, you know, these cards with Salesforce with sales teams?

Matthew Roberts: I've done it for like team building stuff before because exactly, that's the whole point is just like you break down your barriers, and you just get to know each other. And to your like, point there. I think people work well together better when they understand each other, you don't really know that person might not be as collaborative as if you feel like you do know them, because you shared some sort of experience together. So yeah, I've done it for team building before, I used to also ask a few of the questions in there during interviews that were just more like personal just to kind of see like, what their response would be. Sometimes people would, you know, really open up and sometimes is very just kind of canned. Like that was fun. Outside of that. I haven't kind of weed that into the sales world that much.

Kushal: Got it. I think, Matthew, this is probably one of my last questions for you. And, yeah, it kind of makes sense, given what you've just shared, what is really the number one impact that you want to drive in the world? 

Matthew Roberts: I'll say, yeah, you tie that to pair for sure. And it was just, you know, to create a more positive communicative environment for everybody, whether that's in there, you know, work life or their personal life, but just, you know, letting everyone know that there's a lot of support out there for people might want to create things. And we talked about all the time, especially when people are starting up companies is it's not many people out there are really trying to be helpful. And I think a lot of people just don't think to ask, but there's a lot of people out there that want to help. So, I guess, just letting everyone know that and also being one of those people that hopefully can help others advance in their personal or career and say, you know, most exciting thing for me and what I love the most about being in sales development, like leadership is like seeing people you know, gradually get better each and every day and then move on to the next thing like that's my, like, I'd rather see someone get promoted and do really well then, you know, sort of anything else in this role. Like that's what really gets me going.

Kushal: Got it. Thanks so much, Matt. I think this has been an amazing conversation. I know we could go on and on. But yeah, I guess we'll cap it for now. Thanks so much for taking the time for this. 

Matthew Roberts: Yeah, absolutely, Kushal. I appreciate you getting this on the calendar and I'm really excited to see how it ends up.

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