Episode 93: Rob Gonsalves – If You Want To Grow In Your Career, Say It!

Don’t wait for someone to offer — Ask! When it comes to elevating your career, Rob Gonsalves suggests taking the initiative, stepping up to the plate, and making your intentions known.

Now a Sales Manager at memoryBlue, Rob knows that gains happen incrementally. Learn new things, tailor your strategies, and set SMART (Specific. Measurable. Achievable. Relevant. Time-based.) goals.

In this episode of Tech Sales is for Hustlers, Rob shares the #1 skill needed to be a successful AE, the best ways to nurture a relationship with a high-maintenance client, and how to use tactical empathy to uncover pain and tee up the close.

Guest-At-A-Glance

💡 Name: Rob Gonsalves 

💡 What he does: Rob is a Sales Manager at memoryBlue.

💡 Company: memoryBlue

💡 Noteworthy: Rob has a degree in marketing from Assumption College. He worked as a solution specialist at Verizon, as a certified personal trainer at Healthworks Fitness Centers for women, and in 2019, joined memoryBlue. For the first five months, Rob was an SDR at memoryBlue, then became a delivery manager, and for the last seven months, he has been working as an account executive.

💡 Where to find Rob: LinkedIn | Website

Key Insights

⚡ Set smart goals and achieve them. Rob has been an athlete, and he has worked as a trainer. As he notes, many things he’s learned and adopted as a sportsman helped him to be a good salesperson; he connects his background in sports with entering sales. “Cross-country was a lot of fun, out of scholarship for that, but at the same time, I was competing in powerlifting; I was prepping for a bodybuilding physique show. Nobody’s asking me to do any of this stuff. You need to set goals with the timeframe that you need to do them. You need to work backward on what exactly you need to be doing to get there. If I’m comparing it to sales, you have an angle. For you, it might be the end of the month; it might be the end of the quarter. You want to work backward on what are the inputs and what are the actions that are going to help you be able to get where you want to go. And if you mess up, that’s on you. There’s nobody else who that’s gonna affect.”

⚡ Tactical empathy is crucial for an SDR. As a former SDR, Rob points out that it is very important to have a broader view. As he explains, you need to develop the ability to see things from every perspective, not just the one you currently have. “A question I would ask on some of my calls would be, ‘What’s the process if something does go wrong inside your current situation that you’re using?’ You want to put yourself in the shoes of the person that you’re selling to. When you’re able to do that, you’re going to have a much better understanding of why you’re asking these questions. So I think tactical empathy really helped out and that customized close, based on their situation.”

⚡ If you want to grow in your career, say it. So many people think they deserve a promotion to a leadership position and privately dream about it. However, they can come across as uninterested, and as a result, they lose out on opportunities. According to Rob, you have to be a little boring and make it clear that you want a position. “For anybody who does want to grow in their career, into their position, don’t wait for somebody to tell you, ‘Hey, now it’s your time to get a chance’ If you’re not the bug inside their ear from day one, they’re going to look at the person that was. So every single one-on-one that I had with Jeremy [leader, mentor], it was, ‘What exactly do I need to do to become a manager? What exactly do I need to do to lead a team?’ And it was just constant nagging, constant talking about what exactly I needed to develop to be ready for the position.”

Episode Highlights

The Transition from Retail and Personal Training to the SDR Role

“It’s not different; just the modalities are different. Verizon, there’s a phrase for their training called ‘earn the right.’ You need to earn the right to be able to pitch any product to people that you’re going after. The expectation whenever we are selling a phone was that 80% of them had to have insurance on it. We had to sell over $70 worth of accessory sales for each device. When our goals for new lines had to be added, I was used to balancing out five or six different KPIs for what I had to do. So discovery was the key there. When I was a personal trainer, understanding the why, understanding the values, or how somebody wanted to get to where they were going.

So it’s just learning how to take the consultative sale. It used to be maybe 40 minutes of working with somebody as a trainer or at a Verizon store to how can I compile this into a two to three-minute cold call. So, I had a massive skill gap at first, but I had some phenomenal mentors around.”

Rob in the Role of a DM

“That’s the hardest position, especially here [memoryBlue], because you’re not just a manager of SDRs. That job on its own is hard enough, but additionally, you’re an account manager. I don’t think delivery talks about that enough, as being the genuine skillset that you’re developing inside your time here. You’re learning how to coach; you’re learning how to interview. I think, over the past couple of years, I’ve probably done over 500 interviews with people, hired over 50, and had to let go of a few people.

On the account management side, you’re learning how to deal with clients; you’re learning how to deal with clients with extremely high expectations. We’re the best in the business. We all know that we’ve done such a good job. Because of that, our clients have massive expectations from any DM who’s listening over here. […]

You’re dealing with the expectations. You’re tempering expectations. You’re talking with clients about that. That’s probably what translates most into the account executive position I’m in now.”

It’s Important to Know Who You Are Hiring in Your Team

“I needed somebody who was going to work their butt off; do they have a past trajectory and history of being able to absolutely grind? It didn’t matter what they did before. I really loved waiters and waitresses. Jessica Simon was a nanny before she started over here, but she consistently had a great work ethic.

The second piece was coachable. I and Jeremy had a lot of conversations about the number of times that I had somebody redo the role-play inside the final interview because I just wanted to see exactly what they would implement from the coaching. 

If I had those two traits, I could teach anybody how to sell, and I could have an extremely successful team.”

Transcript: 

[00:00:00] Rob Gonsalves: So, for anybody listening that does want to grow inside their career, into their position, don’t wait for somebody to tell you, “Hey, now it’s your time to get a chance,” to leave it to you.

[00:00:10] If you’re not the bug inside the ear from day number one, they’re going to look at the person that was, so every single one-on-one that I had with Jeremy, it was, what exactly do I need to do to become a manager? What exactly do I need to do to, to lead a team? And it was just constant nagging, constant talking about what exactly I needed to develop to be ready for the position.

[00:00:30] Marc Gonyea: Rob Gonsalves in the house. Gonso. We were, uh, doing a team outing yesterday, Rob’s holler, and we’re working out. 

[00:01:16] Rob Gonsalves: Gotta do it. Gotta keep the people motivated. I agree. 

[00:01:19] Marc Gonyea: I appreciate that. You were keeping me motivated. All right, Rob, this is another good one.

[00:01:24] Yeah, because Rob’s got a great history with us doing different things. This is gonna be good for SDRs. People fear about coming here, people who are SDRs now, people fear about being DMs, DMs who work here now, but maybe want to be considering looking at some other things and why someone with as much success as you has DM rolling into the sales world that we want to get in all those things.

[00:01:45] So, before we do, share with us a little bit about yourself. 

[00:01:49] Backstory, grew up in a small town like Massachusetts, father big into sales, basically your whole family works for Verizon, whole family in sales, whole fit.

[00:02:00] Rob Gonsalves: So, father’s in sales, brother’s in sales, mother was a teacher, but grew up in Southern small town. I had a dad that was a massive influence on me. So, might get deep right off the bat with you guys too, growing up, extremely sick kid, in and out of hospitals pretty consistently, had a few tumors,

[00:02:16] but to be honest, later on in life, recognize that that’s kind of a blessing, you got a chance to learn so much for experiences earlier on that I think set me on a path later on in life. 

[00:02:26] Marc Gonyea: How old were you? 

[00:02:27] Rob Gonsalves: So, first one that I got diagnosed with was around, like, 9, 10 years old and came out of the hospital from that one, at 12 years old got diagnosed with the second one,

[00:02:37] couple of years worth of surgeries, follow-ups, but sets a level of dedication and kind of motivation that I think really has helped me out in my career. 

[00:02:46] Marc Gonyea: Yeah, you’re, 

[00:02:48] we’ll get into that a little bit ’cause you, I don’t know if you want to talk to me about personal health or working out and those things, chat with you about it,

[00:02:55] Marc Gonyea: so I’m sure someone understands when it’s about your childhood. Absolutely. But, what was your spirit like as a child?

[00:03:01] Rob Gonsalves: I, always energetic, always outside playing a sport, doing something, try to be the goofball of the class, wanted to be center of tension inside the household, but always kind of looked up to my big brother too.

[00:03:13] Marc Gonyea: How many siblings 

[00:03:14] in your house? 

[00:03:15] Rob Gonsalves: Just one. 

[00:03:15] Marc Gonyea: Okay. All right. So, you and your big bro? 

[00:03:17] Rob Gonsalves: Me and my big bro. Even after college, we’ve been living together for the past, like, three or four years now, too. So, we’re keeping a really tight relationship. 

[00:03:26] Marc Gonyea: I don’t have a brother, so I wouldn’t know. Chris has got two of them, so.

[00:03:29] All right. So, in high school,

[00:03:30] some people do sports. Some people have jobs, some people do, like, what were you like in high school? What did you think you wanted to be? 

[00:03:40] Rob Gonsalves: Yeah, so, I was motivated by athletics. I think most people that enter into sales has some level of athletic backgrounds at some degree. Started off with football, but because of how I was growing up and being a little bit sick, I was the lightest comet.

[00:03:57] I entered high school weighing about, like, 98 pounds. Entering onto the high school team, I, I got my butt beat time and time again, but it was a good time. Two years later, my buddy convinces me to join the cross-country team, and that’s, that’s really where I found myself. So, cross country, winter track, spring track continued to grind,

[00:04:17] we had a really fun team, uh, also got really involved in, um, program called DECA. So, a massive business program for those that don’t know it. Had a chance to compete, did fairly well on it. Got a chance to go to the internationals. 

[00:04:33] Marc Gonyea: Talk about that. Like what, would you compete? I mean, I’m familiar with DECA with some of the might not be 

[00:04:37] the freshmen.

[00:04:38] Rob Gonsalves: Yeah. So, essentially, what you’re doing for DECA is you’re, you’re prepping out case studies, you’re prepping out business use cases. Sometimes you’re making a 30-page document to present out a entrepreneurship idea, starts off with competing at a district level, if you place well enough, you get a chance to compete at a state level. Place

[00:04:57] well enough there, you’re getting a chance to go to internationals, which as a high school kid, they would fly you out to Orlando, Florida. So, in the two years that I competed, I had the chance to do personal finance me and my team placed fourth at internationals for that, that was really good time.

[00:05:13] I did sports, marketing, got fourth internationally inside that as well, and then had a team that did entrepreneurship, we had a really fun idea together, collaborated we ended up winning at internationals for that one. 

[00:05:24] Chris Corcoran: Number one, number one, what was the business?

[00:05:26] Rob Gonsalves: It was called Forgotten Treasures.

[00:05:28] It was a vending machine designed to be right next to a beach that holds everything you could potentially forget when going into it, everything from beach towels, sunscreen, and then we wanted to do, like, a Wi-Fi hookup inside it too, but when I was a kid, I was thinking, “Ah, this is going to be a massive investment to try to get this started.”

[00:05:46] I couldn’t imagine where I could get four grand to get this going, and now, looking back on it, it’s like, I wish I would have actually started and done something with it even if it completely flounders would have been, an amazing experience would have had it. Yeah. 

[00:05:58] Chris Corcoran: Wow. Number one.

[00:06:00] Marc Gonyea: So, so what’d you 

[00:06:01] think you wanted to be?

[00:06:02] So, your father was in sales the whole time growing up? 

[00:06:05] Rob Gonsalves: Father was in sales the whole time. He was enterprise, a manager for Verizon for the Northeast, um, but I wasn’t really sure. I don’t think anybody has that defined path for what they want to be doing. DECA definitely made a difference to understand that I could be successful in business overall,

[00:06:23] but when I enrolled in college, I started pre-med. Yeah. Pre-med. Did not go well. 

[00:06:30] Marc Gonyea: Doesn’t work out for most people. 

[00:06:35] Rob Gonsalves: Chemistry kicked me. Got fairly sick the freshman year, knocked out 20-days worth of classes, and then I was so far behind and I didn’t want to make up a whole extra semester,

[00:06:46] a whole extra year, recognized business was going to be for me, and I would be successful in it, so I chose to run that route.

[00:06:51] Marc Gonyea: Still thinking sales at all or no? Did that still, had come across, like, I’m kind of curious. What’d you major in? 

[00:06:58] Rob Gonsalves: So, majored in marketing. 

[00:06:59] Marc Gonyea: Okay. Got it, and what’d you think you’re going to 

[00:07:00] do with the major?

[00:07:02] Rob Gonsalves: I knew sales.

[00:07:03] Marc Gonyea: Yeah. Oh, you did? Okay. All right. 

[00:07:05] Rob Gonsalves: I think past experience watching my dad do it, watching the way he interacts with people, he was always fun, joking-around guy and recognized that that’s the environment, that’s the people you’re going to be surrounded with, so I didn’t think there was any other path I was even considering going down.

[00:07:21] Marc Gonyea: What’d you do in the summers when you were in school? 

[00:07:23] Rob Gonsalves: So, I did I training for cross country. I had a scholarship to go to college for that. So, on top of that, I’d primarily picked up, uh, construction gigs, so I’d work construction multiple summers, I’ll pick up extra shifts with my cousin to do landscaping, champion weed wacker.

[00:07:44] Marc Gonyea: So, you’re a runner?

[00:07:52] Rob Gonsalves: It was a lot of fun. Um, had a roommate who was actually getting married this weekend. Best man at his wedding really said for the speech. Hopefully, we’ll watch it, but, uh, he really taught me what it’s like to be a division-two athlete, especially one with a scholarship.

[00:08:07] He would set alarms at 4:35 o’clock in the morning, do a five, six-mile run, and he just was consistent. He would spend five, six hours stay in the gym. Now he’s competing in IRONMAN’s, wants to do double IRONMAN’s. I, his mother was, like, fifth in the world at the double IRONMAN’s. So I, no matter how much I did or how much I trained, like, I recognize there’s always somebody in another league above you, which was just a lot of fun to be exposed to.

[00:08:32] Marc Gonyea: Yeah. When 

[00:08:33] you, how do you relate, the, being an individual sport athlete, there was just, like, somebody, a team sport, how do you relate that discipline into kind of getting into sales, you know, coming to work in memoryBlue or any place else? ‘Cause I’ve always admired athletes, but then I have a higher admiration for these swimmers, runners, tennis players.

[00:08:59] Rob Gonsalves: So, I think there’s, there’s a level of just personal persistence that you want to have. Like, whole life dedication has been like, that’s what you gotta do. That’s what you gotta do to be successful. There’s nobody that’s going to be standing over your shoulder to have you wake up extra early to the gym or whatever you gotta do,

[00:09:15] but you create a network in group around you. I, cross-country was a lot of fun, I had a scholarship for that, but at the same time, I was competing in powerlifting. I set two world records in powerlifting; I was prepping out for a bodybuilding physique show. Nobody’s asking me to do any of this stuff.

[00:09:31] It’s you, you need to set the smart goals. You need to set goals with the timeframe that you need to do. You need to work backwards on what exactly you need to be doing to get there. If I’m comparing it to sales, you have an angle, right, for you it might be the end of the month, it might be the end of the quarter.

[00:09:47] You want to work backwards on what’s the inputs, what’s the actions that’s going to help you be able to get where, where you want to go. Um, and if you mess up, that’s on you, there’s nobody else that’s gonna affect. You’re the person that if you’re doing a physique show, you’re the person walking down on stage inside your swim trunks in front of 200 people.

[00:10:05] Marc Gonyea: When did you start doing that?

[00:10:07] Rob Gonsalves: So I did my first physique show when I was 17 at the Cutler Classic, uh, in Boston. That was a really fun one, um, but it also taught me a ton about what not to do inside prep work. 

[00:10:19] Marc Gonyea: Wow. Well, I don’t even know. I’m still training for my first position at risk. What about you? 

[00:10:25] Chris Corcoran: That’s something that I will never do.

[00:10:28] Rob Gonsalves: I 

[00:10:28] saw you, Chris. You got it. 

[00:10:32] Marc Gonyea: All right. So, you’re in college, majoring in marketing, wide variety of interests. What did you think the secret to sales when you got out? Right. How, you know, God’s great Earth, did you hop upon memoryBlue? 

[00:10:46] Rob Gonsalves: So, that was stroke of luck. Yeah. Um, starting out in some of my career, I obviously asked my dad for advice.

[00:10:54] He helped me out get into a, uh, a retail store at Verizon Yeah. So, I went straight from college, working at this retail store at Verizon, crushed it, had a lot of fun over there, had phenomenal mentors, I think I recognized the importance of a strong management layer above you.

[00:11:10] No matter what you’re doing, whether it’s retail sales, B2B, any path that you’re going, having a good manager changes everything. So, had a chance to do that, found my mentors, we were, like, the top three people, and we constantly competed, and that to me reminded me of the same sports that I was doing growing up. I had Walter Berk, and I mean that was tops inside the store.

[00:11:31] We had one retail rep making over a hundred K per year, so to me, I was, just under him, I was making, like, 80 K per year working at a retail store, but hitting 190% of quota, 160% my second year, but no matter what, I always saw the next person in front of me. So, I did that for a while, uh, anybody with exposure to massive corporate environment understands it’s different when you’re trying to grow inside your career, trying to progress,

[00:11:55] doesn’t always matter on everything, it’s just a lot of time to be able to do it. If you’re two years averaging, like, 175% of quota throughout that time, I never got an opportunity. Soldiers, wait, continue to do it. I got burnt out. Like, that after hustling day in and day out doing well, I, for a moment, thought the sales wasn’t going to be for me.

[00:12:15] Chris Corcoran: Interesting. What 

[00:12:16] Chris Corcoran: was your brother’s when he was in sales? Right? So, he was in retail as well, or was he doing a different, some different? 

[00:12:21] Rob Gonsalves: He started as a door greeter at Verizon. Moved his way up to account executive, he’s now chief of staff for Verizon, so he has grown from a door greeter to an amazing opportunity in his career.

[00:12:31] Chris Corcoran: Is he doing? So he was at open doors, and that’s retail, right? Yeah. 

[00:12:34] Rob Gonsalves: Open doors, retail sales. 

[00:12:37] Chris Corcoran: Retail, retail.

[00:12:38] Rob Gonsalves: Nope, so. 

[00:12:39] Chris Corcoran: How did he, so he ended up going more to enterprise? 

[00:12:42] Rob Gonsalves: Yeah. So, if you were, your dad was too. Yup. Uh. 

[00:12:45] Chris Corcoran: Did you think at all about trying to make that 

[00:12:47] transition?

[00:12:48] Rob Gonsalves: Tried, they didn’t want to take a chance on retail rep.

[00:12:51] So, I don’t know. I hit my wall there and just mentally said, “I’m done.” So, putting my two weeks. And from there, I started to come up with a path one week into that two-weeks notice. Loved fitness, did all that stuff growing up, moved into personal training, found the best-accredited program I could go to for it, went to it for four months,

[00:13:13] Rob Gonsalves: I dropped, like, everything I hadn’t set my bank account at that point to learn as much as I could. Um, blessing, blessing that I’ve learned everything that it did at that personal training and then found the gym that was going to be hardest for me to do well. I was powerlifting, bodybuilding, and I was like, where am I going to mess up the most?

[00:13:30] So, I went for an all-women’s gym to be a trainer at the gym over there because I recognized that was my biggest skill gap that I had to, uh, had to overcome. 

[00:13:39] Marc Gonyea: Well, what was that? what did you have to overcome? 

[00:13:41] Rob Gonsalves: So, people come to a trainer because they, they want to be the image of that trainer.

[00:13:46] That tends to be a lot of why people will choose who they want to work with because I was bodybuilding background because I was powerlifting background, but doesn’t typically fit in, so I had to change my whole style. I think it taught me so much about leadership, and I know we’re going to get later on into how I lead my team over here,

[00:14:04] but, yeah, a lot of how I coach is the level of empathy that I had to learn inside that ’cause it wasn’t just raw. It was, “Walk me through, what exactly are your goals? How are you trying to get there? How can I help you be able to get it?” So, I think that taught me so much sales tactics. You’re doing that and making $15 an hour living in Boston, you can understand very fast

[00:14:23] why I left. 

[00:14:25] Marc Gonyea: Yeah. You got into personal training, self-financed, that, like, starts, I guess, then, like, the research and the knowledge, then you went into your approach to render at an all-women’s gym in the city, okay, and how long did you do that? 

[00:14:42] Rob Gonsalves: So, I did that for one year.

[00:14:43] Marc Gonyea: And what did you learn specifically?

[00:14:45] Like, you give me a couple of things, but, like, what are some of the more practical, very fascinating? 

[00:14:51] Rob Gonsalves: So, it was a lot of fun. It was a ton of learning, not only about the body, how it moves, how to exactly coach it to individuals, know two people that you’re working with aren’t going to be exactly the same,

[00:16:03] some of them have problems in specific areas, so you adjust out how you’re personally training them, how you’re working with them, how they’re coaching them through movements. Again, you learn about everybody’s personal lives ’cause they use that as a chance to vent and talk about this, so you understand how to coach different name when somebody is having a tough day.

[00:16:21] versus when somebody is having a really good day, how are you going to adjust to that, how do you work backwards from somebody else’s goals ’cause I was really used to working backwards from my own. So, that was on the practical side when I was working with people. The other side was, how do you get clients?

[00:16:36] So, at this gym, we were self-generating our own leads. So, I got really creative with it, and I had a lot of fun. I, during Halloween, I dressed up as the devil when I came in, and I made a spin wheel that just says, “the devil’s deal” where you spin it, you can either win sunglasses, or you can win a free personal training session,

[00:16:54] but one of the things was, like, you got to do a plank for a minute. So, I constantly was hosting tables, workshops, um, talking to people inside the gym, coaching them, guiding them through movements. When I talked to, SDRs on team, it’s a little bit less nerve-wracking to talk to somebody on the phone,

[00:17:13] they might hang up in a minute, then interrupt somebody mid-workout. So, I think when I was starting as an SDR, that just seemed like such an easier transition in comparison to, nobody wants to mess with you when you’re at the gym. 

[00:17:26] Marc Gonyea: Yeah. Yes. 

[00:17:28] Chris Corcoran: Yeah. Well, I mean, I can just imagine, you know, someone’s headphones on mid-exercise.

[00:17:35] Rob Gonsalves: Excuse me, sir.

[00:17:39] Marc Gonyea: It’s funny. So, you did it for a year, and you asked, what did you realize you wanted to make that change? 

[00:17:45] Rob Gonsalves: So, I actually got put on a PIP. So, performance improvement plan. I, I wasn’t doing great. I did fairly well. Initially, I was building up my client base, but as I mentioned, this was probably one of the hardest markets for me to do welling,

[00:17:57] so I wasn’t learning at the rate that, that I had to, to be very successful in it. Management layer, they were okay at first, and this is really what solidifies why I need great management and I was struggling, I was asking for help, and it would be, “Oh, we might have this person chat with you.” Never got that.

[00:18:14] So, in my last month that I had over there, they said, “Hey, you need to get 40 new personal training hours this month; otherwise you’re going to be out,” and getting 40-hours worth of client work, build a, like, $110 an hour, that’s a lot. I hustled that month. I did well, beat out every one of the other trainers that we had there,

[00:18:34] Rob Gonsalves: I got 20 new personal training hours inside that month and had a commitment, but I wasn’t going to be enough, and for me, it was either I make a pivot, or I just try to find the next gym that I can transition to and especially with COVID and everything that happened the other year, I think I made the right choice by transitioning out.

[00:18:53] Marc Gonyea: Yeah, 

[00:18:54] sure. When did you decide, “Okay, I’m not making, I’m not going to another gym.” 

[00:18:59] Rob Gonsalves: Yeah, I, that one was kind of a struggle. Um, I think I recognized that probably the, the month before I hit PIP, where it was just, if I am going to have to transition out of here, I don’t think I want to do it like this, making the money that I was making didn’t seem worth it for the additional time that I was putting in.

[00:19:19] Keep in mind, hours of a trainer is insane. I was up at 04:30 inside the morning so I could open up the gym at 5:00 AM, so I could clean up the equipment before people got in, working night shifts on Saturday until 10 o’clock and then having to wake up Sunday morning right away. I lost my entire social life at the same time

[00:19:37] Rob Gonsalves: and maybe I’ll pick up, like, additional, additional shifts as a trainer somewhere over, like, weekends, I had some personal clients that have kept later on inside of my career, but I don’t know, it, it’s still interesting to me, still love the concept of it, wasn’t a long-term. Yeah. 

[00:19:53] So, what, how did you find us?

[00:19:57] Shotgun applied on indeed to a bunch of different jobs that I saw that was available. 

[00:20:01] Chris Corcoran: So, before we, so did you, was there any thought when you made the decision to leave the personal training world, was there any thought of going back to Verizon or retail or try to get in B2B? Did that thought ever enter 

[00:20:17] your mind?

[00:20:18] Rob Gonsalves: So, B2B absolutely, can tell now that, that one’s a trap. Uh, it’s, it’s a great career for a lot of people to get into it, apologize for my phrasing there, but it’s something where it’s really hard to break out of once you’ve entered. And I say, you kind of get typecast. Yeah. I got so many friends that stuck with that channel.

[00:20:35] That’s, that’s what they’re continuously doing, and it’s so hard for somebody to trust a, I mean, imagine you have a person applying for a B2B sales role for your team that’s only had experience selling cell phones inside a retail channel. You don’t trust it because they don’t know lead generation.

[00:20:50] They don’t understand anything. I recognize there’s a skill gap I was missing, just wasn’t sure what it was.

[00:20:55] Chris Corcoran: I see. So, you go out onto indeed and just carpet bomb?

[00:20:58] Rob Gonsalves: Yeah. I applied to probably ten places inside that week, and memoryBlue was one of the names that, uh, that popped up, um, I mean, bless it timing, right,

[00:21:09] because if it would’ve been, uh, a month prior, not even sure the positions would have been opened up, it was just as Boston was opening, so it worked out really well.

[00:21:18] Marc Gonyea: Everything was on Zoom.

[00:21:19] Rob Gonsalves: Yeah, it was.

[00:21:21] Marc Gonyea: Who’s your recruiter?

[00:21:22] Rob Gonsalves: Abby Curtis. 

[00:21:24] She, 

[00:21:25] amazing. Loved her. Loved the chance to work with her throughout everything.

[00:21:29] Yeah, absolutely. I want to stay in touch with her for the rest of my life. She was amazing. 

[00:21:34] Marc Gonyea: So, how, what, what do you remember about the process? So, it was all Zoomed, there’s no office, yeah, you know, what was taught you told? 

[00:21:44] It was a level of trust. It was a, trust me, we’re, we’re a real thing. I was interviewing all my interviews with Jeremy Wood, that I know is doing another podcast here too,

[00:21:55] he’s incredible. Like, not, not only as a leader but inside the interview process, I never questioned things. I was a little bit nervous ’cause I’m like, I’ve never seen an office. I don’t even know if you have an office. I don’t really know what’s going on, um, but it was the impression that Abby and Jeremy booked me, and I was getting offers that was much higher offer, but again, the leadership makes the difference.

[00:22:21] Rob Gonsalves: So, I saw exactly how Jeremy was like, saw the way that he was talking to me, and I had trust, and then the role-play pulled me apart. I had some couple of years of sales experience, and I thought was hot shit. I thought it was going to be really good. Yeah, but then when I do one role play, and then I find out that, “Hey, you’ve done X, Y, Z, here’s your areas of opportunity,

[00:22:41] here’s what I like, what I didn’t like.” I’m like, “I see where I’m going to go from here.” 

[00:22:46] Marc Gonyea: Did you see the B2B path too, or is that, did that come until later? Because as people get into the role of it, they don’t really know what they’re doing. 

[00:22:52] Rob Gonsalves: Yeah. I think that’s where I was blessed to have the family, that was either account executives in it that I knew that, like, okay, I do this job,

[00:22:59] nobody’s going to enjoy cold calling for the time that you’re going to do it, but I do it, I grind out, same thing that I’ve done some in fitness career, cross country career, work backwards, I know I’m going to get to where I want to go if I go through this to be able to get there. 

[00:23:12] Marc Gonyea: What were those early days

[00:23:13] like? Well, tell us about the commute. Like, so, so you’re back. So, you accepted the gig?

[00:23:19] Rob Gonsalves: Accepted the gig.

[00:23:20] Chris Corcoran: Yeah. I just want to make sure, so the whole interview process was all over Zoom? So, you never met anyone. Okay, this is pre-COVID when that was much different. 

[00:23:30] Rob Gonsalves: It was weird.

[00:23:31] Chris Corcoran: You’ve never seen an office?

[00:23:33] Rob Gonsalves: Never saw the office. I don’t even think the office was ready to be opened at that point, even after, I mean, even after starting my first day inside the position, Jeremy gave me a call and said, “The office isn’t going to be ready for your first day, you willing to fly out to Virginia to start with us inside of the office over there?”

[00:23:50] I was like, “Do I have to pay for my own ticket?” That was my first question. He was like, “No, we will, we’ll set you up.” And I hopped on a plane on the Sunday before my first day and then, uh, met all the, uh, me, Tiffany, Tom, and you got a chance to have that office. 

[00:24:08] Chris Corcoran: What an unbelievable experience, because I remember now, we flew you down to the Virginia office for a week so that the Boston office could get finalized,

[00:24:20] that next Monday, you guys opened it up. 

[00:24:22] Rob Gonsalves: Yeah. And you guys don’t realize how much of a blessing that truly was as a, brand new person to be able to step in there. We wouldn’t have been able to learn from anybody that’s having more experience with us, right, it would have been a lot more challenging to try to reach out to mentors if you’ve never met them before, but, like, Ely Kaplan, amazing, Brenda Gandin,

[00:24:43] that’s how you pronounce the last name. Caroline Sullivan. James Manning also, uh, they were all people and also Joe Trapasso, but yeah, all of Jeremy’s old team I constantly would be reaching out to for advice continuing on, especially where Brenda and Caroline were both on the same client that I was on.

[00:25:02] Uh, had I not had a chance to go over there, I would not have seen the success I would have had, finding good mentors, find a good team around you really helps you solidify who you’re going to be as a salesperson. 

[00:25:13] Marc Gonyea: Wow. What clinic were you on? 

[00:25:15] Rob Gonsalves: So, I was on two. I was on TalkPoint, which was an amazing experience, um, and then I was on a company called Empow, which was a brand new SIM that was entering into the market,

[00:25:28] um, weren’t big enough to get on Gartner’s magic quadrant, they had a great product, we’re building everything from the ground up. They had no SDR program, we had to come up with email scripting, phone messaging, we had to communicate that with the client to what exactly was happening. Um, when I got promoted, I had a chance to run with the Empow campaign under me for a couple of years worth of time, that was a lot of fun. They eventually got acquired by, uh, I think the company’s Cyberreason that they got acquired by, but even the account executive on that campaign and I’ll, I’ll ping him with a messenger every once in a while.

[00:26:00] Chris Corcoran: Great. That’s great. Yeah. So we’ll, we’ll cover a lot of that in a few minutes, but Mark brought this up in, in, I definitely want the listeners to hear

[00:26:09] about your commute, because in order to do that, you know, how bad do you want it? If you showed every day, how bad you wanted it by, like, just getting to work? So, talk a little 

[00:26:21] bit about, about the commute. 

[00:26:23] Marc Gonyea: And put them up and down for this. 

[00:26:26] Rob Gonsalves: Um, so for anybody that’s a new SDR that’s used to the remote culture,

[00:26:29] that was not a thing. There was no option to be working from home. You had to come into the office every single day. I entered into this company without a car, and I lived like 20, 20 minutes away by car realistically, and I did not think it was going to be that bad by public transit. I was used to doing that for every other job that he did before

[00:26:48] ’cause I was always on the city. We’re slightly outside of the city, so for me to start off on this commute, I had to take about a three-mile walk to get to the bus stop, to wait for the bus, to hop inside the bus, to go for about a 45 minute to an hour commute to hop off the bus, go for another two-mile walk to be able to get into the office.

[00:27:09] Now, I’m from Boston, had to do this when it was getting closer to winter time, that was miserable. Every day. This was every single day. So, every day I did that exact same commute, bus doesn’t always come on time, so you gotta be 20 minutes early just to make sure you can get there and get on time. I think I was only late twice.

[00:27:27] Um, but I was late twice because I hopped on the wrong bus, and it dropped me off at a completely different spot, which was, yeah, but, I don’t know, there, there’s something special about here, especially at that time, because I was one of three SDRs, I had a manager that was actually the managing directors, so there was a lot to be learning from them,

[00:27:50] Rob Gonsalves: um, so I recognized how much I could learn, but also I’m getting a chance that nobody else has. There’s not that many people that can help build an office culture, not that many people that have a chance to watch an office grow from three people we started with up until, guessing we’re closer to around 60 right now, inside Boston. Making that impact, having a chance to do it has, I mean, that’s going to be a use case for the rest of my career for what I ended up doing.

[00:28:14] Chris Corcoran: Definitely. 

[00:28:14] Yeah, definitely. So, it was all told, uh, uh, how, how far, how long the time would be from when you left your house to you walked into the work? 

[00:28:23] Rob Gonsalves: About two hours.

[00:28:24] Chris Corcoran: Two-hour commute, one way, 

[00:28:27] what would you do on the bus? I mean, could you take advantage of some of that time? 

[00:28:31] Rob Gonsalves: Yeah. So, listen to some audiobooks, had a chance to read,

[00:28:36] I went down the YouTube rabbit hole one too many times when I was sitting on the bus, but, um, it was my chance to learn. It was my chance to even listen back to some of my calls that I had the, uh, the day before. I’ll email it over to myself, listen to it on my phone, um, do myself some coaching and feedback, chance just to use that time for whatever I could. Best book that stood out, so at that time, for anybody listening, the Alchemist, fully recommended, helps you with your own personal journey, where you want to be going, a lot of takeaways from that one. That’s great. 

[00:29:04] Marc Gonyea: That’s great. So, you were in, in SDR role all that long? 

[00:29:08] Rob Gonsalves: No, no. I cruised out of that. 

[00:29:11] Marc Gonyea: Five months.

[00:29:12] Rob Gonsalves: So, after two months being, I mean, I had a chance to be a team lead, two months in. We were a team lead of a team of seven. 

[00:29:19] Marc Gonyea: Hold on, hold on, sorry. But you got to learn to do the SDR job, right? So you’re on a Pal. You’re on TalkPoint. TalkPoint, it was a longstanding, very successful client, but it was, that’s a hustle, right?

[00:29:31] ‘Cause it’s not, it’s not some super unique, nobody’s heard of tech before. Well, they, something’s different. Like, how does you transition from retail, to personal training to outbound SDR world? 

[00:29:45] Rob Gonsalves: So, it’s not different, just the modalities are different, right? Verizon, there’s a phrasing for their training called Earn The Right,

[00:29:54] you need to earn the right to be able to pitch any product people that you’re going after. I mean, the expectation whenever we are selling a phone was that 80% of them had to have insurance on it. We had to sell over $70 worth of accessory sales for each device. We had our goals for new lines that had to be added.

[00:30:09] I was used to balancing out, like, five or six different KPIs for what I had to do. Carol had to worry about one. So, discovery was key on there. When I was a personal trainer, understanding the why, understanding the values or how somebody wanted to get to where they were going, what’s the soft perhaps going to be for there?

[00:30:26] So, it’s just learning how to take the consultative sale. It used to be maybe 40 minutes of working with somebody as a trainer or at a Verizon store to how do I compile this into a two to three minutes cold call? So, I mean, massive skill gap at first, but again, I had some phenomenal mentors around me. Like, I could ping Caroline any day.

[00:30:46] I could ping Brenda any day. I was collaborating with Emie and Tiffany all the time, probably the, the best manager in the company at the time, no disrespect to anybody, full love to Simone Comer, who was probably my mentor for most of my time as a DM, but Jeremy was exceptional, so I had a chance to take everything that I learned, learn how to compile that into a quicker window.

[00:31:09] Marc Gonyea: What did you get good at as an SDR? Like, what was your flex? 

[00:31:15] Rob Gonsalves: Tactical empathy, I think, is something that, yeah, something that I leverage a lot more inside my career now as an account executive is understanding the why behind the other perspective. So, if I was putting myself inside of shoes that this, uh, VP of investor relations that are reaching out to, what’s going to personally be most important to me?

[00:31:38] What could potentially be my concerns with an upcoming event? Now, TalkPoint was an event management tool with video broadcasting, so number one, it’s on my head, what if something goes wrong? So, question I would ask and said, some of my calls would be, well, what’s the process if something does go wrong inside your current situation that you’re using?

[00:31:56] ‘Cause somebody to think about a slightly different perspective, again, you want to put yourself in the shoes of the person that you’re selling to. When you’re able to do that, you’re gonna have a much better understanding to why you’re asking the questions that you are, so I think the tactical empathy really helped out and then customized, close based on their situation,

[00:32:13] since you mentioned, you’re potentially having problems inside these specific areas, this is exactly why I’m reaching out to be able to help you out with your issues. Yeah. 

[00:32:20] Marc Gonyea: All right. 

[00:32:21] Chris Corcoran: Empathy, bring it down. 

[00:32:23] Marc Gonyea: He didn’t even blink. 

[00:32:24] Chris Corcoran: No. 

[00:32:24] Marc Gonyea: You just have to think about that.

[00:32:26] Chris Corcoran: He’s waiting all 

[00:32:27] morning for you to ask. 

[00:32:30] Marc Gonyea: What were Tiffany and Emie good at 

[00:32:33] that you learned from them?

[00:32:35] Rob Gonsalves: I mean, he just so caring, but I think that caused a lot of struggles for her at first, me and I mean, we’re on the same client, so it was a lot of fun, a lot of time on it full-time in any week that I had maybe one more book than her she knew it was half time so that, um, but she was highly empathetic and she was learning everything from the ground up.

[00:32:57] So, she had hustle, and she had an ability to work far later than I ever personally could. I mean, it wouldn’t be a surprise to see her inside the room until, like, 8:00 PM at night, and then she also had a crazy commute. She was probably an hour and a half, two hours as well, but she had just drive to want to do it.

[00:33:18] She never truly knew what she wanted to do inside her, uh, her career at that point and, like, she was developing that as she was having the exposure, which I thought was brilliant. I had my experience before, but watching somebody else have to learn everything from the ground up was an amazing experience. Tiffany was interesting,

[00:33:34] like, I, I loved working with her. It was a great experience. I think that the biggest thing that stands out to me about her is one time, I think it was maybe second or third book meetings, she was talking to somebody on the phone, on the fly, her to transition over to speaking Mandarin. Oh, that was wild to see

[00:33:50] and we’re just listening, and all of us has dropped our headsets and was just watching Tiffany call it, and she got to book of meaning out of it too. So, she was just very able to adapt on the fly to any situation. 

[00:34:01] Marc Gonyea: So, what had his project red team, project blue team? I remember hearing about this when he was trying to scale.

[00:34:08] Yeah, just talking to Kristen. What was your role in that?

[00:34:11] Rob Gonsalves: Yeah, so it was me and Emie, co-team leads, uh, again, this is two months into us being inside the position, and then, uh, Tiffany and Faith Emery, love her, such a sweetheart, um, but it was our team versus their team on any given, any given month, any, any given thing that we’re doing.

[00:34:31] We had a stellar team. We got to really build up some, some strong people that were, that were with us and I got a chance to learn from. Katie Lowery, potential candidate for alumni of the year, unbelievable. It was actually kind of brilliant how she did her messaging to people. It was highly customized, highly targeted,

[00:34:49] Ryan Carey, just a absolute goat, but he was a workhorse. I never have the met somebody more, more motivated when they’re seeing success, right? Like, he’s three months into the position. It wouldn’t be a surprise to see him at 10 o’clock in the morning. He’s 85,000, and he’s got three books on the day,

[00:35:09] sometimes, you can see somebody throwing the towel or SDRs be like, ” Hey, I’m good.” He’d be like, “Nah, that was just my AM blitz,” he’d go back and call again. Yeah, and then every month is less tied to reset to a brand new target, so you got to get rid of all of his past leads, reset list building,

[00:35:23] so there was nothing that was stopping them. Then I like Ryan Graziano, Tim, we had a great team, and we got to learn a lot from each other. So, we crashed, from what I remember, we just dominated inside of the first month, it led to Jeremy taking us out for a $500 steak dinner as a reward for it,

[00:35:38] so anytime I get a chance to win it there, I’m in. 

[00:35:41] Marc Gonyea: So, this was happening, the office was growing fairly quickly, right? 

[00:35:45] Rob Gonsalves: Yeah. Wild. I mean, there was a reason why I moved up so fast into the position. Like, I was, I wasn’t ready after four months of being an SDR to become a delivery manager. I was still learning how to cold call,

[00:35:57] right, um, I hadn’t even gone through my personal tip yet, not seeing success. I had maybe experience with the two clients. I had one PBM that I booked for, but we moved from, like, three SDRs to close to 20 inside a four-or-five-month window. Okay. 

[00:36:15] Marc Gonyea: Yeah. Yeah. 

[00:36:17] Rob Gonsalves: Give the story a few times during interviews. 

[00:36:21] Marc Gonyea: Still, still, keep, keep going.

[00:36:23] So, yeah, it’s the companies, office is growing, offices looking for some leadership help. Why do you think he came to you? Why were you interested? 

[00:36:31] Rob Gonsalves: Oh, I bugged the crap out of them. Um, so, for anybody listening that does want to grow inside their career, into their position, don’t wait for somebody to tell you, “Hey, now it’s your time to get a chance,” to leave it to you.

[00:36:44] If you’re not the bug inside the ear from day number one, they’re going to look at the person that was. So, every single one-on-one that I had with Jeremy, it was, what exactly do I need to do to become a manager? What exactly do I need to do to, to lead a team? And it was just constant nagging, constant talking about what exactly I needed to develop to be ready for the position.

[00:37:04] When I had a chance to be a team lead, I got a chance to learn a lot, and so I had one-on-ones with people. What I started to notice is, like, my own, my own phone calls from my own wins were exciting, but it was a lot more fun to watch somebody else get their first book. There was something we’re seeing the whole team get around them, slamming the gong for the first time, that is something special. 

[00:37:23] Marc Gonyea: And why is that so special to you?

[00:37:25] Rob Gonsalves: I don’t know. I, I’m guessing it stems from, like, the personal training, the stuff I used to do there prior to even college, I had my whole group of people that are used to work out with all the time, that I was the trainer for all of them,

[00:37:39] so watching my buddy get 2.25 on bench for the first time and just seeing the excitement out of that, um, it just reminded me of the exact same things I was getting out of the career path that I thought it was going to love, but in a, in a way that it didn’t take away from my hobby that I also loved.

[00:37:55] So, it was just very similar to my past job. 

[00:37:58] Marc Gonyea: You were DM for over two years. Yeah. So, what’d you learn in that role? 

[00:38:04] Rob Gonsalves: I don’t think there’s a way to summarize it. 

[00:38:06] This position, especially here, because you’re not a, you’re not just a manager of SDRs, that, that job on its own is hard enough, but additionally, you’re an account manager. I don’t think delivery talks about that enough as being the genuine skillset that you’re developing inside your time here. Yes, you’re learning how to coach,

[00:38:26] yes, you’re learning how to interview. Think over the past couple of years, I’ve probably done over 500 interviews with people, hired on over 50, had to let go a few people. 

[00:38:36] Marc Gonyea: Let people go. 

[00:38:38] On the account management side, you’re learning how to deal with clients. You’re learning how to deal with clients with extremely high expectations.

[00:38:44] Rob Gonsalves: We’re the best in the business. We all know that we’ve done such a good job. Because of that, our clients have massive expectations. For anybody that’s a DM that, that’s listening over here, I understand. You’re going through hell day in and day out working with these clients that you might have an SDR that’s,

[00:39:02] I mean, I’ll use Brian Carey again, as an example. Dude was booking 40 meetings per month and occurring them, we had Tyson Maddix, who delivery manager here now, also on that same campaign, getting 20 meetings per month. We had Ellie Miller, who was also on my team, getting 25 meetings per month,

[00:39:23] they were like, “Hey, you guys aren’t getting us 10 times the amount of investment on every single given month on closed deals. We need to cut your program after two years’ worth of time and a partnership together.” Cut just like that because not getting over $250,000 since I closed deals every month from outbound.

[00:39:39] So, you’re dealing with the expectations, you’re tempering expectations. You’re talking with the clients about that. That’s probably what translates most into the account executive position I’m in now.

[00:39:50] Chris Corcoran: For the listeners, I just want to say that that was an all-star team.

[00:39:57] And in some, sometimes you can have the best team in the floor and producing results, and it’s just not good enough. That says more about, I would say, the client or the company than the team because that team is a bunch of winners.

[00:40:11] Rob Gonsalves: Yeah. We, I pulled up the numbers before moving into this other team,

[00:40:16] so I’d have everything in front of me in the future, but my team matched 97% of quota attainment for two years straight. I mean, we had some absolutely rockstar SDRs that had chance to learn from, uh, Jonathan Duffy, Carly Prunier, Justine, Terry Loe, I don’t know his last name, Curtis Giles, like. 

[00:40:36] Marc Gonyea: Seriously,

[00:40:40] you think you’re going to put together a team on your own while you’re creating your software better than someone like that? 

[00:40:50] Rob Gonsalves: Yeah, we had rockstar SDRs, but it was due to, I got really good at formulating team composition, that’s something that’s really over, might be overlooked, I think it depends which team that you’re talking to, but there’s a level of knowing who you’re hiring, why you’re hiring them, how they’re going to be interacting with the team overall, knowing what sacrifices you’re willing to make for a team.

[00:41:13] Like, an example would be, I knew my intangibles that I was looking for inside any SDR. I needed two things for anybody that I was going to hire. That’s a bit I can, I can figure it out for them. I needed somebody that was gonna work their butt off. Do they have a past trajectory and history of being able to absolutely grind?

[00:41:29] It didn’t matter what they did before. Sure. Really loved, like, waiters, waitresses, but, like, even for Jessica Simon was a nanny before she started over here, but she consistently had great work ethic. Second piece was coachable. Me and Jeremy had a lot of conversations about the amount of times that I just had somebody redo the role-play inside the final interview because I just wanted to see exactly what they would implement from the coaching.

[00:41:52] If I had those two traits, I can teach anybody how to sell, and I could have an extremely successful team. Then you learn, well, who am I going to have sitting next to who to drive them for better results? That’s a really fun thing. It’s like, well, Carly probably had one of the greatest mindsets in terms of motivation for moving forward,

[00:42:12] Ryan Carey had the exact same thing, and it will be fun, let’s have them sit right next to each other. Drove a ton of great team composition with each other. Example would be on a pick class, which was a long running client of mine, a more recent example for, like, current SDRs that might be listening to this.

[00:42:28] It’s like I, Colin Jones, Noah C., and Matt Lamar, they, I put them all in this client for a specific reason. Noah had exceptional work ethic. Colin had past experience in, like, sales, and I understood that he was going to be very good in terms of tactical. Noah, I knew it was going to have the work ethic.

[00:42:48] Matt was learning, and he was very green. Put them alongside two people that’s going to be work ethic, somebody that’s going to be more technical, you’re going to drive the best out of each one. So, I don’t know. I thought team composition was a massive part of what makes a team successful inside of the time.

[00:43:03] Marc Gonyea: He’s 

[00:43:03] a professor, right? ‘Cause you kind of have your term, tactical empathy, team composition, composition, so you didn’t stray too far from maybe organic chemistry scared you off, but you’re like a little medical diagnostic professional in terms of putting together these 

[00:43:19] teams. 

[00:43:20] Rob Gonsalves: Well, you learn from experience when you keep yourself open to what other people do.

[00:43:26] I, I would never truly tell an SDR what to do. I would always say, “If I was in such a situation, here’s exactly how I’d go about it,” because I don’t know everything. I’ve had experience managing 20 different client campaigns, 50 different SDRs, but I would learn something new from somebody on their first week.

[00:43:44] If they tried out something, it’s not a mildly different way than what I had before. I don’t want to limit somebody screed at freedom to be able to do that. So, I had a chance to learn through every single person that was on my team, and that was an absolute blessing to get a chance to do that because you’re not an expert yet

[00:43:59] if you’re a DM for six months. I might have had your experience before, but learn from everybody that’s on your team, and it’s going to create a better manager out of you in one year’s worth of time. 

[00:44:09] Marc Gonyea: So, you’re doing this role, helping build an office, upset the other offices, but, like, an office I was very 

[00:44:19] proud of. 

[00:44:19] Rob Gonsalves: Oh, best office in the company.

[00:44:22] Marc Gonyea: I wouldn’t say it’s the best office, you know, my family’s from my peers always kept it with that, but possibly potentially my favorite, but when you were looking for, for what you wanted to do, kind of where you wanted to go with things, what was on your mind too? So, short stint as an SDR, so, I mean, for you, I think it’s great

[00:44:40] you had this experience before. Right?

[00:44:43] Rob Gonsalves: Oh yeah. 

[00:44:44] Marc Gonyea: And, I always talk about how with people who are career switchers or transitioners, but the experience you had before it’s going to help you, even more, when you get out of the SDR role, but you prove you can do the SDR role, that other perspective is going to kind of help you with things. But you spent time, quality time in a DM gig, learn from Jeremy Wood.

[00:45:04] Right? What did you think you want to do after that? 

[00:45:08] Why, because, yeah, because we’ve got 50 DMs at the company now who we want them to continue to grow and delivery, and you learned so much in that job over two years and maybe potential open office, maybe not, maybe take over an office, maybe an MD’s office,

[00:45:25] Marc Gonyea: or join the sales team and, right, I want to talk about your transition from being a DM and why you decided to kind of go into sales and so on and so forth. 

[00:45:33] Rob Gonsalves: So, this is a question I tend to get a lot whenever I’m doing one-on-ones with people, and for anybody listening that wants to have one of those, you’re talking about career path trajectory, I’m always open to helping out, always willing to have a conversation,

[00:45:45] just this ping me, send me an email, send me a LinkedIn message, all that’s open, but I think for, for the first, probably year and a half, I was a delivery manager, the only path ahead of me or the only thing that I saw was, it’s, it’s managing director or, or I need to leave memoryBlue. I need to figure out what I need to be doing from here.

[00:46:02] Um, I hear that a lot even when I’m talking to current delivery managers, that’s figuring out, like, what they want to be doing next. I got rocked by one client, and that one got me extremely frustrated. Literally, drop, so it was a situation where things weren’t going well with the client at all,

[00:46:20] I would take, like, one day of PTO, um, I didn’t respond to, to an email, I got a six-page note that day back that got sent over to her head of delivery. It, it was something that wasn’t fruitful, the conversations that he was having with the SDR wasn’t going to be helpful for him. He was trying to take on fully coaching

[00:46:38] the SDR, I was losing control of that specific one on my team, SDR Garrett Mack, amazing guy, ton of, ton of work ethic. Um led even to the point where we had to sit down, and you were like, “Rob, what the, what the heck are you doing? I’ve never seen something like this from you.” And I, I wanted to be back in control a little bit ’cause that, that hit me,

[00:47:03] and then I recognized that if I’m going to be a managing director, this is the situation I’m going to deal with more often than not; it’s going to be the challenging ones. It’s going to be less about the individual coaching; it’s going to be less about everything, which recognizing now, that’s only partway true.

[00:47:18] Uh, you’re dealing with a lot of that, but there’s a lot of individual coaching and helping. So, for me, that was really the, the final straw to me wanting to transition out of it. I think I walked into Jeremy’s office fairly soon after that, saying I’m done. “I’m, I’m ready to be at memoryBlue. How can I get started up for the rising stars program?

[00:47:36] He said, “Take a couple of days, think about what you want to be doing. Let’s revisit this conversation. I’m going to bring Kristen in.” Kristen’s amazing. It’s really, truly nothing but love for how much she taught me throughout my time here, um, but she walked me through the, what exactly are you looking for?

[00:47:53] What are your goals? How do you want to get there? Where, where do you want to see yourself going? Which I wish I used a lot more of the tactics on some of our past SDRs that I had, but I started to really think about my career path and where I wanted to be going similar to fitness, similar to across country,

[00:48:08] what’s my goal? How am I going to work backwards to get where I want to go? Well, the more I thought about it, the more I’m like, “VP of Sales, Chief Revenue Officer. Find, find a way to, to lead an entire organization. I want to learn how to do that.” Then the more I’m thinking about it is, if I’m going to be trying to get into a VP of Sales position, how the heck can I do that

[00:48:30] if I’ve never personally closed a deal? I might’ve been one of the, one of the top managers at the time, it was great at account management, I was great at the SDR work, there was a massive skill gap, so I sparked up conversations about joining the AE team and about potentially wanting to try to lead an AE team for us over here,

[00:48:48] so I reached out, I had conversations. I had these conversations for months before my actual transition onto the team, and I’m so glad that I did, um, because I felt like I stopped learning, come like a year and a half into the position, transitioning into the AE team here, they care about coaching and feedback in the same way we do for the SDRs and recognizing other companies, they don’t get anything like that.

[00:49:13] It was a massive pickup to transition from one team to the other initially because I was talking some in class on one, I’m entering into the beginner, I got to learn again, and to me, that never mattered. It’s all about what am I learning? How’s it gonna set me up for the future and future growth? Had a chance to hop into the scene,

[00:49:29] and get rocked and rocked on the phones, getting rocked on, deal cycles, trying to figure out how do you take something from intro phone call to DocuSign close. It was like an entirely different perspective shift. So, for me, it was more working backwards on where I want to go and then taking this as an opportunity to truly learn, hone the craft, talk with people that know me, that know my experience,

[00:49:53] it can help teach me to get to that next level, and for anybody that does do the transition from DM to account executive and your goal is to grow outside of the company, the experience is invaluable because you already know the product so well. That, that translates instantly into how you’re selling your, you understand account management, you understand the problems,

[00:50:11] so it’s going to be better for you to be able to learn how to sell this product that you’ve had exposure to at first, get the coaching, the guidance be able to grow alongside from there. So, it’s not just a linear path of DM to managing director. You can make your own path, you can communicate it.

[00:50:28] Marc Gonyea: And how, how’s the team supported you with that? Was it the same kind of process when it was just you and Tiffany and Emie and Wood learning to sell? Did you go about the same way? Did you learn differently? 

[00:50:42] Rob Gonsalves: It’s so much better, I think. We, AE team here is amazing. Do you mean, like, Nick Callan closing close to a million-dollar deal from the outbound cold calls?

[00:50:54] Uh, Alex Rodriguez, who’s absolutely crushing Sutton Craft. Connor Keeley doing well for so long inside his time here, like, but, and Billy Jacob’s used to be on my team, Tara, like, everybody I’m having a chance to, and Ben Faulkner, I know he would rip me apart for not bringing him up on here, but I could set a pride of West Virginia, pride of West Virginia in the swim truck,

[00:51:17] but I could reach out to any one of them at any given time and say, “Hey, I want some help. Let’s listen to an intro call together. We’re going to dissect the call together.” We’re constantly bouncing ideas and feedback off of each other. Everybody has a different way to be positioning the product.

[00:51:32] Every time I’m listening to an intro call, I have 30 to 45 minutes worth of content to be gathering from what somebody else does different versus two minutes worth inside of cold call, and not only that, these are the elite of the league, there was 350, 400 SDRs we’re recruiting from for this very specific team of, like, 10 people.

[00:51:51] Yeah. Um, we got the genuine best of the best from SDRs into this position that’s honing their own graft and learning it. So, we’re constantly bouncing ideas off of each other. Sales leadership team here is insane. Brandon Eyring, uh, amazing, amazing first manager that I have on the sales team actually used to be one of my clients.

[00:52:11] So, Katie Lowry was working on his client at Zero North when I first started as a delivery manager, and I would go to him as the point of contact. Fast forward a couple of years later, he’s now my boss. 

[00:52:23] Marc Gonyea: Yeah, you know, there you go. Yeah. I want to go back to this because, I mean, you’re selling something that you, you manage these campaigns for over two years, 

[00:52:33] so 

[00:52:33] that’s,

[00:52:35] how do you view corporate, that and kind of how you build credibility with prospects? 

[00:52:41] Rob Gonsalves: Honesty, transparency. I mean, there, there’s a level of bringing up case studies, right? Just the, “Hey we’re selling into the event space. Can you walk me through any examples, or cybersecurity space? Can you give us any examples?”

[00:52:53] Like, well, I was the delivery manager that only focused on cyber security in my first year because I felt really passionate about it. So, we align up who wants to claim work to what they’re going to be in with passion for, what they want to be selling. You’re building it up because we’ve had the experience.

[00:53:08] They talked through how they have an SDR making $40 a day, and they’re like, “I don’t really know what to be doing without them” “Well, here’s how I personally coached. Here’s how I personally dealt with these types of people that were working on my team.” It’s a lot of, you understand the problems ’cause you’ve been there.

[00:53:22] You’ve done that. You got a brand new, say, a 25-person company, you’re talking to a CEO that’s saying that they’ll just hire somebody onto my team. “We’ll get an SDR for fraction of price,” is outsourcing. Then it’s well, “What’s your recruiting process looks like? How are you going to filter out?

[00:53:38] Who’s going to be a good or a bad SDR?” In my experience, I did probably five to seven interviews per week consistently on every single week, I’d maybe hire on a new person every two weeks. How much time do you have to separate for hiring on an SDR? How are you going to vet them out? How are you going to coach them?

[00:53:54] How are you going to train them? Here’s the exact amount of time. It turns into a more consultative conversation about, well, what’s the logistics of you’re doing things like this? Because you’ve seen it. You’ve been through it, and you understand the, the actual challenges to be able to get there.

[00:54:09] Marc Gonyea: Yeah.

[00:54:09] And that’s, I would imagine that resonates with the right proper, should resonate with most prospects. It’s not going to evolve, but I would imagine that gives you an instantaneous level of credibility that other folks who you’re competing against. So half. 

[00:54:23] Rob Gonsalves: It will eventually resonate with every prospect because I, I’ve lost a ton of deals so far,

[00:54:29] right, I’m still, I’m still learning everything. Yeah. 

[00:54:33] Marc Gonyea: We don’t make too many cold sweats. 

[00:54:35] Rob Gonsalves: Um, but I’m learning a ton inside the process, and everybody that I’ve lost a deal to I understand why I’ve lost it. I asked for, for notes and feedback after I’ve lost something and being like, “Well, where, where exactly did we lose you?

[00:54:46] What you ended up going with? Why’d you end up going with that?” Using that is personally a chance to be able to learn for myself. Secondly, that’s a follow-up. Yesterday I just did an up cadence on a bunch of opportunities that I’ve lost inside of the past, and now I have timelines for four or five of them towards when they’re going to be reconsidering the situation because they went with either another vendor internally

[00:55:03] that’s not working out. 

[00:55:05] Marc Gonyea: Yeah, it happens quite often. What’s your favorite part about the new role? 

[00:55:11] Rob Gonsalves: New role, you’re in control of everything. One of the, I think the biggest, prideful moments that I’ve had inside this new role is, um, one week I closed a $500,000 deal which was exciting, and it was really cool.

[00:55:24] The following week, I closed an $11,000 deal, $11,000 deals stood out a lot more to me. This was the first deal I’ve ever gotten that started with an outbound cold call. Wow. I’d been spending two years preaching the importance of outbound cold calls, preaching the importance of the outbound, what it actually means for yourself and for an organization.

[00:55:44] You can only believe it’s so much until you’ve done it for yourself and have the exposure of watching that DocuSign to say, “signed.”

[00:55:52] Chris Corcoran: Originated from an outbound. 

[00:55:54] Rob Gonsalves: So, since then, I’ve probably been an aide for about six months over here, have closed over 350,000 inside outbound calls so far, so it, it makes a difference in, I don’t know.

[00:56:05] I think it was just the culmination of everything that I taught works, and now when I’m walking up to SDRs, they either used to be on my team, I’m constantly still trying to help out where I can with the SDR role, it’s not just, “Hey, you should do this because it will get you a more meeting.” It’s, “Hey, when you transitioned to AE role, here’s exactly how it’s going to translate and make a difference for you.”

[00:56:25] Marc Gonyea: What’s the biggest skill you’ve developed in the past six months in this role?

[00:56:30] Rob Gonsalves: Organization, because when I was a manager, you have to be organized with your calendar, you have to understand how to space out your time. I had 17 SDRs under me at one point, I was managing an external company BDR program along with my full team here, and all the clients and SDRs, that you have to be organized at the individual situation. Here

[00:56:49] you might have 25, 30 different deals that you’re having touchpoints at different times with, so understanding when to follow up, what’s an appropriate follow-up, what’s the importance of taking good notes inside the initial call, so, you know two months later when they said to follow up, you know what to be doing, because you’re going to forget after the next week when you’ve had five or six more calls.

[00:57:10] So, continuously taking good notes, blocking off of my calendar when I’m going to be doing follow-ups with people versus just keeping the notes somewhere else, so I can just stay on top of my workload and what I’m doing. 

[00:57:22] Marc Gonyea: Nice. So, the plan is learn, continue to build this skill, go outbound, selling, run your own sales cycles, outbound deals, inbound deals and then take the managerial experiences

[00:57:36] then transition to a manager on the sales side. And how do you see those two jobs being different? 

[00:57:44] Rob Gonsalves: One of them is going to be having a little bit more control because the sales cycle, especially when you’re teaching somebody up front, I had Brandon helping me out a lot on my calls when I was starting out, I got Bobby Han

[00:57:56] who’s helping me out a lot on my calls right now. Um, you, you need to know exactly where everything is, when they’re going to be inside pipeline. I think the biggest differentiator is going to be managing pipeline, especially to that extent of having a full team under you. For the delivery manager role is just focusing on coaching, developing the SDRs, tempering expectations with the client.

[00:58:17] I think the tempering expectations and all that, it’s going to transfer into the disco calls, and I think the learning how to coach the SDR gives a slightly different perspective in how you’re going to be coaching the AE. So, I think it’s still to be learned, especially after a little bit more exposure to, to this role, but I think I’ll make a ton of mistakes and learn from each one. 

[00:58:37] Marc Gonyea: You will,

[00:58:38] and what I know about Chris Robyn, the, uh, Rob is you’re booking a lot of meetings for yourself, whether you work here or whether you work at a technology company, and people are still always gonna be about outbound. 

[00:58:52] Rob Gonsalves: Yeah. The, no matter what, your number-one goal is to get new names into your cadence. That’s the first thing.

[00:58:59] If you’re an SDR that’s struggling, first thing to check out is how many new names have you uploaded last month. Um, that I tend to notice being like the biggest differentiator to those that’s doing very well and those that weren’t. So, consistently, every single morning, 8:30 AM, list building 25 new names per day. Continuing into the role as an account executive,

[00:59:21] that’s a massive reason to why I’m still generating success on the outbound channel. I’m getting, I think on average, I’ve been around like 14 or 15 meetings occurred every single month since I’ve transitioned onto this team along with balancing the new pipeline. Not all of them are winners, but you getting more at bats, more opportunities from learn to each call

[00:59:39] and at the same time, you got more people you can follow up with. So, outbound is going to be key for everything that I do. It’s a skill set most other companies don’t have. Yeah. 

[00:59:48] Marc Gonyea: Particularly you sell it. Yeah. That’s the core of our offering. So, you’ve been booking 14 outbound for yourself. 

[00:59:56] Rob Gonsalves: Give or take, every month.

[00:59:59] Marc Gonyea: It’s a healthy body of work, for sure. 

[01:00:01] Chris Corcoran: For sure. So, what, in your opinion, is more challenging, closing, finding, or leading? 

[01:00:07] Rob Gonsalves: I think leading’s easiest. 

[01:00:08] Chris Corcoran: The DM role is easiest.

[01:00:10] Rob Gonsalves: So, more leading people, the account management side is something different, but that changes based on your personality trait for, for really who you are.

[01:00:20] So, I think on the leading side, that really meshes with who I am as a person, how I try to match up with people, that tactical empathy, you’re using the exact same thing when you’re working with a team, it was always something that was very good at. Booking meetings it’s effort. I mean, if you’re, you’re struggling, let’s say you’re at a hundred dollars a day,

[01:00:38] you got one conversation, you’ve got no booked meetings. How do you fix that? You got more, right? You’re, you’re eventually going to get somebody, you can test out different tactics, you’re going to be able to get more, no matter what, that’s fully inside your control. Closing’s a bit more challenging inside the sense that it’s less inside your control, right?

[01:00:56] When it’s going to be up to another person to finally do that DocuSign, you’ve been inside control the sales process for helping somebody out all the way through it, but at the end of the day, they need to be the one to sign that paper. You can’t make that up by doing an extra 10 dials inside of the day.

[01:01:10] Rob Gonsalves: So, I think for me, closing has been definitely the most challenging out of the bunch. That being said, DM was a mildly more challenging role just because there was a lot of moving parts to consider while you’re doing it. 

[01:01:23] Chris Corcoran: Leading in account management and simultaneously.

[01:01:25] Rob Gonsalves: Yup. Your calendar is every half an hour,

[01:01:27] it needs to have a purpose, and if it doesn’t, you want to make sure that it does so that you’re doing something better for your team, right? Because if you’re not using that, if you’re just using that time for yourself, you’re taking away from the person that trusted you with their career when they’re first getting started. You have a responsibility to everybody that you hired to coach them inside the way that you would want to.

[01:01:45] be coached.

[01:01:45] Chris Corcoran: Exactly. Well, 

[01:01:46] it was great. Very good wisdom today. 

[01:01:49] Marc Gonyea: Yeah. Rob, Chris, and I are fortunate that we had Jeremy work here, we’re fortunate that Jeremy and Curtis, anyone else involved in your interview process, get you to come work here? Right? 

[01:01:59] If your body, if we could get everybody at memoryBlue to have a body of work like yours, it’s fine, that’s what we’re working towards, and I’m thankful that you, you’re helping the market understand how to do these campaigns the right way, for actually doing it. So, I think that that’s your best value add to the sales cycle.

[01:02:19] So, I’m, I’m happy to see you can do that. 

[01:02:21] Rob Gonsalves: Happy to be a part of it. 

[01:02:22] Marc Gonyea: Help them,

[01:02:23] help them get where 

[01:02:24] they want to go.

[01:02:25] Rob Gonsalves: Let’s do it. 

[01:02:26] Chris Corcoran: I’m excited about the future, for sure. Sky’s the limit. 

[01:02:29] Rob Gonsalves: Yeah, absolutely. Kind of an additional mark is, nobody hesitates to reach out if you need help, like, genuinely, I’ve always been there for other people,

[01:02:39] always will be, so if you’ve been struggling on a campaign for a while, if you’ve been debating what you want to be doing next inside your career, send me a message on LinkedIn, we’ll, we’ll coordinate some time to, to talk through. 

[01:02:51] Chris Corcoran: Very good. I encourage listeners to do just that. 

[01:02:54] Marc Gonyea: Thanks a lot, 

[01:02:55] Rob.

[01:02:55] Rob Gonsalves: Appreciate y’all.