53. Think You Want to Be a Sales Leader? Gabrielle Reveals the Dark Side | Gabrielle Blackwell

Speaker A: How am I going to get four of my people to their number? Right? And how do I support people who are on a coaching plan who might be on their way to performance improvement plan or, you know, if I need to let someone go, like, how do I do that with dignity? I think the weight of an SDR manager is just a lot more than with an ae. Plus, you can make more money as an AE too, with a lot less stress.

Speaker B: I'm, um, thrilled to have Gabriel on the show.

Speaker C: A sales leader whom I have admired and has done what most SDR managers dream about. Making the leap from SDR leadership to AE success. With a career spanning gong airtable, cultureramp and now common room, Gabriel has built, coached and led high performing sales development teams at some of the biggest names in tech. Here's the twist. She did not just stay in management. She made the jump back into an AE role, flipping the script on what's considered the natural career progression in sales. Today we are diving deep into why she left SDR leadership for an AE role. The harsh reality of being an SDR manager versus an AE to transition from SDR leadership to closing deals. The number one mistake SDRs make when trying to level up, and why mental health and work life balance played a huge role in our decision. Gabriel does not hold back and this conversation is packed with insights, real talk and actionable advice for anyone in sales figuring out their next move.

Speaker B: Without further ado, Gabriel, welcome to the show. Welcome, Gabriel. Thank you so much for coming to the show. Truly, truly appreciate it.

Speaker A: Yeah, I'm glad to be here. Thanks for inviting me.

Speaker B: Yeah, so I'm a huge fan and I think I've been following your journey for a while. It's an honor to have you on my podcast. And you know, I think I've been following you because, and I've seen like probably all your hairstyles. You know, I want to probably start with that. You know, what's up with that? Like, how, how often do you change the hairstyle and uh, how do you, how do you find, you know, uh, what hairstyle to go for? Like, do you, are you like, do you like a follow fashion a lot?

Speaker A: Oh, that's funny. Yeah, I was wearing braids, uh, for a bit because over gong days I had a.

Speaker B: That was the best one, by the way, I'll tell you that.

Speaker A: Thank you. Thank you. My boyfriend disagrees. Uh, um, but, um, no, I had, yeah, I had really short hair and I would dye it all different kinds of colors. And then I realized that when you dye Your hair too much, it compromises the health of it. So ended up switching to braids to grow my hair out. And so I was like, I miss having color though. So I would just change the color of my braids like every time I got it done. And that was about every six to eight weeks. And then like maybe middle of the year last year, uh, I was kind of like, I think I'm going to pause on braids. And so I've just let my hair be out and that and I just decide how I want to wear it depending on how ruly or unruly my hair wants to be. That's about it.

Speaker B: I was going through your videos in the past. Your previous podcast with C Anns, you did one with Morgan in, uh, the office of LinkedIn. And one thing, uh, and that is where I kind of noticed this. In every video you had a different hairstyle. So I thought I should probably ask you, how do you do that? Yeah, I mean, I'm rocking this hairstyle for years. I don't know. I can't change it.

Speaker C: It's.

Speaker B: It's so hard.

Speaker A: No worries. I've got the gift of my hair. Can do a bunch of different things. And then I do think that the styles that you'll see that are typically for like black women, they allow for a lot of versatility as well. So it's, um, it's nice to be able to have some level of self expression through hair. And I can remember during COVID times as well, I started picking up hobbies like with makeup. So I used to wear, I would probably spend 30 minutes in the morning because I was working central time, but the majority of my team was in Pacific. So I would have four hours before I started work and I would just play around with makeup and see what was possible. So it was just before work activities and fun, before I got into the grind of the day.

Speaker B: Thank you so much again for the background. Appreciate it. Gabriel, would you please be kind enough to give us a quick rundown of your career journey? Because I think that's worth talking about.

Speaker A: Yeah, absolutely. So I started in sales. I was 24, I want to say. So previous to that, I had actually been living, living and working in Paris, France, uh, as a under the table person because I did not have the right to work as an immigrant there. Um, and then when the time came to start thinking about like, what did I want to do, what did I want to create, I moved back to the US to, uh, Chicago, where I'm from. And I wasn't sure exactly what I wanted to do, but I was like, let me start in sales. That seems like a really great place to go. Uh, so I started as an outbound sales development rep at a company called Cloudwards there in a satellite Chicago office. Ended up doing really well. Ended up moving with our leadership team to the next company called Acton. Got fast tracked from SDR to ae. Uh, did really well as an AE there, but ended up being a part of a, um, what do you call them, layoffs. So yes, a reduction in workforce. So ended up moving to another company called Cloudability, which has been acquired by Aptio as an outbound. BDR got promoted to a manager bdrs two months later. So I was only an IC for about a year and a half before I got promoted into management. So, ah, Cloudability in Futor as well. I was um, building sales development teams, outbound sales development teams from the ground up, creating all the operations behind it. Like was the head of the department on that side. In 2020 I moved over to Gong. And so I've been at a few different tech darling companies. So GONG was one, Airtable was another. Uh, then it went to Culture amp Lattice. I've had a lot of experience from, you know, commercial segment to strategic segment for outbound sales development. And then more recently I've moved over to an AE position at Common Room. So, uh, getting back into the individual contributor life, uh, and here we are.

Speaker B: That's amazing. I think, uh, that's hell of a journey, I can tell you that. And you're the first person I know personally who has made the transition from SDR manager to ae. Uh, back in the day when I had an option to become an SDR manager or an ae, I always wanted to become an ae, I think just like everybody. But um, my manager said, you know, uh, the other SDM manager quit. You're it and you know, you become the SDM manager. I enjoyed it so much. I can't think of any other position I would want to ever acquire. But you made the jump. And I would want to talk about that today because lately I've seen. I'm m seeing a lot of other SDR leaders who are thinking about it. So walk us through your journey. Like why did you make the jump? What really helped you? And I had tons of questions.

Speaker A: Yeah, definitely. So I'll say this. I remember when I made the move over to Gong. So that was in 2020. I had got a mentor through Revenue Collective, which is now Pavilion, this guy named John Gilman. He's awesome. And so I was just kind of talking about like my career trajectory and what I wanted to accomplish. And I had this, uh, mindset that I was going to continue to rise up in leadership within the sales development department. Amber getting introduced to Lars Nielsen, who was over at Snowflake at the time by John had introduced me and I was like, yeah, like, Lars, what do I do? And he had just shared with me, he's like, you know, do really great work, but also try and get experience, as much experience across all the different segments and all the different sales motions in sales development. And you'll essentially be so good that people can ignore you, you'll start to get dragged into promotion. Uh, so I had that mindset and I was kind of executing against that plan. So, you know, gong I did commercial airtable. I was strategic enterprise culture amp I was mid market. And I think as I was going through these things, I also was like, where are the opportunities to continue to move up? I was also looking around at folks on LinkedIn and not from a matter of like jealousy as to say, oh, other people are moving ahead at a faster rate than me. Wham. It was just more like, you know what I'm seeing the kind of investment that I'm making into sales development leadership in pursuit of these goals that I have. And I feel like it's taking me a lot more work and efforts than I necessarily have capacity for. So by the time I had gotten to Lattice and I moved into a senior manager position, I, um, won't say that I was burnt out yet from the position, but it did feel a bit like, you know what, this isn't exactly what I thought it was going to be when I initially made these plans. So I think for me, big things that changed were like values. It was also looking at, for me, like my relationship with stress and how I wanted to start to disentangle, like, I think like an addiction to it. Um, and so even as I remember like starting to step away from Lattice, had some personal things pop up where I'm like, I just can't ignore the fact that it does take a lot. It's a lot of emotional capacity to lead sales development reps. It's a lot of emotional labor to manage all the different stakeholders internally. It is a lot of like, to me, like mental anguish to consistently need to advocate for a department that not at every single company, but a lot of times isn't given the same level of respect and credit and merit as other teams in the go to market function. So as I really started to just think about, all right, well, what do I want my work experience to be like? Just me as an individual, not thinking about a brand, not thinking about a title, not thinking about anything like that, but just, you know, what's going to be the best thing for me, my health and what I'm trying to accomplish without needing to completely blow up my career. And so an IC position as an AE at, uh, a company where I'm like, hey, if I was a sales development leader, I would want my team to have the solution. So it just ended up working out really well. Plus, my manager is someone that I knew previously. So, you know, it just seemed like the right move where, again, I'd have way less stress, a lot more flexibility, a lot more control over my destiny as well, versus needing to influence my destiny through other people. And just thinking about those kind of things started to give me a lot more peace of mind. Um, so at night, the things that keep me up before I start going to sleep is like, all right, I had somebody who wants to extend a trial beyond the freeze, the two weeks that are free versus as a manager, it was like, how am I going to get four of my people to their number, right? And how do I support people who are on a coaching plan, who might be on their way to performance improvement plan, or, you know, if I need to let someone go, like, how do I do that with dignity right towards them? So when I think about, you know, the weight of the job, I think the weight of an SDR manager is just a lot more than with an AE. Plus, you can make more money as an AE2 with a lot less stress. So those are a lot of the things that came into consideration as I made or committed to making that switch.

Speaker B: That's a different perspective than I definitely expected because I was expecting a lot more of, oh, you know, I want to make more money. The way you're m balanced. This is phenomenal because you obviously put your mental health, your overall health at first as well, and obviously, and I totally agree with you because I've been an SDR leader for six years. It stacks saying it's a timeless job and the, uh, grind never ends. Uh, as an A, you could probably meet your, uh, you know, quota in two months and get, get away with it, probably have a month off. But you can't do that as an SDR leader because there will always be a new month. So I totally hear you. Anybody who's watching this, and I'm pretty sure there was a recent chat in One of the SDR leader community I'm part of, where two people actually brought up the same thing. And I told them, I'm chatting with you, uh, and they might have also reached out to you and you know, you. Because you were the only person who came to my mind who've done this, uh, who've taken the journey. What kind of, uh, let's say if you were to tell somebody, hey, this is the right time, or these are the things which they need to look at before they make the switch. Besides, obviously, you know, the stress or let's say the money part, is there any other for which you want them to consider?

Speaker A: It's a great question. So I can only go based off of my own experience. Right. So this is how I've typically gone about making decisions when it comes to my career is a lot of it is going to stem M from, okay, what are the things that I value and what's important important to me. And once I've kind of outlined that, what I'll start to do is almost take, um, inventory of, okay, well, what are the things that I'm doing on a day to day basis, what are the decisions that I'm making or what are the choices that I'm making and do those align with my values? So when I first got started as an SDR manager, the thing that I valued was, you know, I was started as an individual contributor and my value was I'm, I'm trying to get promoted as quickly as possible. I was 26 at the time, right when I joined this new company, um, or I just turned 26. And so I was just, I was just thinking, like, how do I get promoted? How do I move up? And I do think a lot of that was stemming from, like some kind of anxiety or maybe feeling not worthy or feeling I had to prove myself. So coming from a place of scarcity big time, and I think within the SDR manager position, at least the experiences that I had, I think it reinforced that a lot. So whether it was, all right, hey, our team is hitting their numbers. Okay, now go do more, right? Or okay, teams are not hitting their numbers. There's some kind of internal reason for that. Like, there's been a lack of planning or whatever, and it's like, hey, Gabrielle or gb, you know, like, why isn't your team doing this? What's going on? And so just feeling like I'm carrying the weight of the world, like, I'm never enough. And there came a point in time for me where it was just like, I can remember last year. Um, I've been on a whole, like, personal healing journey as well, overcoming some PTSD stuff too. Just asking myself the question, when do I get to be enough? Right? I just realized that, you know, it kind of was living aligned to not being enough. So when I started to work through a lot of that, then I had to look at my career choices and go, how might my career choices be reinforcing that? And so when I started to, like, let it go, right, where I'm like, I don't need to be promoted. I don't need to rise up in the leadership race. I have nothing to prove whatsoever. Like, I can if I'm being honest. Like, one of the things that I told myself was, I'm allowed to be average. Like, I'm allowed. I'm allowed to be average. And I don't have to be in the limelight. I don't have to be promoted. I don't have to be exemplary. Like, I can just do a job and I can do a good job and I can just take care of myself. And if I can do that, that is success. So you know what I really like the big value change was just I started to value me over everything else. That's. That's really what it was. So, like, how can I just take care of my person, take care of my human and as well as. Because I do have a certain lifesty style, right? While also being able to see that the lifestyle that I have or that I want to build is also a form of caring for myself too. So the AE position just aligned a lot more. So I'm not, I'm not having to deal with. I shouldn't have essentially not having to deal with the politics that, you know, management includes, especially sales, development, management. I don't have to, you know, be in those conversations to try and advocate for the validity of the department or feel like I'm my me and my people are being threatened, employment wise. I don't have to, you know, put everybody else first because that's how I let as well. And I think that's a lot of reason why I had a lot of success too. So I'm like, I don't always have to be in service to other people, right? In order to be in service to myself. Let me just prioritize me, right? And that's where it's like, all right, within an IC position, I can, as an ae, I can accomplish all the things that I want to accomplish. I can meet all the needs that I need to Meet and I can still value myself and have a lot more space and time to do things that I need to do in order to continue my healing journey without that impacting how much I'm able to show up at work and the people who might report to me. So, uh, I know it's a little bit long winded, but like, that really was kind of how I thought about things. And I think the second part to this too is just realizing like sales AE life is like, it's not rocket science. A lot of the lessons that we learn in sales development, uh, management and how we, you know, affirm our people, how we coach our people, develop our people, but also teach them the kind of mental resiliency in order to withstand an SDR position and do really well. Like it comes in handy. So, you know, I'm able to be a much better coach to myself and a much better advocate for myself and cheerleader for myself now, since I have a lot of practice of that, doing that for other people. So that's a bit of a long winded way of answering your question.

Speaker B: No, thank you. I love that. In fact, you answered one of my next question, which was the question I'm going to ask actually has two parts. Number one, which you already answered that it's not rocket science. Anybody can learn it. Now, you did have an unfair advantage, right? You had a good brand, everybody knew you, right? So it was, and I'm sure there was opportunities which were lined up for you, but that might not be the case for everybody who is currently an SDR leader. There are other factors at play, which is, and I'm seeing this a lot, uh, nowadays across the globe where people are putting like an age limit where they would not put, you know, to put it out there, however, mentally they are actually checking you out if you're above a certain age. North and other SREA leaders are actually above 30. Now, I know in the US it doesn't really matter as long as you can, you know, perform the job. But globally, I've seen that this might be a case where, let's say SDRs over 30 are not given the first preference versus somebody who is, you know, 25, 20, 25. My first question would be, how did you prepare for the E role? You had a brief role earlier and you obviously had good mentors. But somebody who's an SDR leader today, how can they prepare themselves to, let's say, transition out of the role to an AE role in the next six months? What can they do to prepare?

Speaker A: Uh, absolutely. Well, I think there's, there's one thing which is like, I do have a brand, but that that brand was earned. So of course, right? So, you know, every. It wasn't to say that, right. To prove a point. It's just more to go. And I think also for me, as a black woman in a predominantly white male environment, like, there's a lot that I do have to prove, just in addition to probably compared to what most other people have to do. And so the things for me, like as an SDR manager, the ways that I had to go above and beyond in order just to be given the same level of respect as somebody who just entered into a position, who didn't even have as much management experience as I did, it was, I had to understand how sales thought about things like if my team is delivering a, uh, less than quality work product in the form of meetings and pipeline opportunities, that reflects very poorly on me. So with my team it was always about, like training on, all right, how do we, how does an AE think about the world? How are they thinking about targeting, how are they thinking about prospecting? How are they thinking about qualifying and what needs to happen and what kind of impact does that have later on in the funnel? So I can think about, you know, when I was at Infutor, that meant, like, on our dashboard, we looked at how is your pipeline that you're delivering progressing and how is this resulting in revenue? As a, as a manager at Gong, it was looking at what are all the different metrics that AES are measured against, like conversion rates and quality of pipeline or quality of their execution, and bringing those AES in to talk about, hey, what is it that they're doing that starts to drive that kind of performance at an above average level? So, you know, as an SDR manager, I was always trying to find ways of bringing insights back to the team that weren't just siloed to our department, but it was going to be things that are going to have an impact on pipeline. So when he looked at what my team was doing compared to the teams that other managers were leading, you know, we had the highest conversions down funnel, we had the largest, uh, deal sizes that were coming through. We had the biggest impact on revenue as well. And so I think a lot of that just came from building a certain level of like, sales maturity. Um, and so when I started to go into the interviews, like, I still had a lot to prove. I couldn't just show up with my name and with my brand alone. I had to show up and deliver at every single one of the interviews. And I also thought about with my manager, it did help that I knew him previously, right, that we had conversations, that he could trust me, could see me as credible as a professional. The next piece of this was making sure I didn't make him look like an asshole. I was going through interviews, right? So that meant like showing up, it meant going the extra mile, right? And it's little stuff like sending over recap emails, not just thank you emails, right? Oh, thank you for the time. But it's like, hey, like here's what we discussed. So really running it like an ae, starting to multi thread the account as well, uh, engaging with different leaders, also looking for ways to deliver insight. So with this, this company, I got a little bit lucky in the sense that how I heard about Common Room was they were selling to me at Lattice and I was really, really interested and I was trying to be an. I was an internal champion. I ended up taking some time away. I did, I went on leave. So the deal got lost. And so I'm retelling our head of revenue when I was interviewing, like, hey, here's how I would have sold Lattice, right, If I were you. So I'm like, hey, like I was your champion, I left. That's probably one of the main reasons things went out. So here, you know, here's what was going on at the organization. Here's how they're measuring success. Here are the individuals that I would have gone to. Here's how to frame the solution as well. So I'm really showing that, hey, like I already have what you need from a, uh, from a skill set basis or a sales maturity basis. There's going to be some learning that I have to do. Plus here are all the strengths that I possess as well that came from SDR management experience. So I really stuck with my strengths. I try to demonstrate as like as much sales maturity as possible, right? So everything from, you know, uh, the questions that I asked, how I responded, the demo that I ran, right? Information that I was sharing in between those meetings, right? Like really managing the deal, like really managing the interview process, getting ahead of objections, right? Asking more questions, getting my, getting my now boss to be the one to go, hey, actually here's the reason why the concerns that others in the organization have are not valid. And here's how we can get over those, right? So getting someone to articulate this is why we should have like this person or this solution, that kind of, that's what we'd want an AE to do. Right. So I think it's just, you know, emulate a really great AE and show that you're a really great AE right now even if you don't have the title, while also realizing you have a lot to offer just based off of the experience you've accumulated in sales development management.

Speaker B: I do have a follow up question on what you just said. It might be considerably easy for example, for an, as your manager, let's say transition and you know, become an AE in the same organization, opportunity arises. And I think some of the tips which you mentioned can also be applied where you're trying to learn a job, you're trying to learn their world and trying to, you know, then apply outside. Do you see people are more receptive to some, I mean like I said, you're the only person I know now I've seen, you know, recently I saw Harry Sims made the uh, you know, switch similarly. But do you see where the companies are actually open for these kind of transitions?

Speaker A: I think so. I think. Here's, here's my thought. Talent is talent and yeah, cream always rises to the crop or yeah, cream always rises to the top. So if you, if, if you're really good as a professional, that's all that matters. That's my take on things, right? So like if you are, here's my, my opinion is if you are a subpar professional, just in general, if you are delivering a subpar work product, right, you're probably not going to have as many opportunities as somebody who does. So as a sales development manager, like think about what makes you successful, what helps you to deliver a really great work product. Great, wonderful, like apply that to the AE position. So maybe there's a lot of, so for example, a lot of the things that I'm seeing is there's a big focus on generating outbound or self sourced pipeline. So if you're an outbound sales development manager and that's all you've been doing, you actually have a head start compared to the rest of the folks. Just because you don't have closing experience or because you're maybe not as experienced experienced with that skill set does not mean that you can't compensate uh, for that in other ways. So like stick with your strengths. I also, something I should say as well is the one thing that I think is super important to share here is that I knew my boss before I joined, before I even knew that I was going to go and interview for an AE position. So we had a relationship like based off of last year as manager to manager uh, he was a little bit newer to the position. I had a lot of experience, so it was very much. We were able to connect as peers. And so there was a lot of respect that was, that was shared. And when he had said, hey, like, you know, I've joined this new company, and I think I had told him I'm considering moving into an IC role, he's like, I would hire you in a second. Because we had the credibility established. We had that trust established. Like, he saw me, I don't know. It's like, you know, saw me as an equal. And it was never a, hey, you don't have this experience, but it was very much a, hey, I can get you an interview, but you need to deliver. Right? So I do think it is important to be able to have people who can be champions and advocates, uh, of you, especially during the hiring process. Um, but again, it's the same stuff that you would want to see from an ae, which is, do you have a champion internally who can sell for you? And if you don't, the deal is dead. Right. Do you know who your detractors are? Uh, and is an, are you and your champion coming up with ways to be able to neutralize the impact of those detractors? So I think if you don't have those people, it's going to be much harder. So I would definitely recommend, like, tapping into the network. Into. Yeah, like, hey, if you don't have a network, develop it. Join professional organizations. Get a mentor, for example, like, really shop around. And like, if you do have any. I had to learn this lesson a while ago, which is, hey, someone's going to come up to you and it's going to say, how can I help you? Right? Have an answer. That's my take. I want to get into an IC position. I want to get into an AE position making X amount of money, right? So, like, if you know of anyone or know of anything, please, you know, refer me to them. And so I think I've gotten a lot of opportunities, whether it's a new job or, like, I had the newsletter called the One on One, right. Which was a new experience. But that first started with knowing what I wanted, knowing where I needed help, and just not being afraid to say that to other people.

Speaker B: That's, uh, that's definitely a very interesting insight. And I, I think I thought I knew you, uh, based on your podcast and based on your social life, but I think I'm getting a sense that, you know, it was a different whole story. And when you narrated that. Thank you so much, Gabriel, for coming to the show. I know we have only two minutes, so I do have a very small rapid fire round for you. Something to keep things like, uh, if you're ready, I can just shoot the question.

Speaker A: Yeah, let's do it.

Speaker B: All right, awesome. So you get only two seconds to think, and if you. If you don't know the answer or if you don't want the answer, just. Just pass. Okay. Ready?

Speaker A: Okay.

Speaker B: All right. Phone calls or cold emails. What's your pick? Uh, cold calls, your favorite sales tool you can't live without, which is not gone.

Speaker A: Ooh, sales nav.

Speaker B: Uh, the best city for networking.

Speaker A: New York.

Speaker B: One sales cliche you love, actually, Austin, Texas.

Speaker A: Austin, Texas, is the best. That's where I just lived. Austin, Texas, is the best for networking.

Speaker B: Okay, all right. One says cliche you secretly love.

Speaker A: One cliche I secretly love.

Speaker B: It's cliche. Yeah.

Speaker A: A cliche. I don't know. I always just say, like, progress, not perfection. I don't know if that's cliche or not, but that's just what I live by.

Speaker B: Okay. Uh, now, it's not that the cliche is higher end, but probably it is.

Speaker A: Yeah.

Speaker B: The last question. The most creative icebreaker you have used in a call. Uh, on a cold call.

Speaker C: I.

Speaker A: Funny enough, I haven't used icebreakers and cold calls. I'm very much a. Like, get to business first with somebody and then do funny stuff afterwards. But as a manager, the best icebreaker that I've heard is it's a guy on my team named Jordan. He would call a prospect and he'd be like, oh, hey, good morning, Rahul. Oh, one second. Like, that's just my dog barking in the background. He doesn't have. He doesn't have a dog. Uh, but people would just, like, warm up to it. He's like, yeah, wait one second. I'm sorry, my dog's barking in the background. You know, but he didn't have.

Speaker B: I'm gonna try that. That's.

Speaker C: That's clever.

Speaker A: Yeah, it was fun.

Speaker B: It was truly fun. Thank you so much, Gabriel. It was a blast. I truly enjoyed and I think I learned a lot. Good luck with your next call. Take care. Bye.

Speaker A: You too.