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Derek: [00:00:00] All right, Gabrielle, thank you so much for coming on the show today. I’m super pumped.
Gabrielle: [00:00:06] I’m pumped as well. Thanks for having me, Derek.
Derek: [00:00:09] you know, I knew, you know, for everyone who’s listening, this is at least the second thing that we’ve done together. You did a talk for the next level sales leadership summit earlier this summer.
you’re actually sort of the inspiration for this podcast because your. Talk like, it was just, it was just like you and I hanging out, you know, that’s the talking, which made will always make sense. But, you know, after that, I was like, it would just be cool to have people on and do it all the time. sort of for the same target market.
But could you, you kick us off by just telling us it’s a bit about your history and how you land, where you are now.
Gabrielle: [00:00:48] Yeah, 100%. So a little bit about my history. I started off in tech sales back in 2015, initially as a sales development rep, I knew I wanted to get into sales. I figured it would lead me down the career that I wanted to go down.
And now five years later, I’ve, I’ve gone from being an SDR to being a sales development manager, to also doing sales management. And so now just focus the on managing SDR and I’m like, well, I’m done trying to. Balance multiple plates all at one time. But Estero management is what I’m doing at the moment.
I’ve been an SDR manager for the better part of three years now. And, and funny enough, I’ll be starting a new role as an STR manager at gong. So by the time people are actually listening to this, I will already be there. Cool.
Derek: [00:01:32] Congratulations on that.
Gabrielle: [00:01:34] Thank you really cool company.
Derek: [00:01:36] how did you know you wanted to be a manager?
Like how did you make that happen?
Gabrielle: [00:01:40] Ooh. I don’t think that I knew that I wanted to be a manager, like, but I knew that I could, I knew it took to be successful as a sales development rep. And so back when I was an SDR, I had quickly kind of asserted myself as one of the top performing reps based on the results and the manager that I had at the time.
Was chatting with me one day and was like, Hey, once you figure out how to operationalize your success and essentially like, make, create a structure that people can follow, like that’s really, when more opportunities are gonna present themselves for you. So, Maybe a year and a half after I had gotten that recommendation, I was in an opera.
I was at a company that was going to be hiring for an SDR manager. I was an SDR. I had a lot of opinions and a lot of ideas as to how sales development should be done, how we should structure it, how we should enable the SDRs. just like what the end to end. Top to bottom program is going to look like.
So that’s really what I raised my hand. And I said, Hey, I think I can do a really good job of building up this program out. So, I didn’t, I don’t think I really knew for sure. Like, Oh, I’m going to be a manager. I’m going to be in leadership. But I knew that I had a lot of thoughts and opinions as to how things should be.
So when the opportunity presented itself, I was like, Oh yes, like, let me, let me give it a go.
Derek: [00:02:56] So you went straight to whoever like the head of your boss and give me a shot. I want to do this.
Gabrielle: [00:03:03] Yeah. So I had, I mean, I had raised, I had a funny enough, I was talking to Kevin Dorsey like a couple of weeks ago about re like, you know, coming in, number one, raising your hand.
And he challenged me to not just raise my hand, but also to raise my voice. Right. So like, for me, it wasn’t just a matter of like, Oh, Hey, like I’m here. Look at me. It was. Hey, to the VP of sales, somebody who had come on board two weeks after I joined the organization. And at that time there was not an SDR.
There was not a dedicated sales development manager. So, and that first meeting that I had with our new VP of sales, I was like, Hey, here’s what. I’ve done this far. Here’s what I have the potential to do. And here’s how I see that looking here specifically at Cloudability. So two months later, the job post comes up for an SDR manager number waiting for somebody to say, Hey, we talked about this two months ago.
That never happened. So I ended up having to like, again, like. You know, raise my voice again. I’m not yelling. Right. But letting people know, Hey, like here’s what I’ve done in the past. Here’s what I have the potential to do. Here’s how I see things looking. And I would like to help. Right. I would like to, I would like to understand how I can move into this position and what you need to see from me in order to feel confident, making that choice.
So, yeah, that was, that was really what happened in order to get into the SDR manager position. Cool.
Derek: [00:04:22] So you, you had to advocate for yourself and. Come up with a thoughtful, I don’t know if plan is the right word, but like
Gabrielle: [00:04:30] talk about what you do in the role. Yeah. I think whether it’s raising your hand or making it known that you want a promotion to become a manager or anytime that you’re trying to present a new idea.
Coming up with a, here’s what it will look like. Right. Here’s how we get there. And here’s what I need from you. If you have that kind of clearly mapped out and you’re able to clearly articulate that, like I do believe that’s going to be incredibly. Influential in getting you to that place that you want to be, or seeing that idea that you have manifest.
So that is the process that I went through was again, sending out an email, like here’s my results, like from the bike for the past, however many years it is, here’s what I’m most like, here’s how I can make an impact right now. I’m like, help me understand, like, what do you need to see from me in order to feel confident and comfortable moving me into this position?
What happened after that was. Let’s do a business plan so much in the same way. If you were to interview for an SDR manager at a lot of companies, right. And it’s not just an internal promotion, usually apart, like usually the, the final interview is, this plan or 30, 60, 90 day plan of how are you going to get yourself up to being successful and how are we gonna prepare the team to be successful in a sustainable way?
Cool.
Derek: [00:05:49] And were there, were they interviewing external candidates as well?
Gabrielle: [00:05:54] I think so. but I, I think I might’ve been the only person who interviewed for all. I know. So. But I think that’s an important piece here because, so, you know, I came up with the business plan. I presented it to our VP of sales.
So the panel, right, who was, who I was presenting to was our VP of sales, our head of revenue, operations, our director of sales, our chief marketing officer, or a VP of marketing, as well as our head of HR. Right. So that was the panel. And what I had shared with him was this, you know, this 30, 60, 90 day plan, I had all the details just in case they ask me any questions that weren’t initially on the prompt.
And the final piece was the close. And so nobody was asking me to close, but my part was what I asked them at the end of this presentation was, you know, like help me understand again, what is it you need to see from me, right. Or what, what else do you need to see from me in order to feel. Confident that I am the absolute best person and that you should move me forward.
and. And, and I also kind of like, almost like, you know, I stuck the knife in and then turned it a little bit more when I said, when I started to paint the picture for them as to here’s why you should not hire externally, like, think about the cost, think about the ramp up. Like I already possess kind of like that domain knowledge.
I know our internal processes. I already know the team. So much more like I’m so farther along than any other external hire will be an ask yourself, like, what is that going to cost you? Or where are you not going to be able to do? Should you go and explore that other option? So like that’s the piece for the internal hire.
Right. but I definitely have lost job opportunities because they promoted internally when I was coming in as an external hire. So I’ve definitely like suffered both ways.
Derek: [00:07:36] You did a good job of answering that objection before it came up. When, when you were the one.
Gabrielle: [00:07:41] Yeah. Yeah. And also, I think as a first time manager, one of the biggest objections that you should prepare yourself for, or if you’re an aspiring manager who doesn’t have people manager experience is.
Are you like, are you, it’s almost like, are you mature enough to get into that position? Especially if you’re a younger person. I got promoted to a manager when I was, I had just turned 26. So there’s Oh, there’s going to be a question around maturity. There’s going to be a question around, like, are you going to know how to manage people?
I think there’s also going to. I think those are really the two big things it’s going to come from a matter of like, you know, not having experience and as this organization, if it’s an internal promotion, right. Is, does the organization feel competent and comfortable that you possess kind of the qualities, and that raw talent or to succeed in a management position?
So like the more that you can prepare for that objection, the better, the better position I believe you’ll be in.
Derek: [00:08:35] Cool. And, how did you learn to manage people?
Gabrielle: [00:08:40] Through trial and error, honestly. No, like I, I, I think one of the things. One of the dis I, I think one of the disservices that I did for myself, the biggest disservice that I had for myself was expecting to know exactly what I was doing without ever having done it.
So, in that, that just puts a lot of stress on. So one of the things that I, one of the things that I kind of wish that I had done more, but maybe did a little bit was recognized. There’s going to be things that I don’t know. And I don’t know what to do. So, it could be everything from, how do I know, put somebody on a coaching plan versus a performance improvement plan.
How do I know to kind of like, you know, pull the cord on an underperformer or somebody who’s not really abiding by the operating principles of this company? what happens when we have a top performer who might want to leave the company, you know, or doesn’t feel challenged by the role? So for me, I’m like, I’ve never, I had never experienced those conversations, from the management point of view.
So. I have a couple of options. I can either try and wing my way through it and then see what happens, right. Or I can go and ask for help. Right? I can go to folks who have maybe already done the job before, who can offer some advice as to how to better. Approach those kinds of situations. so that’s why I think about the trial and error.
Like there’s times that I tried on my own and it didn’t feel right. It wasn’t a great response from somebody that I was managing. So I go back, I go to my mentors, my advisors, my boss, you know, those supportive people can provide productive and constructive feedback. And then try it again. And so taking notes, documenting the process, thinking through like, all right, well, what is the objective that I’m trying to get to?
And as I’m communicating with people, whether that’s the people I’m managing or the kind of cross functional peers that I have, like, are we driving towards that objective? Or is there something getting in the way? So it’s like, or if there’s something getting in the way. Like, here’s how I can adjust my approach next time and see if that might, that might work.
So it really is just a matter of like AB testing, different approaches depending on what the situation is presenting.
Derek: [00:10:43] So can you talk about, tell us a little bit more about what the errors right
Gabrielle: [00:10:48] on the trial,
Derek: [00:10:48] on their side, like your steak that you made and tell them you put your foot in your mouth, something like that.
Gabrielle: [00:10:56] I think, I think my first time being a manager. so this is Cloudability era 2016 or 20 early 2017. And I had a person on my team who, the best way to, like, I don’t want to like, talk bad about anyone, but I think one of the challenging parts was going from a peer to now being somebody’s manager someone’s boss.
And especially if that peer is someone who’s been at the company longer than you. Right. So I think in that kind of situation, you only, if that person feels as though they have power in the situation because of how long they’ve been at the company, or maybe they’ve gotten better results, something on those lines, like to meet that person with that same energy of like, Hey, like they’re coming in with a power move and now I’m going to come up with a power move.
We’re never going to really come to the same page. So for me, I think one of the challenges was I need to better understand how to deescalate situations. Rather than pour fire on them. So like that to me, was it like, so whether it was again, like. Someone doesn’t agree with how like with, with, you know, with a new territory model.
Right. And how do we deescalate that situation? How do we reassure them that they’re still going to be successful versus it coming off as though, or, Hey, all this change is happening. There’s all this chaos that’s happening. And this person has all of the fun defensive. I, I I’m, I misinterpreted that person’s defensiveness as.
A personal attack against me and not just this person reacting to a very chaotic situation. So I then that showed up in a bunch of different ways, but like that to me was like the biggest. The biggest source of frustration is like a first time manager. It’s like, why is this person not agreeing with me?
Why don’t they like me? They’re not going to work on my team. It’s like, Oh no, my job as a manager is really to help them understand, well, number one, it’s to roll out plans that should improve productivity and performance. Right. And then. And then share that vision and reinforce it over and over again that it’s like, Hey, like this is, this is we’re going to create conditions for you to be that much more successful and reassure them along the way, rather than saying, listen to me and listen to me now.
Derek: [00:13:10] Yeah. Yeah. It’s really good point. You can’t fight fire with fire, so it doesn’t work.
Gabrielle: [00:13:17] I was, I’ve been reading, Oh, this book, pitch anything by Oren Klaff or cloth, whatever his last name is. And there’s this idea of frames, right? And everybody’s going to come into a certain section as soon as you have like one, like two people, each person is going to have their own kind of frame of reference or frame of mind and their.
And in that, like when you’re coming into like the same area, you’re trying to have a conversation with someone it’s those frames that they can start to be combative. So it’s either like I have a choice. I’m either going to just come back to this person and like, what does that actually going to do? Or it may be taking a step back.
Better understanding, like what this person’s frame of reference is, where are they coming from? Are they worried about this change? Because they’ve been in another organization where there was a territory change and they lost their job. Like, are they just responding to like things that happened in the past?
And it has absolutely nothing to do with me or the situation right now. or, you know, like, or is there something that I might be missing because they have a better perspective or closer to spec perspective is something that I haven’t yet considered. So I think I just. I had to take a step away from just seeing my frame of reference as the end all be all and say, all right, this person that actually helped me can help me better understand how to roll this out effectively, if it’s a new plan or it’s also an opportunity for me to engage in a way that builds more trust and confidence between the person I’m managing right in me, because I’m taking the time to listen to them and really understand where they’re coming from, rather than just assuming.
And making a judgment as to what their frame of mind is.
Derek: [00:14:54] So how do you open that up? How do you uncover somebody it’s frame?
Gabrielle: [00:15:00] I think it’s just kinda, it’s like discovery, right? I mean, I think more than anything else you want to understand people’s motivations and drives and, aspirations. I think that’s really all where it starts.
but in order to get that information out, it takes time. it’s almost, I don’t think that’s, you know, I don’t think it’s appropriate to say like a boss and the person who’s reporting to them. It’s like a, it’s not like a romantic relationship, but think about like, if you’re going dating with somebody, right.
you need me to build, hold up a relationship and build up rapport and learn about that person before you’re able to truly commit. To being in a relationship with them. And so to come into a situation and just because you have a title doesn’t mean that you have a relationship with this person. So like, just because I’m a manager and I’m their boss, like I was like, I still need to go through the work and show, Hey, I’m personally invested in your success now, but the thing is, I need to understand what success means for you.
So over the course of the next, however much time, like I would like for us, Talk through, and maybe even do some exercises to further reveal. Like what does success mean for you? And what’s the best path to getting to that? So like that is a dynamic process. there’s there are like questionnaires, that’ll ask people at the very beginning.
So this company that I’m just left in Futura, when I first came in, I did a new manager questionnaire with the reps. They inherited a team of three people. And so in this questionnaire I’m asking like, what do you, where are your goals for the next year? Three years, 10 years, then I wanted to know, like what had been promise to them.
Right. Is there, have there been promises around raises or promotions or increased responsibility, something like that, those lines like help me understand, like what, like, where are you tracking to that? When are you expecting these kinds of things? Like, why is that actually happening? And so the more you can dig into like, well, Hey, you told me that your one year plan is to do this.
And why, why is that important? What does that opening up to you? And some, I want to make more money. Why, where are you going? Like where is that money going to go? Oh, I want to buy a new house. Because like, that’s incredibly important to me. It’s like, okay, cool. Well, what do you need to get there? And what does that mean?
Like what results do you need to hit this year? What were your results last year? How are we going to bridge that gap? And so now you’ve become a partner in their success and they’re like, Oh shit, I’m not alone in this. I got somebody who like, understands why I’m moving the way that I’m moving and where I’m moving.
So like, and that to me is like where we’re going to actually drive alignment.
Derek: [00:17:32] That’s solid.
Gabrielle: [00:17:35] I was like, I was like, did I black out a little bit when I said it?
Derek: [00:17:40] so I read pitch anything like five years ago and I’m like, I don’t remember any of it. So thanks for the refresher.
Gabrielle: [00:17:46] Oh yeah, no worries. I, yeah, I’m only on page 30 right now, but, and there’s a lot of stuff in here. It doesn’t. I haven’t gotten into like specific tactics, but there are a lot of concepts in there where it’s like, Oh, this is definitely good to know.
Derek: [00:18:01] Yeah. Smart dude. I remember thinking he was really smart and tried to implement some of the things, but I couldn’t tell you what they were like. I have no idea if that worked or not, you know?
Gabrielle: [00:18:14] All right.
Derek: [00:18:16] What would you say, Gabrielle? What would you say is your super power as a leader?
Gabrielle: [00:18:20] I’ve gotten this question. Maybe, have you asked me this question? You might have asked me this question. I don’t know somebody I’ve gotten this question a few times in the past few months. I think I really, really liked this idea of a tuning to another person. And so, and, and, and I’m probably gonna butcher like what attunement actually means, but the way that I conceptualize it is, It’s almost like, imagine like a mother and her baby, right?
The baby can’t talk, baby. Can’t tell you whether it’s hungry or not. and so there’s mother, like mother has an opp, like has an option like this baby is crying. It’s freaking out. Does it know like. Can’t can articulate itself. The mother can either be like F all of this. I don’t know, like walk out that room.
And that baby is basically going to learn that, Hey, my needs are never going to be met. So why even speak up? Like, that’s going to be like, that’s the reinforcement that’s happening, or this mother can. Attuned to the baby. Right. And making it temp, understand the baby, recognizing that the baby is not yet in a place articulate itself.
So like what this mother is going to do is respond to what’s happening. Right. And try different almost like different stimuluses out to see like, alright, is this what’s going to help Sue the baby and get this being back into a kind of a calmer state, into a more comfortable state. And like that to me is what I think my super part is with my reps.
Cause I’m like, I forgot a rep. And again, like if this rep is like, Hey, I don’t feel challenged. I want to leave. I want to, but I think there’s a bite, you know, I gonna say bye. And so maybe the rep doesn’t actually want to leave. Maybe the rep hasn’t yet understood how to articulate. What’s really going on.
It’s Hey, I really appreciate this environment or really love this team, but yet I’m not really, I don’t really know what my place is next. And can you help me figure that out? Right. So with me, I’m going to start asking some questions like. Or I’m going to say, Hey, like here are a few paths that I think are available, right?
I’m gonna give you some stimuli. Let’s see what we can do to challenge you in the SDR role itself. I’m going to go and have conversations and like, let’s get you prepared for that next role for some kind of enablement planning or program. if those, like let’s at least go through these things and then keep in touch while on the way and kind of track what that engagement is like, what that morale is like, what your enthusiasm for the role, what your commitment for the role or this company looks like.
And also know that if you truly don’t see a place for yourself here, like that’s okay. And we will, like, I will personally, I will be personally invested in getting you to a spot where you do feel like you can engage and commit, like whatever that is. And that means like recommendations, helping with resumes, getting you like interviews introduced, like socializing your, your, your resume all over the place.
So like that to me is like a certain process of attuning to that person, really understanding what’s going on and trying to further reveal like, okay, well what’s really going on here. And like, let’s agree on what this piece is before, before I just start dismissing anything. Wow.
Derek: [00:21:18] Okay. And that’s sort of the same thing you were talking about before, where it’s like a
Gabrielle: [00:21:22] discovery.
Conversation. It is, it is. I think one of the things like a first time. Okay. Let’s, let’s kind of contextualize this in sales. what’s like the difference in my mind, there’s more, I’m going to make this super simple, right? So, the difference between a rep, who’s been at a company for five years, like a sales rep and eight E in a rep who just got to the company.
Right. I think the main difference is the insight it’s that our rep who’s in such as a representative, like, you know, coming in and checking in and checking out the difference between the two. It might be just a matter of insight. So they developed through those five years tenure at the time organization.
So it’s going to be like the product, the accumulation of insights developed through having conversations and seeing a lot of things, just a matter of exposure. Right? And so this, this new rep. Might not have that confidence, that insight would bring, like, I was like, all right, Hey, I’m learning everything.
I haven’t quite understood all the different use cases. Our platform can support. I’m not, I’m not familiar with all the different ways that our customers are leveraging our platform. And so therefore can’t provide those insights. Same thing goes for a new manager, right? The difference between a new manager and maybe more experienced manager is.
I’ve just had a lot more, I just had a lot more conversations right. With these people. So like once I’m, once I’m more familiar earlier with those conversations and what to expect from it, I can have a better response to it. So. It’s like, all right. Hey, like, I can’t tell you how many times I’ve had, I’m struggling with managing my time.
Like conversations are so like, it happens all the time. So I’m like, all right, cool. Like this to me, I have an automatic response to it now. So, and then I also can better, I given the fact that I’ve had those. Had this conversation so many times have had a chance to see what’s working. What’s not working.
I can also provide options for all the different personalities that I might come across as I’m managing different people and potentially in different teams.
Derek: [00:23:23] What’s something that you either, you wish you would have done it earlier, or you could recommend it to somebody who say, wants to learn faster than just.
The experience of having the conversations and screwing up and trying again.
Gabrielle: [00:23:40] so here’s where I think has been super beneficial to me right now. Right. So, I mean, I think there’s, there is one piece where like, experience has truly helped me build confidence. I think that’s like one, one key piece. And so I think you can learn a bunch of stuff, right? You can go to all the conferences, you can have the mentors and things like that.
And also probably feel as though you’re failing because you have nothing to. To compare yourself against. so I think with that, like what I wished that I had done or something that I wish I had no known is that it’s okay to not know all of the answers. It’s okay to not know everything you don’t need to.
I wish that I had, like, if I can go back in time, I wish I had like delegated more. I wish I had said no more. Like, I wish that I would like manage my time a little bit better. I wish that I had gone and found. not just any and all mentors, but really great mentors who were going to align very well with how I talked.
How I thought how I presented myself. It’s like, if you have a mentor, who’s just judging you. Like, that’s not helpful. I’m already beating myself up. I don’t need to include somebody else in here. Yup. As well. So, that’s like, that was the experience for me. Right. Cause when I first became a manager, but I feel like my biggest struggle was.
I like kind of like lacked faith in myself or like, didn’t believe in my ability to eventually figure things out like that, that took some time to really develop that.
Derek: [00:25:08] Cool. Well, thank you so much for coming on the show and sharing all of that. Man I of having you on. So thanks for thanks so much for me.
Gabrielle: [00:25:18] Yeah, no problem. Thanks for, thanks for having me on board. I love talking about this stuff, so thanks for creating the stage to do it. Of
Derek: [00:25:25] course. Hey, where can people learn more about you?
Gabrielle: [00:25:29] So the only social media you will ever find me on is LinkedIn. So, let me just, just look up the sales development staff stress.
Gabrielle, linkedin.com/in/gabrielle block. Well, that is that’s my profile. So that’s where you can find me.
Derek: [00:25:49] Cool. I’ll also include that in the show notes, everyone.
