Putting the Sass into SaaS with Gabrielle Blackwell

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Oh my God, that's so exciting. What a great introduction. Thank you.

I've been told that that's the only reason Some guests. Come on. I'm just here for that 10 second intro. Just makes me feel good.

So, yo, I'm like living my best life right now. Thank you for hyping me up. I needed this going into the weekend.

Hell yeah, girl. Hell yeah. Well, let's. Let's do this. And we're gonna kick this off here of like, what does it mean to be a Sastris? Like, I love that term and I love how you identify with it. What does that mean, to be a Sastris?

Ooh, that's a good one. So one part of it, of course, is like, SaaS, right? Like a solution as a service kind of thing. And then I actually, funny enough, I took a break from work from like 2018 up until last year. And as I was taking a break, I was trying to think about different ways of, like, healing and recovering and like, bettering myself and improving myself. And so I really stumbled into magic. Like, everything from like Wicca to tarot cards to oracle readings, like Reiki, Anything that has to do with energy and flow and connecting to, like, a higher power or swords. And so there's this term that comes up, right, that I've seen, which is enchant. Enchantress. I can't say it right now. Yes. And so I'm like, all right, how can I have, like a play on words here of like, sass and enchanting and like, you know, having that charisma or something along those lines. And Sastris is really the name that came up for me. So it was very much like a blending of the two worlds, both in, like, you know, working as an SDR in SaaS base, but also combining that with this, like, all right, what do I do during my five to nine time as well?

So this took a massive right turn. And I'm excited because I was not ready for. I was not ready for magic and enchanting.

Oh, my gosh. And all those things.

So here we go.

Here we go.

I just threw all my questions out the window here because now we gotta talk about.

Funny enough, I have, like, people. Cause I do like a Tuesday tarot tip. Like, that's one of the things that I post on, on LinkedIn. And so I've had conversations with other professionals that I'm coming across and I let them know, hey, I'm. I'm kind of into tarot and I'll do tarot card readings. I've done tarot card readings for people I've met on LinkedIn as well. So, like, I'm into it. That is.

That is amazing. This might turn into a session here real quick where you help me figure out my life.

I was like, my cards are downstairs.

We might get there if we have time. So let's talk about this. Let's talk about where they overlap, right? Like, is, if you talk about enchanting, if you talk about, you know, tarot reading, a lot of it comes down to belief, which then leads to behavior change. So how do they overlap? How do you take some of the things that you've learned, diving into those things, and apply them to the sales world?

So I'll use tarot cards as an example. So there are, I believe, like, 78 cards in the deck. And the way that I interpreted the cards is each one of those cards is a representation or an archetype of the experiences that we will be exposed to or endure during our lifetime. Right? So if we were to bring this into, like, maybe the sales world, it's like the equivalent that I think of it as, hey, like, here's a playbook, and here are all the kinds of objections that you'll face, like, let's do flash. And then also, here's a way of being able to overcome that objection. So the tarot card in itself and say, hey, listen, like, here's something that you might experience. Here's something that you can anticipate. And then also, so here's some guidance as to how you can overcome a situation or better navigate and maneuver in that situation as well. So it's not to say that, like, you know, the tarot cards are going to read your future and everything is going to come true. It can give you a frame of reference as well as maybe some guidance and wisdom to help you manage through a specific situation.

Okay, so, Gabrielle, you definitely threw a little curveball at me here, talking about tarot cards and enchantress and magic, should we call it? And so now. Now we got to go down this path, because I want to know the overlaps. Something that I love about learning about different, you know, trades and crafts is the overlap and how they can be applied to my career in sales. Where's the overlap between what you've learned in some of those acts and those skills that carry over into sales?

Ooh, that's a good question. So, so funny if I have a coach who also does tarot card readings, and so he's been doing it for probably 40 years now, and he was talking about the, like, what, working with tarot cards or any kind of, like, divination tools Allows people to do. And that's to be able to tap into some, like, universal source of truth or knowledge. So if you can get like past the specifics, right? So like, let's say in sales, if you're only speaking the language that your company is speaking, how can you actually resonate with the marketplace, right? So, like, what's the way of tapping into the market that might be looking at analysts reports or tuning into the publications that people are connecting with the most? And so with like tarot cards, divination tools, tapping into this kind of universal source of truth, you're able to like, abstract your language enough to be able to connect with more people and at a deeper level as well. So it's not quite as superficial. So like, that to me has been the communicate. Like, it's very much like a communication tool to help me better resonate, right. And attune to other people. Other people.

And that last part there is where I was going to go next. The attune to other people. I would assume that, like being coached like that or going through that, like, your level of EQ goes up, your level of awareness goes up to read people and feel people's energy and kind of that sort of stuff. Like, do you feel that as well?

A hundred percent. So, like, when I think about the tarot cards, something I had read a couple years ago was like, the tarot cards, each card represents some kind of experience that we can go through in our home, in our human experience, right? And so these 78 cards are going to represent all the kinds of experiences that someone can go through. So it's almost like reading a book. Like, hey, if I can understand this theme or this experience, right? If I can understand the challenges, the obstacles, as well as the rewards that this experience can give, I think at that point you're able to then translate that over to, like, whoever you're meeting, right? Everybody's going to have a story. Everybody's almost like a card right at that point in time. And so in learning about the cards and learning about what they mean and being able to better interpret them, I think you have the ability to better connect with the individuals that you're coming across. Whether that's like me as a manager with the individuals on my team, right? Or as a salesperson connecting with somebody who I'm just now meeting. Like, how can I interpret them? How could I read them, how can I be very present with them? And also what can the cards maybe enlighten for me in my engagement with them?

So the real Question I think everyone's probably thinking, and by everyone, I mean is, have you ever busted out a tarot card on, like, a prospecting call or a demo? Like, have you ever.

No, no, I haven't been in, like, a. In a frontline position during the tarot cards, but I have been on. I have been, like, a meetup. So there's a. I think it's a Toronto Marketers of Toronto meetup that I got invited to. I went to a session, and they're like, hey, everybody, tell us a little bit about yourself, something you're interested in. And I was like, hey, you know, I'm really into tarot card readings. So the organizer actually reached out to me, so I did. I did a tarot card reading on LinkedIn. So I've been in groups where someone's like, hey, can you do a reading for me? So I've been able to do in the professional context, but never with a prospect.

Okay. Okay, well, I'm gonna put that out there as a new life goal to see if you can pull that off. You pull that off. Like, I'm a fan for life. That'd be absolutely.

No, that would be amazing. Like, think about it. Someone's like, oh, hey, you know, here's. Here's what I'm challenged, funny enough. I just did a tarot card reading for someone the other day, someone I connected with on LinkedIn. And so they were talking about their business. He's an entrepreneur. And so I use it like. I use the tarot cards to, like, it was very much more so a validation tool. He's like, you know, here are the things that I'm trying to do. Here are the ways that I haven't been able to succeed, and here's what I'd like to do moving forward. And so it's very much like a coaching tool. Like, hey, here are the things that are blockers for you right now. Maybe here's some of the influences, right, that are making those blockers present. Maybe here's something in the past, right, that might have happened that you need to resolve. And so you're still carrying that energy with you so you can translate to that, to a prospect, right? Like, hey, what are the main things? What are the main challenges that people are going to have? Okay, so, like, you had your unselling the status quo, sticking with status quo, realizing that, hey, the things that got us where we're at might be the same things that hold us back from getting us to where we want to be. So using the car to Then say, all right, hey, like, let's walk through the themes right now. And then let's, like, apply this to, like, how do you. How can you get a solution? And if your solution falls into it, wonderful.

That is amazing. But it's true. I mean, I think everyone listening, like, I hope, really what it's about here is discovery. First of all, finding, like, what it is someone is trying to achieve, asking great questions, and then helping paint a path of how they can get there. So that's really cool. And I was not. Like I said, I wasn't anticipating this. I had no idea coming into this. Right. One of the things I loved and was so excited to talk to you about is how authentic you are. This is a whole nother level.

Thank you.

But it's also, I think, a good segue to leadership, because a lot of leaders, where I think they go wrong is they try to make their team like them, right. They're always trying to create mini versions of them. I think early in my sales leadership career, I did the exact same thing, right? Like, try to do it my way. And what I'd love to hear from you is, you know, you are so authentic and unique to yourself. How do you help your team, like, embrace their authenticity? Like, how do you help your teams embrace their creative soul? Like, their creative, like, nature, like, who they are so they can bring it out into their sales world?

Yeah, that's a good question. And so if I think about. So I'm at my. I'm. This is my second time, right? Being in the SDR manager role. So I'd still say I'm pretty early on in the leadership journey. And so when I had first become a manager, I think I knew I didn't want to, like, make copies of myself, right. I didn't want to enforce people to, you know, follow the model that I had and do exactly what I wanted, like, that I was doing. And so. But I didn't know. I didn't know what to do instead. So I kind of, like, I think I just gave. I almost, like, stepped back, right? And so I wasn't really taking my. Like, I wasn't holding on to the power. The control. Power, control, but the influence that I can have in people's lives and in the performance of sales reps. And so I think over time, I just had to learn about, like, what does it take in order to help somebody realize their best potential? And I had to go through that journey myself, right? So, like, a lot of therapy, a lot of tarot card readings, a Lot of just having conversations with people. And so what I started to realize is like, hey, you know, there might be something that someone believes. There might be an agreement that someone makes with themselves way back when that says, hey, I'm not deserving, I'm not worthwhile, I'm not a value, or that my value is dependent upon some specific outcome. So the way that I work with my team right now, so I have. I have a few people on my team who are like, hey, listen, I'm having a good time if I'm winning. And winning looks like hitting my quota. And so it's like, okay, well, what would happen, right, if maybe we had a different definition of what it means to win and what it means to succeed? And like, hey, can we actually control if we win when that's just an outcome that's dependent upon the activities that we're doing? So, like, how can we look at the things that we're doing today, the things that we have control over, how can we look at those as opportunities to succeed and opportunities to build momentum? So it's much more conversation about, hey, like, succeeding equals progress, right? And here's how you can track progress over time. And so that's something that I learned in my personal life as I was kind of like battling my own demons. And so thinking about that in the professional context, right? Because people are like, hey, I have expectations for myself, especially salespeople of, I want to hit these goals and I need to hit these goals. And until I do that, I will never be satisfied. Like, if we, if we maintain that mentality, we're likely going to burn ourselves out, right? And we're not going to be able to realize the things that we want to realize. So let's take a moment and reevaluate the ways that we're setting our goals or expectations for ourselves. And so that to me is like the journey of how can we unlock. How can we unlock that peace with our people?

No, I like it. You know, but I'm, I'm a pressure here because this is why people like this show is. We don't say high level. We get tactical. A lot of people talk about the idea of, like, you know, controlling your controllables and setting goals that you control. Could you give an example? Right, so what would be an example of helping a rep see their wins that aren't just tied to, you know, the demo meeting schedule?

So I'll give a specific example. So there's a guy on my team, one of the guys on my team, so he Joined the company in May. And then also he was, he was our seventh hire for a program built for six people. So this all to say is I had not yet right sized the team right or optimize our territory plan. And so I knew this because I'm like, hey, listen, Ben, this is going to be tough, right, for a while until we can get this right size. And so until that time, until a time where we can actually right size, he's not actually put in a position to succeed. So what we did is just like map out month by month. Here are your milestones. So milestones equals activities by call, email, social. It looks like responses had. It looks like meeting our accounts, worked contacts, works, meetings booked, meetings completed, opportunities generated pipeline. So map out that full process. And so in order to tell a story of progress for him, right? Especially as we knew that he's not going to hit his quota quite yet. It's like, hey, let's look at month over month. What are the conversions, right, from let's say an account work to a meeting booked. So let's say month one was 642. He might not like the fact that I'm taking these numbers right now. Let's say the first month that he was in there, it's 642 accounts that he has to work in order to generate one meeting. And so now like last month, it's 222. I'm like, dude, like, that's a huge improvement. So, like, these are like the little things that we can look at just to see, hey, for the activities that we're doing, the way that we're distributing them, are we doing that in a way that is eliciting like an improved performance, right. Even before hitting quotas? Like, that's one very specific way of being able to track the milestone or track the progress by tracking milestones.

I think that's really important. And for anyone like listening to this, like, it's so important as you're leading that you focus on behaviors, not just outcomes. If you only you can't manage outcomes, you actually can't even, you can't even change results. All you can change are behaviors and skills. That's all you can change. If you can change those, then the results change for real change, right? Because we all know reps can get lucky some months. They also can get unlucky some months. And so you'll have a rep, have a great month. But if the right behaviors weren't in place, they're gonna come crashing right back down versus big time. Focusing on the right things there. So that's really cool. So then let's step to the next start. Like, you know, behaviors and skills. What are some of the ways you help develop those with your team? Like, what do you do to make sure that the right behaviors is in place? And then what do you do to make the behaviors better? Right, like, what do you do for the skill development side of things?

That's a good question. So I'll give an example. So it's kind of the exact same illustration that I had with Ben. And so let's go to the other side of the spectrum with one of my reps named James. And so James, a high flyer, right? He's an exceptional performer. And so, but last month, what we saw is like, normally if he's hitting, let's say, 120% of his quota month over month, and now, you know, in one month he hits 90%. It's still good, but it's like, all right, this is a little bit uncharacteristic. So, like, what's actually happening here? And when I look at. So when I start. So when I'm looking at the numbers, right, And I'm trying to find some kind of trend, and all of a sudden I see, all right, hey, his. His account to meeting conversion rate went from being 13 or 14% to now being 7%. And I'm having those conversations in our one on ones or in our team meetings. And I'm asking about what accounts he's focusing on. And he's telling me, oh, hey, I'm trying to experiment with like, healthcare on demand. And so I'm like, all right, hey, this is a really good experiment. But hey, like, these have a much lower conversion rate, right? So I think the first part in terms of understanding behaviors, I don't know about understanding behaviors exactly, but being able to drive specific behaviors is to show data, right? And give people almost a formula like, hey, the reason why things aren't working, I think, is because of this. And so how, you know, how do you see things changing? How do you see, like, us impacting that number? So that to me would be like that to me is like one method of being able to, like, attain or align to changing behavior. And in terms of the skills, I don't say, I don't know. I don't have anything specific, right? But one of the things that I think is helpful is to show is to have a peer, right? So if I'm managing SDRs, rather than me saying, hey, do this different, right? I'm like, you know what I think? I think Whitney has a really good method. It's one slight adjustment from what you're doing right now. But, like, you should talk to Whitney about these key things, ask her a few questions, because she's. And I know that Whitney has a super solid structure for, like, how she's structuring her day and how she can start off her week with, like, you know, with a really. With a head start. So, like, those to me, are kind of the ways of, like, all right, let's look at data for behaviors and then terms of skills. And how can we. How can we create a culture of collaborative learning and where the SGRs are really taking the spotlight in terms of sharing what's working and what's not?

And I love it. And it's a perfect segue to the next thing I want to dive into, which was metrics and analytics. Because you're talking about some metrics that not a lot of people actually pay attention to. Not a lot of people even know the account to meeting conversion or know the dialogue to meeting numbers. Right. And I saw this in actually in one of your recommendations, right, Your eye for analytics. I love that now we're speaking, like, my language, because I also love the data side of things. And so where does that come from? Because a lot of sales dev leaders are honestly atrocious when it comes to metrics and the math of sales. Where did that come from? Like, where did that level of, like, awareness or analytical thinking come from? And then what are some of the key metrics that you track for your team?

You know, so, okay, so I start. So I started off as a sales development rep back in 2015. This company called Cloudwards. Absolutely loved working there, Loves everything about it. People, product. It was disruptive in the marketplace. It was a lot of fun. And our leadership changed. And with this leadership change, we had this new person come up into, like, you know, the head of marketing and sales. And this person did not believe in the value of sales development, right? So they ended up killing the entire sales development program. So I'm like, wait a minute. I look like we were killing it? We were doing an amazing job. Like, how could someone rationalize, like, getting rid of the sales development program? And I thought to myself, I'm like, what are the metrics that matter, right? Like, how can. How can you position, especially sales development? Like, how can you, like, what is. What is needed, what needs to be shown in order to completely eliminate any doubts about the sales development, the value that sales development can bring to an organization. So that's really what launched me into, like, what are the metrics that matter? What are the different ways that we can look at the business? Because here's what I think is if you, as a sales development leader are not asserting what the metrics should be and how the value should be defined, other people are going to make up that story for you. So like that to me, like, I'm like, it's more so about, like, what is. Like, what happens if I don't. If I'm not data driven, right? Somebody can misinterpret the data. And I'm the subject matter expert. I'm the one who should be informing people as to how we should look at the business. So, like that, to me, it's just. I'm just like, all right, if I don't do this, I could have an entire team who doesn't have a job tomorrow.

It's true, y'. All. I hope y' all grab that. If you don't understand your metrics, someone else will write the story. I mean, that is absolutely gold because it's true. If you can't speak to the value of your org, if you can't also know what levers to pull to improve your org, you're just flying blind, right? And so what are the metrics that you look at? Like, what are the things that you measure frequently, look at frequently to know, one, the value of your org, but also two, like, okay, this is where we can improve or this is where we can get better, right? Like, what are some of those key metrics you track?

So I think there's. There's one part, right? There's like the one like nuance or asterisk that you have to put there, which is you have to align to your business, right? So if, let's say if your CFO is like, hey, the measure of effectiveness of the sales development team is based off of closed 1 revenue, right? I think the things that you're going to track is, okay, well, what is the process and what are the milestones in order to generate revenue? What is the SDR actually or what can the SDRs actually touch and influence? So it's everything from, you know, the accounts that you're targeting, right? So there you're looking at the conversion rates on the accounts, the titles that you're targeting. You're going to track the conversion rates there. But it's also looking at, okay, what are the. What are the activities that need to be done, right, based on conversion rates in order to generate Opportunities and pipeline. And I think the one piece here, there's a few other things that I think an SDR or yeah, sales development leader can look at, which is what happens after the handoff because not to throw salespeople under the bus. One of the things, like I was having a conversation with Trish Bertuzzi the other day and she says, she theorizes this, which is there's a lot of AES out there who don't know how to launch a sales, like an outbound sales engagement off of a discovery call. So for us there's a huge leakage in between discovery and qualification. 50% of the opportunities SDRs pass over dropping, right? So at this point in time you also want to look at, hey, like, how are we qualifying? What questions are we asking, right? What are the actual qualification? I guess factors that matter that are going to drive things forward. So like those are ways you don't have specific control over it, right? We can start looking at the data and asking questions around, hey, how can, essentially, how can I make my team look better, right? What's the work that needs to be done on our end to make sure that we're covering our basis and then how do we partner with our, you know, with our, with our peers in sales, for example, in order to make sure that these metrics align across the board?

I think that's so important. And like, in a little bit of a nutshell there, right, you had conversion rate by title, you had conversion rate by activity, you had conversion rate of account and you also had like, what's happening post handoff or like, where are they dropping down now? I could spend 30 minutes ranting on qualification because what, like, I think it's something where, you know, being a former SDR myself, I'll always have that part of me in there of like, I'm not going to let AES just be DQing shit because it wasn't interested or they didn't have the budget right now it's like, unless my AES are taking back to back demos every single day and they just can't take another one. It's like, no, like it's our job on the closing side to build that interest to help them find the budget, right? So there's not this massive drop off because it just crushes strs, right? They work, they work, they worked, they get it, they finally break through, they get them there and then they get that email to Slack from the AE saying, yeah, like I'm not gonna flip this one to qualified because they can't do something for six months.

Yep.

And it's like, what?

What did you want?

Right. So. All right, I'm gonna stop because I will go for 30 minutes.

Yes. Yeah, I, yeah, I can't go for 30 minutes. But that's because there's some things where I'm like, just be diplomatic, Gab. It's gonna be okay.

Everybody knows I took off my diplomatic hat a few years ago. But this isn't about me. This is about you.

Yeah. You're also Kevin Dorsey, so you're allowed to right now.

I guess eventually I get to earn that right there. Now, something was very interesting with your cross career trajectory. Right. So you were an sdr.

Yes.

You got into enablement. Sorry. I believe you went str, SDR manager enablement back to management. Correct.

Yeah. So I was doing enablement and SDR management at the same time. Don't ever do two roles at the same time. People don't do it. It's not a good thing, I guess.

Unfortunately, I've done that my entire career. But it's something. So I thought it's interesting because one, there's actually a pretty interesting trend happening in sales development leadership right now. I'm watching a lot of sales development managers move into sales enablement. Like they're getting out of sales dev management and into sales enablement, which I think is a very interesting trend. I'm keeping my eyes on of like trying to find like why that's happening. But where do you see like, you know, kind of like enablement and management have always kind of been treated as two different things. What could managers learn from enablement, but also what could enablement learn from sales managers? Because there's always seems to be this gap, you know, like enablement sits somewhere else. They do something else and they come out like the person come out with the Persona cards. And then sales is like, what are these? I've never said, like this isn't how they talk. Right. So like how can we actually do a better job of, I guess bridging that because you've, you've played in both fields how that works.

I think I, you know, so I think I've even before this holding the title of like sales enablement manager. I think actually let's go back to when I was in SDR at Cloud Words. I, I think, you know, I'm having conver. I'm having a lot of conversations over the phone. I'm receiving these emails. I'm starting to see trends and themes. There are questions that are coming up over and over again. And so I'm like, oh, hey, why don't I just make. Like, why don't I just create some resources for myself, right, So I don't actually have to think about these things. So I started creating documents, right? Like, literally just a piece of paper with sticky notes on it. And so the sticky notes corresponded to, like, a value pillar that we. That our product fulfilled. So maybe it's campaign management, maybe it's translation or it's, you know, storing, you know, storing words and languages and things like that. And so I'm like, all right, hey, for each one of these kind of, like, solutions that we can provide or these value pillars that we can fulfill, there's a certain set of keywords and themes and trends in the conversations. And like, if someone says this, this means, oh, hey, they're actually really interested in our. In our content repository. So I just started building resources for myself. And so then when I was in a management position, I'm like, okay, well, I already have these structures. Why don't I just input the data right from the company that I'm at right now? And so as I was doing this one for myself initially as an sdr, then it's like, okay, now I'm a manager. Let me share that, right? Let me have people enhance that. Like, enhance that information. Let's actually make this something that is presentable. And so for me, it started off with, I want to get better. I don't want to have to think as hard, right? I just want to have information at my fingertips. Now I'm a manager, and it's like, all right, these are the things that were really beneficial to me as a rep. So, like, let's see how this could work for my team. So I think the thing here is sales enablement. You can't create content in a vacuum. You can't create resources in a vacuum. You actually like. So in the same, like, I had, I had direct exposure to the conversation. So, like, enablement, you might not have that direct exposure. Or actually, you probably do. Go talk to customers, ask them what's going on, speak with the reps, jump on a call with an account executive or a CSM and start to note down what's going on here and then interview your reps, right? Like, hey, how often are you having this kind of conversation? Or where do you feel like you are getting hung up on? Like, the same kind of questions that I would ask as a manager to my reps in a coaching conversation is the same kind of questions that I feel like sales enablement should be asking the reps that they're servicing. So like, you know what? I think one of those challenges. I'm going on a tangent here, but when I think one of the challenges with sales enablement as I understand it and what I see it today is they're getting their orders from leadership and management as to how content should be built instead of servicing their AES and their SDRs and their CSMs and speaking with them and bringing that information back up to leadership. So like that, that's my rant. Like where I think I. So I'm like, I don't know how to build. Like, I don't know exactly what the bridge looks like, but I'm like, I think that's how you get the, that's how you get to developing content and resources as a sales enablement professional. That's actually going to be used, adopted. Right. It's going to drive the results that you want to have. I think there's other things that are there. Like for instance, if you have a really good sales manager who's very. Or leader who is data driven, like, look to see over time is the content that you're creating, the resources that you're delivering out, are they actually having the desired impact that we thought they were going to? Right. And so if not, why is that? And so you go through that process again of, hey, you know, like, like, hey, are you having this conversations? Or like, hey, maybe we need to take a different angle. Maybe we need to look at it by accounts or industry or vertical or by title. I don't know. But that's. Yeah, I get, I get really frustrated when I'm like, hey, listen, like we need to talk to the people because they're the ones who are really the, they're the masters of information.

They are. I got in trouble a few years ago again, I had taken off my diplomatic hat and I came out and said like, sales enablement needs to change their titles to sales performance.

Yes.

I don't care about enablement. If all your enabling. But most sales enablement isn't even held to a number.

Yes.

Like, so unless you can change it to salespeople performance, if you're enabling, performance should go to go up. And you should know performance is going up because you're doing the right thing.

Yeah.

You know, like if you're rolling out these Persona cards. Okay, why, what number, what metric is supposed to go up because of this? And if they were being held to that, things change real fast.

So there is something I came across because like I came into sales, I basically was just creating stuff for like the sales development team. My sales development team was doing very, very well. And then the VP of sales is like, hey, like, like what's going on here? Your team is ramping up really fast. And then over time he's like, hey, how do you feel about taking over sales enablement for the whole, for the whole team? And I was like, all right, let me do some research just on what sales enablement is to begin with. And the definition that I felt was like the most appropriate or what sales enablement should be, it's focus on effectiveness. And effectiveness is measurable. Right? So like there are specific skills that AES, SDR, CSMs, customer facing reps can become measurably better at. Right. So for example, I'm talking about this quality, you know, from just like from qualification to discovery, there's this 50% dip. Like from like the Esther handoff to the AE handoff. And I'm like, what the hell is going on here? Like, you know, the team is doing very well. They fulfilled all the qualification criteria. What could it be? And it AE's just like, well they don't have budget. I was like, okay, well did you. What, like what did you ask them? Like, what's going on here? Are we just like, that's one thing I really appreciate you about UKD is the focus on like building up a pain before you can ever talk about value. Right? So like are we actually understanding what's of value to them or are we assuming what's valuable to them? And of course they're not going to tell us that they have budget because they're not going to do business with us because they have no reason to. We haven't built up a reason yet. So when I'm like, hey, sales enablement, right? What, like what can sales enablement do? It's not just teaching a sales methodology, like how to manage opportunities. Like how do we actually manage the call? What needs to be accomplished, what questions need to be asked. Exactly. Like how do we extract that information as well and how do we ensure over time that reps are actually doing this and what happens when they're not?

Mm, yeah, I think it again, it's back to that awareness level. And so something that I say to my managers all the time is I don't want you to be micromanagers, but I want you to be micro aware.

Yes.

I think you're showing exactly what micro awareness is. Right. Where like, you know the nuances, you know the Small details of like, wait, we have a 50% drop off here, right? And I think that's something that I hope people listening, SDR managers and even SDRs, right? Like, because you were thinking this way as an sdr, which will be kind of like the next question I'm dive into. But the micro awareness of what's working and what's not and what the sticking points actually are, and then going and solving those things is key here. And so one quick note I just want to pull out that also you said was like, make sure you're documenting things, right? You said it was on sticky notes and then you took it and then you wrote it down and then you shared it. So like managers, reps, write down what's working, write it down. Don't just keep it in your head because one, you'll forget it over time and two, you can't share it. So write down everything, document it. If it worked, write it down. If it didn't work, write it down. Start building your own playbooks as you go through your roles so that you get into leadership, right? Like that way, when you step into leadership now, it's not like, oh shit, what do I do? It's like, you've got your playbook now you can start teaching people how to do it. And so then how did you make that transition? Right? So how did. Because you did it fast. At least what I can tell on LinkedIn. It looks like you went from SDR to management pretty quickly.

Yes.

How did you do that? And how would you recommend SDRs that are SDRs now, accelerating their path to leadership and management?

So my first day as an sdr, remember we had a zoom call with our CRO and our VP of Strategic alliances. And I just remember the one thing they said is, come in number one, raise your hand and tell us what you want. I think the easiest way to get what you want is to over perform. Like, don't just do, don't just do the job at a satisfactory level. Over perform, right? It's almost like you have to put pressure on leadership to see you and to recognize you. And then the most important piece is raise your hand and let them know what you want. If you don't let, if you don't let people know what you want, how are they ever going to know, right? So I feel like I come across whether it's really great SDRs or really great AES or whoever, and they're killing it. And I'm like, okay, well you've been in this role for like two Some years, like, why is that? It's like, okay, well, I don't know. I just figured if I put my head down and worked, it'd be great. I'm like, okay, did you let people know what your intentions were? Like, did you allow people to be a part of your dreams? And so that's. I think that really is the key piece here. That being said, though, like, what is going to make you a very successful or an exceptional SDR might not be what, like, helps to be a great manager. So I think it goes back to, right, hey, you find a way of becoming very good. Actually, I have an idea in the sdrc experiment as much as possible, right? So if you figure out a way, a surefire way of getting things done, try other ways. Go talk to other people. Like, go talk to other people on your team, learn about what they're doing. If you have an opportunity to share with them something that you know that they don't know yet, that you feel is the. That you feel will help them, share that with them. That's the easiest way to get some leadership experience, right, is be the leader on your team already. So it's something as simple as someone's on the phone, they're struggling with an objection, write the answer on a sticky note, put it on their desk. We're not wearing Covid times right now. But, like, those are the things that I did as an sdr. See, if there are ways that you can have your manager delegate some of their activities to you. So anything, like from training and onboarding, for example, or skills development or coaching or leading role plays, like, these are the things that you can do in the role of as an SDR that will help you so much more when it comes time to being promoted, right? Because you're already demonstrating those characteristics and those things that people are going to want to see in the management position and then something that I didn't do until I actually became a manager. Learn about leadership, Learn about management. Because, like, right, as an ic, you're so focused on, okay, like, I'm trying to drive results where results equals, you know, meetings completed, opportunities generated and pipeline generated. And so if you're only singularly focused on that, right, like, well, what happens when now you need to figure out how to work cross functionally, like, what needs to happen? Like, what's going to happen when you need to have a hard conversation with somebody? Like, what happens when someone's like, hey, listen, I think that you're a shit boss, you know? So, like, you know, I think There's. There's a. There's a lot more to learn, I believe. Right. I think there's a lot more to learn in terms of how you work with people, how you work within a business, how you work with numbers, how you manage performance in the management level. And so the more that you can study that or get exposure to that and low risk environment, the better your transition is going to be.

And one small nuance I want to call out there that I think is important because I think it trips people up, is the difference between raising your hand and voicing you want something. Because raising your hand more often implies someone asked a question, right? And then like, okay, who wants to be a manager? And now I raise my hand. They may not be asking that question. This is where a lot of people get stuck, especially unrepresented leadership and unrepresented, like, you know, minorities, women, sexual orientation. We wait to be asked and then we'll raise our hand. That implies we were asked. And so what I would encourage people to do is you need to voice it. Whether the question was asked or not, you need to say the moment in your head you want to be a manager. You don't wait until someone asks you if you want to be a manager. You don't wait until a role's available. You say it. And so that would be something I'd like to call out is like, don't raise your hand, raise your voice.

No, that's. That's super key. And you brought up. I totally, for a moment, I think I blocked out the experience of becoming a manager and what I had to do. You just brought it to life for me. Because here I'm gonna tell you, this was at a company called Cloudability. I came in as a sales development rep, or BDR, whatever they called it, in December of 2019, I became a manager. In February of. No, not 2019, 2016, I became a manager in February of 2017, two months later. So something that happened in between that time was two weeks after I started, we had a new VP of sales who came on board. This is another tip that I would recommend is if you have a new leader come on board, get to know them before. Like, just get to know them. Like, ask, like, you know, see if you can get a coffee or a zoom call, something along those lines. But. And let them know what you want to do. Right? Like, yes, I share what you want to do with them. Raise your voice. That's key. That's exactly what I did. And so I did that in December, early January, they posted that BDR manager position maybe three, four weeks after I had, like, raised my voice about it. And I was waiting for somebody to be like, hey, listen, Gab, we got this manager position open, and we know that you said that you want to do it right, like, come over. That never happened. Like, and I just remember, like, waiting. I was like, okay. Like, they posted on a Tuesday or posted on Monday. I'm like, Tuesday, I'm like, nothing. Wednesday, nothing. And I woke up, I'm walking my dog. It's like, five o' clock in the morning, and I'm like, walking into. I remember spraining my ankle as I was typing out the email, trying to figure out how can I communicate that I, like, I need to have this job. Like, I'm the best person for this. So, yeah, I remember spraining my ankle while walking because I was paying attention to what I was doing while I was typing an email to the VP of sales.

That's pretty epic there. But that's also dedication. That's how much you're just willing to sacrifice for the role. But I really hope that's an important takeaway. All is raise your voice, not your hand. If you're waiting for someone to sit down and go, hey, Gabrielle, what do you want to do with your career six months from now? We think we may have a manager opening. Would you like it? It's like, no. Like, you have to be not only raising your voice, but then, as you mentioned, your actions being promoted internally should actually be a pretty anticlimactic event because you've already been doing it. And so when they're like, hey, everyone, Gabrielle's a manager. The response should kind of be like, yeah, like, that makes sense. Like, she's already. She's already been putting sticky notes on my desk, and she's already been taking me on walking talks.

You know, she's like, yeah. I mean, I had. I knew someone where they were like, oh, hey, I want to be promoted into the manager position. It's like, okay, well, walk me through what you're already doing. Like, how are you preparing yourself for that? And they're like, well, I'm not. I'm like, well, then you must not want it.

Right? And they say, well, well, I'm not it yet. So, like, you know, and this is. This is a flaw with a lot of people. Even SDR to ae, same thing.

Yes. Big thing. Yep.

They wait to develop themselves as an AE once they are an ae. Right. Like, we just went through this process right now. I promoted some SDRs to AES. That was one of our questions is, what have you been doing to prepare to be an AE before this? Like, you've been working with an AE for the past year, year and a half. Like, what have you learned? Have you learned anything?

I think the big. Yeah, the biggest thing here is start doing the job before you're ever asked to do it. Right. I think there's. There's a level of discernment that you need to have, right? Because you don't want to just, like, pick up another job and not get paid for it. Right. Um, but I do think that there is merit in, hey, start. Like, if you see yourself moving into position. So if it's SDR to ae, this is what I tell my reps. Like, hey, listen, I want to be an ae, and I don't feel challenged by the SDR role. And I'm like, okay, well, what parts of the AE role can you just do in the SDR role? Oh, well, I can run these calls. Okay, well, let's run the calls. But, like, what if it's not an opportunity? Like, just ask the AE to come on board and essentially act as the, like, director, the executive sponsor internally, right? And so then they can start mentoring you up. But, like, it's almost like, just be creative, right? Think, like, outside of the box. Like, yes, you have your role and you have your job responsibilities and things that you're paid for, but if there are things that you want to do that you're not currently doing, like, it's like Oprah said, like, you have to sometimes have to do. You have to do things. There's some things you have to do until you can start doing what you want to do. I'm paraphrasing there, but, like, that's, like, that's the biggest message now for sure.

And I would say just start learning. You can even start learning before you do. Right? Like, and I actually, I would encourage people before you start trying to. Like, before you start trying to lead your fellow SDRs, maybe pick up a leadership book, maybe start reading on management before you start to do those things. Start reading on communication before you do. Because also, too. And I've made this mistake, like, you try and you get shot down, right? Like, you try to, you know, you try to help someone else. You try to, like, you know, step up a little bit, and someone shoots you down, and they're like, dude, what the hell are you doing? But if you did it the right way, I think that's really, really key. And so like with that, sorry, go ahead.

And also, you have to give yourself the opportunity, space to learn. And so as you're learning, know that you're going to fail. So like, if you're an sdr, for example, you're going to get shot part of the job, right? But are you going to quit your job? Maybe. Right, but that's probably not meant to be an sdr. It's like, hey, listen, if you are, here's what I truly do believe. It's like, if you have figured. For me, I try to figure out a system to operationalize my own success, right? Like, that was it. And I was like, I wasn't just thinking about what works for me. It's like, what is a system of success look like, right? And so like, if you are over performing, if you have a system of success and you're just like, I mean, there's a part of being a likable person, an approachable person. If you're an asshole, like, nobody's gonna take information from you. So, like, don't even try, right? But like, if people, like, if you are agreeable and folks are having a hard time, hey, you know, like, I heard you say, you know, I heard that you said this specifically. I just had a conversation with someone, they asked the same question and here's, here's what I try, and they seem to really like it. So I think it's even in the delivery, right? So the delivery of the feedback, potentially. But yeah, as you're learning, know that you're probably going to mess up, right? So, like, keep pushing through.

So what are some of the best resources you've had or found or utilized to learn how to be a better leader? Like, how do you continue to grow?

Ooh. So I like having conversations with people. So if there are leaders that I'm following or leaders that I know in my network, I would just start having conversations with them. So I don't. When I became an sdr, I didn't, I didn't have any. Like, I'll be honest, I didn't have this, you know, what's my next two roles going to be? And like, is that management? I wasn't even thinking about that really. And so I just had, I would just have conversations with my manager, like, why are you doing this? Like, what is it? Like, why'd you get into management? What do you like about it? What are the challenges? Like, how did you learn about it? And so as I'm having these conversations and I'm starting, you know, and people are saying hey, like, here are the things that were helpful for me. I feel like then I had, like, a game plan of what to do and so, you know, questions that you can ask leaders. I think, number one, like, what is your management or leadership style? Like, one of the number one things that I hear right now is servant leadership. Learn about it. Read a book about it. Like, what does it actually mean? And see if that's something that aligns to what you believe in or if it's like, yeah, like that. That to me, has been the process. I haven't. I'll be honest, I haven't read a bunch of books, right? The only books that I've read thus far that I think speak to management is like, cracking the sales management code. And then good to great, right? And so, like, this to me was important. So, like, I wanted to understand what separates the best, right, from the worst or even the second from the first. But then after that, it's been mostly having conversations with people. The people who I think are really great managers, but also the people who I think are terrible. Right? I'm like, why'd you get into leadership? Like, why does that matter? And, like, I'm like, these are the things that I want to steer away from.

No, I think. I think that's important is, like, you seek it out, and you seek it out from many people, different types of people, different types of leaders. All those things. Like, I have some very close mentors, and even my mentors have changed over the years because I've needed something different. Yeah, I'm at. I need something different. I need a different type of insight, a different type of challenge, a different type of push. Right. Like, you can outgrow a mentor.

Yes.

And that's okay, right? They help you get to one level, and then you say, okay, like, I need to get to this next level. And you find new mentors and go, but seek it out.

Yeah, mentorship is huge, right? I like to engage with people. I mean, I can learn theories and concepts in books, but I'm gonna have so many questions after that. I'm like, I need to talk with me through this because that's how I'm going to process something. So having a mentor, whether it's the person that you're reporting to, whether it's somebody else in the organization or if you're finding. I would even advocate for mentors outside of where you work. Like, that, to me, was incredibly helpful in my first, like, in my first role of being in management is like, I would just ask anybody and Everybody that I came across, like, what? Like, what are you focusing on? Like, why did you. Like, why even did you choose the company that you chose? Like, why is this value important? Like, why is servant leadership important specifically? Just become incredibly curious, like, interrogate and inquire into anything and everything. And I think that's really what's going to mold, like, what kind of manager, what kind of leader you're going to be, assuming that that's the path that you're going to go to.

I love that. And so I think that's a good segue to the final two questions here. Right, so. So the first one's the big three, right. And this would be a fun one. I'm excited for your answer because we've covered a lot. We've covered tarot cards, which I did see coming. Enchantress, the Sastris, the Sassy. We've also covered things like leadership and cold calling and analytics and sales development, and all this across this. If there were three things that you wanted people to take away from this episode, three things. If they forgot everything else but these three things in terms of, you know, how to be a better salesperson or how to be a better sales leader, what would those three things be you'd want them to remember?

Ooh, good question. I think the biggest piece here is, like, get curious about yourself and others. Like, for me, I would have never known that I had an interest in tarot cards until I started actually questioning, hey, you know, like, what are the things that, like, bring me joy? Like, what does play look like for me? Like, I think that's the biggest one. So I think the more curious you are about yourself, the more that you satisfy that curiosity, the better able. You'll be able to be curious with other people, too. So, like, that to me, is probably, like, the number one that I would share there. Number two, get. Yeah, get analytical. Funny enough, like, I've run into some folks who have been like, all right, hey, you seem really analytical. What about, like, the qualitative side of things? So, like, the analytical piece has been a little bit of, like, a criticism. I'm like, timeout. No, I'm not listening. Yeah, yeah, yeah. So, you know, like, know your numbers, know your business. When I came into being an sdr, the number one thing that got communicated from leadership was like, you're the CEO of your business, and you have to know your numbers. Know your numbers, know your numbers, know your numbers. So, like, know your numbers. Know, like, what they actually are, how they're changing over time. And what that means, like really understand what the data is informing you of. And then if I had to choose the third option, become a student of whatever it is that you're trying to do, right? So whether, whether being a student means like going to conferences and workshops or like picking up a book or listening to podcasts, anything like that, just highly recommend, like really studying. Look at what you're doing as a craft and study extensively and don't stop learning.

Sorry, my dogs are messing with each other right now.

No worries. No, I saw that. I was like, he's either talking to a kid or a dog right now.

Yeah, had to do the quick, like get the dog out of the entryway. So anyway, last, and the last question here, right, is you know the name of the podcast is live better sell better, Right? Focusing on the person in salesperson. You know, this weird idea that if we are better people, if we live better, that also our sales will improve as well. What would be your live better advice for everyone listening? Right? Like how to get more out of life or out of themselves, More fulfillment, more joy. Like, what would that live better advice be?

So I'm gonna get, I'm gonna be very tactical. I'm not gonna talk in theory right now. So there's a bunch of things you can do. Get a journal and ask yourself three questions, either one every day or three times a week. And write this down. The three things are, what was I like? When did I feel most like myself? My best self? Today. What was I doing? Who was I with? You do this for a month, two months, you'll start understanding what the themes and trends are of when you feel your best, right? And then you can start focusing on like, all right, hey, like, this is best, this is better. And here's like, and here's what I can focus on to create more of that in my life. So I think like a lot of times when I'm coaching up my reps, funny enough, I had a one on one session with one of my reps yesterday and he was talking about like, he's like, I don't know, I'm feeling burnt out. I don't, you know, those kind of things. It's like, let's think about the things that just inherently bring you joy outside of hitting your quota. Like, what are things that you can be doing right now in this role today? Or things that we can start introducing into your role today in order to make sure that you're remaining fueled. So without that awareness, Right. I think people run the risk of dispensing other energy into things that are not actually going to fuel them. So that's my one very practical tactical advice.

I love it is self awareness is everything. If you don't know yourself, how on earth can you accomplish anything that you want to accomplish, right? Like, how can you even take care of yourself if you don't know yourself? So I think that is a phenomenal piece of advice, Gabrielle. Holy smokes, right? Like, you know, like, I try to be a pretty, you know, open. Not even open book. That's the wrong term. But, like, you know, not make assumptions about people. But I wasn't even ready for all of this. And everything that you said, like, this was amazing. Where can people get more of you? Like, where can they, you know, get more of you, follow you, talk to you? Like, how can they get more Gabrielle in their lives?

Just like LinkedIn. Connect with me. Follow with me. Funny enough, someone from Australia hit me up yesterday and we talked about how there was like a crow versus a hawk fight right in front of my balcony. So, like I said, I'm definitely. I'd say I enjoy engaging with people. I post content there and I don't have an Instagram or Twitter, so you'll just have to find me on LinkedIn. Yeah. Gabrielle Blackwell, sales development. I promise I'll engage.

Hell yeah. Sounds good. Well, Gabrielle, thank you so much for your time and your insight today.

Yes, thank you, Katie.

All right, later.

All right, peace.