Meet Amanda Long, our newest Pipeline Consultant

0:00One of the cool things that Outbound Squad is we've gotten a chance now in the last five or six years to work with 250 plus sales teams. And it's been companies like Shopify, Zoom, Rippling, Gong on the large end. And as small as companies rolling out their first SDR organ everywhere in between. The thing that's really cool, there's two things. One is seeing people get promoted during that time. So there are people that we worked with that were reps five or six years ago that are now a VP of sales somewhere, uh, seeing sales leaders, uh, work their way up into bigger companies and bring us along for the journey.

0:37And the third thing in today's episode, and what this is all about is a couple of people that we used to work with as clients now work for us at outbound squad. And Amanda long is one of those people. She's our newest pipeline consultant. So she's recently led a really large engagement with iHeartMedia, trained hundreds of their reps. We saw a 44 % increase in first-time meeting set. So just massive, massive value there that she was able to bring to iHeartMedia. And in today's episode, we're going to get into her backstory. So I'll talk a little bit more about that. But before we get to it, my name is Jason Bay.

1:14I'm CEO at Outbound Squad, and we're all about helping you turn complete strangers into paying customers. So what we talk about on this podcast is pipeline generation. You might call it PG, might call it pipe gen. For SDR teams, that's typically the cold stuff, right? The net new business creation. So if you're running a team of SDRs or you want them to be more strategic in their outreach, break into more enterprise accounts, maybe land meetings with more senior folks to improve the meeting quality and the conversion through the pipeline, those stage twos, threes, et cetera, you're definitely in the right place.

1:48And if you're running a sales org and you have account executives that you want to self-source more pipeline, or maybe there's some account managers on the team that are going, you know, quote unquote outbound into the existing customer accounts, you're definitely in the right place as well. So Amanda, what I'm really excited about to talk, to share with you rather, is we unpacked her entire journey in person a few weeks ago when we were in Seattle having our first official offsite. So we brought her into town and we impact her journey as a first time rep in 2015, what it was like being a first time manager, right when COVID happened, she shifted into an enablement leader.

2:29And during her entire career, she's been a top rep and always had one of the top teams as a manager. And in the last four years, she shifted into enablement. So she's really the enablement brain at outbound squad. So when you think about like the programs, how to make them stick, how to reinforce it, she really helps a lot with playbook creation. She helps with all of the content creation here too. So at Outbound Squad, a big part of running a firm like ours is we have to do our own enablement, right? We have to enable our pipeline consultants, our trainers on how to deliver this. And there's slides, there's worksheets, there's content.

3:08We're customizing that content for our client, right? So it's really big. So some of the big things we talked about in this podcast were the importance of relentless practice. Talked about how AI fits into that. We talk about how to advocate for yourself and your career growth. So if you're a rep or a leader listening to this, like how to make it really known to your leadership that you want a promotion. We talk about leading her team through COVID, building enablement programs, making training stick, all kinds of really fun stuff. So let's get to the interview. I got two things I want to give you beforehand.

3:42And one, we have a free outbound mastery course and workbook. It's three hours of content. It's our very best stuff at the moment on how to do outbound in a modern way. You can grab that at outboundsquad.com slash masterclass. Again, it's free. It's three hours of content. It's everything from targeting and prioritizing your accounts to what works on the phones, what works via email, and everywhere in between. So if you're running a team or if you're a rep, you're really going to love it. Outbound squad dot com slash masterclass. The other thing is if you want some of the implementation around a lot of the things that we're talking about today around pipe gen and you're looking to maybe shift the team to be more outbound centric, maybe inbound is down right now and you've had to really push the team to do more outbound.

4:33We'd love to chat with you. We build custom programs from scratch. We work with your enablement team. We train the reps and most importantly, we train the managers on how to reinforce it. And we do everything from building that outbound mastery program. We do really intensive work with managers. We build onboarding programs, all kinds of fun stuff. So if you have a goal to really increase pipe gen right now, hit us up. You can just email me directly, Jason at outbound squad.com. All right, let's get to the interview.

5:11It's been so good to meet you in person. Yeah. So we've known each other, I want to say for four, maybe five years at this point. Yep. You were a little baby sales manager. I know. I know. But I was so excited to welcome you, well, officially welcome you to the team here. It's been a couple months now that you've been full time. But I was so excited to reach out to you again because you just like were a standout when I was working with Manolo. And it was like your vibe and your energy and like your ability to really get shit done and how much you leaned into the engagement and all that stuff. So I'm really excited that we're working together.

5:50I'm really excited, too. I mean, I followed your work for a long time before we actually brought you into Winaldo. So I was kind of a fan and I wanted to impress you. So I guess I'm glad it worked. So let's unpack your career a little bit because we were talking about, and as I've gotten to know you a little bit more on a personal level, sales, I'm really curious, like, how did you get into sales? A lot of people get into sales on accident. Was that the case for you? Or was there a different story? I feel like I was kind of intentional about it. Yeah. Growing up, I was always very social. And I loved the connection aspect.

6:33But in college, I was a double major. And I chose business economics and psychology. Okay. And thinking about the two, I wanted to be able to use this knowledge in a way. And it kind of led me to sales. The business acumen, understanding demand and supply and cost and negotiation. But then on the other hand, really understanding people and what they care about and how to motivate them. So it was this natural path. And I went, I was an overachiever. I kind of still am. I'm in recovery for it. We're working on it. Yeah. But I went to a career fair my fall semester of my senior year. Yeah. And I walked out with an interview.

7:19And then I walked out with a job and it was, I didn't, yeah, I didn't interview anywhere else. I just immediately got the offer. This was Insight Global? Yep. It was Insight Global. And so I had a job my entire last semester of college. I was just kind of waiting to start and it was my entry point into sales. And I learned so much in such a short period of time. and that's where I realized how like hungry and competitive that I was in the sales world and how fun it was to hunt and pursue and close. Um, that validation just kind of like sparked a fire for me. Yeah. So was this first role, was there a lot of cold calling and yeah.

8:03Okay. What did you think of that? It was an interesting role because I started as a recruiter, which is like their entry point into sales. So on one hand, I'm focused on basically cold calling applicants, candidates trying to sell the position and get them in for the interview. Which you think would be really easy, but people do not like to interact with recruiters. No, absolutely not. So that was a challenge and had its own objections and arc of the conversation. But on the other hand, as you wanted to level up your skillset, you had to start cold calling and setting appointments with local businesses for the account managers.

8:43And so that is where I was terrified, but I really leaned into that fear and I, I was almost like afraid to fail. So I over-prepared overachiever and basically figured out a way to make it work for me and got promoted into sales and really never looked back from that point. So had you done any, you know, like in high school, I remember going door to door to sell Christmas wreaths to make money for the basketball team or anything. Had you done any of that kind of stuff that made you? I sold Girl Scout cookies when I was really little. No, I was a hostess at a restaurant. So like I had the interaction element, but I wasn't, I never did any sales before I joined sales.

9:26What was the rejection like at first for you? Oh, I think I had a lot of ego that I needed to work through at that point. in my early career. Yeah. I just, I was used to excellence as much as I could control. And so when a meeting would flop, which happened, of course, when I would like fail a cold call, that sat with me a lot longer than I wish it did. And I was really focused on like the the fail points instead of what did go right and what I could learn from it. So that took me probably like a month of like really struggling and breaking down my ego so that I could just kind of just see it as another at bat and keep it moving.

10:17So when you say ego, was this like, I have to separate this failure. Someone hangs up on me or rejects me or says they're not interested or whatever, separating that from like your own self-esteem in terms of like how you feel about yourself, like not taking it personally. Is that what it was? Yeah. And I think the way I could describe it is like my early career, honestly, even up to probably a few years ago, a lot of my identity was wrapped into this construct of success in my career. And I needed to be successful in my career because that validated my worth. And so when I would have these like failure points, it wasn't that I failed a cold call.

11:02It was that I wasn't good enough to do it in the moment, which I realized is not accurate. And I've worked through that. But that was a big challenge for me early in my career. Yeah, I think that this is a very common challenge for a lot of people in sales. I mean, to give the people listening some perspective, since Amanda's joined, she is literally working with our largest client right now, iHeartMedia. So you've led all of the engagements with iHeartMedia after that initial pilot that I did. And I've worked with some really cool companies since then. But you've gotten to see now, and one of the things we talked about initially when we met was you said impact.

11:41I really, like what really intrigues me about this job is I'm not just leading a team or doing enablement for my company. I get to do this with a lot of different companies and like really make an impact. And so you've gotten to see a lot of that. I'm curious, do you see this showing up with our clients and the reps that we work with and the leaders that we work with? The fear of failure and like, yeah, I see it all the time. And what's really interesting is one of the things that we do is we teach an entire new framework and that's uncomfortable to learn something and kind of deprogram the way that you've operationalized and seen success.

12:22Yeah. And so when you try new things, especially like a new cold call framework or a new cold call flow and you're role playing, there's this moment of vulnerability where you do have to kind of put your ego aside. And, and I make mistakes in role plays all the time, but I see that it can really, really derail reps in the moment and they're being really hard on themselves. And my message in that moment is this is, this is the place to fail. This is the place to practice because I don't accept or expect excellence. I expect you to lean in and I expect you to get comfortable being uncomfortable because that's really where growth says.

13:06Man, there's so many different ways that I want to take the conversation. I think the first thing as we kind of go through your career, the stuff that you learned as a rep around, you mentioned role play and really it's kind of like the larger kind of theme there is around practice. And you were a cheerleader. Did you do any other sports? I was a cheerleader and I ran track, but really I, I just liked going to practices. I didn't actually like the meets. The meets always kind of sucked because you're hanging out for five hours to do like a 10 minute event or an hour event or however long you had to run.

13:41And I just would get really, really anxious. I would get so anxious. I just could do homework. I would, I would pace back and forth and like try not to puke. So there's this really, in sports, there's this well understood concept of like, yeah, of course you would practice. You wouldn't just run a 5K without preparing for that. You wouldn't do a cheerleading competition or a game or whatever without practicing. I played basketball. It's just like you wouldn't do any of these things without practicing. Yet in sales, it's like the onboarding is purely education-based. It's the equivalent of watching YouTube videos about how to do cheerleading moves or basketball stuff.

14:26And then they just kind of throw you out in the wild to just practice like on actual buyers. Like the most risky way that you could possibly learn how to do something is how most sales reps learn. So can you walk through, this is a really key part of your success as a rep and share just some of the things that you've noticed and that you've taught some of the reps that you've worked with, whether in previous roles or in this current role. How do you think about practice and what impact has that had in your career? When I think about practice, first and foremost, I think about consistency because you can't just practice one time and be like, okay, Jason, I'm, I'm locked.

15:06I'm ready to crush this and expect that it's going to be perfect every time. So the consistency I think is really critical there. And you know this, but I've seen that play out with my brother too. So my brother is a professional athlete and he's he's done what less than like one percent of athletes are able to do what like point one percent of people do yeah and it's i think seeing the capacity to overcome such significant odds because of intentional and deliberate practice and this like resilience despite all odds, I've seen that be successful. And that has really had an impact on me and my career because I don't see quitting as an option because I know what happens when you're on the other side of it.

15:56So in my sales career, what I always did was a lot of role plays. I would role play with my husband. I would role play with my friends. I would practice. And this is just like Calls, talk tracks, openers. Yeah, because I think I was so afraid of the negativity of the failure and rejection that I overprepared. And I think that's probably a through line for me as well. But I would role play a ton. I would sit there and I would think about who I'm selling to. And I would physically write out my own scripts and just practice it over and over in the car. I would voice record myself doing the scripts and play it on my Bluetooth in my car as I'm driving to work.

16:36Like this became kind of a ritual and it was every day I am either role playing in some capacity. I'm listening to my own calls, which is actually very uncomfortable to do. It's really hard. Because we have a tendency to be our own worst critic a lot of the time. Plus hearing your voice sometimes. Oh, I hate it. It's nails on the chalkboard there. But what I really loved doing is hearing where the call went wrong. because I feel like I can diagnose my own calls and sometimes better than the way other people give feedback because they're nice with their feedback and I'm relentless with my self-feedback.

17:14So I can pull apart what needs to change and then apply it immediately because I'm doing this almost in real time. And then the other thing I would do is listen to top performers, the peers around me that are seeing success. What are they doing and how can I kind of emulate that? And I think one of the benefits when I was in sales, I was in a sales pit. So everyone's on the floor. There's this like, there's a ton of energy. For someone that has only done inside sales work from home, what's the sales pit? Oh, man. Everybody is on the floor. And you maybe have a cubicle, maybe not. Most of the time it's open office space.

17:53Yeah, most of the time it's very open and it's very loud. And the energy is just kind of intoxicating. You can't just sit off in the corner and be quiet because that is more noticeable than when you're cranking dials and having conversations. But what I loved about the sales pit, not only is the energy, it stimulates competition, but learning happens in osmosis. I say that all the time with sales. And I think that's something that we miss out on in this remote sales culture. if we're not intentional and proactive about listening to our own calls, listening to our peers calls, if our managers aren't facilitating that level of knowledge share, I feel like it's a deficit for a lot of reps.

18:36And that's where I saw a lot of success. Yeah. I love that. So this is one of those things where the, if you really care about getting better about something, we don't need to talk about like, yeah, you should time block this and like do this. It's like, no, before you start work, you should think about like practicing this. You should have time blocked off at the end of the day to like debrief and like review this stuff. And it's like, this is not like rocket science really in any way. It's, I think most people know that if I practice something out loud, I would get better at it. If I listen to my own recordings, that would help me.

19:14If I listen to other people's stuff, It's really more about the attitude. Yeah. Like the attitude around self-improvement, I think is a really big thing. Well, you know what that reminds me of is the article that we just read through. Yeah. Are you actually trying? It's like a lot of reps complain, oh, this channel doesn't work. Phones are dead or email doesn't work. But are you actually trying? Are you doing everything in your repertoire? Are you using all of your resources to actually like change the dial and see success? Or are you just okay with things not working the way you want it to? You know?

19:51Yeah. Like that's what I am taking away from the conversation. Yeah. It's the, hey, I can, you know, hit the phones for an hour and talk to a couple people and spend the same amount of effort in scenario A where I go through the motions or scenario B where I'm like really being resourceful during that time. Mm-hmm. Yeah. And like really trying, you know? and like the practice around this and all of that.

20:19If we were to zoom ahead into the future real quick, I'm curious, related to practice, where do you see AI fitting into all this? That's a really good question. So I love using AI. I think AI has a wonderful place in scaling efficiencies and scaling productivity. I don't see AI as a replacement for human judgment. And I think that sales is a science. You can use frameworks, you can have tactics, but it's also an art form. And there is so much nuance to success with sales. The way I sell is going to have my own spice and my own flavor. and the way that you sell is going to be like subtly or significantly different from there.

21:10And I don't think AI has the bandwidth to fully scale that, I guess, variety, that nuance. I do think, though, that AI is great for a starting point. So maybe I create a scorecard and I upload a transcript from a call. It can give me some high-level pointers. And then I still need to go and listen to the call. And I need to really understand, like, is this aligned with how I experience the conversation? Is this aligned with how I would give myself feedback? And if it is, like, great, I'm going to move forward with it. But that opportunity to not just digest the feedback that's given, but really internalize it and then make it your own, I think, is important.

21:56And I don't feel like AI has that right now. Yeah. And then if we're throwing a manager into the mix, their ability to deliver that coaching to someone and make it stick, it's interesting because if we were to break apart a task, this to me reminds me a lot of reviewing game tape in a sport, let's say. there's so much data that i'm not even really i don't even really follow a bunch of sports these days but the the analogy i think is a good one you know espn can like with basketball they can tell you all kinds of different crazy stats that like the computer will just generate now and that people don't really have to think about like where they shot the shots and what their percentage is shooting from three point versus like from the post versus mid-range it's just like all of this data is just being automatically collected.

22:44But a coach still has to like create a game plan. A player still has to go practice that stuff. But the mundane parts of the task, if it's analyzing a sales call or whatever, like finding the key highlights and the things like that's gotten really, really fast with any conversational intelligence tool. So let's fast forward a bit. But you're a rep in 2015. You become a first-time sales manager in 2020. So you go through – I mean, just learning how to become a sales manager is very hard. I was really bad at it. I was very good as a rep but very bad as a manager the first six months. You're not only going through that learning curve, which I'm curious how that went for you.

23:29You're also going through it like through COVID, which is interesting. If we talk about kind of the buildup to becoming a manager, we talked a lot about advocating for yourself and career growth and essentially this idea of like, hey, I'm going to start doing the job before I get the job. And I'm going to fucking raise my hand and just be like, let everyone in leadership know that I want to become a sales leader. So tell us more about that. I thought that was pretty cool. Yeah. So I, and this maybe is another one of my ego moments, but I was a top performer. Okay. So I had, I had seen consistent success as an AE.

24:14I was closing enterprise deals. I was leading the charge in like talk tracks and what was landing. I was giving my peers feedback. So naturally, I assumed that that would, of course, lead to a promotion. And of course, leadership is seeing me in that capacity. So I just need to be humble and I just need to wait. And I think I had a moment where I realized if I don't advocate for myself, I'm going to get left behind. And I had a kind of difficult conversation with my leader and Jordan, you know, Jordan. and Jordan is so funny. I know he was not expecting this conversation, but we're in our one-on-one and we're talking about performance.

25:01And I was like, well, what feedback do you have for me? And he essentially was like praising the things that I was doing well. And that's the ammo that I really needed. He was like, yeah, just keep doing all the right things. And I was like, okay, so why don't we talk about what comes next? and he, I think, saw a ghost. I felt empowered and terrified at the same time. Your heart must've been freaking racing you. Yeah. Because it was something I really cared about too. Like if I was detached from the outcome, then like, yeah, I can be bold and whatever, but like I genuinely cared and it was really important to me.

25:38So I was nervous. I felt like bold and spicy. I was feeling empowered, but I didn't know how the conversation was going to go because our sales team wasn't that big. And I knew that my colleague, Michael, who you also know, was like naturally the next person for the role. He'd been there longer. He'd been very successful. So I already knew that. But going into the conversation, I was like, well, let's talk about what's next. And he kind of looked like he saw a ghost for a moment. And I was like, what about sales leadership and it got a little bit quiet and I could see the wheels are starting to turn and I knew that there was panic under the surface but because he didn't want to hurt my feelings but what he wanted to say was we've basically already picked our guy and we don't need more than one so you just need to wait he did not say that I want to be very clear but I know that that was what he was struggling with.

26:37And I said, I kind of cut to the chase because I didn't want him to feel this discomfort. So I was like, listen, I know that Michael is the guy, like there's no part of me that is trying to convince you otherwise, or like circumvent his success because he deserves it. And I fully, that's another one. I have these thesaurus buzzwords, But I was like, I'm not trying to take anything from him because I support. I think he'd be a great leader. My goal, Jordan, is to make it impossible for you to not also promote me as well. And you could kind of hear a little bit of a pin drop. And I just like stood in it.

27:22I wanted to fill the space. I wanted to rush in and like keep talking. But we just kind of sat there. And he was like, well, you're doing the right things. And I can't promise anything, but like I have a lot to think about now. And then we ended up getting promoted together the same day. And yeah, so we started our sales leadership journey and career on the same day together. And we, it was actually really nice because we were able to navigate those challenges together. And, you know, Michael, so the way that we are as people And the way that we process and the way that we lead is very different.

28:00But the challenges that we were going through were the same. For anyone who is navigating this or wants to navigate this life transition, going from an IC, going from an AE role, where you are really good friends with all of your peers and you're hanging out constantly. And yes, you're a top performer. So there's credibility there. But you have the credibility as a rep. So then when you transition into this leadership capacity, you think that that credibility follows you. But in reality, it's almost like you're starting over. You have to earn their respect and their credibility by showing up as a leader, showing your capacity to lead with empathy, but also accountability.

28:51Accountability is really challenging to figure out in that transition because these are your friends. So that was a really tough learning curve. and I think it doesn't set a lot of leaders up for success in that transition because we didn't go through like any kind of formal leadership training and that's what happens in so many sales orgs, revenue orgs. You go from being a really competent and credible IC into this leadership capacity and there's no roadmap. You just kind of have to figure it out. So on top of that, navigating this kind of friction point of transitioning from like a friend to a leader and the emotional challenges that go through that and the mental tax that goes through that.

29:44And also realizing that the way I saw success as a rep was unique to me. It's scalable. There are learnings there. But again, everybody has their own flavor. So then having to figure out how do I lead my former friends who are still my friends, how do I hold them accountable and how do I teach them in a way that's unique to each of the individuals on my team? That was quite a challenge. And then throw in a global crisis, a global pandemic of COVID. we went from being in the office where it's a lot easier to facilitate difficult conversations and an accountability oriented conversations build relationships establish trust like on the spot live coaching like that works really well in an in-person environment but then we went fully remote and none of us had ever worked fully remote at least for me and my team and the revenue New York.

30:41So that was a major transition. The world was shut down. So a lot of the businesses that we were selling to were kind of hunkered down. They weren't looking for labor and that was the space that we sold into. So it was really challenging. Yes. Let's unpack some of those things. So you mentioned the, which I went through as a sales manager too, where all of a sudden now I'm leading some of my friends. And you also might be leading people that have more career experience than you. Which like any young sales manager is going to, like that's going to resonate with them. Talk about that a little bit more, that transition.

31:25Did you have like conversations with them about it? Did you have to kind of rethink about that yourself? Did you create distance? How did you work through that? That's a really good question. So if I'm thinking about the transition, it was still important to me that they saw and felt that I still cared about them and the relationship that I had with them before it was a friend, peer-to-peer relationship. And I wanted to maintain at least a level of that connection when I transitioned into leadership. So I made a point to continue the relationship. I made a point to be really intentional about like asking about their families and understanding what they're working on and working through outside of the job, because that connection is where trust is built.

32:19And so if you trust that I genuinely care about you as a person in your career and outside of your career, and I make it clear that I am willing to go above and beyond for you, advocate for you, coach you and support you, that makes the transition actually so much easier. Because once you have trust, then they're going to be open to coaching. They're going to be open to hearing feedback. They're going to be open and at least feel safe in difficult conversations as opposed to feeling this defensive posture of who are you? You just stepped into this role. You don't have the capacity to lead me in this regard.

33:01Like I think building trust is really the foundational point of that. so it it is still about maintaining the connection and deepening the trust it just instead of going out at happy hours I'm building that through like our one-on-one time and I'm building that trust through my clear dedication to your growth yeah do you have uh for someone that's listening this maybe uh wants to become a manager or is a first-time manager or honestly just any manager, even the experienced ones, how, uh, what's the tips that you might have for them to like build that personal connection? I think it actually is so important for leaders to lead from the front.

33:46I am an advocate for vulnerability, but when I say vulnerability, I, I still mean strength. So I don't want to just break down and lose my mind. I want to be able to still have this executive presence, this strength, but I want to show that everything doesn't have to be perfect. And I have things I'm also working through. I have areas that I'm not the most comfortable in. when a leader breaks that fourth wall and exposes kind of like the the softness that you don't always see it makes it so much safer for reps to be able to lean in and do that as well and i think i honestly think the vulnerability and like the emotional connection that comes from that is that's where you build that trust that we were just talking about you have to lead from the front.

34:46You have to be willing to be uncomfortable and show that vulnerability in this environment is safe. Yeah. It creates that psychological safety that's been kind of a theme that we've talked about in the last couple of days. Absolutely. So you doing that first, right? You sharing that first, I think is a really big thing.

35:10Accountability was a word that you used. Mm hmm. What was that part like learning how to have tough conversations with people when you need to have the tough conversation? Well, let's be honest. Sales is a numbers game. It's always going to be a numbers game. And if you are not doing what it takes to be successful, you can't blame it on bad luck or bad territory. Like there is an ownership mentality that high performers have. And it's I'm going to be successful because I'm going to make it happen. Not I'm going to wait for success. I'm going to wait for inbounds to land on my plate. So accountability is a natural counterpart to that.

35:53Where I think a lot of teams get it wrong is this like one size fits all method of accountability. So I had actually a really big unlock when I kind of came across sales math and really individualizing what these numbers should look like for every rep on my team based on their strengths, based on their actual numbers. And I had a really close relationship with our RevOps team at the time. And we built this very cool calculator where we also were considering the coaching mechanism associated. So it was really dynamic. I could show a rep, hey, if we just want to focus on increasing the number of calls that we're making, what that means is our conversations are going to be a little easier.

36:47It's going to lift this metric. And we could kind of gamify the experience for them. So if we were really focused on driving next steps and being really firm in that, like bringing a mutual action plan into the closing process, like that's going to drive your win rate up. So maybe you have to make less calls in that regard. And so it was really cool to be able to connect the this is what we're focused on from a coaching mechanism. And this is actually how it plays out into your success and what you need to do on a daily, weekly basis to see that success. So I think gamifying accountability is actually where a lot of leaders should lean in as opposed to just saying, hey, Jason, everybody makes 250 calls a week.

37:33And so you got to hit this number. yeah you know yeah it reminds me of I don't for some reason I thought of like therapy like when you work with a therapist it's kind of like you control the agenda you show up and there's no agenda outside of what's on your mind and what you want to talk about and that works in that context that's like how I think a lot of managers will work with their reps where the one-on-one is just the rep shows up and like what do you want to talk about and where do you feel like you need help. And then the manager will cater to that and coach to that, right? Hopefully they do some coaching.

38:10And what we're kind of talking about is more of like blending, like training and coaching together where there is a system around how we produce the outcomes that we need to. And like, we both understand the system and the system's going to reveal different, you know, leaks in your sales pipeline that we can fix. And like, you have some autonomy or for how you want to fix it. And that's going to cater like, you know, how I approach the coaching. And it's really like a manager meeting the rep halfway. Yeah. Where it's like, I'm part of my job is to guide you, not just like help you when you ask for help.

38:48So the individualized coaching sounds like a huge unlock for you. Oh, yeah. Where you're able to provide this like very catered coaching on the individual level, which back to your point around building the personal connection. I mean, like, that's like the next thing, right? I build a personal connection. I understand what motivates this person or what's important to them. And I'm able to individualize the coaching. And that's just the next level, I feel like, with leadership. Yeah. I completely agree. I feel like when you are doing a one-size-fits-all coaching motion, a flavor of the week coaching priority, if you will, it doesn't land as authentic to reps because it maybe is not relevant to where they need the success.

39:33But I know every time I had a leader that took time to understand how I worked and where I was very strong and recognize those strengths, but also where I could shift the needle a little bit and see success, I actually trusted those leaders so much more. Yes. Because they took the time to make my reality a part of their priority, you know? So I think that's so important. And for leaders that feel like they don't have time to coach on an individualized level, I would really challenge that because I think it actually is doing yourself as a leader disservice to do one size fits all coaching exclusively one size fits all coaching.

40:21But I think it's a really big disservice to the reps that you're leading. I think you, we talk about ownership mentality. I think one of the ownership mentality, like pillars that is critical for leaders is deep understanding of their team on an individual level and owning the transformation on an individual level. Yeah. It's like, if you don't have time for this, that means that it's not a priority and it needs to be the top priority. Like if there's one thing, you know, um, let's talk about, so you crushed it for a couple of years as a manager, um, and you decided to get into enablement. Yeah.

40:59So tell us about that. How did that transition happen? This was another one of those moments where I advocated for myself. And I, I think that is another through line in my career. And it's a skill set I had to learn. But one of the things that I challenged myself with early in my sales career was I don't have all the answers. I don't have all the insights from a leadership standpoint, from a coaching standpoint. I need to level my skill set up because if I don't level myself up, then I can't level my team up. And so I started doing a lot of like self learning off to the side. One of the courses that I took was a summer school program for sales enablement.

41:49It was remote and it walked through creating the program, scaling the program from initiation all the way through like leading huge enterprise orgs through change management and enablement focus. So it was really cool to get that baseline. And I actually brought a lot of that into my leadership style. Like it changed the way that I was running one-on-ones. It changed the way I started to do sales math and I started to see data and metrics differently. I was looking for trends. I was able to understand what those trends actually meant from a performance standpoint and how to connect that to coaching.

42:29and so this kind of became like a passion project for me and it's just so funny and I like stress tested it with my team yeah and I had another conversation with Jordan I was like Jordan I have a question for you and every time I would say that I mean he's like oh my gosh where are we going but I was like why don't we have an enablement function and he's like well that's a really good question. I mean, we've talked about it, but like, we don't have it built. And I was like, yeah, I think I should own that. And this was another one of those moments where he was like, what is going on with this girl asking for all of these things?

43:09But I felt very motivated and inspired to pursue this. And so I ended up shifting over to our marketing team working under Susan and I love her. I think she's wonderful. And, and I just really credit her. I credit Jordan. I credit Lori with the opportunity to expand my, my career because I loved being a leader. And this is another conversation we've had. One of the through lines of my career is impact. And I think impact is so important. So when I was a rep, my focus was driving the most impact for the business. How can I close the best deals that bring in the most revenue? And then when I became a leader, I was so excited about the ability to drive impact with my reps and coaching them and seeing these aha moments.

44:02But enablement, I think, is a unique role because you drive impact holistically when you do enablement well. So it's the entire sales motion. It's post-sale. It's partnering with product. It's helping to spearhead go-to-market delivery. It's navigating change management. So your impact explodes when you move into enablement. And it lit another fire for me. I felt like I got a second wind when I moved into the enablement world. And I mean, it was a very difficult decision and it was risky. Like I took a pretty big pay cut to move from sales leadership into this unknown because we didn't have enablement.

44:49So I built it from the ground up and I learned through some bumps and bruises like what I was doing. And I just kind of figured it out. And from there, I've built and scaled enablement functions. And that is part of my DNA now in my career is I think about things from the enablement perspective. And I think about how can we take this theoretical, abstract, kind of challenging, like learning or training or framework. And how can I make this so easy for reps to learn, so easy for them to practice and adopt and see the transformation. But also, how can I make it easy for leaders to reinforce? Because without that aspect, leaders are multipliers.

45:39So if you're not pouring into your reps and you don't know how to coach your reps, everything that we're working on is going to fall flat. So that became a passion of mine and ultimately, I think, helped lead me here. Yeah. One of the things that I really admire about you is your ability to have almost no direction with something outside of, hey, here's your role and the outcomes that I need to get. Whether that's you being a first-time sales manager or working as a rep in some of these orgs and not having a lot of direction. And then the enablement function, creating that from scratch within an org.

46:19I really admire that about you. The thing that you've crushed too is for those of you watching and listening that have been a client before, you understand the journey that we have gone through from a curriculum standpoint. And when I was doing all of this stuff by myself, like when we met for the first time, there's a version of things that happen. And since you've come into the company, it's significantly up-leveled. I mean, our whole reason to meet framework and how we're able to really simplify like the messaging approach and you've really spearheaded a lot of that. I have loved every minute of it.

46:59And it's selfishly one of my favorite things about this project has been that I can input some of my DNA and some of my like I'm making an impact here. But it's not just making an impact with Outbound Squad. It's actually making an impact with every client that we work with moving forward. And that is the most exciting part of it all is I know what we've leveled up and changed has significantly impacted the teams that we've already rolled it out to. So I'm just so excited about the scaled success that our clients are going to see because the content was wonderful. I remember how great it was years and years ago when you led it for our team and just seeing the metamorphosis of the content.

47:54Metamorphosis. I know that's another one. Just seeing how it's changed. But it hasn't changed. It's just become easier and it's become more scalable. And that is exactly what I look for and try to bring to life from the enablement perspective. So let's talk about some of the things that you – you're the enablement brain at App on Squad right now. I'll love that. Let's talk about some of the themes around how you think about enablement. You've mentioned some of them. Hey, making it incredibly easy. We use this phrase eating complexity here, right? How do we remove all of the extra steps, whether it's the org can do it on behalf of the rep or a tool can do it or, you know, addition by subtraction.

48:40We just take out some of the unnecessary stuff. You've talked about the managers and making sure they can reinforce it. What are some of the things that you think about from an enablement perspective? Perspective? So the inside joke here for everyone watching is we have been making fun of each other because there's like buzzwords that each of us says a lot. Perspective is Clara's word. How do you think about that from an enablement point of view in terms of themes around how to make stuff really stick and land with the org? Yeah. I think one thing that a lot of enablement programs get wrong, and it's easy to do this.

49:20You put all of your time and energy into this great training program, and you're so excited to roll it out. And then it falls flat. And you're like, what? This is great work. Like what's going on? And it's because training can't live in a silo. Learning can't live in a silo. Growth can't live in a silo. And so I think that one of the most important things that I think about from an enablement standpoint is how can we reinforce the narrative? How can we make this so consistent? And that goes back to the practice conversation we had. And it's this consistency that really drives the behavior change.

49:59So we should have a really great training program. That's part one. But we need to make it tactical, not theoretical. We need to make it actionable. We need to help reps make it their own so they feel this freedom and they feel bought in and they feel like they're co-authoring alongside you. that increases the buy-in with reps which I think is really important if they're not bought in then they're not going to adopt they're not going to lean in the same is true with leaders so where I saw friction early in my enablement career was when I assumed that I knew best and again this is like an ego thing that I had to kind of learn the hard way the best enablement programs are programs that are built in lockstep with your partner organizations.

50:50So sales, BDR teams, AE teams, like you need to create and co-author alongside them, get their buy-in, see their gaps, see what they're excited about and give them responsibility and autonomy there. See where their weaknesses are and provide supports and structure and resources to help combat that. But when you just try to throw a program on reps or leaders in a one-time capacity and expect it to drive change, that's never going to work. So it's this continuous motion. We'll do a training program. Is that it? Are we doing anything else? Are there resources? Is this a mini series? Are we doing snackable content as I like to call it, like short videos?

51:35Like what are you doing to reinforce the narrative here? It can't just be one time. And the same is true with leaders. So when we train something, when we roll out an initiative, a new framework, whatever the case may be, leaders have to own the carry forward. They have to keep like driving it home, if you will. So the partnership is huge. The reinforcement and consistency strategy is huge. and I also think you need a very strong perspective when you're in enablement because it's easy to be kind of bulldozed by the teams you're working with they think they know best they see these gaps they want this but is that actually the best solution for the team does the team need like discovery training or do they need to focus on like trap questions like do they need to set better expectations when they're meeting, when they're booking the meeting?

52:33Do they need to refine the qualification process or is it discovery? Like really being able to understand the trends and the gaps, have a point of view, surface that to leaders and really partner and lean in. I think that is what sets enablement teams up for success. Yeah. The co-authoring is big. Yeah. You've seen that's a big part of how we do things. It's, you know, hey, we need to spend three, four weeks customizing the content with you. We're going to come with a really strong point of view on what we think things should be and sound like and all of that kind of stuff, but you need to participate in the creation of it for sure.

53:09And then it needs to be built with reinforcement in mind. What are some of the other, if we were to kind of spitball for a little bit, what are some of the other themes that you have seen in, you've had some massive successes with several of our clients. You know, like iHeartMedia, you know, one of the cohorts you worked with, I think increased first time meeting set from account executives, people that don't prospect full time by almost 50%. Yeah. You kicked my ass in the first cohort. That was my goal. Yeah, with that group. Massive success there. Optimizely was another one, like massive success.

53:47When it really works well, what are some of the other themes that you have seen with some of the clients that we've worked with? I actually think there is a theme that I've seen with our clients, but I've also seen like externally as well. It's around change management. So especially for teams that don't have a strong pipe gen motion where Albound is not built into the culture and the DNA of the sales team, that's actually quite a friction point to lean in. And And it almost feels like a 180 for reps that have never really had to do a lot of prospecting and then flex this muscle and be expected to be excellent at it overnight.

54:28And a lot of the times the goal is lofty, like two, three X pipeline within a very short window. And people want to do it within the corner. And you don't feel like you have the tools to do that. And so I think change management actually is really critical and it's so easy to get wrong. And co-authoring is actually a big part of change management. When you bring the impacted team members into the fold and at least give them the capacity to have an opinion and share that opinion and shape the direction, that really changes rep mindset. And I think that's something that we do really well. because when we are in our workshops, yes, I've got frameworks, I've got examples, but I want you to make it your own.

55:19I want you to practice it and you give me feedback and then let's riff on how we can make it better. How can we make it more authentic to you? So now you trust that I actually care about your growth and your experience. I'm not just trying to force something on you and say, Hey, Jason, good luck. Figure it out. This is, this is the way we're doing it moving forward. Yeah. The make it your own is something you've brought up a couple of times. Could you share some of the stuff that you've been working on recently with the content we've been revamping around this idea of like, what is a framework that allows someone to make something their own versus, you know, if we're using cold calling example, hey, here's the script, here's your permission, permission-based opener, your PBO, say this, how have you seen through your career and just, you know, kind of recently with some of the stuff that we've been working on, like what does that mean to help someone make it their own?

56:12And like, what does a rep need from us and from enablement in order to have something that they can make their own? Yeah. So when I think about making it your own, I never worked well when someone gave me a script that I needed to follow. I needed to understand what's the script accomplishing? What's the story it's trying to tell? And how can I tell that in my own authentic way? And I think that is something that we bring in to everything we do. So we've got frameworks that break out. How do you do a permission-based opener? How do you do an RTM, a reason to meet? But what I think is so important is you have to make it authentic to you.

56:57So when I am, for example, thinking about reason to meet and we talk about our cold call opener, cold call intro, the way that we've done it, I think, makes it so easy and kind of gamifies it for reps too. So I've got examples. I've got frameworks. I've got scripting you can lean in if you need to. But really, Jason, what you need is you've got to have a greeting. You have to have at least one of the three T's. The three T's that we refer to is either a trigger, tension, or trust. And then you need to wrap your permission-based opener by asking for permission. The way that I might do it would sound probably different from how you would do it, but we're still following the framework.

57:43So if I am cold calling, I would say, hey, Jason, I noticed you just opened a new branch in the Nashville market. It's Amanda with iHeartMedia. Do you have 22 seconds so I can tell you why I called? Like that, I'm leaning into a trigger. That is my opener. I just need one T, but I could shift it. I could change it. I could focus on the tension that you might be feeling entering a new market. You've got to expand your brand awareness and you need to do that quickly because you're competing with local brands that already have that trust. It's Amanda with iHeart. Do you have just a minute? Like it doesn't matter how you get there.

58:21It just matters that you have a roadmap that's going to keep you successful. So I always advocate for reps to make it their own because if you sound scripted, you're going to come across very uncomfortable. And I never want a rep to sound like an AI robot on the phone. I want them to sound like their human self. Yes. And one thing that we've talked about a lot is this why, what, how framework where anytime we're teaching something, they have to understand the why, which is like the objective. If we're talking about the first – the intro of the cold call, it's like the objective is like I need to like make an entrance and get permission and pattern interrupt usually in some sort of way to like get them to understand that I'm calling you on purpose.

59:07I researched you. I'm not like every other sales rep. Like give me like a minute or two to just like share why I'm calling you because this is a really good reason. The what is like the permission-based opener and like the reason to meet framework that we've talked about. Yeah. And then the how is like the tactical execution that we're giving you some examples. Like here's what that might sound like, but we're really empowering them with the what and the why. Yeah. And that's the mistake I think that almost all training makes, especially a lot of the internally stuff is they just give the how.

59:39They just say, I want you to do this how. You don't need to understand why it works. It just does. Yeah. Trust me. Yeah. And there's no like building blocks of like, how do I make this my own? And why should I do this in the first place? Yeah. Like, I think that goes back to change management. You can't just expect someone to change behavior unless they understand what's in it for them. Yeah. Like, what is the benefit here? Why should I open a cold call by asking for permission? Like, who would do that? That sounds weird. But we need to realize that our prospects aren't expecting us to call them.

1:00:14They didn't ask us to cold call them in the middle of their day. We are creating friction for them when they realize that it's a cold call. So the best path forward is to give them autonomy in the conversation. Let them opt in, make it safe to say no. And what that actually does is it makes them more inclined to lean in and say yes. And so I think when reps understand the why and they understand that the way they get there, they can have their own blueprint. They can have their own spice, if you will. Yeah. But this is the structure that provides success. That covers everything for reps. Yeah.

1:00:56It's giving them, we've used this analogy a couple times this week, the sandbox or the bumper guards or whatever. Like give them like a space to play. Exactly. This has been great. Yeah. So I got a couple surprise rapid fire questions for you. Okay. You ready? I haven't prepped for these. Yeah. How do you like to decompress after a long workday or workweek? Oh, you probably already know I'm very woo-woo. For those in the audience that care to know, I am very woo-woo. So I have like a sound bowl that I'm listening to if I get really stressed. I've got red light therapy that's going on but I will say my guilty pleasure when it comes to like decompressing I kind of dissociate and I read a lot so I love reading I wish I could say I was reading more like self-help yeah yeah I'm reading a lot of fiction and it's just kind of nice to to get out of my body to get out of this whatever is causing stress in the moment and just kind of live in a world that doesn't exist but sounds so wild and crazy like yeah that's what i do when i need to decompress or if i'm being honest i binge watch trash tv so love island bravo like yeah yeah the fiction is really great for developing empathy yeah so it's something I'm trying to lean a little bit more into as well, because the self-help books are, they're great, but you don't get to hear a lot of internal dialogue.

1:02:36And I think in sales, it's really important to like understand the internal dialogue that a buyer is having, especially because you're already dealing with the fact that you don't really know this person that well as a person. And there's this like guard up that's going to be in any interaction like that. What's one thing you have to bring with you on a work trip when you're traveling? Oh, that's a really good question. Let me think about this for just a second. So when I think about traveling for a work trip, I – this is like kind of subtle and probably a dumb answer. But I am a comfy girl at heart, and I need to be able to feel comfortable.

1:03:18And so I will bring – every single time I have to bring my like ratty, tattered sweatshirt because it is home for me. It feels comfortable and it's a way for me to like just feel that like warmth of home when I'm away from my family. So I would say probably just like a real tattered. It's a Tennessee sweatshirt because I'm go Vols. I'm a Tennessee alum. So, yeah, it's just like a janky sweatshirt if I'm being real. I love it. Lastly, what's your fuck you money purchase? We talked about this. So I think I have actually two and my goal is to be swimming in cash so I can obviously do both of these.

1:04:03But my first, I think, is a really souped up and like pimped out golf cart because I have found. To drive around your neighborhood. Yeah, I have found myself living my dream. I'm in a neighborhood where people drive golf carts. And I just, I think that's so funny. And I want to have the golf cart that like stops people in their tracks, you know, maybe like pastel blue or something like real, real snazzy. It's got to have good music. I want lighting. I want lots of seats because it's going to be the whip that is transporting all of the children to the pool and back. Yeah. So that is one. And we also talked about the fact that I would probably have my husband, Zach, drive the golf cart and I would be holding onto a string off the back and just use it like using my longboard.

1:05:01And he would just like drive me around. So that's probably my first. And then the other one that I would say, another vehicle actually, is a really badass, renovated, like mid-century modern Airstream. I just think that would be so cool. Yeah. Yeah. Because Airstreams have this like vintage flair that I personally find myself very drawn to. And you probably are not surprised by that because you said you think that I was actually supposed to be born in the 60s or 70s. Yeah, totally. So Airstream is my vibe all the way. And I want it to feel really cool inside, like disco ball and like mid-century modern, like wood finishes.

1:05:48Like, yeah. Hell yeah. So those are my purchases that I'm manifesting it now. My woo-woo side is going to manifest both of these purchases. I don't know when. It's not really my call, but it's coming. I love it. Before you take off, where do you want people to go to connect with you? I'm on LinkedIn. so I would love to connect with anyone on LinkedIn I'm trying to do a better job of sharing my voice and sharing my perspective not for any gain other than putting myself in an uncomfortable situation and and honestly just leading with a little bit of vulnerability to make it a safe space for others to feel like they can find their voice and do that you have a lot of really really great things that you share with our clients and I'm looking forward to getting stuff like this is kind of the start of But I'm looking forward to getting more of this on you.

1:06:38So I want to challenge myself there for sure. It's great to have you on. Thank you. It's been so fun.