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Index/Sales/Bold Calling
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From SDR to Sales Leader

Bold Calling · 2025-04-18 · 31 min

0:00--:--

Key moments - from our scoring

Substance score

18 / 100

Five dimensions, 20 points each

Insight Density4 / 20
Originality3 / 20
Guest Caliber3 / 20
Specificity & Evidence4 / 20
Conversational Craft4 / 20

This episode features an internal conversation at Orem with two high-performing salespeople who progressed from SDR roles to leadership and AE positions. Kevin Wynn leveraged Orem as a customer before joining as an SDR, winning Rep of the Year in his first year before advancing to team lead and eventually account executive. Brayton Riley transitioned from a teaching background with no sales experience, rising to SDR Rep of the Year and team lead within 18 months before breaking into enterprise deals. The discussion covers critical themes for early-career sales professionals: finding mentors within your existing team, managing the emotional transition from peer to leader (including managing guilt around leaving the team), maintaining positive energy as a leader using the principle "attitude reflects leadership," and practical time management across competing priorities. Both speakers emphasize the importance of self-care (exercise, social connections, community involvement through groups like Alluvians), asking for feedback when deals don't close, adopting an abundance mindset to avoid fixating on difficult prospects, and building discipline through calendar blocking and audit processes. The episode serves as a practical playbook for SDRs considering advancement into leadership or AE roles.

Key takeaways

  • →Transition from SDR to leadership involves managing personal guilt about leaving the team behind while trusting promoted peers to carry the responsibility forward.
  • →Maintaining visible positive energy as a leader is critical - your mindset and mood directly impact team morale, requiring deliberate self-care practices like exercise, social time, and community involvement to refill your own cup.
  • →Abundance mindset prevents you from getting stuck on prospects who won't convert; instead, expand your list and focus on new opportunities to maintain momentum.
  • →Time management shifts dramatically moving from linear SDR schedules (prospecting blocks, cold calling hours) to non-linear AE work requiring end-of-day audits, priority checklists, and next-day prep.
  • →Asking prospects directly what you could have done better after unsuccessful pitches is a high-ROI learning habit that accelerates skill development and builds rapport.

Guests

Brayton RileyKevin Wynn

Topics in this episode

Enterprise salesCalendar blocking and time managementSDR to account executive career progressionSales team leadership transitionsAbundance mindset in salesEnd-of-day audits and next-day prepMentorship and team enablementOrem (the company)Self-care for sales leadersAlluvians sales community

Questions this episode answers

What advice helped Brayton Riley get unstuck when she was in a rut with her pipeline?

Aeralee, the SDR manager, introduced her to abundance mindset - instead of fixating on a few high-value prospects who weren't answering, Brayton shifted to expanding her prospect list and calling fresh leads, which immediately improved her booking rate and mental state.

How did Kevin Wynn adjust to the shift from SDR work to account executive responsibilities?

Kevin transitioned from a linear schedule (four hours prospecting, three hours cold calling) to non-linear AE work by implementing end-of-day audits, priority checklists for the next day, and disciplined calendar blocking to ensure all prospects and tasks receive appropriate attention.

What is one consistent practice both Kevin and Brayton use to maintain energy and positivity as leaders?

Both prioritize self-care through physical movement (Brayton runs/goes to the gym, Kevin is part of the Alluvians sales community), social connections, and ensuring they fully disconnect from work in the evenings to recharge before the next day.

Did Brayton Riley plan to move into team lead or leadership when she started as an SDR?

No - she initially wanted to focus on her own performance after being burned out from teaching management. She naturally transitioned into the team lead role because she enjoyed supporting others and being a cheerleader, despite lacking the technical mentorship skills Kevin brought to the role.

What is the core piece of advice Kevin Wynn emphasizes most often when coaching others?

Don't be afraid to fail forward and ask questions - when deals don't close, ask the prospect directly what could have helped you book them, and remember that "closed mouths don't get fed" when seeking feedback or opportunities.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

4 / 20

The episode is packed with well-worn sales platitudes ('fail forward,' 'abundance mindset,' 'closed mouths don't get fed') with almost nothing a working B2B operator would not already know. The few concrete tactical points - such as blocking calendar by AE or doing an end-of-day audit - are surface-level and underdeveloped.

don't be afraid to fail forward
abundance mindset, abundance mindset. And I've known about this, people say it all the time in sales

Originality

3 / 20

Every framework or piece of advice offered is explicitly acknowledged as common ('people say it all the time in sales') or is a recycled pop-culture reference. There is no contrarian argument, no first-principles reasoning, and no take that challenges conventional sales wisdom.

abundance mindset. And I've known about this, people say it all the time in sales
don't be afraid to fail forward

Guest Caliber

3 / 20

Both guests are junior-to-mid-level practitioners (an SDR team lead and a newly promoted AE) at the host's own Series B employer, making this effectively an internal company content piece rather than an expert interview. Neither has led teams at scale or across multiple organizations.

my Aurum journey started off as a customer. I leveraged Aura, my original, at my first SDR role in tech
I became team lead at an interesting time because we had just, like, created a whole new team

Specificity & Evidence

4 / 20

There are almost no metrics, dollar figures, or data points that would be useful to an external operator. The only concrete specifics are rudimentary scheduling details and headcounts that apply only to the guests' specific situations.

Four hours of prospecting, two hours, three hours of cold calling
I only support two AES, so it's nice

Conversational Craft

4 / 20

The host asks consistently soft, open-ended questions, frequently inserts lengthy personal anecdotes about himself (his own career goals, running habit, partner's morning question), and never challenges a vague claim or pushes for a specific example. There is a noticeable audio dropout mid-episode with no recovery of substance.

I want to ask you guys about that, like, kind of filling up your own cup
I love it. This is fantastic. Kevin Brayton, thank you both so much for joining me today

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B38%
  • Speaker A36%
  • Speaker C26%

Most-used words

team61lead27kevin25feel16sure15brayton14start14leader13role12different12mindset12first10leadership10love9success9sales8

Episode notes

Featuring Kevin Nguyen & Brayton Riley Host: Adam Sockel | Presented by Orum Episode Overview In this episode of Bold Calling , we're joined by two standout Orumites who've made the leap from SDRs to sales leaders: Kevin Nguyen , now an AE, and Brayton Riley , now a Team Lead. Host Adam Sockel guides a candid and insightful conversation about their career progression, leadership philosophies, and the lessons they've learned along the way. If you've ever wondered what it takes to rise in sales, lead your peers, or just show up better every day - this one's for you.

Full transcript

31 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: You are listening to Bold Calling, an award winning podcast presented by orm, where every episode we're bringing on the biggest and brightest minds in tech and sales for a discussion about their biggest challenges and the unique ways they are working to solve them. Today I am joined by two absolutely fantastic Oramites who I kind of bullied into doing this. I have Brayton Riley and Kevin Wynn. They have incredible experience going from SDRs to leaders here at Orem. So we're going to talk about their stories and how they got to where they are. Kevin, Brayton, both of you, thank you guys so much for joining me today.

Speaker B: Of course, literally no bullying was needed, by the way. Yeah, we love Adam, you too.

Speaker A: All right.

Speaker C: Ah.

Speaker A: So what we're going to do today, like I said, Brighton and Kevin both started out at their aurum journey as STRs and they have since moved on to other roles because of their incredible success and talent and capabilities. And we want to give everyone else a playbook for how they can expand into new roles from their careers if they're just starting out in SDRs, if that is what they want to do. So we're going to start by how you guys got to where you are, from where you were and just go through a whole bunch of stuff. So first things first, Just because one of you has been here longer than the other, we'll start with Kevin. Tell me about your path here at Aurum into your current role.

Speaker C: Yeah. Um, so my Aurum journey started off as a customer. I leveraged Aura, my original, at my first SDR role in tech. I sold to DevOps. Sold, okay. But really saw the value of Aurum and reached out to my CSM Patrick, to get my foot in the door. My OREM journey was a really fun one. I found a lot of great success in partnering with my AES to be Rep of the Year. My first year here, getting promoted to senior, then to team lead, helping onboard Brayton becoming a top rep herself before jumping onto the AE side of things. Now, the two and a half years here has been super fun and incredibly rewarding in so many different ways.

Speaker A: I love that. Speaking of, from one STR of the year, I believe, to the. To another STR of the year, Brayden, tell me, tell everybody how, uh, if anyone has seen our social media, I've made Brayden talk a few times about her path from like, from teacher to here. But talk about your journey and how you got to where you are now.

Speaker B: Yeah, definitely. I mean, Kevin was a huge part of it. Like he said, uh, when I got here, I had no SDR experience at all, really just came from a teaching background. That's what I thought, you know, most of my career career was going to be. So joined the team. Kevin was a senior SDR at that point, not team lead yet. Um, a few months later, he ended up getting promoted to that team lead spot. But I felt like he always was kind of a mentor to me. I had a few really strong senior SDRs on the team that I kind of looked up to because didn't really know how to, like, set the pace myself. I had no SDR experience coming into this. So, you know, I had Kevin Dom, who's now an ae, Julie, who is killing it elsewhere. So definitely had a few really strong mentors that I looked up to. And that's kind of all I knew was, like, what they were doing. So got ramped up pretty quickly. Like I was hitting the phones here second weekend, just faking the confidence, you know, listening to all of their calls, figuring out what's working for them and kind of making it my own. Just, yeah, faking it till you made it. And yeah, I felt like I just kind of picked up momentum. Didn't, um, have the best first quarter because I was just figuring out the text stack, but second quarter and beyond, I just kind of kept, kept scaling up and I would say was, what, a year and a half into it, I got promoted to team lead and then around the same time also broke into the enterprise space. So a lot of change in the last three months for me on the SDR team.

Speaker A: I'm curious and, uh, Brayden, we'll start with you. Like, was was this your goal when you start out here at Orem? Obviously, like, you know, I don't mean like your end goal, but when you start out as an sdr, was it your eventual goal to say, like, I want to go from SDR to team lead? Or were you thinking, like, I want to be eventually a CSM or an account executive? Like, what did you have in your mind was going to be the path you would take?

Speaker B: Honestly, no, I didn't consider doing team lead or any sort of leadership in this role. I think honestly, teaching kind of burnt me out. Like, I didn't really want to be in charge of anyone else's, you know, abilities or success at first. I just wanted to be able to, like, go in, do my own thing and, like, crush it at what I'm doing. And I think I just kind of naturally got into that team lead role, if I'm being honest, because I enjoy, like, supporting others and, um, being everyone's cheerleader. And so I might not have had, like, the technical background or the things that, you know, Kevin was really good about, like sitting down with us on a one on one and being like, hey, what, what are your goals? Like, what do we really need to do to get there? And giving us, like, really technical tips that we can use and great talk tracks and things like that. And I was kind of like, okay, like, yes, maybe I could jump into that role. But, like, I think I have a different set of, um, you know, it's different asset to the team. So I think me being more of a support system for the newer reps and, yeah, being a person that, you know, people can lean on and helping with the enablement piece because being a teacher background, so just kind of finding what works for me and where I'm an asset to the team. And I kind of just got, you know, pushed into that role and I was happy to take that on, but definitely my goal is just to really get into that AE role and kill it as an individual contributor. For sure.

Speaker A: I love that. Kevin, how about you? What, what was your initial like, hey, here's where I want to get to when you started here.

Speaker C: Yeah, um, this is a really interesting question because as I was completing my first year as an sdr, um, I really did not know what I wanted to do. And kind of similarly to Brayton, I really enjoy, like, helping out the team. Like, when we got new reps, like, my goal was to always help them be as good as we are. Like, if I could find success, how much can I share that? And I think a lot of that, uh, turns back on talking my own history. I've mentored teams or cohorts of fresh grads to help them break into tech. I, I have always had, like, that older sibling type of energy. Um, and even now as an accounting executive running through pilots, like, I find so much joy. And when the reps get that aha moment, like, Orem is unlocking so much for us. So when I jumped into the team lead role, I really wanted to ensure that Brayton and Sean, who is now our senior sdr, was able to find their own beat and their own way to sell and really capitalize it with OR's capabilities. And then even now as an account executive, like, being able to help the new SDRs find their own voice and how I used, like, was able to be successful, like, being. If I'm not a leader now, like, I'm still a leader to them. Because they're helping me out.

Speaker A: Yeah, I. And I want to clear. Like, I want to clarify. I asked you both, like, if this was your goal, and to be fair, if someone would ask me in my first marketing role, like, what do you want to be when you grow up? I would have been like, I don't know. I just. Please keep paying me every two weeks so that I can pay for my insurance. Like, but now if you were to ask me, like, I want to be a CMO someday, I want to be a Chief Marketing Officer somewhere, whether it's here or elsewhere. And, like, you do start thinking, like, okay, in order to do that, like you said, uh, even if you're looking out for your, like, stuff that you're doing in your own pipeline, you're. It's also you. You're like, okay, how do I take the time to make sure I'm doing that enablement? To your point, Brayton, you're like, I'm helping lift up other people. And I. There are. It's this unique thing of, like, I want to look out for number one quote, unquote, but I also want to, like, lift everyone else up. And it all really does end up paying off. And, you know, those are. Those are some of the challenges, obviously, that the people experiences. They're kind of taking on leadership roles. But I'm curious for both of you, like, what is. What was. Has been. Slash, what was Kevin, for you? Like, the biggest challenge? And Kevin, Kevin, we'll start with you. Like, what was the biggest challenge in going from someone who was on the team to kind of leading a team in real time?

Speaker C: Yeah, the biggest challenge was kind of just. It was a lot of personal guilt. Like, it was a really big transitionary period of leaving the team without real leadership, um, and ensuring that they could be successful while still wanting to achieve my own goals. Um, part of me, like, I'm really glad to see where things are going now, but a part of me still feels a little guilty for not being able to. To support the reps as they are when I did move over to the, uh, AE team. But the other side of it, too, is, like, I had a lot of faith and trust in Brayden and Sean, and I knew that they would be able to, uh, carry on the flag just on the conversations that I still have with both of them. Um,

Speaker A: I know what you mean. Like, as a person who is both a individual contributor and like a strategist, it's like, it's so hard to let go of some things to focus in Other areas. And, like, it can be challenging to kind of take a deep breath and be like, okay, these people got this. And like, Brayton, for you going from a member of the team to leading the team, like, what. What did that feel like?

Speaker B: What were.

Speaker A: What were the challenges you experienced? And then kind of, how did you address them in real time?

Speaker B: Yeah, I. I think one of the biggest challenges for, for me is remembering that, like, now my energy that I'm bringing into every day is gonna impact the rest of the team. So there might be moments where it's like, yeah, I wanna vent about a change that's going on, or maybe I'm not having the best week. And it's like, I'm not going to bring that onto the team and let that energy bring the rest of everyone down. Cause I wanna make sure I'm lifting everyone up. And so now it's maybe going to Kevin or, you know, talking to my manager or, you know, really figuring out, okay, who. Who do I want to bring these issues to? And, like, the energy that I'm making sure I'm bringing to the rest of the team, right? And making sure, you know, now I'm like, uh, gathering the troops for, for the sales floor, making sure, like, I'm showing up every day, um, and not just in my own little island, keeping my head down. I'm grinding. Especially when it comes to, like, end of quarter, making sure I'm still, still prioritizing time every single day. Because I do think that energy is felt if, like, I disappear. The whole team's, you know, not bringing their all every day. Like, that's definitely felt even in a remote environment.

Speaker A: I want to ask you guys about that, like, kind of filling up your own cup, because there's this quote from. It's actually from the movie Remember the Titans. This is so cheesy, but the movie Remember the Titans, which came out, I think probably before either of you were in the working space. I'm. I. Oh, Kevin's giving me the faces. Like, no, what are you talking about? Anyway, there's a quote where they say attitude reflects leadership. And, like, this is where I will give our, like, head of our sales team, Colin, a lot of credit. Like, he's always so positive and, like, I'm sure there's got to be days where he's tired and, like, having a rough moment. And, like, I feel like I'm pretty well known around here for being positive and, like, reflecting. Um, hang on one moment. You still there, Kev?

Speaker C: Yeah, I'm still here.

Speaker A: You there?

Speaker C: Kevin, I am. Can you hear me?

Speaker A: Okay. There we go.

Speaker B: Yeah.

Speaker A: Um, anyway, there's this quote. Attitude reflects leadership. It's from Remember the Titans. And it's like, our leader, Colin, our sales leader, he's always super positive, and it's like, I'm sure there are days where he's having a rough moment. Um, like, I think about this personally because people always think of me as, like, a very positive person on slack and in meetings and trying to be, like, Mr. Positivity. But I definitely feel some days I'm just like, oh, my God, I don't want to do this. I don't have a team under me. I have a team that I work with. But, like, how do you guys. Where do you go to kind of fill up your own cups and, like. Braden, we'll start with you. I, uh, think you and I may have talked about this, like, going for walks and, like, having, like, a Zen moment at the start of the day. But how do you refill your own cup to make sure you can be that source of positivity and energy for your team?

Speaker B: Yeah, I definitely feel. Feel it on days where I'm, like, working too late or I don't move my body. I, like, feel it coming into the next day. And so I'm big about, like, once my laptop shut. Like, I'm not gonna keep opening it after dinner or looking at emails before bed. Like, once I shut my laptop unless it's really urgent. Like, the rest of the night's for me. So going on walks now that it's spring. I live in Seattle, so for me, I've just been hitting the gym and running on the treadmill every day. Day, which isn't ideal, but, like, moving my body in some capacity. And I even notice on weeks where I'm, like, more social with friends, like, I show up better at work. So I'm big on, like, planning my week out with friends, doing a lot of, like, one on one, um, you know, friend dates throughout the week and catching up with people. Like, that's huge for me, just having my social time outside of work.

Speaker A: Yeah. Kev, how about you? How do you make sure you're ready to be energetic and positive for your team? And especially when you were a leader before.

Speaker C: Yeah, I mean, I still think it's the same today. Like, even if I'm not. I may not be leading a team, but I'm still, uh, a leader. Both here as an account executive and then in campaigns, uh, with my prospects, like, if I'm not showing up for them Then m. Who else is going to do it? Right. So uh, but I lean on a lot of my communities and like shout out to Alluvien the sales community that I'm a part of. That's really helped me like shape my vision and uh, ground myself to be able to show up as my full authentic self and really to keep the energy up. Brayden couldn't test this. She's seen like pre Alluvians and post Eluvians and just like how much that has affected the way that I show up for myself and for the team.

Speaker A: Yeah, I love that. I will say I'm very much like Brayden. My partner asks me every day, the start of the day, what does self care look like for you today? And every day it's going for a run. Um, that's like a, like that's how I have to, I have to move my body or else I'm gonna go crazy. So I definitely appreciate that very much. I would love to hear advice you guys have had, have been given from your leaders that you are using in your daily jobs now that will that are, that's helping you out. Like for example, I'll give you leadership one from a previous job I had like I had a SVP of brand marketing and they like, they just reminded me that when somebody gives you feedback who's above you, you have to remember that you don't have them, you don't have the context for why they may be being harsh about one thing or another and you can ask them but they may not be able to tell you. But just understand that like where they're coming from maybe from just a different angle from you and it doesn't mean what you're saying and doing is wrong. It's just maybe not right for the this moment. And that's always been that's helped me take a deep breath. Anytime I create a piece of content and someone above me is like no. Because like I, I, I wait. So that's been really helpful for me to remember that like they are coming at anything from a different point of view. And I'm curious for you guys now that I've vamped for a little bit and I can let you guys speak. Kevin, is there a piece of advice that's been really beneficial for you that you think about often?

Speaker C: Um, I have the only thing I really think think off top of my head is just like don't be afraid to fail forward.

Speaker A: Mhm.

Speaker C: You learn a lot from failure. And I think too like when I was an sdr. When I wouldn't book meetings, I would and I still have prospects on the phone. I'm just like, hey, what can I do better? Like mhm. What would, what would have helped me book you that I can book the next one? And people are always receptive to answering that question and I guess like a two part thing where like closed mouths don't get fed so just not being afraid to ask questions. And I, I'm pretty sure I've told Brayden that probably a hundred times when she was ramping.

Speaker B: Yeah, it's a big one over here. Yeah, don't ask, don't get.

Speaker A: I love that. Is there, are there other ones Brayton, for you that like from a leadership standpoint people have told you?

Speaker B: Yeah, I actually think back to, I think it was Aeralee's like second month here. She's our SDR manager. She's amazing. She. I wasn't having the best week that week. I was just kind of in a rut cuz that happens to me as well. And it's just, yeah, once you're in that like it is uh, it's. You have to have a mindset shift. And she was talking about abundance mindset, abundance mindset. And I've known about this, people say it all the time in sales. Like we constantly are talking about abundance mindset but it's really hard to like understand how to actually do that. And so she kind of walked me through it. She's like, okay, well we have all these accounts you're going after. You're talking about these people that you know, you'll convert to a meeting if you get them on the phone. Right. But they're not answering. So like what are we going to do? We, we can't just be relying on these, you know, few accounts. Yes, they might be great prospects and could really use Aurum, but like it's not working right now. So we need to think there's so many other options out there and so many other people that could have a need for us. Like go up after them and you won't be so stuck on these few people that you're not getting in contact with. And so you know, just having this like fresh list of leads, like it honestly just was like a weight lifted off my shoulder and then I was booking more. Like I wasn't focused on um, what's not converting. I was focused on like the possibility. And so I've kept that like if I'm in a rut and things aren't going well for me, like Go out there and add a ton more prospects. Like just that mindset shift of calling a fresh list. That is all in a step one of my sequence. Like I go into it with a whole different mindset. Um, and so, yeah, I think like, actually understanding, like how to use your abundance mindset every day, um, has been, been huge.

Speaker A: I love that. Uh, I want to ask you guys a little bit about time management because obviously you're building your own pipelines, you're leading other people. Kevin, now you're like doing demos too, and there's a whole bunch of stuff going on. And like, I know you're both in different roles from one another at this point, but I want to hear how you guys are managing your time, whether it's like blocking out your calendar. Kevin, we'll start with you. Like, Kevin, how do you approach time management your schedule usually look like, so that you can get all the things done?

Speaker C: Yeah, as an sdr, it was pretty linear. Like I had. It was straightforward. Four hours of prospecting, two hours, three hours of cold calling, and like that was it. Um, and those hours, like I would go account of account, maybe, um, do some LinkedIn stuff here and there, like my last hours, my uh, end of day audit. Something that people don't tell you when you transition to AE is just how going from a linear to a non linear day can be really jarring. So a lot of it has to do with like your end of night audit and your next day prep list and like, what else can you get done that is priority one that you need to get down now. And being disciplined with your time has been really hard, but we're getting the hang of it. And just having that checklist is really the most important thing for me to knock off to make sure that no stone is often turned and that everyone is getting the attention they all deserve.

Speaker A: Yeah, I was laughing. We were talking about linear linearly and non linearly. Because as a content person who's usually doing 17 different things, like, forget linear nonlinear. Mine looks like, like a scatter plot or like a novel that has 15 different timelines and no one really knows what's going on to the end, that's how I feel. Like my day is like, um, Brayton, um, I'm curious if you like, as you're also leading a team, but like focusing on your own pipeline, how do you split up your time so that you can be present for everyone who might need you while also realizing that you do need to have that abundance mindset for yourself as well?

Speaker B: Yeah, I Definitely. So I break my day into like what AE I'm prospecting for and kind of Monday's more like understanding kind of my workflow for that week. Things, accounts, I need to prioritize all of that and then I break it down into I only support two AES, so it's nice. The, the other four days I go back and forth so I know, okay, today I'm really focusing on prospecting tavers. The next day I'm doing Sam's. So I'm not switching too often within one day on my book of accounts. So that's been really huge for me. And then honestly like I, I have my typical calendar that I've had since I became an SDR and that's kind of what I stick with. But, but I do have like my two other you know, tasks as an SDR that I do or team lead every week is I do our Friday meeting where I'm um, doing our shout outs for the team and going through all of our stats. So I know I have a little block on my Friday morning, like put together your slideshow. And then I also know that you know, every Monday I'm doing my one on one with aerily where I'm going to be, you know, bringing up ideas for the team or maybe new enablement ideas into. So I also Monday morning when I'm like going through my workflow for the week, like that's something I have like a little brainstorming session, um, morning. So aside from really the those two, you know, team lead blocks that I have every week, I'm pretty much open. Like if I'm in a prospecting session and people want to huddle me or slack me, like I'm pretty good at just doing it right away and kind of moving on with my tasks. So overall it hasn't really changed. Like I stick with my calendar block from week one as an sdr.

Speaker C: Yeah, I think the difference like when I was a team lead for Brayton to um, where she is now is like there's different leadership and our previous SDR leader leaned on me pretty heavily to like take a higher leadership role. And I think what worked really well for me is the taking the time to see like what does each rep need right M. With the newer reps it was definitely more heavily on being creative with enablement, trying to up level them in an additional skill outside of what they're currently working on. I was an enterprise rep with our senior reps, um, at the time. So like our one on ones were really like two on one. So all three of us were having prospecting blocks together because that was the most important use of our time while still brainstorming on how to best, like, build pipeline together. Um, even now, like, if I'm meeting with the reps, I'm just like, how can we be, uh, both be productive and. And enable you to be more productive?

Speaker A: Yeah, I love that. That kind of goes into. My next question is wondering if you guys perspectives have changed now that you're not just focused on your own like KPIs okrs, but you're also focused on team and company ones as well. Like, is there been a mindset shift? Braden, we'll start with you on this. Like, knowing that, yes, you're still responsible for everything that you're doing, but you also are responsible for other people, people who, like, there's some variables that you can't control. How does your perspective change knowing that it's not just you that is building into what ultimately are your goals?

Speaker B: Yeah, I mean, when I'm. Even when I'm prospecting now, like, I'm constantly thinking about what could help the team. So if I find a lead on LinkedIn and I go in and see someone's at a SDR on the account, like, I'm pinging them right away, hey, this is the context that I have go after this person. Um, I feel. Feel like I'm more actively, like, seeking ways to give the rest of the team, like, a, you know, uh, a lead in an easy win any way I can. So I think that my mindset has just changed or, you know, if there's someone that I see on Orem, someone booked a meeting, like, I'm actively reaching out to them. Hey, great job. Loved your line of questioning. Like, I'm giving one little thing that I thought they did really, really good in that call, where maybe before I'd only mention it if I was on the sales floor with them and, hey, nice job on that call. But, like, I. I know that that can go a really long way, especially being like, a newer rep on the team. Like, even one positive compliment can really, like, make the rest of their day or week and honestly increases everyone's productivity. So I feel like it's just those little things that I'm, like, really trying to actively do every single day.

Speaker A: Kev, how about you?

Speaker C: Yeah, I mean, I think this mindset when I became a leader, like, was still, like, their success is my success. Like, even if I hit my number, like, it's not as great as we all hit our Number. Um, and that might just continue to stay with me as an account executive. Like, the reps that I help their success with, my success, I want them to hit their number and I want them to break records and take home a lot of money. So, like, similar to Brayton, like, I'm cheering them on whenever they get it. I may not be listening, listening to the calls, but, like, I'm making sure that they feel seen. And then if things aren't working, how can we reverse engineer a way to make sure that it's not so much of a thing that's holding them back, but a way that they can continue to lift them up?

Speaker A: Um, have there been challenges? Did you guys either experience or are currently experiencing challenges going from being someone's peer to technically being their leader? Like, they. That feels like such a interesting situation where it doesn't really. It's very rare that it happens on other teams. Like, in marketing, we all have our sort of paths, but it's not like they get to. We get to the end of a year, and it's like, okay, Adam, you were the most successful. You're the VP of marketing now. And Ting Ting isn't anymore. Like, it doesn't. That doesn't really happen on other teams, but obviously in, like, the SDR role, like, the most successful person who also is interested in the path of leadership and has, like, what it takes, they become an STR leader or they become, like, they become a team lead. And then all of a sudden you're looking at these people that you were on the sales floor with, like you said, like, rooting each other on, but now you're kind of responsible for their success. Like, how. What are the challenges and how do you approach that? And Brayton, we'll start with you. Like, is that an interesting feeling or I guess, uh, take me through the psycho. The psychology of that.

Speaker B: Yeah. I mean, I became team lead at an interesting time because we had just, like, created a whole new team. Essentially. The only person on the team with me is Sean from when I. Before I was a team.

Speaker A: Oh, yeah, yeah, yeah.

Speaker B: So I actually haven't really had to deal with that. I will say, like, with Sean, I doesn't feel like I'm a team lead over him. It's like, he's senior. He knows what he's doing. Like, I kind of come to him if I need, you know, to vent. He's kind of my. My go to person on the team, so I don't really look at him as being below me in any way. So they just kind of naturally, everyone else was just on the team knowing me as a team lead only. So I feel like Kevin might have a better perspective on this one.

Speaker A: Um, all right, Kevin, be honest.

Speaker C: It's really funny because Brayden and I have had this conversation multiple times. Like, in the what if scenario, if I became her manager and what that would look like. Um, but I think the cool thing is when I did transition to team lead is I was very clear. I'm like, hey, I may be your lead, but I am your friend before your lead. Um, at any time that you need me to take off the lead hat, I will take it off and I will be here for you on a personal level. Um, and that's still. She did, like, to this day, like, I, I am Brayton's friend before I am her ae. Um, and that kind of mindset is like, where I'm going to right now, where I have a new leader who was my peer on the SDR team and then my peer on the AE team. So it's like that kind of situation where we, like, made it very clear we have, we can separate the two. Um, but at the end of the day, we're all looking to succeed together.

Speaker A: Go ahead, Braden.

Speaker B: Well, I, Yeah, I also feel like, like, Kevin, the fact that you're able to also be our friend, like, I feel like we respect you more when you're a little bit harder, harsh or blunt or, hey, like, that was a terrible call. You need to do this, this, and this instead. Like, I listen to you because I know you care about me because we're friends, you know, So I actually feel like it kind of works in a way. You're able to be more, uh, blunt and tell us what we need to hear.

Speaker C: In times, I always ask for permission if they're open to feedback and how and what kind of feedback they're willing to receive today.

Speaker B: And it's always a yes.

Speaker A: I suppose I should have brought on, uh, two less like, like, like compassionate and psychologically aware people to be like, give me some spiciness. No, I. But I totally understand what you're saying. Like, ultimately, especially at, like, a series B startup, which we are like a growing but still new, ish company, everyone wants to win together. And, like, ultimately rising tides lifts all boats. Like, if one of us, somebody on the team books a million dollar deal, like, yeah, there's a little bit of you that's like, damn it, I wish that was me. But also, like, that means that the team goals are probably going to get hit and it's like, okay, kick ass. That's awesome. Yeah. So that makes sense. Um, all right, last question for you both. Is there one piece of advice that you wish. Is there one thing you've learned that you wish you would have known before you started as a team lead that's been really beneficial for you now? And, Kevin, we'll start with you. Like, is there something that you didn't know going in that now you're like, oh, that would be helpful to know. When I first got started,

Speaker C: I think the most beneficial thing is, like, there's no right answer. There's no right way to lead. I had a very clear, clear picture of what I wanted to make out of it, is because it's the things that I needed when I was a fledgling rep, and it worked out for the team. They're all promoted now, so I'm very happy about that. Uh, but taking that pressure off and being able to ask for permission to focus on the things that I needed to focus on, whether it be like, hitting my own number and advocating for myself, for my own growth, like, that's really been beneficial for me and just, like, not being afraid to do all that? Yeah.

Speaker A: Braden, how about you?

Speaker B: Yeah, I think I definitely get imposter syndrome with things. You know, I'm like, uh, am I really the best for this job? Like, I haven't been doing it as long as other people that might be way more senior than me. But it's like, you were put in this position for a reason, and people see you as a leader and trust you as a leader, and so just really stepping into what I'm actually good at, uh, and the value that I have and not comparing myself to previous team leads and what they've offered and been great at, because I'm, you know, I'm not going to be great at all the same things Kevin was as a team lead. But, you know, I have different value that I add to the team. So really stepping in that and then doubling down on it, like, the enablement piece really gives me a lot of joy. And so that's where I get to brainstorm and have creativity. And same with, like, the being a cheerleader, like, I'm coming up with different PowerPoints every week, and just being able to use my creativity instead of stepping into what was already built for the team lead role and, um, kind of creating it my own, is something that I wish I thought of in that first week. This imposter syndrome's not real.

Speaker C: And before, as I transitioned, I did push, you into being the lead, and I thought you'd be a fantastic lead. And yes, here you are doing the thing. Here I am.

Speaker B: I'm doing it.

Speaker A: I love it. This is fantastic. Kevin Brayton, thank you both so much for joining me today.

Speaker C: Absolutely. Anytime.

Speaker B: For you, Adam, um, always a pleasure.

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