The Pros and Cons of Moving Up to Management with Daisy Chung
31 Jan 2026 · 34 min
Podcast episode (Dec 19, 2022) of "Live Better Sell Better" hosted by Kevin 'KD' Dorsey featuring Daisy Chung (Director of Sales at Orem). The conversation explores Daisy's career path between SDR/AE individual-contributor and management roles, how she decided to move into and out of management, practical lessons for first-time managers (hiring, coaching, tough conversations, recruiting for team balance), differences between SDR and AE management, pay/lifestyle tradeoffs, and advice for people weighing IC vs. management. The episode includes a sponsor mention (Clary) and caller guidance to Daisy's LinkedIn and YouTube.
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Awesome. Thanks Katie. Super excited to be here and super excited to talk about this topic as it's a, it's a very positive popular question in sales. Which one should I go after?
So then let's actually start with your journey a little bit because it looks like you've asked this question and answered this question differently across your career you've gone from IC to manager, but then back to IC but then back to manager. So walk, walk me through the decision making process there a bit.
Yeah, absolutely. Well, I started off as an IC as a SDR sales development rep as that is the entry level role to get into sales. So, so that was an obvious no brainer from there. Very typical a lot of times when you're in SDR. I was young when I was in SDR, I was about 22 years old. Everyone was trying to be an account executive in the team and I thought, hey, I want to be an account executive too because I think that's what everyone wants to be. And so that was the path I was going towards. And at that time I was the top scr. They promoted me to a team lead role and then I was interested in the A role. But my managers at that time actually said, look Dan, Daisy, I think you'd be a great ae, but right now you probably could gain different skill set and we'd like you to try this team lead role where you can start like leading a team and seeing where that takes you. I think the hindsight was I was kind of young. They're like, okay, let's get her a little more work experience before she takes on like a closing role. But after that team lead role, I was still pretty interested in a role. Not sure why to be honest, but I was like, I think I want to be an ae and my VP manager at the time, one of the best managers I ever had told me, look, Daisy, we do have a spot for you in A role but I think your strengths are to be a manager. I think that you, you know, you're leading a team right now, let's make you a full manager if you're interested. And he was teaching me that look. In account executive role you're one of many and you're do awesome. But in a management role you could really impact people for a long time coming. It's a different role and in a sense I felt like I was kind of guided towards management role I really respected, looked up to my, my manager. So I took that role without thinking too much. And being a first time manager, especially being a young first time manager, I was about 25 years old, you learn a lot. You learn that one all because you're really good at your individual role doesn't mean you're really good at being a manager. Or it could be mean that, but it's a completely different role. You can't. I think a lot of times you think that, oh, I know how to do this role. I'm be a great manager. I'm just going to teach them exact exactly what I did and everyone's gonna crush it. No, that was my first mistake. It's a completely different role. You have to learn how to, how to work with people, how to understand different strengths and skill sets and know that all because you did it well does not mean they can just mimic what you did and they're gonna do it well as well. So that was my first taste of management and from there, why I decided to. After, after some time I raised my hand again. I said, look, I want to be an account executive. Now my reasoning is clear. I'm managing a team of SDRs. Love them, they're great. But all my SDRs want to be an account executive and I've never been one. So how can I be the best manager getting them ready for promotion if I can't even relate or get them there? So before I even consider what I want to do in life, I know that to be the best SCR manager, I have to be in the role that all the SDRs want. And so they put me in the account executive role. And then it's back to the individual role where I realized, like, slowly but surely, all the management, all the worrying about people dissipates and you're focused on your number, how to crush it. And then, and so I did the A role for, for a couple of years, then transitioned to Aurum, where I started off as an AE as well. And then why I made that decision myself to go back to management was because after some time being individual role, especially being ae, loved it, had a great time, love my clients, love the process, also love the commission check. But after a certain point when you're doing really well, there's did start feeling like I'm just here to make money. Like, sure you're still learning different things, sure you still learn different ways to navigate close a deal faster, sure you can close bigger and bigger, more complicated deals, but after some years and you're doing well and you've broken records, it's like it felt like a, like a paycheck. And I was like, I'm at a point in life where I want to do more in my care and, and that could be management again, where it's, it's, you have to impact the team. It's a lot of creativity. It's a lot of, you know, I want the challenge of how can I get a whole team to blow it out? It's a lot harder than it sounds. And so I raised my hand, got back into management. This time was my decision. And from there I've always gotten a lot of questions like, hey, should I be a manager, should be a rep, what's the difference? And, and I've learned a lot throughout the years.
Well, then let's. Because that's a hell of a journey and you don't always see it the second time around. Right. Where you go, I see manager. Go back to ic, you tend to stay there. Right. Or you go, I see the manager and you stay. So it's been, it's interesting to watch that full journey. So let's break this down a little bit. You look back at, you know, that first time going into management, what are some questions you wish you would have asked yourself? Or what are some things that you would have thought about more before just stepping into that leadership role? So you knew you were making the right decision?
Yes. So now in hindsight, I, what I would have done, why I tell people now is talk to other managers in other departments. Because when you're in a management role, you have a lot more similarities to the HR people manager role, to the head of client success role, to the engineering manager than you think. You think that you can relate to everyone in sales, but really your, your, your skill set in that management role is going to relate a lot more to other people. Manager and how to hire correctly, how to train correctly, how to fire when you have to. All those things it takes to be a good manager, how to motivate, how to inspire, how to level set all that fun stuff. So that's what I would have done differently is to talk to other people and understand different management styles, understand the pros and cons when people who have done it, especially if it's your first time managing, especially if you're managing in the sales department. Because it's just really, really different than just being a rep who books meetings.
Or closes deals and you hit on something that's just a huge passion of mine. Right. Obviously what I do right now is management coaching and leadership coaching because no one teaches us how to do it. Sales training is still not nearly where it needs to be. Manager training, like it doesn't even exist. Right. So what are the things? And you kind of mentioned it, but I'll ask it anyway. Like what are the things you wish you had been taught before stepping into that leadership role? You were touching on them a little bit, but like what are those things you wish? Man, if someone had just taught me this before stepping in, that would have made my first pass as a manager so much more successful.
Yeah, no, absolutely, Katie. I feel the exact same way. There is no training for managers, especially when you're a first time manager. Second, third, fourth, fifth time, you start to get the hang of it the first time manager. Especially a lot of times in the sales world, usually you're pretty young. Usually your first time managing is a SDR manager role or team lead role. You're usually pretty young in your career. So it's a lot to be responsible for other people. And so I wish I had learned that one. You can't be. You're not friends with everyone here. So when you make that first transition, you're usually. I was managing my peers when I first made the transition and they were my friends, friends first. And so it got. It could get sticky because even yourself as a person, it was hard to delineate like my friends, their co workers or my direct report that I have to promote, retain, et cetera. And so striking that balance and knowing right away to differentiate that relationship is super important. And I learned the hard way because I was a young manager. And so understanding that you are not friends, you could become friends in the future after, you know, you guys don't have that management relationship but in their best interest, you have to be a manager first and look at things holistically. Number two, I'd say understanding how to recruit and what that means because a lot of times as a manager you're responsible for a team and good key players make a team go really well and even one bad player can hurt your team. So when you're hiring it's good to have, you know, you have to recruit hard and have good players. But also how do all the good players talk with each other, especially in sales. I'm a high energy type of person, super passionate. And so when I started hiring I kind of hired people with similar personalities. But when you look at things holistically, you realize can you have eight super passionate, high energy, a little more aggressive people on a team or do you need some other folks to balance that out? That's something I learned. You can't just hire a bunch of super a player that's one personality because it doesn't add dimension to the team and create feelings of, of, of, of diversity and just learning and, and different personalities actually really good for a team. So that's lesson number two and I'll wrap up with number three is learning when it's time to put someone on a performance improvement plan and transitioning them out. I think as a first time manager, you've never fired someone before or had those tough conversations and it's really hard because a lot of times you're a little naive and you believe in the best of everyone, but realizing at the end of the day that's your job as a manager and that's also your job. It could help someone. Sometimes a role is just not right for someone. They're probably not happy if they're not doing well and you have to be responsible to have a hard conversation.
That's true. And that's what's crazy to me with like managers is these are hard things to do and no one teaches us how to do it. So either you learn from experience, but unfortunately most people actually don't learn from experience. They just keep doing the things that they've been doing and they don't know if it's right or wrong. They just keep doing it and that's it. And so let's come back a step here then of like if I am in the situation that you were in, Right. I'm listening to this episode and I am, I'm a top performing rep. What question should I ask myself if leadership is right for me? Right. My manager comes to me, I'm doing well. What are the things I should be asking myself before making that type of decision?
Yeah. So a couple of questions that you can ask yourself is one, if you are interested in a management role, why is that? Be really honest. Be brutally honest. Like why would you be interested? Is it for, you know, the, the higher title? It's nice to have a manager director title. Is it for the more pay? Because you imagine a promotion equals more pay, you want to keep going that way. Is it because you want to eventually be the top person in your department from vp, director v, CRO, et cetera. And you have that, that passion and drive to do that. So be brutally honest. What is your reasoning? Or do you like working with people? Do you like, you get a high from when someone does really well? Are you just a natural coach that likes to just improve and help others? So what is your why? Why are you interested? Be brutally honest with yourself to where you are in life outside of work. What Is your lifestyle? Like, are you the type of person that really likes just working, you know, start to finish, like a nine to five day and then from there work is done. You want to focus on other things or are you someone that likes to travel a lot, that appreciates the flexibility to, especially in sales, if you're doing well, you could take time off as it makes sense usually. And if you're not doing well, you're on it. Do you like that flexibility? Do you have a family? Are you planning to have a family? You want less time with work. So these are important questions because in an individual role, if in sales, if you're doing well and you have a good manager, usually you can take all the time off in the world. It's all about your performance. You have flexibility. You block off your calendar for four hours, take demos for four hours, crush out your number, whatever the case is. If you're a manager, you can't just block off your calendar for four hours. You got to be there for your team. You gotta make sure you're present. And sometimes you work extra hours even if your team is doing well. And so how does that strike with your life balance and goals is question number two. And then question number three. I'll say this because sometimes it's not obvious to folks, especially if you're a high performing rep, is if your interest is to make more money and climb that corporate ladder, be really realistic. Because the highest paying people in a company is usually the top performing sales rep. They will make more than the CEO if you are crushing it. And so yes, you get a bump in base if you're a high performer. I bet you you're going to get a pay cut. And the higher the performer you were, the bigger that pay cut is. Again, that's not to say you can't make more and more money. Because when you become a manager, a director, a vp, that base does increase and you have a little more security that way. But you're never going to make as much as a top performing rep. And if that's okay with you, and then absolutely, you have the right reason. But if you're in the intent of I want to make more money, that's not the way to do it.
I love it. And these are the real questions, y'. All, because if you don't pause to ask these questions, you'll make a wrong decision. Right? Like I asked anyone on my team when they said they want to become a manager, there's a set of questions that I asked them every single time, every Time, it's, I want to be a manager. Okay. Got some questions. Just let me know what your answers to these are. Right, so the first question would be, are you ready to put your paycheck in someone else's hands?
Yes.
Are you ready to put your paycheck in someone else's hands? Right. Because as a closer, as an sdr, it's all up to you. As a manager, it no longer is. That was my first question. Second question, are you ready to work harder to make less? It is easier to be a top performing sales rep than it is to lead salespeople. Salespeople are hard to lead. Right. They've got, you know, egos, and they are top performers and they like to go, go, go. And they don't always listen as well. Like, gotta think about it. You ready to work harder to make less? Third question. Are you ready for me to be upset with you because of what your team is doing? Are you willing to fall on that sword? Are you willing to be the person that steps in and actually sacrifices for them? Because as the manager, you don't get to blame your team anymore. You don't get to point fingers at them. Right. And I would walk them every single time. At least half of the people that said they wanted to be a manager after those questions were like, oh, geez, I don't know if I want that anymore. And it's like, okay, then let's talk about the difference between leadership and management. Doesn't mean you can't still be a leader, but as a manager, you're responsible for these things. And so what are like. So when you think about those questions, what maybe are bad answers? So you ask that question, why you want it? And you mentioned things like, you know, is it tight title? Is it like, if your answer is this, maybe leadership isn't the best for you, what would be maybe some bad answers to that? Like, well, why do I want this promotion? What would be kind of a red flag of like, ooh, maybe management isn't the path you want to go down?
Yeah. I say, I don't know is a really good one. A lot of times people don't know. They'll say, I'm not sure I think that I want that. And with your response for people, you have to know, not that you have to know 100% why, but at least have an inkling or a feeling of why you're excited for this role. I think, yeah, if you're in it for the money, that's. That's the wrong answer. Because you're gonna make less. Again, I'm gonna caveat this because if you're a okay performer, you actually could make more as a manager. You could actually also be a really good manager. Another misconception is, you know, only usually top reps get offered that management role or that management option. But they don't always make the best managers and sometimes a middle or even a low performing rep can make a really strong good manager. So I think there's also, there's also that because sometimes you could make more if you were not a top rep and you're like an okay rep. But what, what's motivating you if you don't have an answer and if it's not people oriented.
I was waiting for you to get to that because that was not in any of those questions asked around like your thoughts on people. Right. And like being responsible for them. I think that's really, really important because if you're becoming a manager for yourself, that's already a yellow to red flag for me. Right. Is because as a manager it's about the people on your team. And so talk to me about the transition back. So you did, you became a manager but that AE role was still calling to you a little bit and so you made the choice to go back, break that down a little bit further. Like why like you mentioned, like, well, I can't be a good SDR leader if I don't become the role that they're trying to become. Was that really the foundation that was it of like, well, I'm leading SDRs, but they want to be AE, so I want to be an AE so I can go back to leading SDRs.
Yeah, that, that was the, the prime reasoning at that time. Because when you're a first time and you're a young manager and you're managing a lot of SDRs and a lot of times SDRs, one of the biggest things is promotion path. A lot of the sticking points in a software company is when it can become an ae. Are there roles for it, Are they actually going to hire me? Becomes such a sticking point between the two departments. And as a first time manager, it was very hard for me to bridge that gap and understand why my SDRs weren't getting promoted or why there was wishy washy timelines and in hindsight that also could have been because I was young and I wasn't at a place to have those serious conversations with the other stakeholders to align on the path forward. There was just a lot of openness in the air at the same time I felt like I could only prepare them to be really good SDRs, but I also felt like, you know, if I were to prepare them better to be AES, that would line them up for a better chance of promotion. But I didn't have the skill set or the knowledge of how to even better prepare them to be AES. And I felt at that point I couldn't be the best manager I could be. And so, and so I made the decision to try out the A role. I did end up falling in love with that role as well. As you see, I was an A for a couple of years. And then you just have another light bulb moment and realize, is this really, you know, what I want to do is continue selling, selling, selling, or do you want to make a bigger impact on folks and see that looks like.
So do you manage closers now or SDRs now?
I manage closers, so this would be a fun one.
This is a loaded question and I'll see what your answer is here. Do you believe an SDR manager can manage closers without having closed themselves?
I believe.
Because this is where a lot of SDR managers get stuck. Is they SDR and become an SDR manager and they now feel like they're trapped in SDR leadership that they can't make a jump over to the aisle unless they go become a closer for two to three years and then work their way back up. So what are your thoughts? You've done both, right? What do you think? Can an SDR leader jump over to the AE closing side? Obviously they have to learn ac, but without having done it?
Yeah. If you want my simple answer, I say you should be a closer first before you manage a team of closers. That's my simple answer. I mean, again, it depends on the company. This is a big company with a lot of resources and the team. If you're the SEO manager making the transition and you're managing a team that can get the resource elsewhere to help them understand closed deals, those can be some exception. You're a phenomenal people leader. I can see those exceptions. But typically you are in the trenches to start with your reps and they meet someone with experience of closing to guide them to that. So yeah, that's my answer.
I'm just curious because there's both sides of that fence because oftentimes you'll see AE leaders step into SDR leadership roles even though they were never in sdr. But you don't see as many SDR leaders get to step over to the closing side. If they haven't closed first. So just curious because you've done both now. So just curious on your take on it.
Yeah, no, that's a, that's a, that's a, that's a good question. I think that, yeah, because, because not everyone has SDR experience. A lot of folks become an AE with no SDR experience. They, they're a 10 year employee at other companies, they've done partnerships this and that, they jump into the A role. And I've seen some of the best AES also have never been SDRs. I've also seen the best AES that were killer SDRs. So at the end of the day I think holistically really depends on the company culture, what kind of company you are, what the resources look like and what your deals look like as well. Like the more complicated and technical the deals are, the more you need those resources, the more straightforward, easier learn to learn the product etc in, in a day or so. I think the easier it is to, to manage those things.
What would you say is the biggest difference in your experience now? Having lead STRs and lead AES. What's the nuances? Right, so you've managed SDRs, you've managed AES. What would be your biggest call it like differentiators between the two groups?
I'd say the biggest thing is there's a lot more managing emotions in the SDR world. Emotions. Can I get that promotion? After 6, 8 months STRs get ANSI, they want that promotion and usually it's a big SDR team so they're competing against each other for a existing or non existing promotion. So it's a lot of managing emotions and creating a lot of processes because a lot of things get sticky with the A world. You know, is my OP qualified, the A didn't move it, things like that. So the emotions, the processes, fleshing it out. So it's black and white to me that's what SDR management felt like. The AE role. It's less that because a lot of times AES sometimes AES want to be AES for a very long time. They're not thinking what's next, what's next? Even if they want that promotion, I want to be a mid market enterprise, etc. They aren't as emotional about it and they're still usually pretty happy in their job. So more of the time it's really getting the trenches and managing deals with them and working with deals specifically.
I'd say I love it, I love it. So what would be your biggest tips to A first time manager. So they did it. First time manager. What would be your biggest tips to them? They're in this role now. They might even be managing their former peers. What would those be like, those top two to three tips you'd give them?
Yeah, I'd say find and create a network with other first time managers. First time management can feel lonely. You feel like you don't have a cohort of peers anymore that you, you can relate with and so create that cohort. There are a lot of first time managers out there. There are other companies with managers and if your team only has you as that, you know, first time manager. So find or create your own network so you know that it's not, it's not as lonely as it has to be. You can, you can find friends and relate. 2. Don't be afraid to be vulnerable, especially with your manager. When you're a first time manager, you feel like you have a chip on your shoulder and you have to know it all. You have to, to be the superhero. But you're human and you need help too and you need to learn. So be vulnerable and don't be afraid to share how you really feel when you're struggling with your direct manager. You have a direct manager on purpose. And even with your team, don't be afraid to be vulnerable. Again, it's a people's job. Like you have to be able to relate with people and to do that to be a good manager. And I think those are the two biggest tips. It's, I guess the third one. The third one. Is that a third one? It's, it's to don't be afraid to be yourself. I think a lot of times when you're a manager you kind of create this facade of I have to be super formal, I have to be this and that to be a good manager or they'll look at me differently. But no, the best managers is just being yourself, whatever that means and being very authentic because that's what you try to bring out of your team. Everyone's individual personality is going to drive the best team, the happiest employees, the best results, all that fun stuff.
So the last question before we start to wrap up here is your second time through? Right. So you're a manager, you went back your second time through. What did you do differently? Right. Because you'd been through it once before. Right. Like what did you do differently when you stepped into this leadership role compared to your first?
Yeah. So everything I said that I had to learn along the way, I did a Little differently. So first and foremost I establish that this is a managing role. You're friendly, but you're not best friends with everyone. So have that separation mindset, it makes your job so much easier. Two, you diversify the recruiting. It's not just everyone who seems like a top, a hungry player. You got to understand diversity in recruiting and how it's going to drive a team dynamic. That's super important. Three, having tough conversations earlier, that was hard for me as a first time manager. And now, you know, the earlier you have it, the more direct you are. It's a win win for everyone. Not being afraid to leverage your own managers and be very open and vulnerable about things you need help with. Those are the main ones, but it's probably a much longer list. Anything you learned the first time around, the second time around makes it a lot, a lot easier.
And if you think through this because like something that I guess we haven't really touched on yet, but I actually do want to tag on is like you made the decision to get out of management leadership, how did you handle, I guess call it not like the pride, but like there's a lot of people I think that would be afraid to do that, right? Like afraid to get out or afraid to like make that move out of it. Like how did you handle those emotions to say, you know what? No, Like I do think this is the right decision and I, you know, I don't care what other people think. I don't care how people look at that resume. Like, talk about that real quick because I do think people get stuck there. Is it like, well, if I go down this path and I'll never get another shot, right? Or if I go back and then recruiters won't try to recruit me. Like talk about that real quick.
Yeah. I think at the end of the day you just have to know your why, like why are you doing what you're doing, what that reasoning is and, and being vulnerable and sharing that. Like this is my specific reason. There's always an awkward moment when you leave management. You go back individual, where, you know, folks that you were managing now are peers or things like that. Like there's always those awkward moments, those awkward dynamics, but that's, those are the moments that makes you stronger. I believe that when you're nervous, when you're uncomfortable, that's when you're stronger and you just gotta lean in on that. And the last thing I will also say is I know both you and I are framing management is tough and it is very, very tough. And like you said, it's a lot of make less money, more work. You know, a lot of these things that could sound a little more negative, but I will say there are a lot of rewards. Being a manager as well. That's very different from just having a high paycheck in an individual satisfaction and just pure joy you feel when someone is learning and growing and they get excited, they close their first deal or book, their first meeting. And that feeling is something that I think is very hard to explain, but you won't know until you feel it. And I've never been a parent before, but I could kind of think it's the same pride and joy you have when you are a parent, a dog parent, a cat parent, a human parent, of seeing someone growing with your. With your coaching. So for everyone out there as well, I also don't want to scare you. It's very, very rewarding. And I'd say if you have any inkling, any interest, you love people and a management position is offered to you. Take it. These are hard to get. Like, it's not offered to everyone. And as I did, you can always go back as well. But don't be afraid. It's a very rewarding position as well.
I love it. I love it. All right, so Daisy, as we wrap up here, right, the name of this podcast is Live Better Sell Better, right? Because I also have this weird idea that if we took better care of ourselves, if we had more energy, more joy, more fulfillment, more happiness in life, that the sales would be better as well. And I also believe it with leadership, right? If we lived better, we lead better. What would your live better advice be for people listening?
Yeah. One of my favorite mantras in life is life is too short for what ifs. So if you have a gut feeling of doing anything in life, listen to your gut feeling. Work related, non work related. Just do it. Because life is really too short for what ifs. You don't want to sleep on your deathbed regretting anything, thinking about, overthinking about anything. So it's super simple. If your gut says do it, try it. No matter if you're uncomfortable, just do it. Try it and you won't regret it.
I love it. I love it. No what ifs, right? That's generally what we regret more far than the what we did. It's the what we didn't and what we didn't choose to do. So I love this, Daisy. This is phenomenal because it's a hell of a journey, right? And I've got to kind of watch your journey over the years and see the different roles and see the different opportunities that you've got to be a part of. Where can people get more of you? Where are you putting out contact with? Can they connect with you? Where can they get more Daisy Chung in their lives?
Yeah. So I am pretty active on LinkedIn so you can find me on LinkedIn. I've also created a YouTube channel last year that I will have to update some more but is on my list this that I talk about actually sales and sales development and all that fun stuff. So LinkedIn, YouTube are the best ways to find me and contact me.
I love it. I might have to get some YouTube tips for you because I'm starting to do that too. I just haven't like made the full jump. Right. But know what ifs. Trust your gut. Go for it. Right? So awesome. I appreciate this. This was amazing. Thank you so much for the energy, the insights and everything you provided. Really appreciate it.
Of course. Likewise. Thanks Katie.
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