In this episode, we sit down with Ashley Zagst, Senior Account Executive 2 at Chili Piper. Ashley shares her journey, challenges, and victories — from her first sales job to buying her own house.
As President of Proud Pipers, Ashley digs into the importance of representation and diversity in the industry. She argues that a diverse sales team is a game-changer in catering to diverse buyers.
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🎵 Jam to our walk-up song playlist on Spotify
In this episode, we sit down with Ashley Zagst, Senior Account Executive 2 at Chili Piper. Ashley shares her journey, challenges, and victories — from her first sales job to buying her own house.
As President of Proud Pipers, Ashley digs into the importance of representation and diversity in the industry. She argues that a diverse sales team is a game-changer in catering to diverse buyers.
✨ Follow Ashley
✨ Follow Katrine
🎵 Jam to our walk-up song playlist on Spotify
[00:00:00] Ashley Zagst: I think that's another thing, is just coming in with a growth mindset. When you're coming from something else, from somewhere else, you hopefully have a growth mindset because you don't know anything.
[00:00:09] Like, I came in knowing nothing and admittedly so and ready to learn everything, which is another way to just level up really fast 'cause you're just so open.
[00:00:18] Ashley Coghill: Hello, I'm Ashley.
[00:01:00] Katrine Reddin: And I'm Katrine.
[00:01:01] Ashley Coghill: Welcome to another episode of Ashley and Katrine's Infinite Revenue Playlist.
[00:01:06] Today our guest is Ashley Zagst.
[00:01:09] I wanna do a quick intro for Ashley before we get started. Ashley started her career in tech as a marketing intern in 2014. Along the way, she climbed the ranks, learned a ton, and helped build hyper-growth startups.
[00:01:24] In September of 2020, she made the switch from marketing to sales, we love to see it, when she began working at Chili Piper where she is now thriving. What was that?
[00:01:34] Katrine Reddin: I just said she came to the dark
[00:01:35] Ashley Coghill: side.
[00:01:35] She came to the dark side. She is now thriving on the dark side as an Account Executive there at Chili Piper. She's also a Leader of the Proud Piper's Chili
[00:01:44] Piper's ERG for LGBTQIA+ Piper and Allies. Ashley, thanks for joining us today.
[00:01:52] Ashley Zagst: Yeah, thanks for having me.
[00:01:54] Ashley Coghill: I'm gonna quick go into one more thing and they're gonna cut out my awkwardness. Ashley is a lifelong learner who is on a constant quest for growth. When she's not working on improving her sales skills and business acumen, you can find her somewhere outdoors, snowboarding, surfing, or hiking with her wife and their dog, Kiwi.
[00:02:12] Katrine Reddin: Or buying really cool upcycled sweatshirts as seen today. Love it. As many of you who've listened to previous episodes know, we have a little bit of a musical twist to our podcast. It's called Ashley and Katrine's Infinite Revenue Playlist for a reason because we have each of our guests pick their own walk-up song, since as sellers and as people in
[00:02:35] other revenue-related roles, we are sometimes referred to as athletes or compared to them. And the walk-up song is really meant to kind of symbolize a song that either pumps you up as you walk into the sales floor or walk to work, or just something that really relates to you as a professional. So, with all that in mind, Ashley, what is your walk-up song?
[00:02:58] Ashley Zagst: So, this was really hard to pick one, but I think when you asked me and, like, just kind of where I was mentally, like, this was the first one that popped into my head. It's Irrelevant by Pink. We can tie things to the professional part of it, but, like, just in general, like, if this was, like, where my mood was at, kind of is at, so, yeah.
[00:03:19] Katrine Reddin: Are there any lyrics from the song in particular that really speak to you as to why you chose it in this moment?
[00:03:27] Ashley Zagst: Yeah. I mean, I'm gonna get real deep, real fast. So, there's a whole, she repeats, "The kids are not all right," like, a lot throughout this song. She wrote this song kind of in response to politicians telling her to just shut up and sing. And it's, like, her first single in a, in a while, and it's kind of addressing a lot of the social issues that we're facing in our country right now.
[00:03:49] Katrine Reddin: Um, specifically, like, or one of the many that she kind of addresses is the overturning of Roe v. Wade and basically just like nothing, it, things aren't okay and like. Yeah.
[00:03:59] Ashley Zagst: It's fucking stupid. Like, she, she, there's a line in there which talks about, "I'll be your heretic, you fuc*ing hypocrite," basically addressing the politicians who are being super hypocritical and taking away our rights every day, so.
[00:04:13] Katrine Reddin: Well, the crazy part is the reason why this podcast exists in the first place is because there's not a lot, all right, in all aspects of life, including just being a woman in the revenue space. And so, this is really meant to create a safe space for any woman in revenue to kind of share their thoughts, opinions on what it's like just being a woman in revenue and so I think that song is very applicable to our entire podcast, quite frankly.
[00:04:39] Ashley Coghill: Yeah. Great. Also, we, we had a session, we do a meetup together outside of this, and we had a session with a lot of women, right? It was the same day that that decision was made
[00:04:51] and we held space for women just to like, talk about it. And it was, there's a lot of vulnerability and, like, fear, and I think it's really important for us to, I, I think it's really cool that Pink wrote this song because it's a really powerful and, like, encouraging song and there's anger in it, and that's a good thing.
[00:05:12] And I, I loved seeing that that was your choice because it's definitely a hype us up kind of like, "I'm gonna go make some cold calls." That's pretty not fun, but, like, in the grand scheme of things, as women, our job as sellers is, is probably one of the easier things we do. At least, I think, so. Thanks for picking it.
[00:05:33] Katrine Reddin: You're welcome. Yeah, that's a good one. If you haven't heard it, go listen. Yeah, it's an absolute banger. I was listening to it right before we hopped on this call.
[00:05:42] Ashley Zagst: Nice.
[00:05:43] Katrine Reddin: So, let's, let's get right into it. Obviously, you're at Chili Piper right now, and I saw you were recently promoted, congratulations.
[00:05:50] Ashley Coghill: And bought a house.
[00:05:51] Ashley Zagst: Thank you.
[00:05:52] Katrine Reddin: And bought a house. Making lots of big moves in the world. Jealous. I'm not there yet, but hopefully, fingers crossed, one day. Give us a little, and we already introduced you, but I'd love to hear from your perspective, like, who you are and, and what your background is and how you came to the current position that you're in.
[00:06:08] Ashley Zagst: Yeah. So, yeah, I'm a Senior Account Executive 2 now at Chili Piper and been here for almost three years. Started as an SDR and this was my first sales role at, was at Chili Piper. I made that switch from marketing back in 2020. I basically, I was at Bravado, I helped build that community from the ground up
[00:06:29] and my job there, like, basically was just to talk to salespeople all day, every day and just kind of figure out what makes them tick, who they are, what they need, what they're looking for, how to support them, and just buy a way of doing that, like, I started to recognize some of the stereotypes that I held about the sales profession and just completely
[00:06:52] was like, "Wow, this is false," you know? Started to meet some really amazing people in the sales world and there were three really distinct factors into my transition over to the sales role. One being that it just seemed like a cool challenge. Like, I was like, "I think I could do this. I'm very curious and intrigued to see how my marketing skills that I've developed over, you know, the past however many years can translate into a sales role."
[00:07:18] Like, that was just like a unique challenge that I was interested in taking on. And then, secondly, I mean, we just talked about this, but, like, one of our pillars at Bravado was championing diversity in sales. So, I talked a lot about it. I wrote a lot about it. I created content, I created videos. I spoke at events, like, I talked a lot about it, and I got tired of, I just wasn't enough.
[00:07:44] At a certain point, I wanted to actually be about it, do something about it. I am a queer Latina woman who I don't see a lot of myself in the sales world, much less sales leadership, so I was like, "Let me go. Let me go do this. Let me be the person that I don't see so that other folks who are in my position could maybe see this as a possible career opportunity."
[00:08:06] I mean, Ashley, you mentioned that I just bought a house. I would've never been able to do that if I hadn't made this transition. Like, it, it's incredible. And on that note, the last kind of key factor was I'm a super high-achieving human. If I say I'm gonna do something, I do it and I do it really well. And it's like nails on a chalkboard to me when I show up and give a 150% at my job and then get my same paycheck every two weeks, where somebody else might come in and do the bare minimum and they also get the same paycheck every two weeks, like, seeing sales as this meritocracy, as this opportunity to like, the more you put in, the more you get out, that was o, obviously also very attractive and has been paying off, so.
[00:08:53] Ashley Coghill: It does pay off.
[00:08:54] Ashley Zagst: Yeah.
[00:08:55] Katrine Reddin: High risk, high reward, right? Sales is stressful for a reason. There's a reason why we make commission.
[00:09:01] Ashley Coghill: Right.
[00:09:01] Katrine Reddin: So, from the transition from marketing to sales, I mean, we've talked about this a million times with a million different guests, but I do really believe the people that come from unique backgrounds or have different experience elsewhere tend to become the biggest, not the biggest, but the most successful of salespeople in their teams.
[00:09:21] And I'm curious if there's specific skills or aspects from your marketing career that you think really helped you succeed as a salesperson?
[00:09:30] Ashley Zagst: Yeah, I mean, first and foremost, my love for and ability to write and write creatively, like, I've never been afraid of writing my own cadences. I've never been afraid of crafting an email. And also, within that, asking for feedback on that work, like, as a creative, as a marketer, and even prior to that, I was a dancer
[00:09:53] and, like, we, that's a whole other life journey, but the ability to, like, seek feedback on your work, whether it's an email that's three lines or it's an entire, like, 17-touch cadence or whatever, like, there's, for me coming in, I came from a place where there wasn't a fear of failure. There wasn't a fear of critical feedback on something.
[00:10:17] Like, in fact, I really was looking for that when, because I know that's how I get better. I know that's how I improve. I know that's how I'm gonna get more demos and win more opportunities. Right? So, I think coming from a creative side of things, like, that in and of itself was just something that kind of leveled me up pretty quickly,
[00:10:37] where some folks maybe don't have that background, I don't feel as comfortable writing, crafting up a new cadence, like, and they're just dependent on other people, which totally not a bad thing and if you've got an awesome sales enablement part of your team, or you've got an awesome marketing team that's helping you do this stuff, like, hell yeah, leverage that.
[00:10:57] But for me, I always, I mean, my first couple months in as an SDR, I, like, didn't even ask my manager, I just took, I did like the 80/20 rule, you know? 20% of the folks I was putting in cadences, I put in, like, an experimental cadence. I was like, "Let me just see if something else works. Like, here's the one they gave me that said, they said like, 'This works.
[00:11:14] Use this, do this as you're learning this role and, like, figuring out your process.'" And I was like, "Okay, will do. And I'm gonna try this one over here." And they, I mean my, my manager Matthew Roberts was like fired up. He was like, "Yeah, hell yeah. That's amazing." And, like, sometimes they were awesome and performed real really well
[00:11:32] and I shared them with the rest of the team. Sometimes they were total duds and didn't get any responses and, you know, it's quick to learn, quick to grow. And I think that's another thing, is just coming in with a growth mindset. When you're coming from something else, from somewhere else, you hopefully ha, have a growth mindset because you don't know anything.
[00:11:51] Like, I came in knowing nothing and admittedly so and ready to learn everything, which is another way to just level up really fast 'cause you're just so open.
[00:12:01] Ashley Coghill: I think a lot of that probably has to do with you also having a different mindset coming from being a woman. I think I, we've talked to a coup, well, quite a few women in our communities and spaces and creativity and empathy and, like, the creativity you're, you had that before you even walked in the door,
[00:12:21] but I feel like a lot of women have the ability to build their own sequences, like you mentioned, or try something new or get creative because it's like ingrained in us. And I, sure, that's generalization, but I feel like some truth to that too, so. I don't.
[00:12:39] Katrine Reddin: I think back to my first sales role in the tech space, 'cause I actually started off selling, this is super random, but oil to different ships in the shipping industry and I quickly realized that was not for me, so I very quickly left and went to tech, but I started as an SDR. I, it's kind of very similar to what you were saying before, Ashley, like, your manager's, like, "Here are the designated sequences to use in these certain scenarios. Have Adam." And I remember reading them and thinking to myself, "I would never talk like this. Like, this sounds so wrong coming out of my mouth." Like, maybe it's just me thinking that 'cause I'm like, "I would never speak or write like this," but I slowly but surely started to tweak all the sequences. I'd copy and paste them, duplicate them, change 'em to my own wording.
[00:13:26] Eventually I was just on blank templates writing my own personalized emails and that's when I really started to succeed. And it was crazy. I did the least amount of activity out of any SDR on the team, and I had by far the most opportunities booked because every single one was creative and personalized and took me a hell of a long time to write, but they worked for me.
[00:13:46] So, I think writing is a really underrated skill that I think all salespeople should have or at least work on at all aspects of the, of the sales career.
[00:13:57] Ashley Zagst: Yeah, I agree.
[00:13:59] Ashley Coghill: I'm glad you're not selling oil anymore, Katrine.
[00:14:01] Katrine Reddin: You and me both.
[00:14:03] Ashley Zagst: Wow. What a, what a shift.
[00:14:06] Katrine Reddin: What a shift. Yeah. Yeah. We're, that's, uh, very deep, deep in the past, you know, in the back of my mind, so.
[00:14:13] Ashley Coghill: Not anymore. You just, you just brought and.
[00:14:14] Ashley Zagst: Dug it up.
[00:14:15] Katrine Reddin: That's true. Hey, anyone could look at my LinkedIn and see what my, uh, my work history is, so mine is all out with it now. Well, love to hear that, the career progression. One thing that I want to ask 'cause a lot of the people that are part of our community and listen to this podcast are people that are hoping for their own promotions,
[00:14:36] and as I mentioned earlier, you're recently promoted. I know we've talked a lot about, you know, having grit and you had that really creative background that helped you as a salesperson, but, you know, what specific things do you think other salespeople, specifically women can do to kind of set themselves apart besides doing, you know, what's asked of them in a hitting quota to also get a promotion eventually.
[00:14:58] Ashley Zagst: This is so good. So, I mean, I'm gonna be cliche at first, but I think, I mean, there's, there's truth to it. So, people say it all the time, but, like the fundamentals, right, go back to the fundamentals. So, we just talked about all this creative exploration within the sales role and, like, that's what sort of helped level me up,
[00:15:17] but also once I understood the process and once I understood my process, like, made my own, I know what works. And so, yes, like, finding the balance between getting creative and experimenting, but also knowing what works and sticking to it and doing what you know how to do. At the end of the day, I mean, there's a 1,000,001 webinars out there about like, "How to convert more elites? How to generate more opportunities? How to better this, that, and the other?"
[00:15:46] There are limited channels for us. We can call someone, we can email somebody, we can hit them up on social, whether that's LinkedIn or TikTok or Instagram, whatever. Right? And maybe if you're ballsy enough, you can cold FaceTime someone, but, like, you, like, there's really limited channels, right? So, you can only do so much within that. There's a lot you can do within that, but there is only so much. So, getting back to the fundamentals, understanding the balance between quality and quantity. Focusing on, you know, really drilling down your ICP. These are all, like, basic, like, table stakes when it comes to sales. Understanding your ICP, understanding who you're talking to, the, the language they use, the vernacular they use, what they care about, why they care about it,
[00:16:31] when they will care about it, that way you're prospecting into the right people at the right time. Like, these are all things you can find out. We have all this information and data at our fingertips. So, that's all table stakes, right? Like, just do the work. You know how to do, make the calls, send the emails, do the research, show up, when you give demos, like, give good demos, do good discovery.
[00:16:51] Now, we could dive real really deep into all of those things, but, like, just in general, these are the basics of sales. What I would say, especially for women, especially for underrepresented groups in the sales industry, have a champion, have a mentor, have folks who are going to help lift you up when you need it.
[00:17:12] Because this is a roller coaster role. Sometimes you're gonna get the support internally, sometimes you're not, and so having somebody, whether they're in your company, outside of your company, it doesn't matter. But having somebody who's there to help remind you that you know how to do what you know how to do.
[00:17:31] Like, that has just done so much good for me in my career and so much good for me in my, like, mindset in this role. 'Cause it can be tough and most folks who are in this role like to perform and so when you aren't, you wanna, like, tear it all down and start from scratch and figure out, "What, what am I doing wrong?
[00:17:51] Like, how do I, how do I do this better? What, you know, I must be doing something completely wrong," and the, at the end of the day, you're probably not, you're probably doing things just fine, you just need to get back to that beginner mindset, back to that growth mindset, do what you know how to do,
[00:18:06] stay consistent and bring that same energy to your calls. And I bring this up and I feel really passionate about this because it wasn't that long ago that I had literally the worst month of my career. So, I got promoted thr, three months after my, like, worst month ever as a seller. And in that month, if you had told me, "However many months later you're gonna get promoted," I'd be like, "All right.
[00:18:29] Like, not a chance. Are you kidding me?" But I had a mentor who basically two mentors that I reached out to who I knew would, like, no bullshit, they would just tell me straight what's up. And they did and it was almost maddening because I knew exactly what they were going to say because I knew, I know this inherently, but basically, they were like, "You have this fear, is, like, palpable, but your prospects and your,
[00:18:59] like, potential customers, they don't know where you are on the leaderboard. They don't know if you're at the top or the bottom, so just show up and do what you know how to do without caring about that. It doesn't matter. Like, what matters is this conversation right here, right now, like, being in that present moment." And that seems too simple, but,
[00:19:19] I mean, it was everything. It turned my, just changing my mindset around it and getting out of this place of fear and, like, thinking that I was failing and this scarcity mindset and shifting into like, "No, I know I'm good at this. Look at every other month before that. Like, the, why am I letting this one moment in time, which I'm not even gonna remember in 10 years, factor into, like, my mood or my energy or my
[00:19:47] activities, like, why am I letting that impact me so much?" And, you know, that plus for me, I, I always feel like I need to, like, learn something more. So, I, like, signed up for a discovery class from Chris Orla, which again, a lot of it is a lot of the same things we hear all the time, but it's a good refresher and reminder and bringing that into
[00:20:06] Katrine Reddin: It's
[00:20:06] Ashley Zagst: the calls.
[00:20:06] Katrine Reddin: always good to get refreshed on the basics.
[00:20:08] Ashley Zagst: Absolutely. Yeah.
[00:20:10] Ashley Coghill: How do you feel about leaderboards?
[00:20:15] Katrine Reddin: Is this a loaded question?
[00:20:15] Ashley Zagst: Oh,
[00:20:17] I mean.
[00:20:18] Ashley Coghill: I am the queen of loaded questions.
[00:20:20] Ashley Zagst: One hand, like I, you know, not gonna lie, I fucking love seeing my name at the top, you know?
[00:20:26] Katrine Reddin: We all.
[00:20:27] Ashley Zagst: And I, and I take a screenshot and I'm like, "That was April, I was at the top," take a screenshot, "That was March." I was at the top, you know, whatever. I hate seeing my name at the bottom, so what do I do to get off the bottom?"
[00:20:39] You know what I mean? So, like, on one hand I could see that that's motivating. On the other hand, sales really should, I hate using the word should, but it would be awesome if sales was more of a team sport than we turn it into, right? Like, we are all trying to drive the company towards a collective goal, hopefully, right?
[00:21:03] So, if my teammate, you know, if I close big number, insert big number here, and my teammate closes, like, insert smaller number here, it really shouldn't matter. Like, we're both contributing to that top-line revenue and the growth of the company and next month it might be flipped, where my teammate's at the top and I'm down at the bottom
[00:21:25] and again, like, it's a team sport in my opinion, and we should be competing with ourselves and trying to better ourselves. And we hear that all the time. That's also very cliche, but, like, unfortunately the leaderboard doesn't, doesn't help with that very much.
[00:21:39] Ashley Coghill: Yeah. It's funny, I, you were talking about, like, your mindset and how that, 'cause I feel like what you're saying about going to your mentors and talking to them and getting that tough love that says, "Okay, but you know what you're doing and you knew what they were gonna say, but you needed to hear it," I feel like I personally just don't really pay attention to leaderboards anymore because my mindset is more important than being at the top.
[00:22:03] And if I'm at, if all the cards fall and I am at the top, awesome, but, like, I truly need to compete against myself and do, 'cause we don't control the outcomes in sales. We control what we put in and we control all the things that we possibly can along the way 'cause there's lots of things we can do to make sure, but at the end of the day, someone's not gonna buy something if they, like, that's not up to us if they actually buy it, right?
[00:22:27] Ashley Zagst: No.
[00:22:27] Ashley Coghill: So, I personally protect my mindset by just ignoring the leaderboard until it's over, like the end of the quarter. Cool.
[00:22:34] Ashley Zagst: Yeah.
[00:22:35] Ashley Coghill: But I was just curious 'cause your, your talk track there kind of felt very much like how I feel about it.
[00:22:43] Ashley Zagst: Yeah, I agree. I think if you can focus on the things you can control, then, like, the outcomes, they aren't in your control. And looking at that and kind of paying attention to that or leaning on that is really, it can be damaging, I think.
[00:23:00] Ashley Coghill: My VP hates it. He's like, "Well, how am I supposed to motivate you?"
[00:23:05] Katrine Reddin: You say, "Buy me lots of pretty flowers" or something that you like. Insert one thing that you would like to have.
[00:23:11] Ashley Coghill: Right.
[00:23:12] Ashley Zagst: Well, and I think it's interesting, like, you know, for example, let's say you hit quota already and then, but maybe you're somewhere in the middle on the leaderboard. You know, unless there's some awesome accelerator that like, if you get a, you know, a certain percentage over a quarter, you're gonna get more money,
[00:23:30] like, mm. I don't know. Like, I think for me, like you said, competing with yourself and trying to get better every day and treating, I, what I'm working on right now, we started this thing called Empathy Project here at Chili Piper, and especially because of where we are right now, just in the macro climate, folks are not, I've said this before, that like, "Oh, the status quo is our biggest hurdle," and that's not necessarily true anymore.
[00:24:00] It's the, like, indecision is still a big hurdle, but the, the reason for the indecision is shifting. Sometimes it's just, "Okay, yeah, we're good with what we have and that's actually real." But now what we're seeing a lot more of is that it's like the, this fear involved of making a bad decision and just as
[00:24:22] much as I was fearful of underperforming because the implications down the line of, "If I underperform again, I get on a pip and if I underperform again, I get fired," like, that's exactly what our customers are feeling on the opposite end of the spectrum. They're, if they make a bad purchase decision, they could lose their job.
[00:24:39] Ashley Coghill: Mm-hmm.
[00:24:40] Ashley Zagst: And so, are not up against, "Oh, well our competitor has this cool feature and we don't." Who gives a shit? We're not up against like, "Oh, well, we've been doing it this way for this long, so we're just gonna." Cool. Maybe. What we're really up against, and I even hate saying up against, but what they are up against is like, they know they need to make an improvement, but they also know that if this doesn't pan out, that then they don't hit their numbers and then they may lose their job, you know, whatever the, the ultimate, like, result is and, like, it's one thing for us to be like, "Yeah, but the ROI and, like, we're gonna help you hit the, like, exceed those numbers by 5 x and." Sure. Maybe.
[00:25:23] But they have to believe that and they have to trust you and none of that happens unless you can be present with them, be empathetic with them, be human with them. And so, that's really what I've been working on. Like, I like to think of myself as, like, a really empathetic human who's conversational can get people to trust me,
[00:25:45] but I think there was a lot of work to do there, and there's still a lot of work to do there to just, like, break down that wall and, like, get on the same side of the table as them, help them buy, but it's like it's more nuanced than that. It's deeper than that. Yeah. I don't know.
[00:26:02] Katrine Reddin: We've talked about this a couple of times, but I think that's why community-led sales is, you know, bigger than ever because it's a great way of really, really getting to know your buyers and prospects authentically long before you ask them to, you know, lay their job potentially on the line and sign the dotted line and take on your new product.
[00:26:19] And I think for companies too, a good stereotype for the salespersons, right? Sell at all costs, right? "I wanna make a lot of commission. I wanna be number one on the leaderboard. I wanna be number one, whatever it is." And so, you sell, sell, sell, even if it's not necessarily the best customer, but really long term, if you sell someone that's not a good customer, that really, really hurts and impacts your team, your company, and it comes full circle to you.
[00:26:45] So, for a salesperson now, it's not just about making a sale at all costs, it's really like, "How do I find the right buyer at the right time who I can truly solve their problems with?" And what better way than like actually fostering a connection or relationship somewhere online to get to know them before they open their wallet and are ready to bring on a new tool.
[00:27:07] Ashley Coghill: It's also a good way to understand, like, all the things that you mentioned before, Ashley, about like the basics. Understanding what they care about, understanding what they're actually talking about, that's what I like about community personally. Like, just not sell. I don't sell in the communities I'm in.
[00:27:22] Like, I'm in a lot of communities and I probably could say like, "Hey, have you considered buying Seismic?" Right? Like, I could do that, but I would completely ruin my reputation, my company's reputation, and I wouldn't be able to see firsthand what they care about. Like, it's more valuable to understand them
[00:27:40] Katrine Reddin: Mm-hmm.
[00:27:41] Ashley Coghill: than set a cold meeting.
[00:27:43] Right?
[00:27:44] Ashley Zagst: I totally agree. I'm in several communities and I have a rule for myself, including on LinkedIn. I don't pitch people unless they ask directly.
[00:27:52] Katrine Reddin: That's a very good rule for all salespeople to know entering any community. The moment you start cold-pitching people, you lose that trust and people will no longer engage with you in those communities.
[00:28:03] Ashley Zagst: Well, and.
[00:28:04] Katrine Reddin: You really have to want to invest in building a relationship, and I think that's gonna set apart the people that continue to succeed in sales and find a way to relate to people and the people that don't necessarily succeed.
[00:28:18] Ashley Zagst: Yeah, I agree. I tried to explain that to, like, I used to help with onboarding some of the new SDRs and talk about social selling with them, and that was always my like, number one rule. I was like, "LinkedIn can be an amazing tool, but as soon as you, we've all heard this term pitch slap somebody like you ba, you do, you lose all the credibility the
[00:28:40] You don't.
[00:28:41] Katrine Reddin: The moment you see that question mark in your inbox, you're like, "No."
[00:28:46] Ashley Zagst: Cool. I mean, I do it, right? Like, people will connect with me and then the next message is like, "Hey, I've got this new thing. You should try." I'm like, "What? No, I thought you wanted to connect with me for real. This is, no, thank you."
[00:28:59] Ashley Coghill: I don't even, I actually dislike it when there's any message that comes with the connection
[00:29:04] Ashley Zagst: Oh, really?
[00:29:05] Ashley Coghill: because that, like, pings into my inbox and then I'm, I'm just waiting for, like, the very end of it to be like, "I wanna, this thing that I can help them with." Like, if it's just, I, like, I know that that's a whole debate whether you should add a message or not, but, like, I personally prefer to not have a message because it's not paying my inbox and making me have 10 million red numbers and then I, my assumption is that if there's a message with it, they're trying to sell me something.
[00:29:31] Katrine Reddin: That's fair.
[00:29:33] Ashley Zagst: Yeah.
[00:29:33] Katrine Reddin: I wonder now if the, if when I sent you a connection, if I had a little note in the.
[00:29:37] Ashley Coghill: I'm pretty sure we met before we connected, so I don't think that counts.
[00:29:43] Katrine Reddin: So, Ashley Z, not Ashley C, I wanna go back to something you said at the beginning of this conversation, that when you started off at Bravado, you were super involved in DIB for sales and writing content and all that good stuff. So, I wanna talk about that a little bit. We know that you're very passionate about it and we'd love to hear a little bit more of, like, why you feel rep, representation matters specifically in sales.
[00:30:10] Oh yeah. Question, but.
[00:30:12] Ashley Zagst: Yeah. So, okay. So, at a Bravado, like, that was really surface level because, like I said, I obviously hadn't been in sales yet, and so I, really what I saw is just a lack of representation, which in short why that matters is because if you don't see people like you somewhere, you're not gonna go there.
[00:30:30] So, like, newsflash to recruiters and hiring managers and organizations that are trying to grow, if you have a picture on your, like, about us page and it's 13 white dudes, and yet you're like, "I wanna hire people of color and I wanna hire queer people and I wanna hear women and, you know, you name it," that's not attractive to us. That looks
[00:30:51] like I'm about to walk into a very toxic environment. Now, granted, I might be completely wrong. That might not be the bro space that I think it is, but that's what it looks like and perception is reality. So, the other thing that I like to say, representation matters from that perspective, right?
[00:31:10] Like, if I don't see somebody like myself at your organization, I'm probably not interested. Mo, because a couple of reasons, right? Like, it's already hard enough for women in sales, and I can dive into that a little bit more, it's hard for us to level up, like, the statistics are real. It used to be, maybe it's not anymore, but, like, a pretty even split at the entry-level sales job, like an SDR role,
[00:31:31] but as you level up and get higher up into leadership, it, that diminishes drastically. And then let's not even get started on the pay gap. Right? And that happens early, right? Like, I already see it. So, there's a lot of reasons why representation matters. And then the reason why, like, one of the first things I did at Chili Piper, I was six months into my SDR job at this company, you know, of, I think there were 70-something people at the time, I was like, "You have no ERGs. And you're a pretty diverse company," right? That's why I went there.
[00:32:08] Ashley Coghill: Yeah.
[00:32:09] Ashley Zagst: And so, I started The Proud Pipers. I wanted there to be a place where, you know, folks in the LGBTQ community could come together and allies as well, like, come together, share, learn, grow, ask questions, you know, just become better humans and better coworkers and be able to support each other.
[00:32:27] And man, little did I know how much that was gonna be needed. That was in 2020, so here we are now. Like, there have definitely been moments where, like, that group has, we've been leaning on each other heavily after all these, like Roe v. Wade being overturned, all these anti-trans bills being drafted and, and passed, and just our community being, like, attacked and having to go to work every day and just be like, "Okay, call some people."
[00:32:55] Right? Like, having something internally where you can go and talk to people and know that you're not gonna be judged, know it's a safe space, know you're, you know, supported, that's really important.
[00:33:06] Giving voices to people who are in underrepresented groups I think is a really important thing too, so I, like, that was another reason why we started Proud Pipers. I mentioned earlier, like, sales is already hard for women or for underrepresented groups. All these companies doing layoffs and, and, you know, it's running rampant, right, in the tech industry. There's layoffs left and right. We hear it all the time. And a lot of what I've heard is, like, these decisions are made based off performance. Okay? Fair. Like, pull a spreadsheet, chop the bottom, call it fair. But then you look back at who's left and you're like, "Wow, cool. There's hardly any women now. We fired all of our people of color and there's no indigenous people, handful of queer people, like, you know, okay, diversity just went out the window because shit hit the fan.
[00:34:01] We had to lay some people off." And the notion that doing it based on performance is the fairest way I call bullshit because that is assuming that we're all starting at the same starting line, right? Like, we're all lined up at the same start line and that person was just 400 meters a ahead to, like, this person that's starting, like, got cut.
[00:34:28] But that, that's a big assumption and it's wrong because we're not. I didn't realize this until I got into the sales role. I had stories, right, but I didn't, you know, I hadn't experienced it myself. And even when I first started, I, I didn't really experience a lot of bias and so I was just like, "Wow, I must be really lucky," you know?
[00:34:48] 'Cause I'd heard a lot of stories. Well, I had my first experience with it come right after I started in the AE role where I had a, a prospect who, at a certain point in the deal cycle just, like, stopped talking to me and wouldn't answer my questions, wouldn't answer emails, whatever. And, and then for some reason something happened, and he ended up booking a meeting with my male colleague and in, in that call, it was like less than 30 minutes, in that call he was like, "Yeah, send me a contract."
[00:35:19] Like, ready to do business, ready to sign a deal. And I was like, "Oh, well, alright." And my, my colleague was like, "No, no, no. I was just filling in for Ashley. Like, yeah, Ashley, here. Like, he wants to close the deal." I'm like, "Great." And then again, it's like radio silence. He, like, literally wouldn't talk to me, wouldn't do business with me.
[00:35:39] And I was really confused. And I reached out to a person at the company who had recently left the company who happened to be a woman. And I was like, "Hey, I might be just making shit up here, but, like, this is happening, and I'm really confused." And she was like, "Well, actually that tracks, like, that's why I left the company.
[00:35:55] This person is pretty sexist and it's hard to do business with him." And I was like, "Cool." Ne, didn't realize that would be so blatant.
[00:36:05] Ashley Coghill: Yeah.
[00:36:07] Ashley Zagst: So, that happened, right? Ended up closing the business. I was like, at one point I was like, "Maybe I just give it up and, like, don't like give it to somebody else and don't deal with it," but the fighter in me was like, "No, the best way to fight this is to, like, I'm, I'm gonna take your money. I'm, I'm gonna get paid by you." And so, I did. And so, that's something that we have to deal with, that my male counterparts don't have to deal with. So, when you wanna break this down to performance, they don't have to worry about getting on calls and basically then being ignored and circumvented in, in the deal cycle. Right? Other things that happen on the daily are, and this is not, this isn't just, like, me speaking for personally, but I mean it has happened to me personally, but, like, in general, men get credit for things women do.
[00:37:03] Ashley Coghill: Mm-hmm.
[00:37:04] Ashley Zagst: And why that matters is, because when you talk about getting promoted, and you've got your internal champion who's looking at, like, "Here's on top of succeeding in your numbers,
[00:37:14] like, what are all the other things that you're doing?" Right? That matters. And so, when somebody in your organization gets publicly recognized for something outside of just the table stakes sales numbers, right? And it's something that a woman did, but they'd get credit for it, that's a big deal. And again, that plays into this uneven playing field.
[00:37:36] Like, we're not even at the same starting line. This person is a mile ahead of me, so we're having to run faster, harder, longer, just to catch up to them to be, like, at the same point as them and then hopefully we keep getting promoted, hopefully, we keep succeeding, but like it's, yeah, this whole notion of performance-based judgements when it comes to that is, like I said, I just call bullshit.
[00:38:03] Katrine Reddin: So, for the meetup that Ashley and I host every month, sometimes when we get on as the icebreaker, while we're waiting for people to join, we'll say, "Hey, share an accomplishment of yours from this week or today or this month." And typically, it'll be about 30 seconds of silence. Everyone sits there, kind of looking at each other, like, "Does anyone have anything to say?"
[00:38:27] And then someone always breaks the ice is like, "I just closed a deal," or, "I just booked 10 opportunities," or, "I hit quota," and everyone's so hesitant at first to share their accomplishments versus when I'm on a team meeting with my mostly male peers at Commsor, which they're all fantastic by the way, but the fact of the matter is they are mostly men on the team,
[00:38:49] they don't hesitate to share any of their accomplishments. And when I look at kind of like the juxtaposition of the two, it just baffles me 'cause I'm like, "Here are all these amazing, capable, successful women that all have something to boast and brag about and they're so scared to bring it up versus all of my coworkers who again, are amazing in their own right, but they don't even hesitate."
[00:39:10] They're like, "I did this. I accomplished this." There's no hesitation in sharing their accomplishments.
[00:39:16] Ashley Coghill: We're told bragging is not ladylike, I think early, and so we're afraid to speak up and say, "I did this really cool thing" and it's a shame.
[00:39:27] Ashley Zagst: I saw a comic the other day. It was, like, two people at computer screens, hand-drawn. One person in the bubble is like, "What's the difference between assertive and aggressive?" The other person says, "Your gender."
[00:39:42] Katrine Reddin: Oh my God.
[00:39:44] Ashley Coghill: Well.
[00:39:44] Katrine Reddin: Ain't that the truth, though?
[00:39:45] Ashley Zagst: Mm-hmm. Yep. And you're right, Ashley, like, we're told to be small, to be quiet, to be less than, like, because that's acceptable or, or whatever. I'm like, I, I just can't, I don't like, no, thank you.
[00:40:03] Ashley Coghill: Nope. No, thank you. We're really close to time and I wanna make sure we have enough time to do our fun part, which is, I don't know if we even briefed you on this, but we typically do a, like, super-fast round of would you rathers and there's five questions.
[00:40:19] Katrine Reddin: But first, first to wrap it up, 'cause we did just go very deeply into, you know, the, the intricacies of being a woman in revenue. If you could leave our listeners with kind of one piece of advice or one final thought, just as a woman in revenue, I'm curious to hear what that would be.
[00:40:35] Ashley Zagst: Keep going. Keep doing what you know how to do. Find your tribe. Reach out to other women, other people in sales that you vibe with and keep going 'cause we need you and we need, and, like, future generations need you. And that sounds super, like, I don't know, heady, but, like, like, Ashley mentioned earlier, I just bought a house.
[00:40:56] Never in my wildest dreams did I ever think that was possible. My mom was a single mom, two girls, like, I was the first person in my family to graduate from college. Like, even then, didn't think I would be making this kind of money. So, because this could be life-changing for people, and I'm so grateful that I was exposed to amazing people in this industry so that I was, like, intrigued by it and wanted to, to kind of make that leap,
[00:41:24] and so we need more of that. We need more people who are doing this amazing work, and, like, who look like you, right? Because, like, we just talked about representation matters. And if it's a bunch of white dudes who graduated from Stanford and, you know, we're like, "Go get it." You guys are awesome. And there needs to be diversity.
[00:41:45] Our buyers are diverse. I don't sell to just old white dudes who went to Stanford, right? Like, I sell to everybody and their moms, so why would the sales team not try to mimic the buyer pool? Just makes sense. So, anyway, that's my advice. Keep giving it.
[00:41:59] Ashley Coghill: Love it.
[00:42:00] Katrine Reddin: I love it. And I agree with all of that.
[00:42:03] So, as Ashley said, we wrap up every episode with a round of revenue-themed would you rather questions? They're kind of rapid-fire, so don't feel like you need to explain your answer. But I'm gonna go ahead and read them and we'll, we'll see what you have to say.
[00:42:18] Ashley Zagst: Okay.
[00:42:19] Katrine Reddin: First question, would you rather work with a product that you're very passionate about, but it's very difficult to sell, or a product that you're less interested in, but it's super easy to sell?
[00:42:31] Ashley Zagst: I gotta go to the product I'm passionate about. I can always figure out how to sell it.
[00:42:35] Katrine Reddin: I agree. Would you rather sell 50 smaller deals to hit quota, or would you rather sell two really big deals to hit quota?
[00:42:44] Ashley Zagst: Two really big deals.
[00:42:45] Katrine Reddin: I always feel like they're a little more satisfying in my opinion. They'll typically take a long time, but worth it.
[00:42:52] Ashley Zagst: Yeah, it's worth it. Yeah.
[00:42:53] Katrine Reddin: Would you rather work for a company that has a culture of mentorship and career development or a company that values individual performance and achievement?
[00:43:02] Ashley Zagst: Mentorship and career development, hands down.
[00:43:05] Ashley Coghill: That was a layup.
[00:43:06] Ashley Zagst: Yeah.
[00:43:07] Katrine Reddin: These are, this next few might be a little more personalized to you. Would you rather have to give a five-hour talk on pipeline management and leaderboards or receive a thousand unsubscribes to your emails in one week?
[00:43:23] Ashley Zagst: Oh, brutal.
[00:43:26] Katrine Reddin: We had to mix it up a little bit.
[00:43:28] Ashley Zagst: Oh, I'd give the five-hour talk. I feel like I could talk for them.
[00:43:34] Katrine Reddin: Hey, I think you're full of knowledge. I think you'd be great at giving a five-hour talk.
[00:43:38] Ashley Zagst: I'm full of something. I don't know.
[00:43:41] Katrine Reddin: And last but not least, would you rather have to include a unique pun or joke about ballet and all of your cold outreach, or would you rather have to send a picture of yourself snowboarding to every person who doesn't answer a cold call of yours?
[00:43:57] Ashley Zagst: Oh my gosh, how funny. Why not both?
[00:44:00] Ashley Coghill: I love that. That's a first for us.
[00:44:03] Katrine Reddin: We'll let you pick
[00:44:03] both. We'll break the rules a little bit.
[00:44:05] Ashley Coghill: Both is perfect. I love it.
[00:44:08] Katrine Reddin: Well, Ashley, thank you so much for joining us. We really appreciate you being here,
[00:44:13] and we really appreciate you talking about diversity and representation because obviously it's incredibly important and I think a lot of teams need to work on that very much, so it is a topic that we are really excited to chat about with you.
[00:44:26] Again, congrats on both the house and the promotion.
[00:44:30] And Ashley, I'll let you wrap. Ashley C, I'll let you wrap up.
[00:44:33] Ashley Coghill: Yes. So, the entire purpose of the podcast is to elevate the voices of women in revenue, so thank you for sharing your thoughts. I think it will be very valuable for people who are wanting to get promoted because, spoiler, we all are and it's important to talk about having safe spaces for underrepresented groups in tech, sales specifically, but also just in tech.
[00:44:53] Thank you, Ashley. And for those listening, you can follow Ashley Z on LinkedIn for incredible sales content. And if you'd like to listen to Ashley's walk-up song, Irrelevant, Irrelevant, did I say that right? By Pink, as well as the walk-up songs of other guests, you can find our playlist on Spotify by searching for Ashley and Katrine's Infinite Revenue Playlist.
[00:45:16] See you next time and keep at it like Ashley said.
[00:45:19] Katrine Reddin: Keep at it.