Christine Rogers - President & COO of Aspireship: Sales Leadership, Having Tough Conversations, and Driving Accountability

Christine Rogers  00:00

If someone is telling you the formula to helping them, like listen, listen to what they're saying, pay attention to what they're saying. And, you know, don't think you know better, and every time and I've had to learn that as a leader myself, like, paying attention, understanding that people are all we're all a little different.

Callan Harrington  00:20

You're listening to That Worked, a show that breaks down the careers of top founders and executives, and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back to a another episode of That Worked. I'm excited for this week's episode, I'm joined by Christine Rogers. Christine is the president and COO of Aspireship. Aspireship is a career development platform that helps you launch or grow your career in tech sales, software engineering, customer success, and many more positions. Christine brings a ton of energy. She is a seasoned sales and marketing leader specializing in recruiting, hiring, training, and managing high performance sales teams. She's a people leader who maximizes team performance and drives results. I have to say, we dove into how Christine does all of the above. We talked about how to have tough conversations, how she holds salespeople accountable, and how she maximizes every member of the team. This was nothing short of a sales leadership masterclass. With all that said, the part that I love the most was how Christine turned what she believed to be a failure at her first goal as a business owner into a massive positive. It's a great example of the power that comes from sharing your story. I'm not going to do it justice here. So, let's jump into the show. Christine, welcome to the show.

Christine Rogers  02:14

Thank you so much for having me. I'm excited for this today.

Callan Harrington  02:17

I'm excited to have you here you have so much energy, and one of the areas where I want to kick this off. So, you had a LinkedIn post the other day. And I want to quote this: "if you know me at all, you know I hate this one, because going to the gym has some past irritation for me- another time, another story." What's that story?

Christine Rogers  02:40

Oh, yeah. Well, you know, okay, so I'll just start by saying that was a post about what I do essentially when I'm kind of struggling. You know, what are those things that I do? And one of them was doing something active and physical. And I do have a little PTSD around the gym and haven't really shared that before. So, I will share this because I do think it has something to do, and can be related to, a business conversation as well. Oh, gosh, it was probably when I was in my early twenties. I had been newly married, and my ex-husband, now he's my ex though, but at the time, I mean, he is just a mountain of a man. I'll just say that. Like, he is the person that everyone looks at, in every room he ever walks into. And more men than women, you know, kind of like where men are like, "whoa, I wish I had that," you know, I wish I looked like that. So, that's him. So, we had- he was like, let's go to the gym, let's do that together. Like that'd be fun. So, um, you know, I hadn't really done that before. So decided to go, and of course, he's very well versed in everything he's doing in the gym. So, I decided to get a trainer to help me to learn, and because I was really not very confident and wanted to be more motivated. So I paid for, you know, about six months of personal training, and went into the gym, and the first time I had my trainer, he was trying to motivate me. And so I'm pretty clear know myself pretty well. I know myself better now. But I knew myself then as well. And he was doing the thing where it's like, "hey, Christine, okay, we're gonna do ten." And so I do the ten, and he's like, now five more. And I was like, okay, and then he's like, alright, five more. And I finally- so we went through this a few times, and I said, hey, if we're gonna do twenty, just tell me twenty. Like, I'm a kind of person that if you're like, we're doing twenty, I will give you my full. He's like, well, no, you really won't. You'll think you'll go harder if you think we're only doing ten. So we get through this whole thing. And I finally kept saying to him over and over, hey, this isn't working for me. This isn't motivating. It's actually demotivating, because then guess what I started doing? I started stopping at ten. You said ten, I'm doing ten. And my husband at the time was over in the free weight area and doing all this stuff. And he's like, "wow, your husband's really ripped," and all this other stuff. And I said, yeah, I know, like, can we focus on me? You know, like, I'm trying to get this and how can we do it? And I finally said, "I know you're trying to motivate me. The motivation for me is about telling me what we're doing, helping me envision, like what I'm trying to accomplish here, and giving me clear direction on what we're doing, and I will absolutely give it 100%." And he didn't listen. I gave him the the formula for me. And he kept doing it the same way. So finally, I said, "okay, I feel like we're not communicating well, and I'm trying here to tell you what I need." And he looked at me very exasperated, and then he looked back over at my ex, and he said, "don't you want to look good for him in lingerie?" And I just like- I said, "what?" And he's like, "yeah, I mean, look at him, don't you want to look good for him and lingerie?" Like, and I said, "you know what, this is so not helpful, and what a strange thing to say." To take everything about all the reasons I was in there about being healthy and learning and trying something new... I walked out of that gym, and sat on the bench out front and waited for him, my ex, to finish. And he came out and I said, "I am never going back there again. I am not going to take part in that again. That was absolutely humiliating." And in all of the regards on why I'm there and everything else it was so diminished down to the fact that I should want to look a certain way for that man, not for myself, and not listening to actually what would work to motivate me. And so I just said to him, "I'm not going back." And that was it. And so it's now you know, almost twenty years later, and I in that post was saying, I now have two beautiful children or they're grown men almost now. They're like fifteen and seventeen. And in the month of April, when I wrote that post, you know, I said to my youngest- He said, "Mom, I need to go to the gym. I need you to come with me, though, because I can't get there on my own." You know, because, um, he's only fifteen and a half. He can't go there by himself till he's sixteen. So I said, like, this is a really big ask, because I don't want to do that. I've been doing Pilates. I've been doing other things. I've had all these things. But you know what I really realized, it came back to that moment, like when I started thinking about why do I hate it so much. It was because of that moment. And my kid came with me and we went the first time. And he was like, "hold on mom." And he's bringing me weights and doing the things, and he's like, "I'm gonna show you what I know how to do." And so he was doing it, and stood in front of me, and I'm like "Kale-" His name is Kale. I said, "I don't think I can do-  these are too heavy, I don't think I can do any more." He's like, "we're gonna do twenty." And I got to fifteen. I'm like, it's too heavy! I'm doing these curls. And he puts his- he puts his two index fingers out. And he just put them underneath the weights. And he pulled him up with me a little bit. And he's like, he counted them out, four, three, two, one. And he goes, "see, I knew you could do it, mom." And he's like, you just needed a little bit of help. And I literally looked at him, and I thought, everything about that moment, like, here's this young man who motivated me more in just a moment saying, like, I'm here for you, I've got you. And all you need is just a little bit of help. And he had no idea how powerful that was for me. And I just looked at him and said, like, "buddy, you just changed my whole perspective about this experience, and you have no idea, but like you are more motivating and helpful than anybody has ever been in this regard for me for the last twenty years." He looked at me and he's like, "cool, let's go to the next thing, Mom." And, it was like, not a big deal, you know, in true teenage fashion. I'm like having a moment, about to like have like a tear fest, like in the middle of the gym floor. And, you know, it just goes to show like, we all have it, we all have some stuff that's happened. And when we're trying to be clear and trying to be motivated and trying to do different things. And sometimes people listen, sometimes people don't. And it really, in that moment, it really just reminded me that like it is important to pay attention. It's important to listen and see people and what they need. And even a young fifteen and a half year old teenage boy who has no idea how to motivate his mom, knew right then that all I needed was just a little bit of help, a little bit of encouragement, and I could do it. And he was right.

Callan Harrington  09:35

I have like 50,000 questions around this and I don't even know where to begin. Right. I mean, obviously on one hand is just, it's unbelievable to me that he would say that just in general. But one of the things that I think is is really interesting on what you just mentioned was if we don't ask questions, if we don't really get to the root of the motivations on somebody, then we're going to fail regardless. I mean, that was destined to fail regardless. That person just didn't know what like, there's no excuses for it in general. But if we, if we don't dive into that, if we don't really understand where somebody's coming, whether that's in leadership sales doesn't really matter what it is. If we don't understand what those motivations are, and take the time to figure that out, I don't understand how you can motivate somebody is that essentially what you kind of figured out within that? Is that what you were saying?

Christine Rogers  10:24

Yeah, yeah, absolutely. And also, in the last twenty years there've been many people who have tried to get me to go to the gym, or tried to get me to be excited about that, or try to motivate me to do it a certain way. And sometimes the how we get to results is not necessarily like the thing. We can get there a lot of different ways. But really, if someone is telling you the formula to helping them, like listen. Listen to what they're saying, pay attention to what they're saying. And, you know, don't think you know, better and every time. And I've had to learn that as a leader myself, like paying attention, understanding that people are all- we're all a little different. But giving the credence that is just because it worked for me, it might not work that same way for you. And I think that that's absolutely right, like truly listening, looking, paying attention and changing our mode, the way that we're responding. And not just thinking we know better.

Callan Harrington  11:21

So true. That was a mistake I made early as a new leader, especially in sales as a new sales leader. When I was trying to motivate sales reps, I did it exactly how I wanted to be motivated. And that worked for some, but that definitely did not work for all and I had to change that and  realize they're not me. So yeah, I think that's such an impactful thing. So I appreciate you sharing that that story. And I think there's just such a good takeaway, and you have to understand what, what are their goals, aspirations. And then one of the things you hit more than anything is, here's how I work best. And just maybe take when I do- what I say is what I work best, because I got a pretty good feeling for that. So I love that. Christine, where did your career start out?

Christine Rogers  12:10

Well, I you know, I've kind of been in sales my whole life. So, I did definitely not take a linear path to where I'm at right now. Started in insurance actually, did that for a little while, and moved into and owned my own business and sold everything there. So, it was a retail store for baby furniture. And so my clients were all pregnant women. I'll just leave that there. And so it was a challenging kind of environment. And then really from then when we had to close our business kind of through that first- and in my working lifetime- recession, like the 2008 to 2010 era, had to close it and then started my first job in sales and tech. And so from that point on, because I'd had some business savvy and because I'd had some leadership ability, I did move pretty quickly around in that organization. Not straightforward. And like if anybody had asked me, day one, do you want to be the leader in this company of like the direct sales team, I'd be like, no, but that ended up being where I was. And I took a very non traditional path to get there did enablement, I also was like the executive assistant to the sales leader at the time, because he said, like, I need a thought partner, and I need someone to teach. And I'm like, I'm not a secretary. And he was like, I understand. And I'm like, I don't actually think I want to do your job. And he's like, okay, however, you can help with a bunch of things. And so I really took a big risk in that regard and trusted him. And then, you know, four and a half years later, I- actually, it was like, within about two and a half years, I was running both the enablement org and the direct sales team of $100 million company, you know, so putting in about 60% of that revenue my team was, so just stayed there for about five years.

Callan Harrington  13:52

Gotcha. So well, one, camaraderie on starting out in insurance. I started out as an agent as well. So, I love it. You know, what's interesting is I still to this day, the use of feed lists and centers of influence and a lot of things that doesn't get talked about as much in B2B, but it's huge in B2C, are things I still use to this day and are hugely impactful. One of the questions that I'd love to dive into is, so you were a business owner in the retail space. And what got you into that specifically?

Christine Rogers  14:30

Well, in that- at that time, I was the clientele. I was like the ICP, you know, I had just had a kid, and he was at that point about a year old, and I was shopping. And I'm like, man, there's not a lot of places to get furniture and different things, you know, and so I happened in there. And it was a cute little place, but it really needed to be rebranded, and all of those things that I just said like, "what are you doing? Do you need some help?" And she was like, "yeah." So, I decided I'd always had, and still do have, a very entrepreneurial bug. And I do love and believe in small businesses and love that as kind of the fabric of our country, I believe strongly in it. And so it was really like the idea of being able to own something or have a piece of something in the world kind of spoke to me. So I made the leap, you know, I actually second mortgaged my house, bought into the business did all the stuff that we did. And then a few years later, it couldn't hold when the you know, gas prices went up. And furniture, getting it even shipped was astronomically expensive. And so just getting a crib to me cost way more than what it was, you know, it wasn't worth it to continue in that market. So, then we had to close it. And that was super heartbreaking, very, very heartbreaking. I felt like a complete failure. So, even in this economy, the interesting thing is how tough it is, I do understand it. And I do understand, because currently, you know, I'm running a business that is predicated on hiring, and helping people get into businesses and tech that weren't there before. And you know how the market has been in tech and hiring and layoffs. And so, I will say that, because I experienced a lot of these pains and this heartbreak before, I'm a lot less afraid of what's going to happen now. And more like, we're going to do everything possible that I've already confronted, I've already confronted like looking at myself in the mirror and going like, wow, you totally failed at this. And it's gonna be okay, and so being able to be moving forward when I think sometimes people are panicked right now and kind of stop, but just continuing to figure out like, what's the next thing I can do? I don't know, ten steps, but I can probably take like half a shuffle forward. And that's what we're gonna do.

Callan Harrington  16:38

I'd love to talk about that a little bit more. What do you remember what some of the turning points are when it changed from I'm a failure to no, I'm not, I'm actually completely okay. Do you remember what some of those were?

Christine Rogers  16:52

So, I actually remember this really poignant moment, when I had the company that I worked for first, you know, that sales role. I will remember, I had been there about three or four months, and maybe like about three months. And I was there really early in the morning one day, because we hit you know, the UK, and we're hitting all different places. And I was there with probably like one or two guys. And as we started talking, he said, I think I bought my crib from you, like from your store. And he started telling me, I'm like you did, oh my gosh, how weird and I hadn't sold it to him. So, I didn't know. It had been my business partner. And he said, "Christine, you understand something that so many of our prospects don't..." Well, this specific company, worked with small business owners. And so he said, "your story is so compelling, you sharing this with the prospects is going to be huge." And I said, "I cannot share this." I was a failure, you know, and I remember having this conversation like 6:15 in the morning on a Tuesday, and it was just he and I having coffee, you know, between calls. And he's like, "you don't understand, like, this is so powerful, so powerful. Tell them that you wish you had had a solution like ours." And I did, you know, I really believed in what we were selling, we were like a small business, sales automation, marketing automation, CRM system. So had we had that, it would have been better. And I did feel that way. And he's like, "the minute you actually open up and start telling people, this, you will do better, you're going to be able to relate to them, stop hiding that this happened to you and understand that this is what makes you so passionate about what you're selling." And I remember I burst into tears. And I went to the bathroom, and kind of cleaned and I came back out and I was like, I'm gonna own it. Yeah, I'm gonna own it. Like, I'm gonna do this differently. And the next call I got on, I just said, like, you know, she was talking to me, and she said, "Christine, I already knew who you guys were, I've heard it." Because I was calling into old leads, you know, I was calling old leads. And she's like, "I've talked to you guys before, I already know this spiel." And I said, listen, I was just like you, like, I have heard all the things, done all things, but I did not take action. And I just told her my story. And I said, so listen, I understand it, but I don't want you to make the same mistakes that I did. I want- and she's like, I have been afraid to do something different. And I think what you're saying is powerful. And from then on, I just realized, like, my experience, and my quote, failure that I was embarrassed about and felt like I had to hide, could also be something that someone else needs to hear. And so not trying to manipulate or use it but also not being afraid to share it. And so it's a little like open kimono, like just alright, I'm just gonna stand here and know that like, I'm ashamed, like I'm ashamed and just be okay. With like, my learning can be your learning. So you don't necessarily have to learn this way. And so while it wasn't the absolute best salesperson there was I was able to convey something that I think maybe others couldn't, in a different way. And also, as I then grew into different leadership roles, reminding them that like, this is people's life. They don't have a budget that's coming down and being passed down from something else. So if you can actually speak to them, like the humans that they are, rather than the prospects that we've been told they are, then it will shift for you and them. That is such a powerful story. What I'm curious about is, after that happened, what happened to your sales career? So, after that, you know, I was I was okay. Like, I'm not the best salesperson there is. But I'm actually really good at leading salespeople. So I think there's a different type of thing that happens there. And I think also some- there's a misnomer that you have to be like A-plus, A-plus salesperson to lead the organization. And I don't think that's true. And so the way to lead people is different. And you have to have a little bit of, I think, like a salesperson, but I'm also very operational. So like, my- the way that I like can support also understand that like, the best salespeople are going to try to break every single thing I ever put in place in a framework, they're going to try to, you know, create anomalies and do it better and faster. And my youngest son is like that, too. And I appreciate it. You know, I don't look at it and go like they're trying to- if I need a problem solved, like, that's who I ask to solve it. I'm like, you know, I'll ask him, because he's like, I literally have told him since the day he was, like, could talk to me and tried to negotiate with me about, "there's ants outside biting my legs as I'm picking up the dog poop, which means this has got to be more than a two dollar chore." And I was like, oh, and so I mean, he was literally, I think seven or eight, when we had that first conversation, where he was just naturally negotiating with me that this was extremely painful. And so I look at that and think to myself, like you're every great salesperson I've ever had. And I am enthusiastic about that. And so I think, from my perspective, that's why I've been good at leading salespeople, because I don't look at it and think, like, they're so hard, I look at this organization of problem solvers, that will do it better than anybody else that has kind of a A plus B equals C mind. And like, that's why like, when my kid, he figures out the game at school, and I just- he like, knows how to play a game called, I'm gonna get A's and not do near as much work. I'm like, cool, as long as you understand the game and the rules, and you're being respectful about it like, that works. And, you know, so I think that for my perspective, that's why did like enablement, and hiring and training and different things like that, and then started really operationalizing the sales organization, and then became the quota carrier for the sales organization, and then moved into different companies where I did very similar things, because I can bring an operational mindset, but also don't diminish the beautiful, creative nature of these people, that I'm serving them, and they're doing something that's very challenging and very hard. So I absolutely respect it, I know what I'm dealing with. And also, I think there's mutual respect, because, you know, a great salesperson, it's like, there's the line, they're gonna dance on that line, and everyone's gonna try to put their foot over the line and see if they're gonna get caught. And if they get caught, then they respect you back again. And then they stay within the boundary. And you know what, I don't look at that as like, I look at it and go, that's who they are. And that's why they're great. And you know what, I'm okay with that, and I'm going to be clear. I'm also going to be very clear about that does not work here. If we do that again, then man, it's going to be a bummer, but today will be your last day, are we clear? Like all good, I don't have a lot of burn around it. Like, I don't have a lot of energy around it. I am not going to allow certain things, that are just in the people's nature, to cause me to have a lot of turmoil. Like I've learned that over time. And just not making everybody bad, good, right wrong, it just either works here, or it doesn't work here. That's it.

Callan Harrington  23:58

How do you balance the giving kind of that freedom, that creativity, the autonomy in the world with here's the process, here's what you're accountable to, here's what those expectations are?

Christine Rogers  24:11

Yeah, so, I wasn't always great at the autonomy part of it. Because especially I think some people that had probably worked with me in the past, when I was first kind of trying to hone in on one of those things. I didn't give a lot of autonomy. I personally believe autonomy has to be earned. So I am very clear about expectations. If we are working from a certain time to a certain time, if we're doing different things. And then after a while, it becomes like I don't really care what's happening if you're hitting your numbers or how you're doing it. Like I am supportive of those things. If you're doing it the right way. If our customers are number one for you, if they are having a good experience, if these things are going on I'm not probably going to micromanage you. However, I don't start there. I start with let me very, very heavily direct your work and make sure that we're good, and then you earn earn the right to have autonomy. And I have made the mistake of being hard throughout and not allowing for those earnings. And I've also given people way too much autonomy at first and then being like, oops, that was too much. And so I've learned over time how to balance that. I don't always get it right. I still don't always get it right. But I think I'm more often getting it, I would say more balanced. And being clear about my expectations all along, like, hey, it's changing. Now, I'm going to go ahead, and I'm not going to be managing this as tightly instead of meeting every twice a week on this one priority that we're working on, I'm going to meet now once a week, because I actually know that you're, you know, we're making milestones hitting timelines, things are working out. So I tried to be a little bit more clear that like, I think communication is so important. So like, for me, it's like I over communicate quite a bit on, okay, so I'm changing how we've done things. So I kind of tell what's about to happen. And then I'll tell you, it's what I'm saying. So I'm like, "hey, I'm actually going to change what we've been doing right now, because this is working. So I'm going to shift this. And this is what you can expect different from me." Even when we're going to have a hard conversation, my team will tell you, I'll say like, "okay, we're gonna have a little bit of an awkward convo, like, I'm going to do the best I can with it., but some stuff I have to say might be a little awkward, I might need a little grace with saying it well, but I'm going to do my best here. And I'll expect the same from you." So then I kind of call out what's about to happen. It takes a lot of the pressure off of everyone in communicating. And it allows us to just okay, this is what's going to happen, you know, and this is what we're at. And so I think sometimes it's almost like announcing- like, what do you do if somebody says to you like, "can I ask you a question?" A lot of people will be like, "why you even say can I ask you a question? Just ask the question." But it's kind of pre-emptive in order to say like, you know, we're about to have a difficult conversation. Okay, so like, here we go. And it allows people to kind of gather themselves, even if it's one to two seconds, and prepare for what's going to happen next. And I think like those types of things, the more we can over-communicate, the better.

Callan Harrington  27:05

You know, one of the things I thought was really interesting that you mentioned was that you shifted from giving a lot of autonomy in the beginning to less autonomy, and then you earned your autonomy, which I think is a great way to do it. And I've definitely made that mistake, I've made the mistake of giving away too much autonomy, having it backfire, and then overcorrecting to more the micromanagement side before kind of figuring that out. For you, was it more based off of feel when this person has earned that autonomy? Or did you have a hard system in place that once you do X, Y, and Z, okay, this unlocks the autonomy? What did that look like for you?

Christine Rogers  27:46

For me, what it looks like is the expectations that I have- call them, you know, either the milestones, or the deliverables, or the dates, things are getting done, and they're getting done with the quality that I'm looking for. So, like from that perspective, I start off really clear. And just saying like, this is the average that overstaying that works. Once you do better than average, you can tell me, hey, you're not gonna have to worry about me, because I've actually seen that in the last X amount of months, you hit your close, you know what you're doing, you're over. So then what I start to see is like that consistent performance earns you the right to say it when I'm doing a one on one with you. And I'm like, you're behind on a lot of things here, you're looking like behind for the month, your projections aren't looking good, your pipeline is not looking awesome, like, what's your plan? And if you have a plan for me, I'll leave you alone. I'll leave you alone. Like hit it, though. Alright, that sounds like a decent plan. If you're phoning it in, and you're not getting it done, you've gotten pretty complacent, then we're gonna have a different conversation. But all I mean, for the most part that works. So it's a mixture, I would say it's mostly are you hitting the deliverables and the metrics and the results that we're looking for? And when you do that consistently, you earn the right to navigate the how your way. For the most part.

Callan Harrington  29:04

Yeah, I think one of the things that I hear you saying is, and please correct me if I'm wrong on this, but it's you're giving them the expectations, you're letting them know what done looks like what good looks like up front, and working together to create what that plan is that you need to do in order to do that. So really, when you're meeting, you're having check ins on that plan. And then when things are going really south, there's no surprises, because when you're meeting with them, it's, here's what it is. Here's what you said you're going to do. Here's where it is. Tell me what's going on here. And then if they are like, you know what, I get it. I'm not hitting plan. Here's what I'm going to do to change that. Great, all right. Or if it's, oh, well, you know, XYZ is happening and everything else and all these other things which, don't get me wrong, sometimes some of those are legitimate. It could be something that's going on at home or whatever that may be, but if they're not, it doesn't really matter, because we talked about this, expectations were set, a plan was created. Am I hearing you correctly on that?

Christine Rogers  30:07

You're right, you're absolutely right. And I have them create the plan. So, that's the plan, is we- the first one on one, every single new month, in my mind, should be a recap of what happened. And there should be numbers that they pull, the plan they put together, if they did well, it's like, what worked? And what am I going to double down on? If they have areas of improvement that need to happen called the results weren't there, then it is, I mean, I can't tell you how many times I've done a simple math equation that's like, well, if you made this many dials that resulted in this many demos, then like back into the number if you need to do more demos in order to get to more revenue. And even very seasoned business people sometimes don't understand that very basic equation. So then I'm like, now how many of you know start with like, well, revenue wasn't there. So revenue to demo it, for instance, or revenue to op, for instance, and then back into how do you get to those ops? How many meetings do you have to set then? All right, then to get a meeting? How many calls do you have to make? Or how many outreaches do you have to do? So now, you know, okay, cool, I have to do forty-two, cold outreaches a day, and I got to get to six demos a week, or I will not be able to hit my target, unless I get better. So get better at your craft, and you tend to be able to do less, that's the point. So, I have them come with that, the first one-on-one in a new month, in a new quarter. What worked? What didn't? I want three to five things that you're going to do differently- your plan. Now your plan is what I will hold you accountable to. So, I am not going to give you- if I have to give you the plan, we're in a different thing. I'm not giving you a plan, we're co-creating a plan together called you make the plan, and I'm gonna hold you to it. If your plan is stupid, and you and I both know what that looks like, it's like I'm gonna make more dials. No, that's not a plan. That's not a plan. The plan is I'm going to make X more dials. And the reason is because my numbers show that I have to. And in order for me to do this, I'm actually going to try three different voicemails, three different things, I'm going to hit LinkedIn differently. These are the things I'm going to do differently to change my outcomes. That is for them to create. They do that. Yes, I'm into that. That's a great plan. I love that plan. And next week, we're gonna look at it. How's it going? Is it working? If it's not, let's change it, you know, so I definitely am all about co-creation with people. I want them to be adults, and make their own plans, and do the things that are working for them or not working for them. And I'm gonna- but I'm also going to teach them how. So this is my expectation here. I just give them a worksheet. If they fill this out, you literally have a like one pager for that for that one-on-one. That's like, fill this out. Here's the math, here's how you do it. If you don't know how to do it, like here's it, I'm not going to assume you know. And if you're looking at me, like, "Christine I know how to do this, like backwards forwards." Great. Yeah, most people know how to pull those numbers from Salesforce that actually don't know what to do with how do I put that into action. So, great, glad you know how to do it. Come to me with your plan. Because until you're hitting consistently or over-exceeding consistently, like, we need a different plan. You know, we got to get you there.

Callan Harrington  33:14

I love that. And very, very, very, very, very similar to the process that I've used. So, I think you just gave a masterclass breakdown of it. So that's excellent. So, one of the things- I'd like to switch gears here a little bit. And so you joined Aspireship, you're the president and COO. You joined Aspireship pretty early in the company's lifecycle, right?

Christine Rogers  33:37

Yeah, our first day.

Callan Harrington  33:38

Oh, you were there?

Christine Rogers  33:38

Well, yeah. Yeah. So, Jason, and Cory, they were basically building the product. The day we launched, I was there. So, building the backend of the product for the first few months, and then yeah, day one, we launched the day before Halloween. You know, so it was like it's a very memorable day for us. And we were all- it was just the three of us that did it. Yeah.

Callan Harrington  33:58

So, here's a question that I have. In another interview that you did, you mentioned that you had went through a health scare. And as you went through that health scare, you took inventory of where am I spending my time? What activities am I spending my time on here? From a personal perspective work perspective and everything else you came out of that and you thought I'm putting my time in the right places and of course work's a big part of that, and Aspireship's a big part of that. What is it about Aspireship in particular that made you take that risk to join really as early as you can join a company and to say I'm doing the right thing? If I have limited time left, this is what I want to be doing?

Christine Rogers  34:44

Yeah, I had like a moment where I thought oh my gosh, like something could be wrong. It ended up not, but it was one of those like awakening moments where you're like, oh. You go through a few weeks of going oh my god, like am I going to be- like what if this does go bad? I did take some reflection time. So, what I will say is, for me having a greater impact, I have loved having teams, I love having people around me, I love being able to work with them, I'm fascinated by the human experience. And business has allowed me to live that in a different way. Like business is a vehicle for me to be around really cool people and doing really cool shit. So like, that's how that's how I've like looked at it. Now, when I think about it, Aspireship hits so many of those things, because literally what we are doing, and as a sales leader, I was always trying to find great people to hire, I was always looking for the diamonds in the rough for the people that maybe didn't look good on paper. But man, if I could find them, and if I could work with them, and then they were loyal, and they were amazing. And they were grateful for the opportunity. And, you know, sometimes people that have done it over and over and over and over and over and become soured and get frustrated. Like they're a little bit harder to like, you know, get into and lock into it do that work with. But like kind of those fresh perspective, people are just amazing. And so when Cory- so Cory is the CEO, he and I had worked together at a previous company. So we knew how we did business together. So, when he came to me and said, "I have this idea, but I'm not a salesperson, I'm going to start in sales, and I need you." And he literally said to me one time over breakfast, I said, I don't know, man, I don't know if I want to do this. And he looked at me and he was so solid. And he said, "Christina, I don't want this to sound creepy. But like this business is built for you." And he said, "and you're gonna say yes, because there's nobody else that this business is built for. This is built for you. And I need somebody that understands sales, because we're going to start in sales." And I remember thinking to myself, this is very- like, he is very confident. He's very confident, but he was right, you know, and so a couple of months later, I said, alright, I'm down, like, I'll help you, I'm going to help you build this thing. I'll help you figure out what the curriculum needs to be, we'll do all of it. And we can figure out what that looks like for me long term later. And so I just jumped in and started saying like, these are the topics that I would want people to know, before they walked in the door. These are the things that I would want. And so I started, you know, we started talking about like, what's the core thing, and also it has to work for any Fast Company. So it can't be so pigeon holed or so tight. And you know, so that's when we started talking about consultative sales, and also the soft skills, and also what is it like to- like, what is customer success? What does it mean to be a team player? What does it mean to have a brand? And different things. And it was funny, because it was like 2019, essentially. And like the concept of personal brand, we weren't even talking about on LinkedIn or any other thing. We were talking about, like when you walk into a new company, and you're the new person, what do you want your own vibe to be? You have about five minutes before you have a brand. So think about it before walking in the door. You know, think about who you want to be, because you have a chance for a fresh start. And maybe it hasn't always worked for you. And we have a lot of arrows in the quiver. Pull out the ones that you want to lean into the most. Maybe you've been a little cocky, because you've been in an industry that you've been like big fish, small pond. Maybe what you need to bring out is more curiosity, more team player, more... So like, think about those things. So, we talked about those things that I always wished I could have said as the VP of sales, the first day when people walked in to my team, but, you know, a little risky to say. I could say it, because guess what, they're not my employees. They're not this. We're providing this service. And I'm like, I'm gonna give you the real real. So everything about the coursework that we're doing is very real. It's very, how can I get you quickly to the most important things quick, that you can actually build on and learn from? Not in the company, the industry, the product, all those things can be taught and learned. But what do you need to understand about how to do this work? This work called sales, this were called customer success, this word called, you know, rev ops. Now we have all these different things now. What's that work feel like? Because if I can actually help you understand and allow you to feel it, as you're going through this process of deciding if it's for you and emulate as much as possible how it's going to feel to do that day in and day out, you're likely going to either self select out, or you are going to be like, yep, I'm in for this, and your likelihood of being successful goes up. So that was our entire kind of hypothesis going in. So you can tell like, I'm really passionate about that. And it worked. We started placing people and people were like, these are the best people we've ever hired. This is great. These are learners, they don't have a lot of ego. They're like teach me anything, you know. And so I was like, yeah, that's what we saw. That's what we saw, you know, so we started seeing those things. It was fascinating because I'd never built it from scratch, literally, you know, I'm sitting here looking at it going, what would be a passing score? I don't know what's passing. I had to pick what percentage is passing and what percentage is failing. I didn't know. So we were literally doing and I'm like, you know what, she was good, but I don't know if she's gonna be able to do it. Like actually when the rubber meets the road, what percentage did she get? Versus what percentage did he get? Versus different things? And so we were going through different things and having to build everything and test, and test, and test, and test. So yeah, that's how we did it.

Callan Harrington  40:11

How much did your experience as a business owner help you for this?

Christine Rogers  40:15

I think it helped me a lot, because I had a very different perspective of understanding the customer differently. So, when you have someone standing in front of you, and you did not set expectations quite well enough. Because people hear what they want to hear, and even if, you know- I'll give you a perfect example of, you know, ordering a lilac crib, that was custom painted, and us saying, you know, it's six to eight weeks for it to get here. And you know, this mom coming in and saying, you guys said it six to eight weeks, it's now six weeks, it hasn't even shipped yet, I want my money back, or I'm gonna cancel my credit card and blah, blah, blah, blah, all this different stuff. And it's like, hey, I can't sell that lilac crib to anybody else lady. That lilac crib is the ugliest thing I've ever seen in my life. Like you're not getting your money back. I had to learn differently how to set expectations really clearly upfront. How to have, you know, conversations called, hey, we're going to custom order this for you, there's probably going to be a day where you're going to trip out on me because you waited till you're thirty weeks pregnant. And this is a six to eight week delivery time. So like, you're going to probably be really close to having your kid and not have a crib yet, and you're going to start panicking. So, I want to have this conversation now, we can laugh about it now, but when you you call me you're probably not gonna be laughing. But I'm gonna have you sign this paper so that you remember that we talked about this, and what you've been coming in for the last six months, and I kept telling you, we needed to order it. So, like here we are at, this is where we're at. So, I learned really, really well how to have hard conversations. In the riskiest time when all I want is her to drop that credit card. That's all I want is to get that credit card. But I needed to have the conversation called this is going to be more painful down down the path if I don't have that conversation. So I will tell you, having the customer experience, having those conversations, being willing to have those hard conversations, in both with my employees and my customers, I think has been transformational. I've learned a lot of that, from being a business owner that the buck stops with me, if she made a review, it was me if it was about my store it was me or my business partner. So, it was very- business people say all the time, like, you know, business is business. No, it's really, really, really personal. So I think it's the ability to be able to look at that, understand where people are at, they're doing the best they can. And we just need to make sure they feel like they matter in this conversation the whole time.

Callan Harrington  42:43

Such a good example. Because you do- as a business owner, you do look at it. It's more personal, it's more, I don't know, you feel it more. And I'm not saying I didn't feel it when I was at other companies versus starting my own business. But I just feel it differently. It's weird. And one of the things that I absolutely love about Aspireship in particular, and you hit on this, was finding those diamonds in the rough. And so often my story was, I was at a bootstrap company, and we weren't selling the sexiest product in the world, and it was really hard to recruit people. Because at the time in Columbus, a lot of VC was getting pumped in here, a lot of all the perks, the resources, everything else. Recruiting people away was extremely difficult. So we had to my thought process was okay, we've got to build a world class training and development system in order to build people up from scratch. And what ended up happening is, we did that, our retention rates were much higher. And when people did ultimately leave, and ended up being the absolute best recruiting ground period, because they would tell other people: go there, figure it out, and then, you know, go somewhere else. But hardly anybody left. What you guys are doing, I think is excellent. And I think it's great for companies to tap into that because you're able to hire off of character and not experience, which in the long term, if you've got good experience, and I'm not knocking experienced by any means, but-

Christine Rogers  44:11

No, me neither. No, no, no. Not at all.

Callan Harrington  44:12

If you've got that experience, that's gonna get you a short term bump, for sure. But in the long term, the character is going to win out if you've got character and experience, great, homerun. But I've found that to be the case. Are you seeing that in what you're doing at Aspireship?

Christine Rogers  44:27

Oh, absolutely. I think and also, we've had amazingly experienced people go through our program as well, who just want access to our network and also maybe want to come in from another sales environment or an industry and want to get into tech and want to get into, you know, working in software, different things like that. So we've seen some amazing people. What I notice is like the same kind of characteristics, they're humble, they're eager, they're want to learn, and nobody's making them do this. They are doing it on their own. So, they self select into I'm going to be humble enough, and I I have not yet spoken to anybody who has said, like I took the course, I completed the course, I passed the course, and I have learned nothing. Even the most experienced people that have come through, and I've even placed enterprise reps before. And so they're like, wow, that was a really strong reminder. I didn't think about those things. And actually, I've always done that or done a version of that. But I didn't know, I didn't actually think about it that way. Or some people just saying, like, honestly, I'd never I'd never conceptualized things like this before. So, it's very, I think it's digestible. And we assume, you know, we take the assumption like everybody is just learning. So, we're not trying to use a lot of vernacular that doesn't make sense. And not, you know, it's the style of it is a little different than quote, somebody just teaching you a lesson. It's a conversation between two people. So you're actually watching us ask an expert about certain things. So, it's just less like, let me get in front of a whiteboard and do all this stuff and show you a deck, and more like, let's just talk, and you guys can listen to this conversation, and hear somebody who's actually in the business in the world, doing these things, tell you, how do you interact with senior leadership? How do you do these things? Like how do you think about those things, and then just getting and gaining those insights from that conversation?

Callan Harrington  46:13

I love that. I love how active it is just as a whole how you mentioned. The last question I have is, if you can have a conversation with your younger self, age totally up to you, what would that conversation be? What advice would you give them?

Christine Rogers  46:29

I think probably the most important thing that I've learned over the last, I would say couple of years, is I'm not for everybody. And that's okay. So, I think I'm like a recovering people pleaser. And you know, really working to make sure that people feel like they matter to me. And sometimes it's just not going to be a fit, we're just not going to see things the same way. And that's okay. And I think I would probably tell myself, like, just give yourself a little bit of a break. You're not perfect. And that's all right. And even the way that you show up is not going to be perfect every time. And that's okay, too. And even if you think you did it perfectly, people are still going to have an issue with it. I think that that would have helped me have a lot more restful night's sleep over time, because the minute you get into anything that looks like, resembles leadership, you're getting criticized and criticized and criticized. And so building that- kind of strengthening that muscle, going like it's in, it's okay. That's not going to be have anything to do with my worthiness, or competency, or what I can put on the board is not determining my value. I think those things would have been a good conversation to have with me, you know, in my mid twenties. I think that's excellent. And one of the things that you said in particular struck with me was, there's some circumstances, it doesn't matter what you do, how good of a job, it doesn't matter. And then once you see that a couple of times, then you can kind of look back and say, oh, okay, it's just about what I put- Am I happy with the work that I put forward and what I did? Because I was never gonna win that. I love it. Christine, I could have this conversation and continue this all day. This has been so much fun. I appreciate you coming on the show. Thank you for having me, Callan. I had a great time too. This is a really fun conversation. I know we were talking about like, how do we feel like we did well in this? And I just- You were so enthusiastic and fun to chat with. So thank you.

Callan Harrington  48:29

Well, I appreciate that. And I feel the exact same way. Thanks for coming on. I hope you enjoy Christine and I's conversation. I loved all the talk on sales leadership, and it is clear that Christine is an expert. If you want to learn more about Christine, you could find her on LinkedIn and the show notes. Also, if you liked this episode, you could find me on LinkedIn to let me know. And if you really want to support the show, a review on Apple Podcast or Spotify is very much appreciated. Thanks for listening, and I'll see everybody next week.