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Derek: [00:00:00] welcome to the show. This week I have Christine Rogers. She is currently president and COO at Aspireship. Christine, welcome to the show.
Christine: [00:00:09] Hey, thanks for having me, Derek. Yeah.
Derek: [00:00:12] Thanks for coming on. if you give everyone a quick background, it looks like you went from, you’re on Infusionsoft and went from rep to senior VP.
Then VP of sales at mind body and head of sales and marketing at Y Scouts. And then, just last year, Ooh, almost a year ago today started aspire shit. That’s really cool. can you give us, can you kick us off by talking about how you first became a sales leader?
Christine: [00:00:44] Sure. So I’ve, you know, I’ve spent a lot of my time kind of growing up in sales.
So prior to even starting in the software space, you know, had done insurance. I also owned my own store. I owned a retail store and was selling there. So when I think about kind of this journey into sales leadership, it’s been very, non-linear it hasn’t just been. you know, those moments where in fact I’m kind of known for saying no first to things and then, getting warmed up to it as I’ve had great leaders in front of me saying, no, this is something you need to do.
This is something that you would definitely be good at and kind of helping me get there. I would say like sponsoring me into believing in myself more and able to get, get on board with really being in a leadership position. So yeah, at infusion soft, I was hired as a sales rep and pretty quickly because I had owned my own business, and done some things previously.
And that was really a business that was tailored towards small business. I saw some opportunities there that were again. Not linear. You know, I didn’t go from sales rep to senior sales rep to, team lead or manager, and ended up taking a very kind of, I would say, a sharp right turn and became an executive assistant actually to the VP of sales at the time, very risky.
From my perspective, I was very nervous about that. And when I talked with him, he said, actually, what I need is a thought partner. I need somebody that’s very strategic and understands people because he understood. You know, all the business, but wasn’t really able to capture that other side that was necessary for leadership.
So he said, I will teach you and I will help you learn everything you need to know. And then you will help me in areas that I need to grow in. So I trusted him. And he did teach me and I learned and became, w w w we created an enablement organization. So I didn’t know at that point, even what enablement was.
So, we created that together and kind of passed, you know, created a path and an entire department and ended up being 15 people. That we’re both, you know, sales, operations and training. And we also had engineering, you know, sales engineer. So we figured all of these things out together. And then, when it came time and he needed a very process oriented and kind of turn up the metrics on efficiency, he asked me to take over, the revenue number as well, and the direct sales floor, which was about 60% of the top line revenue of the company at the time.
Derek: [00:03:21] I keep seeing this theme, not just in people that are coming on the show, but I feel like more broadly in life where I’m not linear is going to scribe it or outside the box. Like not the standard path of became a sales rep right out of school, then director Mark, step up. And it seems like that there’s a huge advantage to.
Doing something outside of what looks like the standard route.
Christine: [00:03:53] I think there can be. I think when I, now, you know, one of the things that I think is really important is not necessarily articulating, you know, maybe what title you want or, you know, I want to be this by this time, but really thinking about what you want to learn.
in order to get to something else. So for instance, for me, you know, it really wasn’t, if you would’ve said, Christine, do you want to be in charge of the direct sales floor within, you know, four years? No way that would not have been my articulation at all. I would have been like, Whoa, that’s a lot. I know what pressure that’s going to be.
And you know, at that point that wasn’t even in my frame of reference, Like it was not even visually possible. And, but as I started understanding what was necessary to get there, What might, what I might’ve been seeing at the time might not have been me. So I was looking at that going, I’m not that person.
I’m not that risky. I’m a little more process oriented. I’m a little different, in the way that I solve problems, I look for sustainable solves rather than like sometimes quick wins. And I think that I had a little bit of a different picture of what it needed to be. And at that time, that is probably what it needed to be.
But as you move and grow and scale going from, you know, when I was a sales rep, we were at 26 million. When I left, we were at a hundred million. There’s a big difference there. And so sometimes what I think we see as you know, right here right now might not be what’s needed for the future. So focusing on what you want to learn and what you want to learn, how to build or create or innovate, or, maybe shave off some of your own sharp edges that you, that you’re, they’re showing up for you.
Then those are some interesting pieces. And I think ways of looking at it that might not necessarily look linear, might open up a different path.
Derek: [00:05:40] Cool. So that’s a good way to think about it. So think about things that you want to learn. You said something in there that, you talked about quick wins versus sustainable solutions.
And even I feel like it’s hard sometimes to decide between those things, you come and do new org, you feel like you should go for a bunch of quick wins and prove that it was a good, you were a good hire. How do you think about weighing those two things against each other? I think the most important thing.
Christine: [00:06:15] And this was one of the things I had to learn through this process, is that you just need to know what the business goals are and you need to be on board with what it is. So sometimes, you know, top line revenue is, is really the most important thing. Sometimes we start looking and going, you know, churn is really the most important thing, you know?
So you need to understand what. For the, I mean, what game we’re playing? What are we doing? So I think that’s a really important piece. And then also knowing that, and I would call it air cover, air covers. Okay. It meaning sometimes we do things in order to get some outcomes that are okay to do, because they might not be sustainable longterm, but they’re going to get us what we need to get for right now.
And those things work as long as we don’t mistake it for. That’s our becomes our every day. I think when we are youth using maybe some different things or testing or trying things, as long as we know, Hey, this actually may or may not work. And w it might be a good learning lesson. It also might be something that we create a product out of, or do something totally different, but make them, so we’re all clear.
So that, what I would say was a kind of air cover, doesn’t become the norm because then that’s when I think you get into, places that maybe it is harder to scale, it is harder to repeat because you’re doing things that are not, kind of like normal. You’re doing some abnormal things in order to make something happen.
Does that make sense?
Derek: [00:07:45] Yeah. I want to make sure I really get it. Could you give an example, maybe a real life example? Yeah.
Christine: [00:07:52] Sure. So I think sometimes, I’ll, I’ll give kind of a simple example, you know, discounting, for instance, let’s say we have to have a certain number of new customers coming in the door and new customer acquisition, is the number one goal.
And sometimes, you know, new, new customer acquisition is more important than revenue because we’re trying, you know, maybe our model is land and expand and that becomes something that we’re working on right now. We’re trying this new initiative, right? So we may discount something. In order to drive that specific outcome that we’re looking for.
So we can test something new, maybe test an upsell item or something like that. And as long as the discount, isn’t something that then becomes so normal that we, we never sell anything for regular price. Everybody just assumes there’s always going to be a discount that gets in the market. Then everybody knows I wait until end a month to purchase because they’re going to give me a discount that that can become.
Problematic. So that’s a pretty like simple scenario. I think that I’ve, I’ve seen happen before. So how
do you protect against that becoming part of something? Like my first thought is like, Hey, we’re only going to run these discounts for the next 90 days, and then you pop the table, but like, yeah. Yeah.
That’s, that’s a good way. I mean, saying, You know, creating some stipulations around it. And also if we are testing something, what is it that we’re testing for with our hypothesis, that’s going to happen and then re you know, communicating that to the team, I think is really important as well. Here’s something that we’re going to try here is a test or going to our hypothesis is that it’s going to drive more units.
And as long as those don’t get real Cherney, Then that may actually work for us to be able to then upsell later, if it doesn’t work, then we want to communicate that as well.
Derek: [00:09:43] Cool. All right. So define the experiment really well, hypothesis, w what, outcome you expecting. All right. That’s really helpful.
can you talk about when you first became a leader? What are some things that. Let’s say the mistakes that you made, things that you wish you had done differently.
Christine: [00:10:05] So I think when in one of those areas, it would definitely be because I am a little bit more risk averse than most people. I am really process oriented and driven.
I think I would have been a little bit more risky initially, but articulated that we’re testing things. so instead of saying, Oh no, I’m nervous about that. Or, Ooh, yeah. You know, and making it real heavy, being a little lighter and saying, you know what, I love that idea. Let’s test that and let’s test it with a very small segment and let’s quickly either fail quickly on this and communicate what we learned or, Let’s roll it out to everybody.
And I remember really, really clearly at the beginning being afraid of that because so many other leaders that were kind of in my same shoes or in those shoes prior to me, had a different personality type that was much more risk. I see, and how much we’re willing to do those things. And I had seen some errors and then us having a really hard time fulfilling dealing with customer experience.
That was frustrating and not, you know, I kind of over-rotated the other way. So I think that’s one, that’s one area I would have been a little bit different on
Derek: [00:11:12] it seems like the sweet spot is experiment. If you have a good process around how to run the experiment. So you can take risks. If you have a good process for rolling out and evaluating the outcomes of those risks.
Christine: [00:11:30] Sure. And yes, and creating, you know, I actually wanted people to document what do we think is gonna happen? You know, make a very simple, I have a very simple, like I created a really simple business case form. Like tell me all the things that we think are going to happen here. And then let’s go back and evaluate if it worked.
And if it didn’t are there tweaks or did we do too many variables at the same time, but not making it. So heavy that people are like Mo this is like awful. I have a great idea, but I can’t get anything past her because she’s made, you know, asking me 7 million questions about it. So it is that balance of like, have we thought it all the way through.
And if you tell me, Hey, Christine, this is going to net us another 50, two grand. and I’m saying, what is it going to cost that you can answer that, you know, what is it going to cost on the front end? What does it cost them back? And what am I going to be paying in commissions for these lower dollar deals?
What are all of those outcomes if you’ve thought it through? Like, but, but that’s, that was for me to help create something. So it’s easy for them to think through. And I don’t want to weigh people down. We’re trying to move quick.
Right. That limits your risk because, you know, well, in the worst case, we’re going to be out a hundred thousand bucks this quarter, but the best case is this might make us millions and we’ve quantified that, so we know.
Yeah. Do you still have that business case?
I do. Yeah. Good.
Derek: [00:12:50] Could you share with me,
can I share with the listeners too?
Christine: [00:12:54] Yes, I will. I will make it nice and nice and simple. It is a pretty simple form, but it does cause you to think.
Derek: [00:13:01] Yeah. W I think that that’s, that’s what makes something like that challenging, because as you talked about that, I realized I want a process like that as I go through and build my business.
Right. Like, how do I know that I’m thinking through it well enough and why should I just invent it myself? If you have something I can just, I can borrow your years of knowledge.
Christine: [00:13:22] You can absolutely have it. It’s funny. Cause I have an example on there as well, and it’s like the car won’t start Y and then it’s like, why, why, why?
And actually when we get to like the fifth level of why it’s because like, you know, I didn’t go take it to the monthly or the quarterly servicing that I actually need to do because the car won’t start. It’s just like there, you know? And so just making sure that we’ve really thought through more solving the right problem.
And that’s the number one thing, what problem are we actually solving?
Derek: [00:13:56] Right. Right. And it’s so easy to run into, like the I’m going to solve a short term problem of, you know, whatever it is, and never solved the root. So I’m excited to see any of the forum. Yeah. what do you think is your super power as a leader?
Christine: [00:14:18] One of the things I’ve always done really well is aligning people to jobs that work really well for them. And so I would use the concept of like native genius, like what they are well attuned to do. and the only way that you do that is through really seeing people, listening to them, understanding who they are, and also.
Being able to have the authority and autonomy to create things as well. So I think kind of that superpower has to go hand in hand with some amount of authority to be able to say like, wow, there are a couple of business problems here that I could really use some brains on and maybe I don’t have the JD that’s perfect.
Or the job, you know, everything’s not perfectly aligned, but I have a couple people that those characteristics and traits and the things that I need to do. That would work here. And so I think, one of my super powers is being able to quickly know, yep. That is not a good fit for this person, or how can we make this specific type of work for this individual?
So they are thriving in an environment that feels really good for them. So
Derek: [00:15:29] I’m going to guess that maybe now it’s intuitive for you because you’ve been doing it for awhile, but I’m going to guess that you probably have a process for that to make sure you think through it really well.
Christine: [00:15:40] Yeah. I mean, I definitely think, it’s spending time with individuals, it’s understanding where they get their energy.
So I talk a lot about energy and adapting, understanding that most people, Oh gosh, and salespeople are so good at adapting. You know, they can do anything it’s like, can do. Of course we can do it, you know, but really understanding, you know, if we’re at level set and I’m at zero energy-wise and you had to just do half your day, are you up?
Or are you down if like, if, you know, kind of that watermark, is that like I’m okay. Is my energy up? Cause I talked to three prospects. Do I feel up or do I feel drained and really starting to help them sort out? Where’s the drain coming from? Now we all know that our pretty much every sales rep is going to say when I have to fill out the CRM or when I have to, no, nobody wants to do those things, which is great, absolutely normal and part of the job.
So I’m not saying, Oh, don’t over-engineer that, but when you start asking people those questions about. You know, when you leave something, when you leave a room after a whiteboard session or after you’ve just spent time with a prospect or after you’ve talked and implemented someone or different things like that, when, when you just felt like that.
But when was that? When was the last time that happened? you can start to really get a sense when you allow people some space to think about that. Maybe dream a little. then that, that starts to point to where they love in our leg really, really tapped into themselves a little bit more. So I think, you know, those are some of the questions that I ask people and is
Derek: [00:17:17] this, so this goes into your one-on-one time with somebody, you ask them anything.
You logged this information somewhere or do you just keep it all up up here?
Christine: [00:17:27] I take notes. Yeah. So, I’m a big, note taker. I have lots of notebooks everywhere, you know, like the spiral bound notebooks and then, you know, other businesses, other companies, I also had forms that I would be filling out in and doing different things with them as well.
So depending on how often we did quarterly reviews or, you know, every six months, a lot of times I would be taking notes. even in like Evernote about the things that we’re talking about to make sure that when it comes time, we we’ve thought those things through
Derek: [00:17:57] right.
Christine: [00:17:59] Also one other thing is frustrations.
That’s another thing that points to w to what they’re great at, what and what they’re energized by and what they’re not. So when you can, sometimes you can spot those frustrations where you’re like, it seems like you’re agitated. What happened here? Like, tell me a little bit about that. And sometimes it’s because you know, of a process gone sideways or, And this is how sometimes you understand where people, maybe aren’t going to be great at leading, you know, when they’re very frustrated about things, but they think that this is the only way to do it as if I become a manager and you need to hire me because of this, this and this.
And it’s like, Actually here, let me help you understand what the day-to-day is going to be like. And the last three times we talked, you were frustrated about those very same kind of things that you’re going to be doing every day. So, you know, making sure people understand that, management and leadership and all of those things, I mean, you’re doing that absent of title when you’re on the floor, you’re leading yourself.
And then you’re like leaking all over everyone else around you and everyone else on your team in a good way or in a not so good way. And you’re leading whether you actually have the title or not.
Derek: [00:19:09] What is it in your experience when you have somebody like that? And they really want that first promotion to sales manager, but you’re observing that, you know, to the person who subscribed.
You know that they’re going to be frustrated by doing the tasks. They want the promotion. Anyway, what’s your take on what they’re thinking? Why do they want the role? And, and then the other side of the coin, I guess, is the reverse when people are really successful, why do they want it? Can you talk about the differences there?
Well, I
Christine: [00:19:47] have a real life example with the first one. So, we were hiring a sales manager. One of the top performing reps on the floor was going for it. I would say kind of a B player was also going for it. and I hired the B player for, a lot of reasons, but. When actually, so they, the top performer he’s he requested a one-on-one with me the next day.
So I met with him and he actually, I’ve never really had this happen before, but he was so angry. He could not keep it back. And I, he started saying, I can not believe you. I mean, he was literally raising his voice and, I just kinda sat there for a second and just said, like, I. I’m going to need you to just calm down and like, then let’s have a conversation and this volatility and this inability to control your emotions actually is one of the top reasons why I don’t think you can lead a team of nine because I need a stable.
Calm individual here. I already have a couple of other managers that are a little more passionate. So like, this is what I’m looking for in, in this full kind of group here so that we can create a more balanced floor. And so as we were talking through it, you know, I said, here are the things that I see in you.
And I articulated for him, the things that I see and where I believe he would not be very happy. And at the time he, he calmed down and he heard me and I said, I actually believe there is another role for you. And it’s not leading people. And we ended up about a month later, I had a role that we had created that I knew it would be exactly what he was looking for.
And it was, on my sales enablement team in a kind of a, I would call it sort of a demand gen slash. He was great at writing great emails, great sales emails. and at the time I was struggling with our marketing department. So I pulled him in and said, you’re gonna report directly to me, and this is what we’re going to do.
And we started seeing conversions come up and I had him reporting. He was great at numbers, graded, understanding and great at writing simple, simple emails. So we tapped into what he was good at. And he will still tell you even to this day, like that was one of the most impactful conversations, because although.
He didn’t get what he wanted. He got what he needed and he did great. It really, really well in his past math took him into a complete, like demand gen marketing side that he’s now doing. He has a consulting business for, so it ended up working, you know, if you trust someone that does really care about you and also might let you misbehave a little in order to like hash it out and get to something together.
he did, we did end up doing something really wonderful that he was really, he really did thrive in.
Derek: [00:22:43] Wow. That’s literally a life-changing kind of situation
Christine: [00:22:47] for him. Well, and for me, I’m going to tell you, having him on my team and having him do that work made a materially big impact on the conversions and on what we were able to do, because I needed him.
I needed him times like every rep. So he was there then available to help all of them, which was amazing.
Derek: [00:23:09] Wow. Okay. I love that. I feel like this happens a lot where, people, you know, I didn’t understand what I was getting into, you know, when I took on the role and I had, I had managed people before, I guess even that first time, you know, I didn’t understand what I was getting into. W what’s something, you know, if somebody is listening to us and they think they want to go become a manager, what are things they should go do to.
You know, maybe they don’t have you looking out for them. What are some things they can do to uncover if that’s the right move?
Christine: [00:23:46] I think one thing is to. re like, look at the individuals that need help on the team. Look at people that are struggling. Cause a lot of times people that are top performers are the ones that think, Hey, I want it.
Maybe my next step is to lead. And there is a segment of people that that is not for them. They should just consistently be an individual contributor and doing that because that’s what really thrills them and excites them. And not just in, you know, thinking about enterprise. SMB reps can do this to mid-market.
I mean, all of those things, account management upsell. So there are people that do that very, very well and should stick with that because they really only need to worry about themselves. If you’re considering, if you’re considering becoming a manager, then I would. Actually start giving some time and helping someone else who needs it, meaning talking with them, spending time, working with them, coaching them, seeing if you like this idea of it.
And typically as long as you don’t come off as like a jackass, like I’m going to be so my help on you. Cause you’re really struggling most of the time, if you say to your leader, like, Hey. I want to help. I noticed, you know, he’s really having a hard time and I’m, I’m interested in possibly, you know, putting my hat in the ring next time a management position opens up.
And I just, I want to know if you’d be open to having me kind of coach him and give him some extra help. I don’t know, a good manager, a good leader that would say no, there’ll be like, heck yes, all day long. Go help. If you can do this, go help. I think it would be important. To make sure that you’re really clear yourself on methodology process definitions, make sure you know, the stages, make sure that you are buttoned up and tight so that when you go start teaching training, encouraging mentoring that you are giving the right information out, there is nothing worse than somebody that tries to mentor somebody on the team that is like lone Wolf, top performer that gives somebody else like kind of bad advice.
And then it all kind of gets a little weird. So I would say. Take on some of those actions, as what good leaders do, but do it absent of title and start working with individuals. I’ve had reps do that before, and it’s really wonderful to see both that bond. And also, you know, one of my top reps at, at the time Booker and mind body was mentored by another one of my top reps.
And it was great to see if he had come from like a. A background that was not sales. It was, he was like loan, co loan collecting pretty much prior to that. So came over. So he really didn’t understand SAS. One of my other, top performers, I kinda took him under his wing and, and man, I mean, it was incredible how he, he really did do an incredible job and that showed me that the other was ready, you know, was really doing it.
I love
Derek: [00:26:33] that. So just go do the job, see if you
Christine: [00:26:35] like it. Yeah. And also alert whoever you’re working with, alert your manager, your director, that like, this is what I’m thinking, this is what I’m doing. Is there somebody else? I’m a kind, I’m feeling like it’s him or I’m feeling like it’s her, but if there is somebody else, like, let me know, but this is what I’m really wanting to work on this and see if I can be of service and help the team.
Cool. Don’t miss that opportunity. Make sure you tell someone that this is what you’re going to do. Right?
Derek: [00:27:04] Cause then if you’re doing a good job, you want them to, to have known that you’re, you’ve been doing that and they can follow the progress.
Christine: [00:27:12] And if you, if they’re seeing something else as an area of opportunity, or maybe somebody else that they can add to it, like, Hey, you know, maybe two of them together could be interesting.
Maybe we do, you know, it’s a once a week, we get together for lunch or we listened to calls together. you know, those are, those are helpful things you want to make sure that you definitely do well for
Derek: [00:27:32] that. Right, right. Any other advice that you’d give to somebody aspiring for leadership or that, that just landed in the role.
Christine: [00:27:43] One of the other mistakes I made is, I didn’t realize that I needed to own my own recruiting and hiring for my team. So I worked, you know, infusion soft was one of those places where everybody was, it was like inbound, you know, everybody was applying. So if you have a strong, you know, demand gen, you might not need to learn how to outbound.
Right. Or you think you don’t. so, you know, transitioning over as a leader, as a leader, in any part of the organization, you need to constantly be looking for talent and as a manager or somebody aspiring, you need to start putting, you know, put that lens on, even before you get there and start going, who would I be looking for?
What is, you know, and notice some different things. I mean, notice the people that you’re interacting with on a day-to-day basis, right? I just talked to one of my hiring leaders for one of our companies. And he told me, he said, Christine, I just hired the guy. Who’s made my smoothie for the last three years to be one of my, one of my salespeople.
And he said, you know why? Because every day he knows my name. He knows everybody’s name, who walks in the door. He knows exactly how I want my smoothie. And he, he manages people. He does different things. And like, I know he is as dependable as they come and he’s got grit. And so, you know, when I think about that, Not everybody would look at the guy who makes their smoothie and thinks I want him on my team.
That’s interesting for me. So those are the things that were, you know, where you’re constantly looking for the people that you want to have. Like, if I could have 10 of these, this would be amazing. This is who I’m looking for. So you’ve got, you have to really shift and start opening your eyes differently to see people really see them.
Derek: [00:29:24] runs me. I tried hiring, my waiter at a restaurant two years ago and did not get him, but I was like, dude, don’t work for me.
Christine: [00:29:34] I mean, you pay, if you’re looking, you will notice there’s some tremendous talent that might not have, like, we talk about that quote, quote experience or the right bullet points, or doesn’t look good on a resume, but man can do the job and are doing the job every day.
Derek: [00:29:49] Cool. Well, Christine, thanks so much for coming on the show. How can people learn more about you? Sure.
Christine: [00:29:55] So you can definitely find me on LinkedIn. aspire ship.com is, our business. That’s our, website. So definitely come visit us there. And, if I can be of help, let me know. I’m happy to connect.
Great. And,
Derek: [00:30:10] I’ll drop, Christine’s LinkedIn and the, The document that we talked about in the show notes. Thanks so much.
Christine: [00:30:19] Thank you for having me.
