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Reskilling and Upskilling to Accelerate SaaS Sales with Christine Rogers, President and COO at Aspireship
Episode 4411th February 2022 • Revenue Engine • Rosalyn Santa Elena
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Sales is a competitive industry. And SaaS sales is no different. Finding, hiring, and developing the right talent is critical to revenue growth.

In this episode of The Revenue Engine Podcast, Christine Rogers, President and COO of Aspireship, shares how organizations can leverage the power of training and enablement to hire the right talent and build a winning team. She also shares how individuals with zero SaaS experience can uplevel their skill set to have a successful career in Sales.

As a powerful sales leader herself, Christine also talks about how love, not fear, is the most powerful motivator. Grab your headphones and take a listen to this inspirational story of leadership, empowerment, and success.


Connect with Christine on LinkedIn or at the Aspireship website.

Follow Rosalyn on LinkedIn.

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The opinions expressed in this episode are the speaker's own and do not purport to reflect the opinions or views of Sales IQ or any sponsors.



How does insurance, baby furniture and sales come into play with reskilling and upskilling individuals to help make a transition to SAAS? In this episode of the revenue engine podcast, Christine Rogers, the president and COO S buyership shares how her background in selling.

And having her own baby furniture store led her to a sales leadership career and with the right champions and the right partnerships, how she is now driving a change in the way companies hire top talent for SAAS roles and how individuals with zero experience in sales can acquire the right skills to be successful in these roles.



So super excited to be here today with Christine Rogers, the president and COO at Aspireship.

Aspireship is a different kind of online training for reskilling and upskilling, designed to really help you make a transition to SAAS or to help advance you in that next step of your career.

So welcome Christine, and thank you so much for joining me. I am super excited to learn more about you and, and learn about what you're building at Aspireship.




ht, when that was going on in:

And you know, when that happened, I was looking for a job. And because it was really small business aligned and I had owned a small business. I joined a software company that was specifically for small businesses as a sales rep. And you know, from that point on, it was a growing fast startup and.

I had, you know, experience and understanding with management leadership and things from owning my own business and also being an insurance. That's what I did there as well. So I, you know, was, was exploring, you know, what are the different opportunities here? I knew nothing about software selling. I knew nothing about those different things, but I could do it.

And it's because I understand. Sales process, even though it looked really different. When I was selling a mom, a crib in the story, there still was a sales Fest, you know, so it's fascinating that I kind of learned through, oh, if the mom comes in the first time and you know, she's just newly pulled me the next time she's gonna bring in a fridge.

And then that's like kind of step to the next time if she brings in her husband, we got, you know, and so I knew, you know, the different things and you know what I needed to show dad versus what I needed to show mom and different types of questions. So I did all this learning through this really interesting experience.

And then you know, started having opportunity to say, you know, in the, in the company that I was in, like, you know, Chrissy, we have a need here, Christine, we have a need there. Would you be interested in helping him? Because I did understand some of those things. Even before I was ready, I started saying, okay, yeah, I can do that.

And created an enablement department. And then you know, took over the direct sales. You know, at that company and then moved into other selling roles at other companies once I got to the executive.

That's awesome.









So I actually raised my hand for a management position and I didn't get it. And I was really bummed and I was right in the last two. So. I was right there and he called me the next day and said, I know you didn't get that, but I actually want to talk to you about something else. And he saw the opportunity.

He said, Christine, there's no enablement here. We have nothing, you know, we're just building. And and also I need kind of like a strategic thought partner and some different things like that. And you're very in tune and have a lot of EQ and so he really believed in me every single time something came up at Infusionsoft, he would be like, I think Christine, he was the perfect sponsor.

He would say, Christine needs to, Christine should be in the room. Christina should be doing this. And I would be like, no, I'm not ready. And before I actually took over the direct sales floor, he had had multiple different leaders and they weren't six very successful prior. And I, so I just kept watching people really haven't had a time. He asked me four different times, four times I said, to take over the sales work. And I said, Nope, Nope, Nope, Nope.

And he just kept saying, you know, this is what you need to do. This is the type of leadership I need there. And he pushed me and believed in me, even when I did it. And I don't think any of the other leaders that kind of level even knew that I was saying, no, he believed in status. You know, he sponsored me that and he w he was an incredible sponsor.

And I think that's the difference between in my mind, a sponsor and a mentor. When I was out of the room, he was still saying my name and making sure I was a part of big company priorities. And then also invested in getting me an executive coach. And, you know, he knew he couldn't provide that, but he knew he could be a great sponsor, but he invested in having other people.

Leave me and was like, if somebody said like the other day, what was the best gift you've ever given? I'm like he gave me an executive coach. That was the best gift anybody's ever given me was, was investing in me that way and having an executive coach that really helped me get to where I need it.


So you joined Aspireship, you know, over two years ago, right? You're the president COO there, you know what first interested you in joining the company and you know, how has that changed if at all over time?


You're going to have your upsell team. I didn't even know. It really was at that point, but the upsale team was supposed to sell into the base and I needed to figure out how to do it. So Corey and I got to spend a lot of time together working on, you know, he was leader of his you know, basically the GM of his product.

And I was the sales leader. My team was selling it. So we got to spend a lot of time. So when he just started thinking about this next concept, he knew that this was consistently a thing where people, you know, in support in different roles would come to me and say, and come to him and say, Hey, I want to get into sales, but I don't know how to train.

I don't know how to do that. Cause I've been in customer success, but I actually think I could do this. You know, my response as a sales leader is like, I am slowly spread, but you understand, like you're going to have to pick up a quota. And if this doesn't work to be a problem, there's really no way for people to like, understand if this would work for them.

And so we started seeing this, like, this is something that we're hearing over and over. So Corey came to me and he said, I have this idea for a company. And I actually, he was so funny. He just said like, I need. Like I need you to do it's funny. Cause we talked about it the other day, but he actually said like, I don't know how to tell you this.

And I I'm afraid this is going to sound. I already know your fashion. I'm like, not yet. No, I'm not sure about this. And he just, you know, he had Jason, who was our product. He had the vision, but he's like, what I need is somebody that can actually save. This is what I'd want people to know before they even walked in the door to my company. And Christine you've been doing this 10 years. What do you want them to know? So actually I helped him build that coursework out prior to ever coming on board.

I'm like, I know I'll, I'll tell you what I wanted them to know. I want them to know these things. I'll help you I'll do the recording. So actually the courses that I'm teaching. In that in the course, I was employed somewhere else while I was helping him.

And I believe they should know, just trust it. But he was right at, at, you know, at the neck the next couple of months I watched, I watched them put the coursework together and I was like, this is what I'm supposed to do because. Also, you know, this, like when you are a sales leader, you talk to other sales leaders, you know, within minutes, if they know what they're talking about.

And so if I'm thinking rightly these individuals and I have graded them, I believe they are competent. Even though he has been a barber, even though he's been a teacher, I believe they're 10 to do this work. And. You trust them differently because we've all been in. As soon as I tell people what we do, other sales leaders, like yeah.

Every minute I can't find the right people. I mean, I can't find this work. So you know, so it was hard for me because I knew Corey, I trusted him and And we had already had a working relationship before. And at the end of the day, I want to do meaningful work with people. I like and people I want to play with and do work with.

And why, so that, you know, that to me is critical. So that's why it's been really fun on this journey.



And, you know, and watching, you know, maybe I would find a cohort that I thought, Ooh, they're kind of all. And then three of them would make it the other four did it. And I'm like, why, why didn't they make it? So there are some things that we built into the coursework to it will, it naturally eliminates people that it's not for them.

So, so I'll tell you a couple of things. I remember you, and I both know you have to be fairly technically savvy to be able to be in this work. I'm not saying that you have to be an expert, but our software is proprietary. Right? So people that get in there actually have to learn how to use it. And so that naturally weeds out people that can't, that don't have any technical capabilities, which I think is really important.

The other thing is they have a time constraint and this is something that we consistently talk about and always kind of, and, you know, because we actually don't need to have a time constraint. And I'm like one, because salespeople need to understand the feeling of having a time constraint in a quota and pressure to complete.

So you have 30 days to complete it. It's if it's, if you can get it done within 30 days. So that helps consistently push and see can they complete it within that amount of. In addition, the other thing is it's very uncomfortable. So in the coursework, you actually, you have to do role-plays and you have to follow.

So the prompts are, are like, this is the information. On this person. So it's very much like what would be similar to reading a CRM note. Hey, Jason, you talked to him last year. He wasn't interested then, but he's interested now. You're going to reach out to him. Also. This is a live call, not a voicemail. I have people all the time, then get into the assessments and they're like, Hey, you know, give me a call back when you can.

You didn't read that attention to detail is. Critical for you to be successful fails, and you will not successfully pass these because you go through segments of the call. So then the next one won't make sense if you didn't do it appropriately. Right. And so built it to showcase the qualities that we're looking for and that we believe make a good strong sales.

So at the end of it, we're able to say, okay, between the multiple choice and also between these you know, different role-plays that we've done, that are uncomfortable. We are going to be able to know whether someone is a learner, if they're resilient, if they have a cynical aptitude, if they're you know, resourceful you know, different things like that, where how they solve.

Because if I say, handle this objection and move them to pricing and package. I'm not telling you how to handle it, I'm telling you to ham, right? So it's interesting to see the creativity and how people solve the problem, which again, there isn't, you know, you, and I know this, you do a role play. There's not necessarily a right or wrong.

If somebody makes something up, I didn't say right. It has to make sense though. It's gotta make sense, but, so it's a fascinating experience and it really gives on the other end. Our hiring partners. Imagine you as a sales leader, being able to watch my people do the same role play and solve this problem called handle the objection.

Totally. And it's fascinating, you get a better sense of who they are rather than just bullet points. So you have a more holistic understanding of them as a person.



So they're really hungry right at the other thing is they're not coming from a lot of experience, so they're not They're not big. They're not like they don't have those pre right. They're like preconceptions and yeah. So they're coming in going, Hey, give me an opportunity. What can I learn before even walking in the door?

So they're a little bit more hungry because they've got something to prove, which I love as well. So like naturally it just kind of lends itself to be that. So you're going to have, I mean, we have very few people, we guarantee our hires for 90. We have very few people that we have to replace in that time.

And that, to me, it shows that we're doing a good and better job of helping stuff out and get the right candidate to the right company. And not just, you know, spitting out 75 resumes to a company that's looking to hire people, but really, you know, we might give you four and say, you know, these are, these are higher quality for what you're looking for.


Now companies are all competing for talent. Everyone's leaving their jobs, they're going somewhere else. And we're just not able to even recruit fast enough or retain really that top talent. What have you seen in the market, I guess over the last two years and what effect has that had on Aspireship?


You know, we were still testing or the classes, right. You know, are they going to go in and know enough to be able to be successful? And we started seeing, you know, the green shoes that yep. They are, they're doing well. So we had our first few placements and then everything went sideways and the spring everybody's.

And then it became really difficult for me to say to sales leaders, Hey, hire my inexperienced, but competent people over everybody else in market that just got laid off. And it's very varying experience that became a very difficult conversation to have. And, you know, we had larger partners at that time.

So really what we ended up doing. Is we shifted down market a little bit because what we saw smaller companies, we're still hiring one to two people because they weren't, it wasn't like they had to lay off 30. If they had four sales reps, they still needed the one or the two. We started shifting and going to smaller companies and saying, Hey, we can help you.

And also at that point, we took the time to really test. I had a few companies that had smaller sales teams, like maybe 10 people. And I think. Let me take your work sales people through our coursework and let's see if they actually get better. Well, so we started kind of changing to see how can we test, how can we make the most out of this time, which was very strange and still get some revenue and be able to test whether our offering was still good.

So we shifted. Fast forward till we start seeing things, start to move, start to move people starting to hire again. And you're right. Like last year it's every talent. And the great part about Aspireship is we are providing candidate and to companies that their own no recruiters going to find our people because they don't look good on.

And that's the beauty of it. They're actually not ready to be found until they have the competency to do the work. So it's really fun because we're co-creating with these people. It's like they yeah. Or aspire shift, they weren't ready after Aspireship, they are ready. And so, and we're providing a resource for them and then we kind of help get them to the front of the line.

So to speak with some of these companies that they're naturally. Kick them out of the ETF, because why would you hire him? You know, they wouldn't have any chance. And so it's great because the companies that are really seeing this and taken advantage of this, they know it's not like we're competing with your internal recruiting team because your internal recruiting team, would it find them gold?

Find the people that are find-able. We will provide you if that isn't. And that is unique, that specific space. So so we've been able to kind of leverage these incredible individuals that are getting passed up left and right, because they don't look good on paper and they're like, I just need an opportunity. And that's been really fun to be able to.



I think it will start to write itself, you know? So we're at. Where, where it kind of comes in, swings back down. So it's not such a crazy market on the candidates. I don't think it's going to be, you know, right away. But I do think that will happen. It seems like things kind of do. Right. The other thing I'm thinking is I believe that some of these candidates that are going into companies and this idea of the great resignation this may be a little bit of an unpopular belief, but I think we can get into.

Is, you know, people are leaving for, because they're being offered more money or being offered something else that they perceive to be good. And they're quickly making these dumps and I believe what's going to happen in six to 10. I believe we're going to see a writing where people are going to boomerang back and be like, oh, I went and chased this thing, which is called.

And I actually didn't. I was in a good spot. I should have stayed there, continued to learn and grow and develop and, and really get to where I am doing. Amazing. Not just moderate, not just barely able to do it because other people are not understanding that if you go into a position where you're getting paid $25 to $30,000 more on a base after just a few months at being at a company you have a very short leash.

You have to hit quota and you will get turned out very, very quickly if you are not. And I actually don't believe that some of these individuals have even had enough repetition to get to where they understand exactly what they're doing in a row before they automatically go, oh, I'm ready to move. And I'm going to jump in because this is good.

And it's like, they're, they're, they're, they're really kind of cutting their nose off to spite the face. Like they're not thinking all that. And the other thing that I'm hearing a ton about is, you know, oh, you need to have a side hustle and you need to be doing all of these things to make money on the side.

And if then your job goes away, you're able to do that. I absolutely think that's a great thing to have. And also you need to remember that, like, what is your core monetary brain? Like, what are you doing from like your own. And I literally saw a girl the other day on LinkedIn posting and things. She was a sales consultant. I and was talking to me. She had been a salesperson for eight months. You are not to be. You that you are is probably selling a course or something to try to get you to buy so that you think you can be, you know, monetizing that I'm not saying that there is no value in that.

What I am saying is I think a lot of individuals that are like, I'm going to go do my own thing and be a consultant, or I'm going to go do this and do contract work, I think in six months or so, we're going to see them coming back to market as well, because it's very hard to do. It is very difficult if you are an expert in your field to be a solopreneur and do this work.

And so I think we're going to see some of these people that have done a bunch of bouncing to really find the best opportunity. I think we're going to see some of them a little bit tail tucked and come back and say, Hey I actually did not know that. To do this well, and I need to, I want to get back into a company.

And you know, I just wrote a post the other day that companies are not villains. Just companies are amazing. Somebody, somebody said this and I thought this was so well said, like a great container for learning. And so if we can position. Working for yourself or working, you know, in this capacity is great.

And also is working for a great company that has a strong vision, a strong leadership team in a place where you can learn. And so I think those are some things that we're going to see happen, where it's starting to, well, it will write itself a bit. It might have is when people are starting to think about leaving.

I always ask, like, have you learned any, you know, all the things you need to learn. There, because if you can honestly say, I think I've gotten everything I'm going to get out of this. I've like squeezed all the juice out of this experience. Next one. And then my next question is, well, what, in order to know what you want to do, what do you want to learn next rather than what's the title you want?

What's this what's the next. Because that's what will help you determine some of where you need to go and how you need to get there. What that needs to look like, what the compensation needs to look like, because of all the things that I've done through the different. Types of avenues that I've taken. It was what was I learning in this role that helped me.

And I, like I said, I didn't go from sales rep to sales manager, to director of sales, to this I wasn't linear. It was very theory. All over the place. And that's what was so important. If you had asked me three years prior, would you want to lead the sales team? I'd be like no way, not in a million years. I signed up for it and I never would have signed up for my, for a VP of sales role.

Just, no, it was not even on my radar, but learn. Sales enablement, learning sales, training, learning, sales, operations, understanding those things gave me the competency to be competent and confident when I took over the team and said, yeah, I know how to get to the next revenue target because it's going to take these puzzle pieces.

And I understand them now you're going to get into the next role. And I have no. You know, signing up for more.


But otherwise I do think we'll probably see, you know, people in in the role six to seven months. Turned out, not, you know, not being successful in that role and being either asked to leave or they leave on their own. So let's, let's, let's switch gears. And let's talk about being a female leader in technology, right.

In tech roles, but especially in sales, right. Women are still the minority, especially as you look at leadership and executive roles. And I'm always being asked, like, you know, what do you, you know, what advice do you have? How do you cut through the noise? How do you let your voice be heard? You know, all of these type of questions.

I'm sure you get asked all the time. So what advice do you have for, you know, for other women who are really looking. Elevate themselves elevate their career and maybe continue to move, you know, maybe it's up the ladder or maybe it's sideways or, you know, however it is, but it's expanding, expanding their reach and their.


So I didn't feel like I had a good understanding of what this would, what, you know, what this would look like. And so I think I tried on doing it like what, or what I was watching, you know, what was emulated in front of me, which was a more masculine way of being, and that works to an extent that worked.

And then I started really realizing. Through some executive coaching and through some of those different things, I really just need to double down and be more me. And that when I actually didn't think of all the different scenarios or, or didn't have everything planned out and perfectly done, but I just was responding as me.

I did well. And so You know, I would get feedback, you know, around, oh, you're doing too much verbal processing or you're doing too many things. You need to be more concise. And you know, Christine, you going in and, you know, being with the team and talking to them and laughing and doing all of those things, like you need to, you know, be more stern and be more of this.

And I actually have. He told me, he said, you know, the biggest motivator is fear. And he said, you need to get in there. And this was not in, it was at a different company. He just said, that is it. You need to scare them. That is how you will get it done. And I said, you know, I am you hire, you all hired me to do this job.

And you know, what I think is caring and like, as much as you're gonna hate this. The bigger motivator is like, it's truly love. Like if people love being around you and they want to be at work, I'm like they will work for me differently because I actually care about them. Spots was so funny. He looked right at me as well.

You have three months. If it doesn't work you're out of here. And I said, All right. You know, it was like, you know, put your money where your mouth is kind of situation. And at the end of the day, I believe that to be true, like I have a big capacity to love. I love to have fun. I want to have a good time.

And I'm also very, very particular. I do not like to miss targets. I do not like to mezcal. I am a revenue driven. I am variant, but I also have a large capacity the left. So I think the most important thing is figure out what are those key components that you uniquely bring to the table and try to do more of that rather than trying to emulate all the other things that you're seeing and even.

Even the other women that you're seeing, you know, if you do it that way, if you're a person that is quiet and isn't like, let's get on the chair and get everybody robber on going that's okay. You know, motivating one-to-one and talking to people and caring about them one-to-one is just as powerful as being able to get on stage and motivate a billion people to do something when it actually is.

And, and, and insights action, right? If I get up there and get everybody excited and then five minutes later, they forget about it. But I have three conversations that are meaningful with somebody that moves the needle for them, because they actually understand what I'm talking about. We get it done, which ones like they're both different, just different styles.

So really embracing that, knowing yourself, it's so much more than being. Just self-aware, but it's actually really digging in and go deep. This is, this is who, what I uniquely bring to this. And I'm going to be more of that and try to do more of that. And then I just told us to a gal the other day, it's like trying on a pair of jeans.

That's too tight tracking. Like, if somebody gives you the feedback and you're like, this is too tight, I actually can't be that quiet,

you know, try and see, like, there's that feedback work is this workable for me, this felt good. And this seemed to work and then do more of that. That's what I think is really important.


How to accelerate revenue growth and literally how to power the revenue engine. So from your perspective, you know, what are the top couple of things, maybe top two or three things that you think other executives should really be thinking about right now to drive that revenue growth?


You hear from a different perspective, you're hearing from a strategic person. And really understanding where the customer pain points are in that process and where the prospect pain points are. And where can you do something to alleviate that friction? A lot of times I think we as sales leaders think about that on the implementation and customer success side.

And I think we really miss it. If we are a part of those conversations, like how can we create something, a package of, you know, something that is going to fill, you know, maybe it's downstream where this pain is being felt, but we can solve it in the process early on. And I think that when we actually taken the time to do that, and we don't pawn it off on customer success or somebody else to do those things, but we as sales leaders get into the mix and actually actually listen to, you know, these experiences and go, wow, this is friction.

This is like 12 weeks in. And here's a giant friction point. What can we do to make that non-existent or what can we do to smooth. And also that is a great way to drive revenue. Find a way to smooth those things. You know, half the time it's like customers data or different things, or it's coming in wrong formats.

We can't get, you know, we need one. We need one solution to get put into our new solution. And we got to get stuff out to get it in and all of these different things where it puts it, the weight on the customer to do. It's like, can't we do that? Can we do anything for them in that regard to make it easier for them to transition?

And yeah, I just think there's a lot of ways that we can do that, that drive revenue that we're just you know, we're thinking from an outside perspective because we haven't actually snuggled that to our customers.


And those reasons can all feed back into your top of funnel activity, your whole entire sales cycle. Right? All of that feeds back into there. Then that's super important.


As you ask the owner, sitting there and going, I'm going to call this customer, I'm going to figure out what I'm going to listen to. These five calls that took place or 25 calls that took place, because there's a really pissed off customer, six weeks in, I'm going to go do the investigation and listen to it myself, because you will hear it different.

Then anybody you'll hear. I know that when I would do that, I would come up, you know, we'd all, you know, sync up on it and I'm hearing something different. Like I hear a different opportunity here. I hear a different lever. We could have pulled here. And it's just because of my unique perspective. And so I think oftentimes we pawn that off on other people to do.

We give it to one of our sales managers or sales directors or training. Hey, what do we need to do in training? Go back and listen and figure out what. Sometimes we just actually need to do we have to get in there and get our hands dirty and golf. You know, these are three things that I heard that I actually didn't know we were selling it this way.

And, and we, you know, somebody might've heard me as the sales leader. Describe something and they heard it with their lens and then said, you know, this is how we need to sell. And I'm not horrified that we selling this way for three months. And I did it because it was a mistake. It was just something that I said that they took more word.

And so it's, I think sometimes we do that and we need to get in the mix and get our hands.



Yeah. Yeah. I had to go into the bathroom and do debriefing breathing. When we worded, we recorded these classes. I never, I actually could not watch them for over a year. I could not even watch them. Yeah. So so it's still something I work on. And I think people think because I'm a really giant extrovert and now I can do this.

And you know, I still get a little bit nervous, but I used to be extremely nervous, like where I would wear different clothes. I would wear clothes that came up high because I would turn bright red. And if I had to talk in public, I would really get turtleneck because I didn't want people to see how flushed and stressed.

And so I started figuring out like cheat the system. So I wasn't being, so I'm like shaking, but, you know, I put my hands probably surprise people because I haven't easy, you know, easy going personality and doesn't seem yeah. Right. Yeah. Yeah, definitely. And the one thing that I would want everybody to know is I think when you've gone through, you know, when I had to close my business and do all of these different things.

I was so ashamed. I was so ashamed of it. And because you know, you're like, oh my gosh, how did I do this? I thought I knew enough. And I, you know, thought that this would always make sense. And so every single day, I think you struggle or I have, I've struggled with do I know enough? It, my reading enough books, I mean, I'm an insatiable reader and I have to consistently work on why am I doing.

So that it's really for the purposes of doing, doing, and being a better human and a better leader and a better mom and a better person, you know, in general, in this space, rather than trying to prove to myself that I'm not. You know, a fraud and this, or I don't know enough or different things. And so I think it's just knowing that you can seem very confident.

You can seem super competent and you can even see like all these things, we're all struggling with like, do, are we doing enough? Is this, does this work good? And that, you know, you're not alone if you've ever had those feelings, because we all feel it that 100%.


And, and the truth is we all have fear and the difference is. How we handle it, right. That we push through it, like you said, and a lot of times, you know, even we jump on calls, we jump on events and there's always that moment of being nervous and like, oh my gosh, you know, what's going on and get the butterflies in your stomach.

And then you take a few deep breaths and you just, you just go, you just gotta push through it.



journey is just incredible.



This episode was digitally transcribed.