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148 – Software Sales to Customer Success Manager with Morgan Mason

TeacherCareerCoach

Morgan Mason is a former second grade teacher who started to feel stuck three years into teaching in a pandemic environment.

On Episode 148 of the Teacher Career Coach Podcast, Morgan discusses how she was facing severe burnout and, with the help of the Teacher Career Coach Podcast and Aspireship, made the decision to start looking for a new career.

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

Mentioned in the episode:

  • Use code “TCC” to get 50% off of everything at Aspireship
  • Our career path quiz at www.teachercareercoach.com/quiz
  • Explore the course that has helped thousands of teachers successfully transition out of the classroom and into new careers: The Teacher Career Coach Course (If you are a Teacher Career Coach Course member, you can also sign up for our one-on-one Career Clarity calls.)

Elizabeth Suto: Today, I interview former teacher Morgan Mason. Morgan was a second grade teacher. She taught all throughout the pandemic and made it three years before she started to feel stuck. stuck. She had severe burnout and craved something more. Morgan found the Teacher Career Coach Podcast when she was searching for teachers transitioning to new careers and was instantly hooked.

She also found Aspireship and She Codes through Daphne’s resources. She dove in head first, which helped her pivot into sales and now customer success. Join us today for a great session about transitioning from teaching to sales and then from sales to customer success. Hope you enjoy.

Welcome, Morgan.

Morgan Mason: Thank you for having me. I am super excited.

Elizabeth Suto: We’re so excited to have you and learn from you today. So we’d like to start off and hear a little bit about your classroom experience. What got you into teaching in the first place?

Morgan Mason: Yeah, great question. I did not think as a little kid that I would be a teacher. Teaching came out of nowhere in school. I actually thought I would be a doctor my entire life. I wanted to be an anesthesiologist. I was really shooting for the stars there. Um, got into college, Was like, this is not for me. I’ve got to make a career transition or figure out what route I want to go.

And I actually got to, kind of shadow a teacher and fell in love with it. And so it felt very natural, very, you know, that care giving type of role, um, came very naturally to me. So went into elementary education, was a second grade teacher, and that’s kind of how I ended up in teaching.

So it wasn’t something that I. dreamt of my entire life. But once I got into it, I was ready to go super excited and wanted to continue that growth, like wanted to become a principal and kind of go up the ladder in that way. And I kind of changed after I joined and started and, you know, reality set in, but yeah, that’s how I got started.

Elizabeth Suto: Thank you for sharing that. I love the correlation between teaching and doctor and and caregiving. I’m curious. What was the point where? You were ready. You knew you were ready to leave the classroom and you were leaving.

Morgan Mason: Yeah. Um, I feel like from the very beginning, I had things stacked up against me. I started the same year as COVID. So I had a semester. the first half of the year, it was normal and it was my first, you know, first half.

And it was great. And then everything shut down. My school was not one to one with Chromebooks or computers. And so we had to do packets. It was in a lot of ways, very startup, like mentality. No one knew what was going on. We. We’re just kind of doing things willy nilly and the second year it was like continuing to just be really rough where no one really had a direction.

We kind of were being told multiple things and I think that just weighed on me a lot because it gets overwhelming after a while, right? You, you’re in a classroom, you’re trying to get into a groove of things. It kept changing every. So often, you know, we’d go in, we would go into, being uh, remote and then we’d come back and we’d go back to remote. And so I think that change really weighed on me. And I think teaching in general is already very stressful. And to then add pandemic onto it, it, it was just a lot. I started seeing myself every day just come home and I wasn’t feeling like myself. And, people around me started to notice that where they’re like, are you okay?

Is, is everything going, everything going okay with like school and teaching? And I just finally had to look at myself in the mirror and just say, something’s gotta change. This is not healthy. I’m not taking care of myself. I’m not prioritizing myself. And I’m not sure this is what I want to do. For 20 years, I don’t think it’s sustainable for myself.

So that’s kind of what made the switch. it took three years to get there and I contemplated a lot, but was finally able to build up that courage and, and yeah, make that switch to the tech world.

Elizabeth Suto: That’s great that you recognize that and could make that switch. And that kind of leads us into our next question with, you know, you had a teaching background and your teaching credential. how did you get into your new role? And pivot.

Morgan Mason: well, I didn’t start off thinking sales was the route I was gonna go. I loved coding it. When I say I loved coding, I I liked teaching code to kids like in a very elementary standpoint. I Was like, maybe I should go that route and maybe try software engineering or something along like front end development. I don’t know how I was trying to think back of like how I came across Teacher Career Coach. I genuinely believe I was advertised it on Instagram Daphne was doing something great. cause I definitely was. Just seeing it as like something she had posted. I, Isaw that and I started listening to the podcast myself and saw a bunch of stuff about, people transitioning into front end development or, being a software engineer.

And so I looked into she codes at first, and she codes is, you know, a women coding course that you can go through. And so I did that, loved it, but coding can be pretty, um, lonely at times. You’re coding for hours and hours and you’re not really talking to anyone. Um, and I started to be like, wow, okay, this is awesome.

I love the challenge, but I’m not talking to anyone. And I don’t know if I could do that day to day. I, I, I don’t know if I want as much. social interaction as teaching was where it was just constant everyone boom, boom, boom talking to you all day, but I needed something. And so I was like, okay, I can take what I learned in coding.

I know. I love software. Let’s get into software, either sales or something that is customer facing. And I knew sales was probably, um, It’s not an easy route but an easier route than customer success at the time, because I saw a lot of teachers transitioning and that was a really big, position that everyone was kind of going for. And so I was like, I’m going to go the different route and I’m going to go straight for being an account executive, which. As you know, Elizabeth, that’s kind of skipping a step. there is a role, a sales development representative, SDR, a BDR. but I knew I wanted to take it like one step further even from that. And I knew I loved presenting. I knew I loved demoing and even like a teaching environment. And so I really set my goal high to do that strive for that. and that’s kind of how I got into sales, but that is a roundabout way of getting there. I didn’t know right away that sales was going to be it.

Elizabeth Suto: Very cool. I, and I love to hear that you started with coding. I didn’t know that about you.

Morgan Mason: Why? Yeah.

I have that, um, up my sleeve. I still can kind of understand the back end, which is really, really cool to know in general, just as like things break at a company, right. You can kind of figure out

why.

Elizabeth Suto: I bet that’s so helpful to have that extra skill, especially at a tech company. I know you mentioned you listen to the Teacher Career Coach Podcast, and then you also took Aspireship. So. in utilizing those resources, How did they help you?

Morgan Mason: I was in sales in a different. Capacity in college, I did retail sales, but it’s not a one to one comparison by no means.

And so going through Aspireship to help me understand the. software sales process. although there’s correlations and there’s even correlations to a lot of teaching skills, I still wanted that training and very black and white training just to what is a recruiter or a hiring manager going to ask me? And I wanted to be super confident in that. So. the sales course that Aspireship offers definitely was helpful. And, the late Skip Miller, rest in peace. He was phenomenal too. And I think that whole course just got me so excited to transition, especially during such a low, low time in my life where. I was still teaching while going through all of these courses and trying to balance both. And every day that I came home and did it, I felt one step closer and I was just a little bit more excited to kind of get out of teaching. And so, yeah,

Elizabeth Suto: That’s so good to hear. And in terms of your transition, so you transitioned out of the classroom. then you transitioned from an account executive role to a very, uh, competitive role, customer success manager.

I know a lot of teachers have been asking, you know, in this space. They’re a little bit nervous about getting a new role out of the classroom thinking, what if it’s not my dream role or what if it’s not the role I’m at forever? Can you talk a little bit about how you left your account executive role and got your customer success role and then the mindset around that change?

Morgan Mason: Yeah. First, let me just say, it is so scary leaving teaching where it is such a stable job as far as just you go into teaching and you can have a job for 20 years and it just be that and, um, job security, you know, right now, or at least you know, in the last 10 years have been pretty stable to then go to startup world where things are very fast paced. Things are changing. companies don’t necessarily always get off the ground and it is nerve wracking, to get into that space. And I, it took probably a year for me just to be okay with that. there was a lot of imposter syndrome. There was a lot of. uneasy feelings of the day to day, like, am I going to get fired? Am I doing the right thing? I don’t even know what I’m doing. The, the business acumen, everything that went into it was a lot. But once you shift your mindset that teaching is very unique where it is, there’s that much job security. And then you realize that the rest of You know, jobs and industries, things change constantly.

People get let go. People might get laid off and it’s nothing to be ashamed of. It’s nothing to, you know, worry so much about. It’s okay. Things happen. I was laid off my first role and that was definitely something that I really struggled with. And then I’m realizing every year that I’m in the tech world, that it’s just, it’s common. And so. You might not be in a role at first that you feel is the right fit, but I truly believe that every role you’re in is a stepping stone to then where you’re supposed to be next, right? I am so thankful that I went into sales for a lot of reasons. It gave me so much confidence in and out of the workplace, right?

And teaching there. Sometimes you lack confidence. You have confidence in a lot of ways and then you lack it in others, especially with business acumen and coming into, um, the corporate side where, you know, a lot of us don’t traditionally have a business background and you talk to second graders or little kids all day or high schoolers, right?

It’s a different vibe and scenario. So I, I felt like sales was giving me the confidence to have those conversations with executives, CEOs, CPOs, CMOs, right. People that I would have never thought I would have talked to. And gave me the confidence to then take that into this next role where I am a CSM and I feel that it aligns more with my soft skills that I have. not that sales didn’t, but sales is a grind and it can be quite stressful. And I am just a worry wart. And I knew that that was weighing on me also in a negative way. And so I recognized that in myself and was like, what can I do? And I knew that I loved. The customer relationship and that partnership, because it’s very similar to how you have a partnership with a child in an elementary setting or in an education setting. So that kind of helped me, um, I guess like to bring it back, just having, having this, like understanding that things might shift, it’s okay. That you’re not in the role. You don’t have to be in it forever. It is so easy to kind of. Switch roles within the tech world. It’s not uncommon at all. I know people who go in as CSMs and come out product managers or go in as product managers and switch to sales, especially if you’re in a a company where it’s very open and they want you to thrive where your skills are. They’re happy to kind of help you make that transition.

Elizabeth Suto: Thank you for sharing. And I love to hear the skill building and how you use that to your advantage, you know, the confidence with sales, you know, the coding background and how it’s only making you a better customer success manager

Morgan Mason: and for your customer success manager position, what was the interview process like?

Yeah, so it was an internal role. So it was a little bit unique. I wouldn’t say I went through an entire interview process where it was very structured, where it was like multiple interviews. It was just an interview with the hiring manager. And we just talked about kind of what I’m doing in sales and how that can kind of come over into the customer success space. I also knew where there were gaps in my company of where I could help. And so I really leaned into that of saying, I know this is where we’re struggling. And this is where I think I can thrive. and I’d love to help you out with that. I didn’t have to do any presentations. Um,

I’d say a lot of people actually do have to do some presentations. So, yeah, it’s a little unique.

Elizabeth Suto: Can you tell us a little bit about your day to day, what you do in your new role?

Morgan Mason: Yeah. as a customer success manager, you’re very much an accountability partner in a lot of ways. So we have clients. I have about 80 ish clients that I work with where I really strive to understand their business outcomes. I work in HR software, so their HR outcomes and helping them connect the dots of how can the software help achieve those goals. very similar to teaching. You have goals in the lesson plan that you’re trying to achieve with students or you have metrics that you’re going to hit and then you basically kind of create lesson planning or project planning to get there. I do that for my clients. So I basically create project plans.

We work backwards. I understand, you know, What are they trying to achieve in this year? What are they trying to launch this year? And then we work backwards of how are we going to get there? And so creating outcomes plans is most of my day. In addition to obviously having these conversations with the customers, I’d say that’s probably 75 percent of the day. 25 percent of the day is like internal meetings. you have to be pretty skilled with the products and understanding that. so I kind of keep up with that and understand, you know, any new releases, which happens often. And then in addition to that, just the, the admin work, the email, the outcomes lands, building out all of that.

There is a good amount of that too.

Elizabeth Suto: And can you talk a little bit about the career trajectory?Now that you’re outside the world of education, what does growth look like, um, at your company and for you?

Morgan Mason: Oh, growth. I have, uh, I have gone to a place where I very much have accepted that I just want to be where I’m at right now. And that’s okay. And I’m not trying to become a manager two years from now, a year from now. I just want to get really good at my craft and the, and the work that I’m doing currently.

things that, you know, as trajectory wise for customer success managers, I mean, there are senior, Customer success managers, there’s managers in customer success and like the director level, the VP level, all of that. Um, but that’s not to say you can’t switch to a different role. That’s very similar.

We have implementation managers at our role. We have account managers. we also, have account executives. I think all of those I often see now that I’m in this world, people switching from one to the other. even coworkers that have just moved on from my, my job are now account managers. I think also companies. Describe account managers and CSMs and they kind of can be interchangeable it. You kind of have to look at the job description itself and, uh, just know that some customer success roles there might be like renewals and expansion sales. Or you don’t do that. And you just focus on, helping the customer in their partnership with your company.

Or you can also I’ve seen it where they include implementation. I think that also kind of is a little gray as far as CSMs and the account manager roles and all of that. You have to look very closely because it’s not always the same. I think as far as trajectory wise, that could change depending on the company you’re at.

Elizabeth Suto: And then I know many of these roles are revenue driving, and you’ve had a lot of experience with that, uh, based on your account executive role. Is your current customer success role revenue driving? And how did you, how do you manage quotas and that sort of pressure?

Morgan Mason: at my current company, that is actually separated from the CSM role. So I don’t handle anything with revenue anymore. When I started, I was an expansion account executive, which is also an account manager role. It’s, um, like post sale you’re helping with the renewals and the expansion, for the product there. With that said, quota carrying is tough. having a number over your head can be tough, but also if you’re money motivated, it can be so exciting and provide so much gratification because you make a sale. There’s no feeling like it, to see that money come through In that way, quota carrying, you have to be very organized and very on top of it and just kind of have a gritty mentality. Like you have to grind all the time, right? You have to make calls, you have to have demos, you have to do a lot of outreach, whether that’s cold outreach or warm. So, my advice there is if you are in a quota carrying role, stay focused, never get, never be too excited about the highs and never get too low. You kind of have to stay focused because it ebbs and flows. There’s a lot of waves to it.

Elizabeth Suto: Oh, I love that advice. And I think that’s super helpful to hear as well. You know, some companies and customer success roles might be revenue driving. Some might not. So it really depends on the job description, what company it is, you know, how they structure. So I think that’s very helpful for people, going into the field to kind of know it really varies depending on where you are.

Morgan Mason: Yeah. You have to look at the job description because even now, Looking at customer success roles, some of them include just a wide variety of, um, skill sets or things you would do day to day that maybe I don’t do right now. I think it also depends on the size of the company. So I’ve noticed that if you are in a small startup like Series A, Series B, maybe you are more likely to do it all. One size fits all like you, you’re doing implementation, you’re doing customer success, you’re doing renewals, but the bigger you get and the larger they kind of branch out and they have separate roles for separate skill sets. Well, let’s talk a little bit about if you don’t mind, your work life balance now compared to where you were. I know you mentioned earlier that, some friends and family members would see you and, You were a bit dejected and weren’t feeling that great. So tell us a little bit about now your quality of life and how things are going.

 first off, being in tech, for the most part, just in my experience, you have so much more time off. and there’s less stress of being, or of taking time off, I should say. So as a teacher, right, you take time off and, You’re like, is it even worth it? Like all the sub plans. I have to come back to a chaotic mess.

Like we’ve all been there. It’s just your way in the pros and cons. Now I’ll never forget like the first couple of times I took off. I, I was like, wow, Like it actually took some time to shut off my brain because I was in a mode of like, there’s got to be something I need to be doing right now. it took about a year to get out of that, but I’d say time off is the best. Working from home is so energizing. I think that’s a 50 50 thing. Very polarizing. Some people love working from home. Some people are like, I mean, human energy and interaction, and it, you know, have that. I personally had a lot of emotional dysregulation or,being overstimulated easy by a lot of people around me.

And so working from home has been such a game changer because it’s very quiet. And the only time I’m, talking is if I’m on the call with a, a client, but it’s very structured, and I get to kind of pick and choose when I do that. And I get to struc, like have a structured lunch, an hour long lunch where I can make like a home cooked meal.

And also at home. I can go to the bathroom when I want, I can do things whenever I want it. it’s super liberating because it can be really, really tough in teaching just to have a moment for yourself. I feel like that’s been the biggest change is I have several moments now for myself, and I have a very flexible schedule.

I can go to the gym when I want. I can, go to a doctor’s appointment when I want, and I just kind of fit it all within my schedule and make sure that I’m still getting all my stuff done.

Elizabeth Suto: That’s so nice to hear.

Well, as we wrap up, we like to finish off with this question. What do you think you learned about yourself during this process as you changed careers?

Morgan Mason: Yeah. I feel like I kind of lost myself in teaching and I think when I left, I, Wasn’t feeling super confident about myself or my ability, and there’s a lot of noise. I think the world outside of teaching have, have become very open minded to teachers leaving. But when I was transitioning, I was faced with a lot of people who said, yeah, like. You can transition, it’s just not the same. You might not get this job. I don’t know going like skipping roles. that’s gonna be really tough. It might not be super realistic for you. And that constant noise of people. Kind of doubting my abilities, I think drove me even harder where I was like, let me prove you wrong because teachers are so underestimated. Our skill sets are very underestimated. I don’t think people really know what we’re doing day to day or what we’ve handled day to day. and If you can articulate that in a way that makes sense with corporate America, which Teacher Career Coach does a phenomenal job of helping with, it is a game changer. And once I figured that out, I felt like I had grit.

I was excited. I, had such perseverance to keep going, no matter what people said, or no matter how much fear was, I was faced with, what I learned most about myself is just how resilient and, how much I persevered and got through this.

And I look back now and I couldn’t be more grateful for my, my past self to just, you know, take a jump, a leap of faith, know that it will all be okay and things will work out, cause life always does. And yeah, I think that’s mostly what I learned. I’m still learning.

Elizabeth Suto: That’s such a nice sentiment for you to leave us with. thank you so much, Morgan, for spending your afternoon with us. And we can’t wait to see what’s next for you and continue to hear about your journey and hope you have a great rest of your afternoon.

Morgan Mason: Thank you.

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