102 - Megan Wardwell: From Teacher To Customer Success

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102 – Megan Wardwell: From Teacher To Customer Success

TeacherCareerCoach

Megan Wardwell is a former teacher who left the classroom after 13 years to transition into a role as a Customer Success Manager. We learn how she picked this path, what resources she used, and what her role in EdTech Customer Success looks like.

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

From Teacher to Customer Success Manager

Daphne Gomez:
Hey Megan, thank you so much for being here.

Megan Wardwell:
Hi. Thanks for having me. I’m excited to be here.

Daphne Gomez:
So Megan, you were in the classroom for 13 years. Do you mind sharing a little bit about your experience in the classroom?

Megan Wardwell:
Sure. I got my degree in elementary education and I started my career in fourth grade. And then actually I moved up with my kids from fourth grade to fifth grade. I was in fifth grade for two years, and then from there on I was in third grade. When I earned my master’s degree in reading education, I then became a reading specialist or reading interventionist. Depending on where I was they called it different things. But then I was out of the classroom and kind of pulling small groups and working with students who were struggling with reading and helping in push into classroom sometimes. So, when I left teaching, that’s what I was doing. I was a reading interventionist.

Daphne Gomez:
How long were you in the classroom before you started thinking about careers outside of the classroom?

Megan Wardwell:
I was in the classroom. Well, it’s funny, because I was in the classroom for seven years. And then I decided that I was going to make a switch. I decided to change the district that I was in, and actually I got that from following you, funny enough. Because I used to follow you way back when and one of the things that you had recommended was about changing districts. And trying to find a place that you knew that you fit. So that’s what I did and I made a change and I went to be a reading specialist and then a position opened up in the district where I lived. And I decided to go back into the classroom and take this position in the district that I lived in.


And I loved it. It was a great change for me. It was exactly what I should have done at the time. And I made new friends there and the teachers that I worked with were great. And then I was there for about three years and unfortunately at that point I wasn’t yet tenured. Because I was just there for three years and their funding kind of went down a little bit and they had to let all of their non-tenured teachers go. And so from that point then I kind of was floating around different places trying to find where I would fit. That’s when I was doing reading specialists, reading interventionist and trying to find the right place. And then COVID happened and so that threw a lot of confusion into things. Yeah, that’s kind of how I worked through all those years.

Daphne Gomez:
And I feel like there are people who completely check out mentally when I give that suggestion. If I say contemplate if changing grade levels, if you just something about the classroom management of that specific age or the team members don’t really mesh well with you or change schools. If you actually really like your district and your admin is awful, but there’s a good admin somewhere and they might be willing to let you switch, try that out, or change districts. There are people who hear that and they’re like, “That is not the solution for me. I am miserable.” But then if you do feel like there’s a chance that you’re going to love teaching in that different environment, I always say go for that because that truly is going to be the easier switch. Not that I’m discouraging anyone to, you know what my whole thing is, but it also gives you the clarity that you gave it your all.
I feel like once you’ve evaluated a couple of different opportunities than you say, “Now I’ve been in these different environments or now I’ve come to this conclusion that I’m ready to move on from this because I’ve gone to these different environments.” Did you feel after you went to that different school district you were a little bit more with closure ready to move to the next thing?

Megan Wardwell:
By the end I was, yes. The one that I had to go from because of the funding issue, like I said, I was happy there. I loved it. I had friends there, the people were great. And from that point on, then I just kind of couldn’t find that home again, if that makes sense. I couldn’t find that same environment to replicate. And then in the meantime, I then had my daughter and then COVID happened, and then in November of 2020 my father had a stroke. And then in December of 2020 my sister-in-law passed away from colon cancer. So, I was kind of teaching online, doing remote teaching when all of this was going on in my family with a newborn then toddler.


And it just kind of all got to be too much. And I realized that my work-life balance was all out of whack and just something had to give. And knowing that I kind of always had in the back of my mind I wasn’t happy with where I was teaching. I was trying to find that place. And I knew that I needed to make some kind of a change, in order for myself to stay sane. Because with everything going on in my life things were kind of turbulent.

Daphne Gomez:
I am so sorry to hear all of that. That is such a extreme perfect storm of very stressful, out of control, out of your control situations. And on top of that the uncertainty of a job switch. I cannot imagine going through all of that. Can you tell me how you started to just look for jobs even during that really stressful time?

How Megan found her new career path

Megan Wardwell:
Right, yeah. I was lucky that at that time when all of those things were happening that I was kind of doing remote teaching. Because there were times when the schools shut down and I had to be working from home and that was important for what I was dealing with, with my family. And then when we went back to school, but COVID was kind of still in the back burner, if my daughter were to get sick at preschool, she had to then quarantine for this amount of time and all the rules that were going on. I was then helping with my niece and nephew as well. And all of that happening, I really just realized that I needed to find something else that was going to let me be better for my family. I didn’t feel like I was the mom that I wanted to be.


I didn’t feel like I was the daughter that I wanted to be or the aunt that I wanted to be. And I was just pulled in so many different directions. And I remember sitting down with my brother and I was like, I can’t do this anymore. I’m not happy with where I am. I feel like I can’t call out of work if I need to. And I feel like I’m kind of judged if I need to go deal with something with my family. And I really just knew that I needed to stop complaining about it and I needed to stop thinking about it and staring over it and coming to your page and reading stories over and over again, and just make that jump. I needed to make the leap and it was scary. I ended up taking a leave of absence from work so that I could kind of regroup and focus on myself and my family and what I wanted to do.


And it was during that time that I took the leave of absence that I really then put everything in one basket. I joined LinkedIn, I started to network. I purchased your course, I did the course and I really just started to say to myself like, “This is it. I’m going to make this jump and it’s going to be good because this is what I need to do.” I couldn’t at that point see myself getting any better in my situation if I didn’t make a change.

Daphne Gomez:
It’s such a hard decision to come to and it’s really hard to hold yourself accountable for something that feels uncertain. You can’t promise when it’s going to happen. And so most people kind of hold back and are filled with fear of, “I’m not going to try because I’m so afraid of failure.” But that step of, “I’m going to move forward, I’m absolutely going to do this.”
Keeping that mindset is what ultimately helps you with all of the roadblocks that you’re potentially going to face during a career transition. When you were looking for roles outside the classroom, I know that you were inside my course, did you look for multiple roles outside of Customer Success at first or did you just have one focus?

Megan Wardwell:
I did actually, when I started I was kind of thinking about instructional design, and Customer Success wasn’t really on my mind in the beginning. I am very good with the computer, I’m good at graphic design and doing the slideshows and things like that. So I thought I was meant to go in that direction. And then just researching more about instructional design and talking with people on LinkedIn that I met. And I attended different kinds of free workshops and webinars and learned more about it and I just realized that maybe that wasn’t really the avenue I wanted to go.
I didn’t want to just sit at a computer and design things. I still wanted to be able to have those relationships with people and consult about education and things like that. So, that’s kind of where I started hearing about Customer Success. And I was lucky enough to meet with Kristi Faltorusso, who’s one of the Customer Success leaders. And she did a Google meet with me and we talked for a little bit and I just picked her brain and I was like, “What does Customer Success mean?” Because I didn’t even really know what Customer Success was at that point. I’m coming out of 13 years in education, I had a big learning curve. And the more she talked about it, I was just sitting there and I’m like, “I do this, I can do this. This is what I do.”
I feel like everything that I did in the classroom and in education, building those relationships, consulting with people and giving my advice on what I thought curriculum should be like, things like that. I thought that this was the avenue that I should go down. And then so I kind of changed my focus and then I just kind of honed in on Customer Success specifically. Because I think at the beginning when I started my search, it was too broad. I had too many things that I was trying to look for and too many things that I was saying I wanted. And I knew that it wasn’t narrowed down enough, I really needed to take that time and figure out what I wanted to do.

Daphne Gomez:
One mistake that I think that is really common, especially you said it yourself, you didn’t have exposure to roles outside of the classroom. We’re so familiar with the employees that are inside of a school district, but when you’re talking about these big corporations you’re not really sure what everyone’s role is. One mistake that I think a lot of people have is they think that Customer Success and customer support is the same role. And they’re very different. Did you start to find yourself making those distinctions throughout your learning process?

Megan Wardwell:
I did, yes. I actually, early on in my process when I had an interview, it was for a Customer Success position. And I kind of treated it like customer service. And I feel like maybe with that interview it kind of was more leaning towards customer service with the way the questions were asked and things like that. But yeah, I mean, it’s definitely not customer service. It’s trying to really first of all get to know my customers and build that relationship and build that trust and that foundation. And then just consulting with them about how I can help make their program successful, their implementation successful. I’m in an EdTech company, so luckily I get to still talk about these educational resources and how they can be used in the classroom and what the best way is for the students to find success.

Megan’s experience applying to Customer Success roles

Daphne Gomez:
Let’s go back to the entire application process. Did you apply to a ton of Customer Success positions?

Megan Wardwell:
No, but I applied to a ton of positions. I actually had a spreadsheet that I kept. I think I applied to 79 different positions. And I’ll be quite honest, in the beginning my resume was terrible. Terrible in the sense that, not the information that was on it, obviously I had a background in different things and I had different skills, but the way my resume was set up was not the way that it should have been for corporate.


And I also was applying to any position that I read and I thought like, “Oh, I could do that.” I applied, I wasn’t really gearing my cover letter to that position, it was just kind of generic. So I know that those probably first, I’ll say the first 20 or so, they weren’t really the best that they could be. And the more I learned and the more I went through trying to teach myself about the process and teach myself about the different positions and the different roles that the positions have, then I think my resume became better. My cover letter became better and I really, when I narrowed my focus, that’s when I felt like I was making more of an impact with my applications.

Daphne Gomez:
Were you able to use the classroom to corporate translations from the teacher career coach course to improve your resume?

Megan Wardwell:
Yes, I did. Yes, I did. They were super helpful.

Daphne Gomez:
Do you feel when you were looking through the course and you found that you had to go back and look at your resume with a different set of eyes?

Megan Wardwell:
Yes, yes, absolutely. And again, like you said, when we’re in education and I was in education for so long, I didn’t know how the words would translate and I didn’t know … Actually reading some of the positions in the beginning of my process, I was reading them and I was intimidated. Because some of the words I didn’t know and I thought, “I can’t do that, or I’m not sure what that means or that’s not something I’ve ever done before.” But then when I really sat down, and again, when I looked at the things in the course and I realized how certain words can translate and how they can be used in the corporate world, then I realized I really did have those skills and they really were skills that I could transfer from teaching into the position I’m in now.

Daphne Gomez:
Did you find yourself learning any sort of tech tools? Did you learn Salesforce? I’m not sure if that’s a customer success tool, but I know a lot of people are taking Salesforce for sales roles, the Trailhead. So, did you learn any tech tools like that just to help you stand out on your resume?

Megan Wardwell:
I did, yes. I took different courses on LinkedIn and as I would talk to people on LinkedIn from Customer Success, I would ask them what kind of tools did they use. And I would familiarize myself with them. As a Customer Success Manager we use ChurnZero. And actually in my very first interview for the position that I’m in they mentioned that they were going to be using ChurnZero and that it was going to be coming along. So, I purposely went out and kind of taught myself a little bit more about ChurnZero so that if I got called back for a second or third interview that I would know more about it to talk about it.
So I definitely, once I focused in on Customer Success and knew that that’s where I wanted to be, then I dove in and try to learn as much about the process and the tools and all the things about Customer Success that I could.

Daphne Gomez:
Yeah, some of these tools take longer to learn. So Salesforce, like I just said, that one I feel like is pretty intuitive for anybody who’s been putting things into an LMS like student attendance and putting all the data in. You’re going to be able to learn it surface level enough that you kind of understand it within a few hours is my assumption. But if you were trying to become a Salesforce administrator, someone who’s just in charge of managing Salesforce for an entire company, that takes a full certification and a lot of training. With ChurnZero, did you have a long time that it took you to learn it, or was it just a few hours?

Megan Wardwell:
No, and we’re actually still learning it. I mean, we still do trainings on it. In my company they still are doing these different trainings with everybody so that everybody learns to use it the way that they think is the best way to use it. So no, it hasn’t taken me long at all. I really feel like all the different platforms and programs that I used as a teacher and a reading specialist when I was out of the classroom too. They all kind of work similarly. So, since I was good with technology, in that aspect I feel like that’s really transferred over and I’m learning things quicker.\

The Customer Success interview process for Megan

Daphne Gomez:
So, it sounds like you were upscaling for the very specific position and you may have gone through one or two interviews. Did you interview for a lot of different Customer Success positions before this one?

Megan Wardwell:
I think I maybe had, this was probably my third, so there might have been a total of three Customer Success positions that I interviewed for.

Daphne Gomez:
Did they all have pretty similar questions that they asked you?

Megan Wardwell:
The last two did, yeah. The first one was more customer service type questions, more like, “What would you say to this customer if they called with this problem,” kind of thing. And I could have really geared those questions too, because maybe I knew more the second time around. Those questions were more like, “How would you consult with the customer and what would you recommend for them? And if this was the plan,” things like that.

Daphne Gomez:
Not as much as someone needs help clicking here and pointing here and opening this.

Megan Wardwell:
Right.

Daphne Gomez:
And that’s one of the things, the course really covers all of the basics of what to expect with the job hunt process. Because that’s something that’s so overwhelming and frustrating is, if you have one instructional design position, it doesn’t mean that any of the other instructional design positions are going to have the same job duties.

Megan Wardwell:
Right.

Daphne Gomez:
One learning designer might be completely different. One corporate trainer is going to be completely different. One customer success is more like a customer service role, and that also means all of these different pay scales that happened with it. Were you able to know what the pay scale was for these roles before you were interviewing, or was it something that you talked about after the interview?

Megan Wardwell:
I think in the position that I’m in now we talked about it. I think I did three interviews for this one and we talked about it by the second one. So, we didn’t talk about it in the first one. I didn’t bring it up in the first one. They didn’t bring it up in the first one and it wasn’t on the job description. But by the second interview we discussed it a little bit more, so at that point I knew what it was.

Daphne Gomez:
And you were in the classroom for 13 years. Do you mind sharing if it was a salary increase or decrease?

Megan Wardwell:
It was an increase for me.

Daphne Gomez:
Was that something that surprised you?

Megan Wardwell:
Yes and no. I mean, I’m in New Jersey so I will say that we’re lucky in New Jersey that teachers get paid a little bit better here than they do in other parts of the country. But also the cost of living in New Jersey is much higher than other parts of the country. Because I was at a couple different districts, my pay fluctuated during my 13 years of teaching. So, some districts were much higher, some were not. But I did, I knew that because I had my master’s degree and because I kind of had that experience that I could make a higher amount of money, if that makes sense. And that was another kind of driving force for me is that I felt like where I was kind of stagnant, I wasn’t going to be making that much more money.
And that was something that was a goal of mine. I wanted to be able to find something that I could progress in and I could keep earning more as I went along.

Daphne Gomez:
Do you see a natural career trajectory within your company of where you can go beyond the role that you have right now?

Megan Wardwell:
Absolutely. Yeah, there’s definitely room for growth in the company, and the team leader that I have is just wonderful. And she really has made this process great. In my interview, even the first interview with her, she and the girl whose position I was taking, they were both former teachers.

Daphne Gomez:
Oh wow.

Megan Wardwell:
As soon as I started the interview she was like, “Don’t be nervous because we were both teachers too, so just feel free, we’re just going to have a conversation.” And it was like right away I just felt at ease in that interview. And I left the first interview feeling like they were friends of mine and it was just a conversation. It was really great. And so I’m learning a lot from her. And yeah, I mean, she herself has grown through the company, so she’s definitely an inspiration for what I can achieve.

Daphne Gomez:
Did they ever give you any feedback about something that you did in the interview that really made you stand out above the rest of the candidates who also potentially were probably teachers who were transitioning?

Megan Wardwell:
No, they never gave me any of that kind of feedback. One of the things I was trying to do on LinkedIn was put myself out there. I applied to so many places, as I told you, and for a while it just felt like I wasn’t getting responses. And it’s definitely a rollercoaster ride that you’re high and things are going great and then it’s like, “Oh my gosh, I’m not hearing from anyone.” Or maybe the interviews aren’t going well. So what I did when I applied for this one was, I saw the post on LinkedIn and I messaged her directly on LinkedIn and I said, “I saw that you posted about this position and I did apply through the portal, but I wanted to let you know how interested I am and this is my name.”
And I applied. And I think that was something she did say to me during the interview process. That was something that kind of stood out for her that I messaged her directly and kind of sold myself a little bit. And so she knew to look for my resume in the portal.

Daphne Gomez:
Especially when things are competitive, those messages show that you are one step more excited than other people. You are going above and beyond. Because if it’s a role that you aren’t that excited about and then it’s like, “Okay, here’s this three step process in the interview we’re going to ask you to create a project and then upload it.” And if you’re like, “I don’t want to do this.” That’s an indicator you don’t really want that job. They’re trying to weed through the people who are just like, “I’m just applying to any jobs.”
And so when they do see that extra effort, does it work every time? Absolutely not. But if it’s a job that you really, really want, does the extra effort hurt? No. When you were going through the course, did you use any of the interview resources to help you?

Megan Wardwell:
Yes, I did. I printed out so many of your things, I can’t even remember at this point. It was so long ago I feel like now. But I printed out some of your charts and I had notes on them and I would use it. Yeah, I definitely used all of the resources that you had.

Daphne Gomez:
Did they ask you why you were leaving teaching?

Megan Wardwell:
They did ask me why I was leaving teaching, yes. And I was honest. I said I’m looking for a better work-life balance. I told them everything that had been going on in my life and that it was really important to me that I found something. I specifically was looking for roles that would allow me to work from home and be remote. So, I told them that that was what I was looking for.

Megan’s experience day-to-day as a Customer Success Manager

Daphne Gomez:
Let’s get into that a little bit more. What does your day to day look like, especially in this remote position?

Megan Wardwell:
Every day is different. I’m able to be very flexible with my schedule, which is great. So, I am able to pick up my daughter and my niece at school and then I kind of just leave my computer, go do school pickup, come back and I can get back to work again. Or if I have to stop and take my daughter to dance class, I can stop and do that. And then I come back and I can work a little bit more once she is in bed for the night. So, it’s very flexible and I greatly appreciate that.
And then some days are really busy and it’s the afternoon before, I’ve not even gotten up out of my chair yet. And then other days things are quiet and I’m able to continue to learn more about the products that we have and dig into my customers a little bit more and my accounts a little bit more. But every day is different. I have had to kind of learn how to manage my time. It was difficult in the beginning coming from teaching where we constantly have all these different tasks to do, so many things on our plate. And you’re having to navigate and drop things to handle this right away or handle this. And when I first started working, my email would ding and I would think, I have to get right to that and I have to answer right away. And then this would go off and I would’ve to do that.
But I really have had to learn how to chunk out my time and just say, “Okay, I’m setting an hour aside and I’m going to focus on the success plan or something that I’m doing right now.” And not answer my email right away and then come back and say, “Okay, now I can answer a little bit.” I had to train myself out of that teacher mentality where you have to be on all the time and everything has to be quick and kind of learn how to manage that.

Daphne Gomez:
Let’s dive a little bit more into Customer Success for those people who have no idea what this is, what is a success plan? So you work directly with districts?

Megan Wardwell:
Yes.

Daphne Gomez:
The admin, the superintendents, the reading coaches?

Megan Wardwell:
The admin.

Daphne Gomez:
And what is it that you do to provide them support?

Megan Wardwell:
So once the sale is made in the company, then I come in and I kind of work with them to decide, “Okay, what are your goals? Why did you purchase the program? What are you trying to get out of it? What will success look like to your school or district?” And then we have that conversation and then I kind of help them decide how we’re going to get there. So, kind of building a roadmap with them of what we’re going to do, how are we going to deliver professional development, do your teachers need training? When are you going to use the program? And things like that. And we just kind of have those discussions and I’m kind of their partner on the other side, so if they have questions as they’re going through their implementation, they can contact me and I can kind of help them through it.

Daphne Gomez:
That’s one of the team members that I worked with the most closely when I was doing my learning consultant position where I was just free professional development, but for targeted accounts that I had basically a Customer Success Manager that said the teachers really need support with productivity using this tool and everything was completely free. But I would just create a learning program specifically for the teachers that were opting in. And then I’d come after school sometime and train them on how to do something, and then we’d team up with the customer success people and say, “Okay, we did this, can you see improvements on their end? Have they given survey feedback?” And we would just have this feedback loop. You work with the learning and development team, you also worked with the schools and you also work with the sales team. You probably get a lot of exposure to all of the different departments with this role. Once you get into a company, you do see it. Are you surprised at how much you’re learning about all of the different roles at the exact same time?

Megan Wardwell:
Yes, absolutely. And to be honest, when I was a teacher, I didn’t know that all of this went on in the background. I used so many different programs and platforms as a teacher. I had no idea that there were these sales … I mean, obviously I knew there were sales people, but the sales meetings that go on and the Customer Success meetings and all the ins and outs of how to make the technology work and how to roster and things like that, I’m learning so much, so, so much about all the different roles. And it’s neat, because I didn’t know anything before and I’m a lifelong learner. I mean, that was one of the things that I loved about teaching that I was always learning something new. And so being in this position really is allowing me to learn so many different things.

Work-life balance for Megan in a Customer Success role

Daphne Gomez:
I heard you say something at the beginning of the interview that I have to bring back up. You said that you were not feeling like you were the family member that you wanted to be or the mother that you wanted to be. In this new role in this time of your life, do you feel more like yourself, the person that you wanted to be?

Megan Wardwell:
Absolutely. I’m so much happier. I feel like my family would tell you the same thing. That I’m more relaxed, I feel like I can accomplish more. And this summer was the first summer that I worked all summer because I usually was, well, I wasn’t always off in the summer. I did have some kind of a side job or tutoring or things like that. But this summer I was working all throughout the summer and as August came around, I was just enjoying the rest of the summer and we just had family time and we just did family events and we spent time down the shore and all these different things that I feel like I wasn’t doing before. Because I was just miserable and I was overwhelmed and I was stressed. And I just feel like now things are so much different and I am proud of the family member that I can be now. Because I feel like my work-life balance has finally straightened out.

Daphne Gomez:
And I feel like there’s so many times where just we just see the success story and we just see this transformation and we’re happy, but then very jealous of the people. We’re waiting for that to happen to us too. But you did apply to 79 jobs, you did persevere through this really intense period of your life. And one of the questions that I love to ask people on this podcast is, what did you learn about yourself during this process?

Megan Wardwell:
I mean, I learned a lot about myself. When I struggled in the beginning of my teaching career I kind of felt like, “Was I meant to be a teacher? Can I do this?” And then changing districts made me realize, “Yeah, I’m good at what I do. I was meant to be in education.” And then kind of going through everything that I went through, and believe me, I mean what I went through was nothing like what my brother went through.
Obviously I don’t try to say that I was the one that suffered the most or anything like that. But going through what I went through and coming out on the other side with this story of, I made the change. And I put the work in and I made the jump and I’m happy where I’m at now. I know that I’m where I’m supposed to be. I believe that everything happens for a reason. And I’m just so proud of the example that I have set for my daughter, my stepson, my niece and my nephew. You don’t have to be stuck somewhere when you’re unhappy. You can put the work in and you can problem solve and you can make a change and it can make a difference. And that was really important to me that I wanted to be able to set that example to show them that success can happen.

Daphne Gomez:
I’m speechless. That was a wonderful answer. I don’t know how to answer you at this point. Honestly, you told me prior to this interview that you were very nervous. You are such a strong, brave, wonderful human being and I am so grateful that you have shared your story-

Megan Wardwell:
Thank you.

Daphne Gomez:
… on this podcast, and especially that you were nervous and did this. Because so many people are going to hear your story and that’s going to contend you to inspire them and motivate them through what they are going through right now. So, just thank you so much for being here and for everything. It’s just been a really true pleasure to meet you.

Megan Wardwell:
Thank you so much. I really appreciate it. And I mean, you’ve been a support to me all along the way without even knowing that you were a support to me. So, thank you for everything that you do. I appreciate it.

Mentioned in the episode:

Step out of the classroom and into a new career, The Teacher Career Coach Course