In this week’s episode of The Teacher Career Coach Podcast, Elizabeth chats with Natalie Williams, a former teacher who transitioned into nonprofit leadership and then into tech as an Account Management Team Lead.
Natalie Williams taught for 13 years before pivoting careers. She’s now an Account Management Team Lead.
She discusses the challenges that led her to leave teaching, how her skills transferred to new roles, and practical advice for teachers considering a career change.
In her role, she is an advocate for people, thrives on empowering individuals and loves building teams.
Join us today as we discuss her journey from education to account management, her career growth from sales to where she is now, and how to make an impact after leaving the traditional classroom. Hope you enjoy!
Find Natalie on Linkedin.
Free Quiz: What career outside of the classroom is right for you?
Explore the course that has helped thousands of teachers successfully transition out of the classroom and into new careers: The Teacher Career Coach Course
Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.
Mentioned in the episode:
- Sign up for 7 days of free access to Orchard
- 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
Episode Transcript:
Elizabeth: Well, welcome back, everyone. Today we have Natalie Williams with us, and we’re so excited to get to know her. Welcome, Natalie.
Natalie: Hi. Great to be here. I’m excited to, to, um, dive in.
Elizabeth: Well, let’s dive right in and hear a little bit about, um, if you wouldn’t mind sharing, your teaching experience.
Natalie: Yeah. So, um, I had a pretty interesting teaching experience. in college, did a study abroad in Jamaica, and so while I’m from Indiana, so Midwest girl here, um, I was ready to get away from the cold. And so during college, I did a study abroad in Jamaica and then and got to work as part of a classroom setting there as well. but, after that experience decided I want to live somewhere warm. So, taught for five years in Florida and then realized, you know what? I kind of miss the Midwest and all the way people are in the Midwest. So came back home, taught more here, in Indiana and Michigan. And yeah, in total, it was about 13 years of teaching.
so kind of across a few different states and, taught everything from actually kindergarten as like a. long term sub while actually my sister was on maternity leave and I had just come back from maternity leave. And then all the way up to working with juniors and seniors in high school in not a tech, uh, not a typical education role, but kind of through a different program.
So, had the opportunity to work with all ages and grade levels throughout kind of my education experience. Yes,
Elizabeth: cool. And I love when you had, have the span from kindergarten up through high school. You, that’s a big age range.
Natalie: very big. So I, yeah, definitely, my last like actual classroom teaching position was with first graders. And at that same time, my oldest daughter, who’s now a freshman in high school. Was a first grader and so I realized during that year of teaching like never again. Did I want to teach the same age group as my children were um Just because I was like I was working with first graders all day and then I felt like I didn’t have like I don’t know the, the energy or like the patience, I guess, to work with my own first grader at home.
And I just felt like it was such a disservice to her. Like she’s the one I was supposed to be able to pour into the most. And I was like done for the day after being with a whole classroom full of first graders. So.
Elizabeth: That makes sense.
Natalie: Yeah.
Elizabeth: And so what was that point after those 13 years where you decided you were ready for something new?
Natalie: Yeah. So I think like many folks in education you begin realizing like, I mean, it was a couple of things for me. It was. Just kind of realizing, A, I I was a single mom at the time, and so I, was like, recognizing it was going to be very difficult for me to support my children, on my teacher salary alone.
and so there was that aspect of it, like just the earning potential. And I also recognize that like, unless I wanted to be a principal one day, And at the time I didn’t know that that was something that I was interested in. I would probably just kind of continue to make whatever that predetermined pay range was going to be.
And there really wasn’t opportunity to grow as far as, You know, as far as that is concerned. And so there was that part of it, that no matter how hard I worked or how well my students did, or, you know, how wonderful I may have been or anything like that in the classroom. Like, I was still just going to be a teacher making this amount the same as everybody else that I worked with.
So there was that part of it. And then I think there was also kind of You know, that piece where so much emphasis was on testing and, you know, different things. And at the time I was working in a title one school. and I had, Oh, I’m, I want to say like 20, somewhere between 22 and 25 students. I was in the first grade classroom. the district that I was working in was, more than 50 percent ELL or, um, I know different States call it different things, but English language learners. And then of course I had others who had IEPs. working with those kids, by the way, but I wasn’t getting the resources and the support that was supposed to be, you know, given to those students.
And so I felt constantly on a soapbox or constantly advocating really to no avail. And it just became like, frustrating for me. I’m like, I can like get on the soapbox till the day that I die. And these kids are still never going to get what they truly need. I remember one of my administrators at the time, she was actually the assistant principal.
She was like, like we’re right there with you. Like we’re, we’re saying these same things at the district level, but you know, resources are being kind of spread throughout. at the same time, like I mentioned, my daughter was in first grade at the same time I was teaching first grade and but she was attending a different school within the district. While my daughter was like very much an on level student, she was actually getting extra resources at the school that she was attending, like extra time, you know, getting pulled out or pushed in with additional resources. Well, the school that I was in, there were students who really, truly needed, you know, they were in that bottom 30 percent and they truly needed the extra, um, help and support and just weren’t getting it just because we had so many students. who fell into that category. so I just kind of felt myself being frustrated with that. So it was kind of a combination of like, where else can I make a difference and impact these students? Um, while not in the classroom. And so, and kind of at the same time I ran into a former colleague who was working at a local nonprofit, the boys and girls club.
And he was like, Hey, we’re actually hiring a director of education. Like, I think you would be great for this role. And so I kind of looked into it and ended up moving into the nonprofit space and then was able to kind of still have that impact piece that I was afraid that I would be missing if I left the classroom, um, but through a different lens and a different context.
And so like, and kind of. While there were still lots of guardrails in the nonprofit space, it wasn’t the same. And so I was able to kind of make an impact and, and really help support those students and their families, like kind of through this different avenue. so that’s kind of, a combination of those three things.
Um, you know, wanting some more, you know, like wanting something that offered a little bit more and some more like growth. Professionally, kind of recognizing where we were at in, in just the education space and then, you know, a really great opportunity presented itself initially, and the nonprofit space that really was a great fit for me for quite a while.
Elizabeth: That’s so cool to hear. Thank you for sharing that. And I feel like that story is all too familiar about how you were talking about the resources and, you know, especially with title one schools, other schools and things just not being divided properly or equal. And it really does become a frustration point because you really want to support those kids, but you need more to support them.
Natalie: Yes, absolutely. 100 percent that. And it’s an unfortunate reality. And I, uh, have had many debates and discussions on how can we fix this, right? And how can we kind of, you know, really focus on, you know, the least of these, so to speak, and, really, you know, Put the emphasis and the support where it’s truly needed.
And, so hopefully like turn things around. So it’s not a, a continuous pattern in the long run.
Elizabeth: And then I’d love to hear a little bit about, your experience As an education director, as I know our listeners would too, because a lot of them are interested in nonprofits and we’ve had a few episodes, about nonprofits as well. So tell us a little bit about, working in education with that.
Natalie: yeah. So, um, it was a very, like I said, a perfect opportunity for me and that, um, And that time and so, you know, it allowed me the opportunity to go into a different setting, still bring that expertise that I had. I actually still have a really great relationship with the now retired CEO of our boys and girls club here locally.
And one of the things that was really important to him was having somebody that could really like. the language of educators in the community while also recognizing that the afterschool program that we offered at Boys and Girls Club wasn’t school, right? And so, for me, that was like a breath of fresh air.
Like, hey, I don’t have to do things in the confines of You know, this very detailed curriculum and we can be really creative and hands on with it. of led the programming efforts there and, and that position even evolved over time to more of a whole club, program manager, program director role. and then, you know, operations and things like that. So, it truly was like taking this expertise that I had from being in the classroom and having the experience working with, with students. So being able to share that knowledge with some of the youth development workers in that space. And then also just like helping to like, you know, be creative and share that creativity with my colleagues and, you know, come up with things that kids were really going to enjoy doing.
As many of you may know, nonprofits are very heavily grant funded. And so, some of that was being creative about how can we, still leverage those grant funds or be able to utilize grant funds. To make this an even stronger program. And so that was something that we really did, grow the, you know, the program offerings at the boys and girls club, because we were like, okay, well, we can bill for these certain programs if we run it this way, or if we just institute some tracking, you know, measures in here and, you know, kind of have a little bit more structure to what we’re doing.
Um, so we were really able to kind of turn it around and, we made some really significant gains too. And the, funding that we were able to provide for our, um, community and for that club based on just kind of those shifts that we were making. So, um, definitely if you have a passion you know, if you still have a passion for kids, but just think like, Hey, the school setting is no longer kind of like fulfilling my, you know, desire, you know, or my career desires or whatever, like absolutely 100 percent recommend, you know, checking out the nonprofit space. there’s things anywhere you go, but, navigating those, I think after being an educator, you kind of know how that system can work and, how you can kind of creatively make it to the benefit of those who you are serving.
So
Elizabeth: That’s so cool. And I think it’s important to kind of, you mentioned, you know, you. You knew someone in the community and got connected there. So I know a lot of people in the job search. Now, a lot of educators are looking, but I often try to encourage them to look in your community to utilize your local network because there are things there that you may not know of exists. So I love to hear you found it that way
Natalie: bless. Can
Elizabeth: I love it. I love all these different, um, it’s like stepping stones and blocks that led you to, to where you are now. And I know you recently got promoted. So can you share a little bit about, um, what you do now as in your role at the software company?
Natalie: so yeah, I just recently to start off 2025 was promoted into, um, an account management team lead, um, for one segment of our account management team. Of the business at 15 five. So, in my current role, I’m actually supporting a team of account managers who, um, at some point or another in my journey at 15 five were my colleagues.
And I mean, they continue to be my colleagues. And so, Really in this role, I’m taking the things that I’ve kind of learned by being an account manager myself, um, and just helping to support them. So I’m kind of like a super rep, so to speak. And so I hop on calls with them when needed, or even just if it’s. to have an extra set of ears or, or, you know, just an extra layer of support when they’re working with different customers. And so, kind of support on calls. I also help with some deal strategy in the background. So like, Hey, this is what’s worked for me in the past to, you know, either get a deal across the finish line.
We also manage renewals as a, as account managers. And so there is a lot of that too, with strategy on, you know, how to make sure that what we’re renewing our customers with is actually aligning to what they’re trying to accomplish. And how do you make sure that that’s kind of like a win win for both of us, right?
Like making sure the customer has what they need to be successful, but also making sure, obviously when you’re responsible for retention and renewal, you, You don’t want to make sure that we’re retaining as much business as possible as well. So really just working with strategies, with my team. And, of course there’s some parts of this, it’s like helping them bring things across the finish line.
And then also working with our now director of account management to like keep track of these things on a more, you know, holistic basis. So while in the past I was kind of just responsible for reporting on my own, you know, deals and renewals now, um, You know, I kind of do that on the front line reporting with each of our team members and then work with him to, you know, have metrics to report back up to leadership. So
Elizabeth: I love to hear that. That, and you’re like a mentor and you can be in this position to really support. Your team and support new members. And I know when educators get into these new jobs, that’s 1 thing they look for as well. Like, will I get in this role and be supported? Is there, you know, development for us?
So that’s so great to hear and. We talked a little bit about at the Boys and Girls Club, kind of how you knew right away you were using those skills from education in that position. So in your position now, what are some of the skills that you use and then what do you really like about it?
Natalie: yeah, um, great question. So there are often days where I’m like, okay, how do I tie this back? I actually have had several teachers or former teachers reach out to me like on LinkedIn and other places asking like, Hey, this is my background. I see you are now working, you know, in tech sales. Like, how does this work?
How did you make that connection going into it? And so, I will say this as a caveat, like to all of this, don’t sell yourself short when you’re going into that initial phase of interviewing and, even like prospecting for roles, because I think that was one thing that I probably could have been a little bit more confident in doing. I had a lot of experience like both in, As an educator, but also obviously a nonprofit leadership that I don’t necessarily know that I capitalized on in my initial role with 15 five. I did come in as an SDR. Which still to this day, I think that experience was valuable and meaningful for me. I was able to learn a lot of the tech stack and so forth. I do think that I, you know, probably was ready for a higher role to begin with, but I think, you know, going into it like, Oh, like I’m totally new to SAS. I don’t, I didn’t even know what SAS meant when I was making this shift. and so spent some time learning that, of course, but yeah, I think I kind of undersold the connection a bit and, and probably could have anchored on some of those experiences that I did bring to the table to probably start off a little bit higher than, you know, like higher in the organization or in the, in a different role than, than where I did. so to kind of bring it back to your initial question though, like. Certainly, you know, as an educator, you do a lot of differentiation, individualization, and those sorts of things. Um, whether you’re working in a new logo sales cycle, or if you’re working on an account management side of the house or with current customers, I think as educators, we are very, very skilled at recognizing the unique needs of students and that translates very, translates very beautifully into sales, like really being curious about what the customer needs, what, what are they currently doing? How can I help fix that? Or how can I help them improve? And so, you know, kind of like your students, like where are they struggling? Where are their needs? What do I have to offer them that can help improve that? And then, you know, helping them to kind of recognize that what they need as well. I don’t know, early on, uh, in my time at 15.
5, I did have a conversation and I was like, Hey, like I used to have to convince sixth graders that they needed to write an essay. Like, it was not an easy task, like, especially depending on, you know, which group of students you were working with. And, You know, you have to be creative in figuring out how can I sell you on why you need to write this essay and how it’s going to benefit you or whatever.
And, um, outside of bribery with candy or, or other things like, well, how can I truly make this meaningful for you as you know, a 12 year old kid or whatever. And so, I definitely think that many of us have these skills that we don’t It’s kind of that saying, like, you don’t, you don’t know what, you know, sometimes we don’t know what we don’t know either, but, I think a lot of what you do in the classroom really, really translates into, technology roles in general, whether it’s customer success. sales, implementation, solutions, consulting, like there are lots of, you know, just kind of easy transferable skills there. Um, so it’s just a matter of really highlighting your experiences and tying it to kind of what that job description and, and kind of what that role will, will, um, incorporate. So,
Elizabeth: There are so many parallels and I love to hear your story and just hear these different stories because there really are what you were doing in the classroom. Take that outside into a different setting, a nonprofit, a corporate setting. You have so many foundational skills and just expert skills that you might not look at as something you would highlight.
But like you said, going back to that confidence. Don’t sell yourself short. Be confident. I love hearing that. And then you’re involved a little bit on the hiring side, um, as well. And I know educators looking for a job right now are busy. They’re applying. They’re also a bit stressed because it’s, uh, Just busy out there and in a difficult market.
So is there anything you can share with us regarding that, about kind of like what you all look for when you’re hiring and what stands out to you?
Natalie: depending on the role, obviously you might be looking for something a little bit different. in our role, um, here on the account management team, obviously somebody who can speak to their experience, like kind of caring, out. So whether it’s a project or, you know, a sales cycle or something, but carrying something out from start to finish and like, how did you almost like project plan that experience? because that really indicates to us, like thought process and like how you can approach a situation. you know, to kind of identify the steps that might be needed. on the other side of that, I think, you know, just the kind of like basic things that you would do and any role or experience, I think sometimes, uh, the more we get to you know, remote and online communication and things, sometimes there’s things that are lost in translation a bit, Or just like not having the face to face interaction, but kind of that old school stuff of like making sure you’re sending follow ups.
I know that that was something that, actually, when I moved into the initial role as an a E at 15 5, it was like, you send a follow up as if you didn’t work here already. And he didn’t already know us, you know, um, where there was like an external candidate that they were also speaking to at the time.
And they’re like, they didn’t even send a follow up. So think that that is important still. And anytime you can pull in specifics from that conversation. Um, I kind of use the parallel of like, if you’re emailing a parent as an educator, like, Don’t just email them, you know, something very basic, like pulling a specific example, right?
So if you’ve done an interview or if you’re reaching out to express interest in a role, like pull something specific and tangible related to that role into your outreach. Um, why you would be a good fit or some experience that you’ve had that has a parallel to, you know, the role and how it’s described. and then, like I said, the follow up, like, if you, you know, if somebody gave their time to interview you and, um, you know, like, let’s say you did a presentation of some sort, or if they asked a really great question. Pull that in and, um, make sure to include that in your followup. I think that goes a long way.
and if it’s sales that you’re interested in, I think anytime that you can communicate, but not in a desperate way that you are hungry and like. Willing to put in the work and show that you will take initiative. Um, I think it’s a big thing when you like really know the company or the organization that you’re applying and interviewing, applying for, or, or interviewing with, know them inside and out, know their product as much as you possibly can, um, know their ICP.
So their ideal customer profile. So like. Who are the customers that they sell into? And why will you be successful talking with those folks? kind of same for customer success roles too. I feel like, like, um, if you have experience, like lucky for me, um, my organization is an HR, you know, we, work with a lot of HR leaders.
And, um, though I never had the title of an HR leader, I wore many hats in the nonprofit space. And so it kind of pull in some of those experiences even today when I work with customers. And so, Speak to those things. Speak to those experiences that you have that can translate into the role that you’re applying for.
Elizabeth: Thank you for those tips and for breaking down ICP and you mentioned earlier, I know you mentioned SAS. So software as a service. Um,
Natalie: Yes. I
Elizabeth: awesome and great, great to learn and hear, um, for those.
Natalie: have fun stories about how I learned what SAS was when I was first exploring like new opportunities and had decided like, Hey, I just need to change. And I need, you know, to do something completely different. I was on LinkedIn just searching and all these roles kept saying SAS and SAS experience. And I remember reaching out to like Somebody I just networked with on LinkedIn and I was like, I don’t even know what SAS means.
Like, can you just help me with that? and then he explained it and was like, Hey, have you heard of Aspireship? Like you should really reach out and like do their program. It might be helpful and it will, if nothing else, help you identify if this is something you truly want to do and get into. And so, once I learned what SAS was software as a service, I was like, Oh my gosh, like I use. Tons of SAS products in my roles in the past, but just never knew that that’s what it was, you know, what, what people called it, I guess. So
Elizabeth: That’s awesome. Yeah. And teaching, we have so many acronyms and then also in technology and you know, outside of education.
Natalie: exactly.
Elizabeth: Well, now that we’ve learned a bit about you and your roles, can you talk a little bit about your work life balance and if that has changed and how?
Natalie: Yeah, absolutely. So, funny, you should mention that. I actually have my youngest, I’m a, I’m a mother of three. And so, as I mentioned earlier, my oldest is now in high school. I have a nine year old and I have a five year old and my five year old is actually sick. And so she’s home with me today. Um, that has been. Definitely a huge benefit of, you know, working in this remote setting, working in the tech space. I feel like most tech customers that I have, as well as my own organization at 15 five, super family friendly and really have kind of priority straight in that regard. you know, when it works for me to still work while she’s home. I can do that. There are days where of course, like I need to just log off and be like, Hey, I I need to be with my child right now, I’ll hop back on later, or, you know, I’ll, you know, find time to catch up, you know, on things that I might have missed out on, or, you know, if I need to reschedule things, so, it’s much more flexible, there’s no lesson plans that I have to create for somebody, or sub plans, that, uh, That was always the worst.
It’s like, it’s easier to just go in when you’re sick or
Elizabeth: Yeah.
Natalie: rather than taking the time to do sub plans. Cause you might as well have just gone and worked the day. Right. so no sub plans. I mean, there are definitely times when you have responsibilities that you still need to catch somebody up on information, but, much less taxing, I would say to do that in this role, and just a lot of flexibility.
So, if I have appointments I don’t have to book my whole entire day around those appointments. I block my calendar when I know an appointment is coming up. If I need to take my kids to the doctor and take them to school after, and then I come back and hop on. and obviously, I think as long as folks aren’t, uh, kind of, overdoing it in that regard.
It’s, it’s usually pretty like expected and supported, within the company. So, so yeah, definitely a little bit of a lot different from your traditional teacher setting where you’re like, uh, my kid is sick. Somebody needs to go pick them up. I know I have a classroom full of kids. Somebody has got to come take them so I can go get my own child.
I definitely remember those days. It was very stressful, right? And, um, you don’t want to let anybody down, but ultimately your top priority has to be your own kids. And so, so yeah, definitely a lot easier to balance on this side of, of things.
Elizabeth: Thank you for sharing that.
Natalie: Yeah, absolutely.
Elizabeth: We love to kind of wrap these up by hearing about what you’ve learned about yourself during this process and this big career journey.
Natalie: that’s a big question. I think one thing that I learned about myself, there’s a lot of things I’ve learned about myself, um, one of the things is I think, and actually I, um, participated in like a, a leadership, A local leadership program in my community the end of my time at the nonprofit and before kind of stepping into this role, um, or into the SAS world and one of the things that I recognized as I was kind of going through that journey was like, I think as educators, we almost like get comfortable living in this box of like, this is just how it is.
And like, you almost just accept, like, you’re just going to go from year to year and I’ll put my 20 or 30 years in and then I’ll retire and, you know, whatever. And for some people that might be absolutely wonderful. And that might be what you want and what you’ve wanted all your life. I was that person who always knew I wanted to work with kids always like that was, I was either going to be like a doctor for, you know, like a pediatrician of some sort or a teacher or a counselor or something like that. So knew that I had this passion for kids and, um, kind of followed that path. But then there was always just something kind of missing for me. And I could never quite put my finger on what it was. Um, until I kind of stepped out of this like box that I was in. Right. And so what I learned when I went to the nonprofit and I had that experience, in leadership at the nonprofit space is like, once I kind of like achieved certain thresholds and I had like done some really cool things.
I kept wanting more, right? And I was like, okay, I’m at the ceiling. What do you have next for me? You know, and if you know much about nonprofit space, there’s not always something next for you unless somebody in that higher level is exiting or, or something. And so, I think I realized that once I was no longer living in kind of that box of an education that like, I truly did kind of have this like passion for growth and, you know, You know, like, I’ve done my Gallup strengths and Achiever is one of my top strengths. So I think I was maybe like stifling that a bit as a teacher, um, not knowing it. And, so now being in this role, I, I can definitely like feel like there’s, when there’s opportunity for growth, I’m just like grasping onto it. And have kind of had the opportunity to continuously grow in the organization that I’m in.
And so I’ve been so, so grateful for that. it’s a journey, you know, I don’t know where, what the next step will be. I mean, I’m happy where I’m at today and I’m really excited about the future of our company too. but yeah, it’s been, once those walls kind of came down off my box, I was like, Oh, wow, there’s like so much out here that I can just grasp onto.
And, Where like my unique skills and talents are truly valued and I have the opportunity to kind of shine.
Elizabeth: Oh, that makes me so happy to hear, and I can’t wait for our community to listen. Thank you so much for spending your time with us today. And, uh, yeah, we hope you have a great rest of the day and that your daughter is feeling better.
Natalie: Yes. Thank you.
