Join us as Gabriele shares all about enterprise sales, selling artificial intelligence, and the connections she makes between teaching and sales.
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: Hi, welcome back to the Teacher Career Coach Podcast. and today we’re really excited to interview Gabriele Sylvie. Gabriele is an experienced coach and facilitator. She loves empowering others to learn, adapt, and grow. After four years in the classroom, she and her husband moved to Miami, Florida with their two Rhodesian Ridgebacks.
And she now works from home as a top performing business development rep at a FinTech company that utilizes AI, living her work life balance dream. Today, join us as we learn about enterprise sales, what artificial intelligence looks like at her company and the different correlations and connections she makes between teaching and sales.Hope you enjoy.
Welcome, Gabriele.
Gabriele: Thank you. Thanks for having me. I’m excited to be here.
Elizabeth: We always like to start these off and hear a little bit about your education journey. What got you into education in the first
place?
Gabriele: Such a good question. I think I just grew up always knowing I wanted to be a teacher. I love school. I had such a good experience through charter school growing up and. I mean, I’ve always loved learning, so I wanted to create that environment for kids that, like, I could impact in. I’m a big, like, impact heart led people person, like, that’s what motivates and drives me. so teaching was, just a natural way to get into that. started off teaching in kindergarten for a year, and then I was in a, fourth grade Spanish immersion classroom, for four years after that. Even in that, like, short five years of teaching, I had some student teachers underneath me, like, was leading the team, um, and teaching, but loved my experience, like, maybe one day, who knows, I’d go back, but it’s, It was, it was a really beautiful season of life, for sure.
Elizabeth: And can you tell us a little bit about that time where you knew you needed a change and a transition and kind of how that came
Gabriele: every teacher who taught in 2020 COVID times probably has some type of story to tell, right? It was, I mean, and as I’m, you know, outside of the teaching world now kind of realizing, Oh, every industry had like everything shaken up. Um, but that was a kind of a time for my husband and I to, to reevaluate like, Hey, what are our values?
What are our priorities? And. We actually decided that we were going to move down to Miami, Florida. So we had, we’re both born and raised in Michigan. Um, but we’re like, Hey, Let’s expand our worldview. We always wanted to move. We, we made the move speak Spanish and Miami’s a great place for that.
It’s like we wanted to explore. and once we got in Miami, I was, I was really stuck in between, Hey, do I, go find another school district? Cause that’s such a big part of like teaching, right? It’s like knowing the district, knowing who’re you going to work with knowing the curriculum, knowing like what they value, do you align with that?
Is that what you want to teach? All of that kind of stuff. and for me, it was kind of a point, Hey, what else can I do? I’ve got lots of skills, got lots of strengths. Where else could they apply? so I had a, I had a great neighbor before we moved. Um, and he kind of just sat down with me and he’s like learning and development specialist.
You know, it’s basically like the teachers of the corporate world. And. I’m like, Oh yeah, yeah. So he like helped me go over my resume. But the thing is like learning in development, like it’s just really hard to get a job in that area. just that, that break in, and I’m sure if you’re listening and you’re either a teacher thinking of transitioning or, you know, maybe you’re in that transition process trying to land your first job, it, like, it’s so doable, but it’s just like, I think Brene Brown has a phrase that I love.
It’s effing first times, anytime you’re doing something for the first time, there’s so much with it. Um, but my husband’s in sales, my dad’s in sales, my brother’s in sales. So it’s like, all right, I like talking to people. I like solving problems. I like listening. I like organization, right? all things that teachers, most of them enjoy.
and so I kind of started exploring sales, right after that for the first time.
Elizabeth: I think it’s really helpful to hear your career clarity on how you narrowed it down. Cause I think that’s so important. You know, when people are looking, it’s like, what is the next step?
Gabriele: Definitely. And I even remember, like, at that point, I had, I think the TCC podcast, like, had come up, you know, in the teacher’s lounge at, at, like, our school, like. Have you checked out Daphne, like Gomez’s stuff, you know? And it’s like, okay, let me go read some of her articles. Like jobs teachers can do.
Okay, great. And you just gotta like start trying it. Right. And so it’s like, step one, create a LinkedIn profile, get on LinkedIn and you will find so, there’s so many people willing to help. And that was my experience. Like you have to do the outreach. You have to kind of like. Step up, show out.
Hey, I’m Gabriele. This is my situation. I saw you did this. Wondering if you want to jump on a 15 minute Zoom call and talk about it. what does your job look like? What do you like about it? What don’t you like about it? Because both are very important. some people love the transition to working from home.
Some people think they’ll love it because they’re so stinking tired because they’re a teacher and then they get there and they’re like, I’m so alone. I’m used to having 30 children calling on me. And now all I have is this computer and. I’m connecting virtually, and it feels really disconnected, right? So you really got to like find your people and reach out and ask for help.
and I was really lucky to like have people who said yes to that and partnered with me in that transition.
Elizabeth: That’s such a good point to, to network outreach, use your resources. And that kind of leads me to our next question, which is, with the Teacher Career Coach or Aspireship, um, how did those resources support you if they did?
Gabriele: No, absolutely. Both of them. I think I remember when y’all posted on LinkedIn that it was merging correct me if that’s not the right language, but I was like, Oh, this makes so much sense. This is a good thing. I had found the TCC podcast first as it was more just like general, “Hey, what can you do?”
But my husband. It’s also in sales. He’s like, Hey, check out this thing called Aspireship. One, it’s affordable. it’s You’re not raking in the big bucks. need something
Elizabeth: Yeah.
Gabriele: Like you that’s like affordable. And then the courses, as I was like browsing through it, it looked doable.
It wasn’t like, Hey, let me go switch my whole degree. Like I wasn’t going back to school to transition my career at that, at that point you just need to like get the language, like learned and transitioning into the business world.
Like every industry has their acronyms. Like, I didn’t know what a CRM was. I didn’t know what like an enterprise versus a mid market versus a small, you know, like, I didn’t know any, I didn’t know what AE stood for. knew none of it, it’s kind of funny because I was like a Spanish teacher, right?
I know how to learn a second language. I can learn the second language in this way. But I remember I, I think our school year ended beginning of June, first week of June, and the end of the school year, it’s really a busy time for teachers. You’re planning parties, you’re, I was a fourth grade teacher, so kids went off to middle school, you’re planning like all these graduation celebrations for them, and, and we had known we were going to be moving.
The week of the fourth. So I was like, okay, month of June, this is my full time job. I’m going through Aspireship. and it was so manageable that like courses were fun. I think there was one, haven’t looked into it recently, but y’all interviewed like three different sales reps and it was like, what’s your day look like, what’s your week?
How do you structure your week? How do you manage your own time? And that that was like the clincher. Like, that was like, Oh, I get to pick how I want to spend my time in a week and when you’re an SDR, it’s like you own your pipeline, you, you’re in charge of sourcing all these meetings for the AE, but you kind of get some agency and depending on the company you work for, of course, like, they’ll give you tools and processes to do that.
But, I was a very, or I’m a very, like, self motivated person. So I was like, that to me was like, wonderful. So, yeah, no, Aspireship and the podcast. I couldn’t have landed my first job as a sales rep without Aspireship. it’s actually how I landed my first sales development rep job. and then I can get into later how that tied into where I’m at now.
And then you do also do your referral program.
Elizabeth: For TCC, we have 50 percent off everyone in the TCC community who wants to come to Aspireship.
Gabriele: Check
Elizabeth: You know, you landed an SDR job right outside of the classroom. Now you’re in enterprise sales. And can you tell us a little bit about what that means and break down, um, the difference between enterprise sales and, you know, in SDR?
Gabriele: I mean, I have the sign behind me. It’s like, you are not an imposter. This is for real. So still even sometimes I catch myself. I’m like, Oh, am I going to give this definition justice? Um, but no, an enterprise is essentially, it’s like a large company, like multi billion that the layout of the company, the roles within the company. It’s, a little more complex. So if you’re calling in and you’re trying to book an appointment, like at a mid market or a small business, like you’re probably calling the person who’s going to purchase the software you’re selling. But at an enterprise, there’s a lot of like warming up in, multi threading that has to be done in order to get to like your decision maker, right?
You, you call one person and they, they’re like, yeah, this is the problem I want to solve. You’re like, great, let’s talk. Let’s build this case on how we can help you solve that problem. but it doesn’t end there. And like the sales cycles, they’re like, 90 to 120 days long. It’s just like a little more slow moving, but a lot more rewarding role. Not so transactional.
It’s like call book, sell, boom, call book, sell, boom. It’s like a little more relational, which is, I think the thing I’m loving most about it.
Elizabeth: are you the person who does those initial, initial discovery calls?
Gabriele: so right now I’m like in there with the AE. I’ve only been at this company just about a year. and it’s a tech startup. So a lot of times like in a startup company, like when you’re looking for different jobs, it’s like, Hey, do I want this really established IPO company that has very, You know, career like paths, it’s very clear, but you’re going to do this. You’re going to make 50 calls a day, all those KPIs, in other words, like key performance indicators that, you’re going to be tracked on. Whereas like, I loved this startup type company because there’s a lot more agency and involvement you have in like, Hey, we’re building this together. But, that’s a roundabout way of answering. No, I don’t run those discovery calls yet, but that’s like where I could go. If that’s, what I wanted as a next step at this company.
Elizabeth: Can you walk us through what the interview process was like? for getting your job as an enterprise SDR?
Gabriele: it was super fun because my first sales development role um, I actually got the job through an intro at Aspireship and was there for maybe a few months, five months, six months. and then was doing outreach to other sales leaders. So I was calling into sales leaders, linkedIn messaging sales leaders. And then one of them, my boss at the time, he, ” Hey, we’re hiring, you’re doing outreach to me. I like your style. I like your grit. You want to apply?” And so, I mean, it’s all about like who, you know, how you can network. Any type of warm introduction you can get into a company goes, or referral goes like miles and miles beyond just, you know, dropping your resume in an applicant pool.
So, I cold called him. I did the job that he was going to hire me to do to him. and I think that just showed a lot of initiative, a lot of confidence. Was it perfect? Was my voice shaky? Yeah, my voice was shaky. No, the call wasn’t perfect. I probably left a voicemail that was way too long.
He never listened, you know, but, all of those things can be taught, right. But it’s like that resilience that go get her that, Hey, is she going to like do this first or am I going to have to like carry her along and be like, all right, time to jump on the phone to make your calls. Like people aren’t looking to hire people they have to micromanage. They want people that are just going to go in and get it done.
Elizabeth: I can tell these personality traits that you have that would make for a good sales position, highly motivated, resilient. Are there any others that you can think of that? Really lend themselves to sales?
Gabriele: Yeah. I think. I say if there’s like one thing I want to be the best at, it’s listening. When you’re a teacher, it’s like essential to listen to your students and know where they’re at and then know where they need to be and then make a plan and hire them and get them from point A to point B.
Who else needs to be involved in that plan? parents? Is it like a parapro? but same thing goes for sales. Right. It’s like, listen to the customer, listen to your prospect, listen to what their pain points are, like what issues they’re trying to solve for. And then who else is this problem affecting?
Right. It’s like, it’s like listening. And then curiosity. It’s like, you’re just always asking questions and never assuming, especially like in an enterprise, it’s like, cause things come up and you’re like, Oh, there’s a thing. I think it’s called happy ears or something. You’re just hearing all the things you want to hear, So kind of like being your own little like devil’s advocate at the same time. but listening and curiosity go a very long way
Elizabeth: And would you tell us a little bit about your company? I know it’s involved in AI, artificial intelligence. You know, and we’re hearing just so much about that. Can you tell us kind of what your company does and what you see as growth potential for the AI industry?
Gabriele: It’s really cool. So I work for a FinTech, startup, but we actually have been in the AI space. Like our founders started the company almost, 10 years ago. So it was kind of like AI before the AI boom, got cool. And GPT came out and everyone’s like, we need AI now or else we’re going to fall behind.
so it’s even interesting when I’m like talking on the phone to people, it’s like, Oh yeah, yeah, yeah. We’ve got AI, but I think there’s still so much, So many misconceptions around like. What that is like generative AI versus, you know, all the different types. But we handle accounts payable. So it’s like, again, I don’t even know what accounts payable was until I got this job if we’re being honest.
Like, um, but the end end AP process we built our own AI algorithms. So we partnered with top accounting firms to, to train these algorithms. Cause something about AI is like, You need a good data set to train it well, Or else it’s not going to learn and do the task you want it to do. but it’s really cool.
And I mean, our whole thing, it’s not like about replacing people, but like our tagline is like more human, more potential, So it’s, what else could we be doing if we weren’t having to manually enter invoices and manually code these things? What else could a sales rep be doing? If they could take their gong, like another thing that records your sales calls for you, so you can go back and watch them and learn from them. What else could we be doing instead of like re listening and writing notes and AI can grab a summary of that, can draft an email for me so then I can use like my critical thinking skills. Um, Yeah, that’s a little bit about what we do a little bit about how we’re using it even in our outreach and how we’re Selling into the finance and accounting space, but in terms of career growth and potential So my desire is to get into like SDR leadership. Something I love about SDRs it’s it’s either like the fresh ones out of college. They’re landing their first job or it’s people who are transitioning careers And they’re like, Hey, I was in healthcare, what else could I do? You know, like,from the teacher heart in me, like helping people on board, training people on how to do a process, man, that’s like my bread and butter. That’s what I love. And so, actually about a month ago, I stepped into the, a team lead role at our job. So I’m like doing one on ones helping like lead call coachings and training our new reps that are joining our team.
And, um, that has been not only rewarding, but it feels like, Oh, this is why I even transitioned to get into something different, you know, because at first it’s like, okay, it’s just a grind. You’re cold calling. It’s not for the faint of heart. And then it’s not always fun if we’re being honest, you know, but it, it’s like a means to an end, you get your foot in the door so that you can go and grow within the company and.
yeah, man, with what AI is doing, it’s like, another thing I love about the company I work for, it’s not like ambiguous AI is AI for a specific this is the problem we solve. If you need help with this, here we go. We’re the best at it. Let’s talk. If not, on to the next.
Elizabeth: with AI, I noticed you mentioned, you know, it’s not to replace the person it’s to make things more efficient. So I just love hearing that whenever we talk about it, it’s, it’s freeing up time for you, for other people at the company to have those more human on human interactions.
Gabriele: Yeah. And I think something, um, when I was joining the company that my manager had challenged me with, he’s like, When you’re picking a company you want to work for, especially if you’re like in sales, you’re like the evangelist for the product because AI didn’t really at the beginning, like interest me, I was like, ah, whatever.
I just want to work for a good boss. I want to work for a good company with good culture. compensation good like work-life balance, all those things, but the product itself wasn’t so much on my priority list of, criteria for when I was deciding which company I wanted to work at. But it’s funny more and more, I’m like, Oh, it was really right because you’re talking about this stuff all day long.
So I think it is a helpful part of the puzzle to, consider and even if it’s not your number one passion now, but like, could you, See yourself wanting to learn more about that. And if not, you know, Hey, like maybe go find a company that has something you have a little bit of excitement around, you know, cause that, that shows when you’re talking to people too.
Elizabeth: if you’re genuinely in what you’re talking about, that shows and that draws people in it sounds like what you’re saying too, is kind of get your foot in the door, like somewhere you’re excited. And, and then there’s room to grow from there. You just, you know, get in, meet people, Kind of this whole theme of network,
Gabriele: Yeah, absolutely. I mean, even I remember my first couple of months, I set up 15 minute meetings with our VP of marketing or SVP of marketing, our VP of people, like our head of customer success, like, Hey, this is where I’m starting in the company and most sales development positions, you’re at ground level, you know, and if you find a company that like sees that role as like, it’s our talent pool we promote from within. We grow from there.
Elizabeth: that shows value. You know, they really value their employees and they’re spending all this time on hiring, they want to hire correctly. can you walk us through a day in the life of what you do?
Gabriele: Yeah. Oh, it’s so fun. Log in about nine o’clock y’all I start my adult, my day with calling, dialing. I would tell you I make 200 calls a day, but we use this thing Power dialer. and we are able to, be more efficient and productive with what we’re doing.
so after about, you know, 45 minutes of calls, I try to hit people in the beginning of the day Take some time and your prospect and what prospecting is, it’s essentially using LinkedIn, using your hunting, honing skills. some companies will give you like a list of accounts that you’re working.
Mine does. So I’ve got specific accounts with like different levels of priorities that I’m supposed to break into and set up a meeting. side tip if you’re trying to be an SDR, prospecting is like the number one way you’ll be a good SDR. If you can like use your time wisely, the people you’re calling.
It goes a long way. we have another like cool virtual tool that we use at my company. Um, where we can like jump in meeting rooms and like work together. Um, so even though it’s all from home, like I could work real time camera on with someone I need that. I like that in person part of the day.
Um, I’m doing one on ones with my team right now. So helping them like. Hey, bring a call recording. What went well? You’re self reflecting, you know? Oh, what do you want to change? Okay. What are we gonna try next time? How are we gonna get this count? Like it’s like that coaching teaching piece. Um, that’s been a big part of my job I’ve been enjoying lately.
And then, you know, you get creative with your email writing. Personalization is key, key, key, key, especially with AI. Like people can mass personalize, I mean, come on. I think we all know if chat GPT wrote an email or if it came from somebody, Use that as a start, edit it down.
And then, been doing some video emailing, like just trying to break through the noise, I always get a lunch break. I go walk my big dogs on my lunch break. I take an hour lunch break every day. If I have a doctor’s appointment, I can schedule it during my time because I know how many calls I need to make, how many emails I need to send, how many prospects I need to add.
But I can get that done within my week when it works for me.
Our whole team jumps on and we call together in the afternoon. That’s probably, in terms of like getting excitement and like rallying around something together, that’s really helpful.
And then it’s admin time. Like I try to spend 30 minutes a day, like continuing to learn, I joined this SDR management course and I’m taking courses on that, like learning about how I could, you know, level up and move on. So,
it’s very flexible. It’s very manageable. I think if you like the people you’re doing it with, it’s enjoyable.
Elizabeth: there’s so many parallels just from hearing you talk to teaching, you know, the coaching, those one-on-ones, you know, your observations in school feedback, um, you know, continued learning that you’re talking about. The teachers are always going through professional development. There’s, so it’s just really nice to hear that all that kind of brought
Gabriele: Oh, man, if you’ve been a teacher, you’ve been trained so well to go be successful in another field. You know, like you can do it. You have all the skills.
I mean, even in the interview process, I remember it’s like, Oh, and how will you manage this? And I’m like, I finished 30 screaming children at a time. How am I going to manage to like, Send 30 emails a day. I think it can handle it. You know, it’s, it’s just, obviously that’s not how you respond in the interview. That’s not like the professional response, but in the back of my mind, I’m like, okay, I can do this.
Elizabeth: Right, like all the connections are there. You can make the connections and formulate and translate it essentially.
how has your work life balance changed? You talked a little bit about it being more flexible.
How’s that been going?
Gabriele: Yeah, that’s a big question for me because I think the crux of why I left teaching just me and my personal story was the lack of that. Right. And so I would get home every day, like. Rewind three years ago, Gabriele would be dog tired on the couch at the end of the day, not wanting to go to the gym, not wanting to hang out with friends, not wanting to catch up with family or like even cook a meal for my, family, you know, it was, it was tough.
And so here we are now living in Miami, like we’ve built all these new beautiful friendships and I have energy to hang out with them during the week. I couldn’t have imagined going out for like a Tuesday night dinner. Or glass of wine with someone. When I was a teacher, like, it just wasn’t, how I operated, where it’s like, now it’s like, because my day job, I work hard.
I’m logged in. I’m diligent. I work with integrity. It’s like, I do the job itself, do everything that’s asked of me. but my capacity has expanded outside of my job. And that to me is, That’s the cake because now even outside of my job, I’m like, we like lead a small group and like, I can do book clubs and do things that like have impact, like for me, like we’re part of our church.
We love that. Like I can do these things and have energy for them. whereas that wasn’t always the case before. So it’s, it was a big, one of my why’s of leaving and why’s of staying at the moment. So
Elizabeth: Well, what did you learn about yourself during this process?
Gabriele: That’s a fun one. I think that another phrase comes to mind, like everything is figureoutable. and people are so willing to. Pitch in and help like I think it was a humbling process to be honest like I had to learn how to ask for help I was pretty self sufficient. I like being self sufficient, but I learned how to ask for help and In the same way you feel confident after landing your first job and getting into teaching or you know You make it through year one and you’re like, wow, I did it like let’s go To transition and then not to like to my own horn, but like to transition successfully like and find it a role that’s like, Hey, no, this is working like I am enjoying it.
I do see myself growing at this company. like this newfound, like self confidence. I did it, you know, and if five years from now I want to transition and go somewhere else, you know, it’s like. There’s flexibility in that there’s agency. There’s so much agency to be had. And like, when it comes to career things and just cause you studied one thing, doesn’t mean that’s what you have to do for the rest of your life.
Like, you can use it, pivot and nothing, nothing is to waste.
Elizabeth: such good takeaways. And I like everything is figureoutable. Gabriele, thank you so much for joining us today. We learned so much and it was really nice, um, speaking with you, learning about enterprise sales, AI, and we were just appreciate your time today and wish you luck in your career.
Gabriele: course. So happy I can be here. Thanks for writing me, Elizabeth.
