The Boyz of Edtech | K–12 Education Insights

In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, and Jacob Kantor sit down with Bobby Offterdinger, CEO of TAM to Target, for a tactical conversation about what actually works when selling into K-12. Bobby shares his journey from elementary school teacher and reading specialist to instructional technology, EdTech sales, and eventually launching TAM to Target to help companies build more effective go-to-market strategies across education and the public sector.

Bobby breaks down why more meetings do not automatically translate into more revenue. Successful EdTech companies still need product-market fit, message-market fit, sales acumen, and a clear understanding of district procurement. The group explores growing opportunities in CTE and career readiness, why some legacy products are leaving room for new competitors, and how founders can connect a specific district leader's pain point to a specific solution rather than overwhelming prospects with every feature their product offers.

The conversation also gets practical about outbound sales. Bobby explains why phone outreach continues to outperform cold email for TAM to Target, how founders should test different messages before scaling volume, and why genuine curiosity and empathy are fundamental sales skills. They discuss researching prospects before meetings, choosing go-to-market channels based on the type and price of a product, and understanding why selling an enterprise-wide system requires a very different motion from selling a smaller solution below procurement thresholds.

Bobby also shares how AI is reshaping the SDR function. Instead of expecting one person to research accounts, build lists, write outreach, call prospects, and manage every other part of prospecting, TAM to Target separates go-to-market engineering from the human conversations SDRs are best positioned to handle. The episode closes with a rapid-fire discussion on cold email, phone calls, sales signals, storytelling, and why the strongest K-12 sales conversations still come back to preparation, relevance, trust, and listening with empathy.

Connect with the Boyz

Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ 
Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ 
Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ 
Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ 
Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ 

Key Moments

03:26 Why Bobby launched TAM to Target

05:55 What separates meetings from actual EdTech revenue

09:53 Why CTE and career readiness are gaining momentum

14:00 Finding message-market fit before scaling outreach

16:01 Testing soft versus direct calls to action

16:28 Why phone outreach remains powerful in K-12

19:02 Replacing the product dump with curiosity and empathy

22:07 Matching your go-to-market channel to the type of product

24:12 The district pain points that change and the ones that stay constant

27:43 Why founders still walk into sales meetings unprepared

29:51 Rethinking the traditional SDR role with AI and go-to-market engineering

33:03 Using AI to create more time for human sales coaching

39:33 Why great salespeople get buyers to tell their own stories

43:33 Rapid-fire lessons on cold outreach, signals, and smarter prospecting

Connect with Bobby Offterdinger
LinkedIn: https://www.linkedin.com/in/bobbyoffterdinger 
Website: https://tamtotarget.com/ 

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 

What is The Boyz of Edtech | K–12 Education Insights?

Explore the latest education business trends, entrepreneurship, and school leadership insights with us. We bring you expert discussions on district leadership, edtech innovation, education policy insights, and K-12 education advancements. Join us for valuable perspectives on edtech trends, startup founders in education, and strategies for effective school operations and relationship building.

Hosted by Dr. Rick Fernandez, Jacob Kantor, Jeff Piontek, Ryan Patenaude, Matthew Millstein, and powered by Old Soul.

[00:00] Rick Fernandez: Welcome to another episode of The Boyz of Edtech. I've got Matthew and the Dodo, Jacob, joining me, and our special guest today is the founder of TAM to Target, Bobby Offterdinger. Bobby, welcome to The Boyz of Edtech.

[00:14] Bobby Offterdinger: Thanks, Rick. I feel like I, like, know you guys but don't in a lot of ways, just from, from seeing your growth, uh, with the podcast here. So I appreciate you guys having me. Excited to, to dive into all things go-to-market in edtech.

[00:29] Rick Fernandez: Well, I mean, absolutely. And I'm especially excited because it feels like every time there's someone, an expert on this side of the table, I get to learn a lot because as a former superintendent, I'm still learning how the private side works. And so I'm interested to hear what you have to say and share. But before we jump in, can you just share a little bit about, you know, your career path? Obviously you're a founder. Tell us a little bit about your company and who you serve and why you do what you do.

[00:59] Bobby Offterdinger: Yeah, happy to start there. I actually graduated about 20-plus years ago from University of Maryland with a degree in elementary ed. So I was a public school teacher out of college. I taught in Alexandria City Public Schools. I started as a 5th grade teacher, so I was elementary ed there. And at that time also got my master's in literacy. So I got a reading specialist degree. And then after being in the classroom for a few years, moved into an instructional technology role. And so I was supporting schools. I had like 2 or 3 schools assigned to me. All of them had kind of focused on literacy needs, which a lot of schools have these days, right? And so they assigned me to a few elementary schools that particularly had some reading score issues. And my job was to help teachers leverage instructional technology, especially in the lens of improving literacy. So Was able to use kind of my love for tech and then also that reading specialist degree in a pretty unique way, and then had the opportunity to kind of flip over to the dark side, so to speak, and start working for a vendor. So I was hired by what's now called Stride; used to be called K12, and even back then was was Fuel Education, which was their internally they called it their institutional business line. But basically all it meant is. They had blended learning curriculum, and that was the big thing back then. And so my role was kind of a sales support at first, and then moved into having an accounts and territory of my own and moving into a sales role. So kind of cut my teeth in sales there, worked at a few other businesses afterwards, always in the K-12 space. And then about 2 and a half, 3 years ago, started having this idea that there are some especially K-12 businesses out there that need help figuring out how to sell into the public sector and how to break into schools and districts. And frankly, also got so tired of the way that buyers were being approached, like schools getting spammed with crappy outreach and this maniacal world where we live in, where you have to spend hundreds of thousands of dollars on a conference to go and like like be avoided at the booth, like the kiosks at the mall type of thing. And I just figured there's gotta be a better way. And so we started TAM to Target about 2 and a half years ago, and our job is to help businesses that sell to K-12, higher ed, or state and local government generate revenue. And we do that in a few different service ways. We've got outsourced SDRs and go-to-market engineering. And recently we also started supporting businesses that are trying to win at AI search. So when superintendents and curriculum directors are on ChatGPT asking for advice about things, we can have our clients show up more in that space as well. So yeah, so at this point we're supporting dozens of businesses that sell into that space. And really, I mean, at the end of the day, the reason we do it is because we always kind of come back to the main reason why we became teachers and educators. And really it's just like, We want to help the world be a better place and we wanna help kids and teachers and people that are, that are like servant leaders and all that. And by helping really awesome businesses get their products into schools, we can do that and still help support students in their growth and all that.

[04:27] Rick Fernandez: Very cool. Jacob, let me kick it over to you. Yeah, Bobby. So we share a couple of edtech solution providers that we both help out. You know, you guys on the SDR side, me kind of on more of like the superintendent and getting them some more strategy on that side. But, you know, what you guys do in the market is fascinating to me because, you know, it's funny, my first client was Stride, so we share that. But, um, this dynamic of like, you know, founders thinking through this idea of like, only if we had more meetings would we close so much more business. And I think the, the 4 of us on the call know that like Sometimes, sometimes that's the case, but sometimes it's also making sure that they're their genuine, thoughtful relationship-building self on those calls as well. So I wonder if you're seeing any trends across, you know, solution providers that are like killing it with you. Like, I bet you're seeing, you probably have more data than anybody around like who's actually thriving in the space and what's making them Actually not just close deals, but let's look at like second meeting metrics or all of these other things that I talk to founders about. Like, I bet you have all that data. Like, what are you seeing the best teams do?

[05:50] Bobby Offterdinger: We're seeing a lot of things. It's hard to pinpoint. There's, it's interesting. You're right. So to kind of back up, like we do have a lot of data and so Because we work in a finite addressable market, you know, 13,000 school districts, right? We are making phone calls and emailing into that district in a very targeted way for on behalf of dozens of clients. I can tell you right now, like who's answering the phones and who's not and things like that, right? So we can get like micro insights. Like I know right now we are seeing an uptick for some reason with like career readiness, like people, There are like CTE directors that are very hungry for specific types of solutions. And we're seeing a lot of our clients see a lot of success there. Whereas we're noticing a drop since the beginning of the year in our ability to get ahold of special education directors for some reason. We don't totally know the why yet, but like we're seeing these kind of trends, right? But to your point, Jacob, like you can have 100 meetings on the table and close none of them, or you can have 5 meetings and close all of them. And it still comes back to like a couple core things like product market fit, message market fit, which is a whole nother like beast that people don't really think about. And then the sales acumen that founders have or don't have. And if you don't, we can tee you up with, you might have the best product out there and we're nailing the messaging, but then if you get there and it's just basic lack of understanding around procurement process or Not realizing that you needed a sole source or that you needed to be on like a cooperative purchase agreement, or just you're not good at selling. Like just kind of call it what it is. Like that can be a pretty big problem. So a lot of the basics are still the same. It's just like we're living in a world where there's so much more noise because of all these different like vendors that are out there. And it's really easy for people to send like mass emails now and stuff like that. And it's easier for people to do outreach a very poor manner. And so it's like, I think there's a reality there where people are doing, like, they're doing worse at outbound in a lot of ways, which is probably good for our business, but there's just a lot of noise. And so it can be hard for founders to figure out exactly what channel to invest in and all that kind of stuff too. But yeah.

[08:21] Rick Fernandez: Yeah. And I'll tell you some of the, for the audience that's listening, right? Like some, I want to double-click into You can have the best tool that's winning across other states. You can have the best call, but you don't do proper follow-up or you don't send a thank you or you don't send the demo that they asked for within 24, 48 hours. Like, the folks we are talking to are busy, right? Like, Rick, when he was a superintendent, was probably getting 200, 300, 400 emails a day from vendors.

[08:57] Bobby Offterdinger: Yeah.

[08:57] Rick Fernandez: If you're not on it right when they are interested and you just talked, that is a barrier because now we're relying on them in 48 hours to remember that they talked to you 2 days ago. And we're all parents on the call. Guys, I don't remember what my kids had for dinner yesterday, let alone what I had for dinner yesterday because I have 20 to 25 calls a day. Make it as easy as possible for folks to remember they just talked to you, right? So like some of the basic things. But Rick, something that Bobby said was all things CTE, all things workforce. I know that's kind of your jam and all things Texas. I wonder like, what are you seeing on the ground where that's getting people to respond and like what's resonating out there? I know you and I and the group always talk on all things CTE. Yeah, I mean, I've probably been saying it for 10 years now. It just took a little longer to get here. But, you know, one of the beautiful things about CTE is that it cuts down all the political issues, right? Because everybody wants to take, you know, credit for any type of growth in programming or workforce or certification. So the economy is always kind of on the forefront. A lot of states, including Texas, have incentivized that CCMR, that Career College Ready, however, you know, however, whatever acronym your state uses. And we get additional funding here in Texas if we meet certain goals and outcomes. And so in a state that's hurting for funding in terms of our public school system, it is a huge win to recoup some of that lost funding for students. And I mean, and we're not talking like, you know, a couple hundred thousand dollars. We're talking most districts are missing out on millions of dollars. And a lot of it is strategy, master scheduling, programming, continuous pathways, all of that stuff that kind of you got to get in the weeds on. But if you're willing to do it and the tide seems to be turning at the higher ed level as well where they're struggling, so all of that market share is up for grabs in my mind. So community colleges and workforce programs should be licking their chops across the country. And any, you know, edtech or service providers that live in that space really, I mean, it's never been so good to be in that market. So, and that's why I love it because I knew this time was coming. It just, it just took a little longer than I first expected. So great question though.

[11:32] Bobby Offterdinger: I think it's also ripe right now because there's a few legacy products that have not innovated that well in that space as well. And so There's like the market's ripe for it and then there's just people are dissatisfied with current offerings. And so there's, yeah, there's a couple that are popping up right now that we're working with that are, you know, it's, they're just really awesome, cool products. And, but everybody can come up with like a cool idea, but the fact that it's really fitting a need and there's an existing incumbent that just isn't cutting it is a recipe for success. Yes.

[12:09] Rick Fernandez: No, I mean, you're, that's right on point. I would make the argument that most of 'em are, misaligned with the persona that they should be marketing towards or targeting. I do not believe our high school counselors are the place to be working with in that regard. And everybody seems to think that. And like, that's a— in Texas at least, that's almost 100% of a fail because they don't have time to be diving into the CCMR component. That's usually at the academic chief academic officer or something along the lines at that executive director level. But Matthew, what are your thoughts? I mean, you get to, you're working with all of your clients like this, you know, constantly and seeing kind of the backend and the progressions. Any thoughts on what Bobby says? Are you seeing the same thing? Yeah, we're seeing very similar when it comes to CTE. Those shows are doing very well. You know, we're seeing a lot of conversations around the tech lash, We're seeing a lot of conversation, hearing a lot of conversations around, you know, we want to get our kids off of devices more than putting them on devices more, right? And I'm curious, Bobby, you know, we're touching on a lot of different components of go-to-market. Is there a framework that you guys use or what questions do you ask founders in helping them develop a go-to-market if that's something that you guys do? Because to your point, yeah, anyone can get an Instantly subscription and send cold emails. They're not gonna be good. You're gonna hit spam. And that's why everyone says cold email doesn't work in K-12. But if you're starting there, I think we'd all agree that's probably the wrong place to start. It all begins with go-to-market. Would love your thoughts.

[13:55] Bobby Offterdinger: Yeah, I think we, we kind of bucketed into technical founder or like salesy founder, right? And so I happen to have been like, I'm a salesy founder, right? Like I'm not as technical as like our go-to-market team and all that. I'm not operational. That's why I have like a COO and all of that. But to use like my own example, I've been good at selling. I'm able to do that well. Some founders we talked to fit that bucket. Some of them in the early stage I'm talking about are Have a great idea. They built it up and all that, and they think it's just gonna sell itself. So how do we how do we help those founders in particular go back to that message market fit? And so some sometimes they don't have PMF yet. They haven't even like gone to market, but we can start with trying to figure out what the message market fit is. And for us, that formula is how do we draw the line between a specific person's pain point at a school district and a specific feature or solution that you have in your product. And that's it. Because founders want to just brain dump the whole thing. It's like your cold email is the size of the Bible or something. It's like this long feature dump, right? As opposed to like, hey, here's what we noticed about what's going on in your district. We can do this. Is that top of mind? That's it, right? And it's like, just lead with that kind of curiosity and connect that. And then you take that and you just do it at 100x and ABCDEF test the hell outta everything using conversations and email. And then all of a sudden you start to figure out over a couple of months, here's what actually matters to people and here's what doesn't. Then you can crank the volume on that.

[15:40] Rick Fernandez: I love that. And I'm curious, have you found with K-12 specifically with cold email, Are you guys running soft CTAs, call to actions, lead magnets? Can I share this report? Or are you finding that there is a lot of success with the hard CTA, book a meeting?

[15:57] Bobby Offterdinger: We try both and then it's kind of product dependent, we found, and like persona dependent as well. In some ways, curriculum directors, like busier people, like, like, you know, CEOs and things like that. I mean, everybody's busy at a school district, but the busiest of the busy, In some ways they actually want the hard CTA because they're like, yeah, this is worth my time. I'm going to book a meeting right now.

[16:24] Rick Fernandez: Yeah.

[16:25] Bobby Offterdinger: Versus like they don't have time to read some lead magnet or something like that. Right.

[16:29] Rick Fernandez: They don't care.

[16:30] Bobby Offterdinger: But to answer your question, we try both and then we figure out what's resonating the most. We still, I mean, I've told Jacob this before, at the end of the day, like 90% of the meetings we book are on the phones. Like phone is king in K-12. And so that's just an important thing to know is You can spend hours agonizing over your different email sequences and all that, or you can spend hours calling school districts and you're gonna get better ROI doing that, I think, in my opinion.

[16:56] Rick Fernandez: And I'll tell you, I think for the audience, what Bobby just clicked into, right? Like for the marketing teams out there, close your ears. Like you can agonize hours and hours on the perfect messaging and does this look good and is the image good? And unfortunately, most folks that are really, really busy are not going to read your emails, right? Like, that is hard to swallow, and it hurts my heart because I do email outbound too, but nobody's going to read it, right? Like, is it— is it solving something? But Bobby, uh, something you said that like, uh, speaks to my heart and all the founders I work with, right? Like, think, you know, traditionally when I started my business, I used to set up these 1-hour meetings with superintendents, right? And I was like, Man, an hour's good. We can like build a relationship for 30 minutes and then we can like tell them about, and then I was like, do we need an hour? I think we need 20 minutes. So now everything I do is 30 minutes and 10 minutes is like learning about them doing this and then asking if they can talk about, you know, their solution and asking if they can demo and all this stuff. But I, one thing I wanted to double-click into, Seasoned founders, new founders, seasoned VPs of sales, you name it, all want to product dump all features on everybody right away, which I'm not saying is not good. Sometimes that's fine, but for most, right, they're not listening to what a district is actually needing to solve for and then positioning the solution to be like, hey, I've read in your strategic plan that you're trying to work on math scores. Tell me more about that, right? Like, I am seeing some outliers between some student populations. Like, that is a much better conversation than let me tell you about all the things we solve for, you know, like night and day different, like listening for signal versus just talking at them.

[18:59] Bobby Offterdinger: The reality is, is that you can go on to ChatGPT right now and ask them, what does this product do for me? Like, they're like, you're gonna know before you get on the damn meeting. Like, the buyer will know that. And so it's almost like insulting that you think you have to like product dump it or something like that. Like, there should be like a couple of little features that maybe you want to talk about. But you're right, Jacob. Like, I don't know why we've moved away from— if you want to label it as solution selling or whatever, but at the end of the day, it's just like being genuine and being curious and It's just asking questions that, and having like legit empathy for the people that you're talking to, like actually caring. 'Cause everybody can tell if you like really care or not. Like, I'll go backwards. So I, when I was a teacher, we had this Character Counts curriculum or something. And one of the things we taught, one of the, it's called Habits of Mind actually, is this woman named Benne Kallick. She started it back up. She's in New England. But anyways, one of the habits of mind is listening with empathy and understanding. And that's like my mantra. Like you have to listen with empathy and try to understand what people are saying. That's how you sell. Like, that's it. It's like literally just be empathetic and listen to them. And then if you can solve their problem, talk to them about it. And if you legit can't, don't BS them. Like point them in the right direction and then things come back to you. Right. And for us, like, I think there's another thing you brought up is really interesting is you should know what that strat plan says. You should know what the discussion was on the cold call before you go into the discovery meeting. You should have done all that research. It's so easy now. MCP into Starbridge or into like our dataset from, to get the stuff from the cold call. It's so easy to figure out what's going on at a base layer of what's happening within your prospect's world. And then you can dive right into the meaty questions around like what's bothering them day to day.

[20:48] Rick Fernandez: Bobby, I mean, this is really for the question for the group because I've just thought about it a little bit as we've been talking here. So You know, I still believe that there is a lot of business done just in, you know, referrals, right? A lot of my colleagues will ask me about certain things and do you have stuff for this or what have you? So I know that's still a very powerful way of doing business. My question, I guess, Bobby, if you want to take first crack at this, is the different types of solutions. So like a, like a SIS or an LMS, right? Is that more of a relationship-needed type of sale? Like, do you have to weight the value of your different mechanisms based on the product? Because obviously, you know, ASSIST is usually 18 months, somewhere in there to try, I mean, to try to get it, you know, done, where some other things can move a little bit faster. And it would feel like, because when you're implementing something like that, it goes across the entire district and everybody's got to have a, you know, a piece of it to say their opinion. So that relationship or the ability to have a kind of a Jacob to lead you in and start in a certain place, does that matter differently based on the product?

[22:04] Bobby Offterdinger: 100%. Yeah, I mean, you think about it like, just like any product out there in the consumer world, it's gonna sell differently. Like there's a different channel for different types of products, right? So like imagine trying to cold call sell an SIS. Can you imagine a CTO being like, Yeah, I'd love to demo a new SIS right now. Like, no, like nobody wants to deal with that, right? And so it's, it's like, yeah, 100%. And I think it goes back to like the fact that there's so many ways to do this. Like you can cold call, you can email, you can work with somebody like Jacob, you can do conference, you can do AI search. And most of the people we talk to, there's, you know, there's, let's say there's 20 different ways to go to market. Most founders are either fixated on one thinking it's the way to do it, Or they're spread too thin across like half of them. And you have to figure out like how much bandwidth do you have to test? And then when it's working, you kind of, you crank it. But yeah, it's totally related to product amongst other things. Can you do product-led growth? Is it a building-level thing? Is it a district thing? Is it an 18-month sales cycle? Can you get underneath the procurement cap and sell for $5K? Like all those things matter when you're choosing what channel to go down.

[23:10] Rick Fernandez: You know, the pain, it seems to be, you know, everybody talks about like trying to find the pain, your potential clients, whatever they're going through. Has that really changed? I feel like it's the same pain that we're always kind of living in education. It's a budgetary thing. It's a, I need to do more with less, or I need to really develop our efficiency and really understand what's happening at the student level.

[23:44] Bobby Offterdinger: Yeah.

[23:46] Rick Fernandez: But it feels like we're still missing some of, like, people don't really understand how to dial into that. What's your take on, like, shouldn't the pain be pretty evident to anyone in the market or even founders that are about to go into the market? It really had, in my opinion, hasn't changed a great deal in terms of what's going on in districts that need support.

[24:10] Bobby Offterdinger: Yeah, I mean, I think it's a yes and a no in some ways. So like, yes, like the biggest problem somebody at a district level is facing is lots of pressure, not enough time to get my job done. And then who's putting pressure on me? Is it like, is it students that aren't performing the way we want to? Is it the community is up because something happened? Is it like, it's that, like that's the constant, but You know, 6 years ago we weren't dealing with the cell phone question of like, you know, how do we help with kids with cell phones in schools? And that's like a new, newish problem that people are trying to solve for. And then you got like the idea of all this AI stuff coming out and we've got districts now saying like, hey, we're not gonna do AI. Or like, how do I do an AI policy? Like, so there's some things that are new just because of the growth of, of, uh, you know, of tech and all of that.

[25:05] Rick Fernandez: Yeah.

[25:05] Bobby Offterdinger: But in general, I agree with you. Like the pain is constant and it all comes down to wearing multiple hats and not having enough money to do what you want to do as a department leader and things like that.

[25:19] Rick Fernandez: Yeah, agreed. Bobby, I'll tell you something you hit on, right? Like the research side of it. I remember COVID times without AI being present. being stacked, right? I had at Varsity Tutors, RIP, I had a group of SDRs booking me meetings. I booked my own meetings. So every half hour I just showed up being my authentic self. And my goal was not to sell anything. It was listen, give them enough info where they booked the second meeting, right? Like my measure of success for me personally, this wasn't like a directive from the company, was Can I get them to agree to a second meeting? If I can get them to a second meeting, then I can actually do a deeper dive on all the things that we talked about in the first meeting. But with this idea of research being so easy now, right? You can set an agent free. I have a daily recap coming into my email of like, here's everyone you're meeting. Here's the last conversations you had with them. Here's what they're working on. Here's what you talked about last. That is so easy now that like, I wonder why some folks, even that I work with, they don't do it, right? They rely on me for the backstory of this person at the district and why they agreed for the call. And sometimes I'm like, y'all, let's do some research in advance and let's try to figure out who this person is. But like one prime example for the group, Wes at Orange County Department of Ed, You know, he's real gracious with his time. If there's a real interesting AI tool, he likes to look at it for me. But when he's on with a founder, he literally starts calls and says, I've done a Perplexity Pro search on you and the tool. Is it true that you did X, Y, and Z? And for my founders, I try to tell them like, he is gonna come prepared for this call. He will be more prepared than you. Show him that you've prepared for this as well. That is how you get his buy-in. Off the bat, not everybody is like Wes. He is a one of a kind person. But like, why do you why do you think that with everything being so easy and at your fingertips now, are folks still not coming into meetings prepared? Is it overwhelm?

[27:42] Bobby Offterdinger: Could be a multitude of things. My opinion of it is that there's there are still some. people that think that, again, like the product will sell itself and I— all I have to do is show up and like, who wouldn't want to kiss my baby, right? Like it's something like that. So there's a little bit of that maybe ego, is that the right word? Maybe a little bit of that. But it's also just going back to that acumen. Like it's easy maybe for you and I, Jacob, because we sold for a decade to know what we need to know before a meeting and know that I'm just trying to get to the next one and to know to lead with curiosity. Maybe it seems obvious to us, but maybe not so much to others. I think I know you and I have talked about this separately as well. Like, it's— it can be challenging for people like you and I who are like, our entire job is to help get you at that and to help you. What I can't always do is help you hit the home run, right? And so like, how do we— How do we help? How do I help people like become good at actually Mapping up that pain point with the solution and all that, it's hard. Like selling is not that easy for some people. So yeah.

[29:00] Rick Fernandez: Bobby, I'd love to move towards the work you guys do with SDRs. And can you share when is an appropriate time for an edtech to invest in SDRs, whether outsourced with folks like yourself or bring them in-house? And then also just if you could speak to the responsibilities of SDRs, I'm sure everyone on this call, we've had those instances with founders where they wanna hire their first salesperson. They expect them to do the laundry list of tasks and close business only on commission. And it's like, well, you know, maybe you'll find the unicorn, but you probably won't. So would love to just see your framework for installing SDRs, ramping 'em, And helping business owners make that decision.

[29:48] Bobby Offterdinger: Absolutely. And it's probably been what we've focused on the most in 2026, right? That's the name of the game is figuring out how to provide a super efficient SDR service. And here's how we currently do it. And then maybe I can tell you kind of how we got there. We believe fully that The traditional SDR role needed to be segmented out into multiple people. And so traditionally, I think about SDRs back in like my sales days, like they were expected to generate the list, find the contacts, research the contacts, make sure that we have the right call script in place, all that. And everything that's on my hand right now, we do with AI. Like all of that, and I'll explain a little bit more about how we do it well if you want. Like later on, that's go-to-market engineering. So go-to-market engineering for us is the act of teeing up that action. So the SDR, an email, a LinkedIn message, shoot, even like telling Jacob you need to go talk to this person and open the door. Like what? Like this? Whatever that action is, that's what go-to-market engineering creates. And so. That part we segment off. Our SDRs don't do any of it. Our SDRs are literally just dangerous on the phones. They do not do anything on email. The only thing they need to be good at is being super curious when they get ahold of a district contact or whoever that persona is and leverage super relevant information to show that they know what they're talking about and quickly get to that curiosity and that pain point to help Like to help basically close that and get the meeting booked. So we segment that out and that's actually been a dramatic improvement in an agency model like we have. It's just good business, but then it's also just great for people to focus on a smaller set of skills versus having to be like good at all of those different things.

[31:54] Rick Fernandez: Do you, so it, If the tech is getting better and the go-to-market can be deployed through AI, does it make sense that where things are falling apart are either the actual sales meeting or maybe the cold calls, like the people interactions? Is that where the bulk of the time should be spent on training folks? And if so, why is— why does there— I don't, I don't really see a ton of— maybe I'm— and maybe I'm just ignorant of it, but I don't hear about or see a lot of just straight sales training or role-playing interactions. You just don't see that type of work going on. Or maybe it is and I'm just ignorant of it. But just your thoughts on, well, for getting better at all of these other motions and items and getting hyper-efficient on being able to pull the data and be prepared. Why aren't we spending the other time with the actual training of the people that are having the conversations and relationships?

[33:01] Bobby Offterdinger: I think some orgs are, Rick. I think the smart ones, the ones that have good strong sales leadership and all of that, it's happening at the manager level. Like, I think that those SDRs and that manager, the manager no longer has to be helping with that leadless pull and all of that. Like, they actually should be able to lean in more and provide coaching. And I think in general, when we think about how AI has impacted the world, we should be thinking about that even from a teaching standpoint. Like, should be able to have more teachable moments with students if you're leveraging AI efficiently in a dream world. But I think it's happening at that level. But I also think what we've seen is the decline of the super expensive consultant that's like charging $100 grand to some business to come and like do 3 sales kickoffs and then like do a coaching session with like your team every month or something. And you know what? Good riddance. I think it never was that great and it never was personalized enough. For us, what we do internally is our SDR managers need to be spending the majority, like 50% or more of their time coaching SDRs on their skills on the phone. And we've been able to do that better by leveraging and creating software internally that allows SDR managers to know exactly what they should be coaching on by listening to the call transcripts, knowing what our framework for cold calling is, and then just basically analyzing it like that. So there's a lot of opportunity for businesses to either work with something like Gong or invest in their own, you know, vibe-coded, if we want to use that word, but software to help them improve on a daily basis for those human interactions, to your point, Rick.

[34:41] Rick Fernandez: I mean, are you guys, is it a formalized process of hearing what is said and then kind of redirecting how that conversation needs to go? I guess the reason I'm asking you, or is it more like, Uh, mentorship or like a, like a manager listening in on a call and then kind of giving some, some pointers, but not really a formalized process. Which, which of those are, are, are probably happening?

[35:06] Bobby Offterdinger: Yeah, I mean, it's a mix for sure, but we, we at least like from cold calling acumen, we don't believe in call scripts. We believe in, we internally, we call it sheet music. The concept was supposed to be that it gives like a guideline for how we should be approaching a cold call.

[35:24] Rick Fernandez: I like that.

[35:24] Bobby Offterdinger: Actually, I like it, but I also hate it as a musician because sheet music, unless you're doing jazz standards, actually like really script. So I'm like, our business development director Trevor came up with it and he's not a musician, but I haven't given him too much shit about it. But anyways, so yeah, we call it sheet music. And the concept there is that it's, it's, um, it's a set of, of potential pathways that a conversation might go. But at the end of the day, like human interaction is not something that you can predict, uh, as well as, you know, maybe AI wants you to be able to. And so you also just have to have the right kind of personality and at the end of the day, just be curious. Like, just be curious about what's actually going on in another person's world and everything from there can fall into place.

[36:08] Rick Fernandez: I think this is a good segment into something that's like top of mind for me. Yesterday I was on this COSIN advisory. I'm on the K-12 advisory board for COSIN. Mind you, I don't know how I got on that board. It's all CTOs, superintendents, assistant So thanks, Cosin, for letting me on. But I'm sitting and doing a ton of learning from folks in the field that are living it, right? And yesterday they had somebody on to actually train the group on storytelling. And A, that's literally like speaks to my heart because all the founders I work with, I'm like, what's the story we're telling on this 30-minute call? A, what is the story I'm telling to get us on the phones with them or on a Zoom call? B, then we have them based on some story we told them. What is the story that they're going to leave with remembering, right? And what's fascinating on that call, they started with an icebreaker for the group. And I don't know about you guys, I hate me some icebreakers on calls, like put your name, where you're from, what temperature it is. And I'm like, I live in LA, it's 80. Sorry for everyone not experiencing Los Angeles. But this one was go to your favorite AI And ask a question about, from all that it knows about you, what TV show character or movie would it identify you as? And I'm not gonna lie, it was pretty good to the point for me, of course, it was like Ari Gold, Jerry Maguire, and Phil Dunphy. And I liked the Phil Dunphy. At first I was like, really, Phil Dunphy? And I was like, well, I do post about my kids and dad mode and all this stuff. But it was funny to see the responses from people because they got like, you know, Ted Lasso, they got Leslie Knope, they got, and you know, Matt and I are in this EdTech Insiders chat. So there was a whole lot of overlap with people, but it got people like really, really engaged. And, you know, I took this to LinkedIn and I was like, hey, this is what I just experienced. You should go try it. And people came out of the woodworks. I had like 30 people text me being like, I just tried that. And I don't know if I'm, Irritated, mad, or kind of surprised, but like, okay, Claude, OpenAI, or whatever, Jebediah, whoever they used. Like, so I wonder for the group and not just for Bobby is like, how much do we think that there's just a lack of storytelling skills, which also kills me because these founders tell a great story when they're raising money. They tell a great story when they're hiring employees. They're telling a great story when they get co-VP, VP of HR or whatever, right? We're constantly storytelling. And mind you, storytelling is the same word as sales in my book. When I'm storytelling and I'm giving somebody some ideas, it's the same thing of I'm telling them about my ideas. It's the same thing I'm doing when I'm talking to my wife about what we're gonna eat for dinner or what vacation we take or all, right? Like we're selling constantly in our lives. So like I open it to the group, like, Where is the lack of storytelling? And mind you, I think we all probably have outliers that are like killing it.

[39:32] Bobby Offterdinger: Yeah, I think I'll take a first stab at it. When I think back to like the best salespeople I've seen, like, yeah, 100%. I think founders can tell a story because they went on a journey. And so it's easier for them to do that versus that first sales reps that they hire is not gonna Tell that that founder's story. They have to tell their own story, and it has to be relevant to what that that prospect is is actually thinking about. I think to add one, the yes and here is a good salesperson also needs to be able to get their buyer to tell their story also. So there needs to be storytelling on both sides, and it just goes back to that questioning. Like yeah, it sometimes as simple as open-ended questioning, but some. Sometimes it's just like, hey, can we just take a second? Like, what's going on? Tell me your story or something, something like that. Like just being really genuine and, and having that, that kind of moment. But yeah, I think storytelling needs to happen on both sides, but curious the rest of the group what you're thinking.

[40:31] Rick Fernandez: I think a lot of people just think it's mutually exclusive and that you can't have storytelling in sales, that you have to reserve that for pitching and when you're doing the keynotes. I also, to Bobby's point, I think there's a time and place when you're first getting into a discovery call. Founders that, you know, this is their baby likely will want to jump into this story too quick. And the prospect on the other side of the call who is there from a cold call, chances are they really just don't care and they're trying to figure out why they're there. So there's opportunities where if you get into that story too quickly, it's like, You're just stage hogging at that point versus the, to what Bobby just said, like if we're able to get the prospect to paint that picture and we can guide them through a process that's repeatable every single time, I think story can naturally come along for that journey simultaneously. Yeah. The, my take is that The stories always seem to take a very similar path, somewhere ending in, you know, I just want to give back to education. So it's got a— it's your story, but there's value in teasing out what's unique about you rather than about what you're— if their story is very similar to kind of what everybody else is It is, right? So I'm always more interested in in the people, and so if I connect with somebody that like like you know you see the my background is about basketball, right? So if I connected with somebody with who they are, that's to me more compelling than than most of the time of the story, right? Because I've heard the stories, and again, most of them end end on. We just want to help, you know, we just want to help kids make a difference, right? Okay, that's great. Um, yeah, we're all here for that, for everybody's here for that same reason. So, uh, I like to know who I'm working with, who they are, why they, you know, why do they get up in the morning, and, um, what kind of person they're going to be, uh, with my staff, more importantly than anything else. So just my 2 cents on it.

[42:48] Bobby Offterdinger: And I think the thing you just brought up, Rick, that's really interesting is like That's the difference between sales in K-12 and maybe like outside in the greater B2B. Like teachers at their heart and educators and directors and all that are, they're caring people and they like, they, there's not an ROI. It's like student improvement or like teacher improvement. Like, like, like versus a B2B going to buy some software. Like they probably don't care that much about like the sales rep's interest in basketball and stuff like that.

[43:19] Rick Fernandez: Right?

[43:19] Bobby Offterdinger: Like they want, But in K-12 sales, you have to build that relationship pretty quickly too, in order to kind of build that trust.

[43:29] Rick Fernandez: It's important. As we start to wrap up, Bobby, if you would be so kind, we'd love to do a little rapid-fire session with you on just some quick questions. And guys, please jump in as well. To start it out, What do you believe the most overrated lead gen tactic in edtech is right now?

[43:51] Bobby Offterdinger: My gut's saying cold email because of the way most people do it.

[43:59] Rick Fernandez: Fair. What's the most underrated tactic for lead gen? There you go.

[44:07] Bobby Offterdinger: Pick up the phone. Do it.

[44:08] Rick Fernandez: There you go.

[44:09] Bobby Offterdinger: Not enough people are picking up the phone anymore.

[44:11] Rick Fernandez: And then similar to that point, how do you get past a secretary when you're cold calling?

[44:17] Bobby Offterdinger: It's, for us, it's, we've seen a dramatic, like a 3x increase when we moved from a generic, like, hey, my name's Bobby, I'm calling to speak with Dr. Fernandez, moving from that to, hey, I'm calling to talk to Dr. Fernandez about the ABCD grant that was released last month. The difference between that was like literally a 3x pass-through. So it's actually dialing people with a reason and bringing that reason up with the admin.

[44:48] Rick Fernandez: Love it. Do you only dial office lines or do you ever dial personal?

[44:54] Bobby Offterdinger: Only office ever, ever, ever, ever.

[44:59] Rick Fernandez: There we go. What is the worst Actually, before this one, how do you define a signal?

[45:05] Bobby Offterdinger: Ah, such a funny word that everybody kind of treats differently. A signal for us is an event or a, it's a reason for reaching out for us. Like, that's all it is. It could be something like as older as a strat plan and you're like, wait, I do wanna go back to that. Or it could be what they talked about at the board meeting last night. But it's a reason or a relevant reason for reaching out that then drives an action.

[45:36] Rick Fernandez: Love it. We use the same definition, reason to reach out. What is the worst signal you think an edtech can use as a reason to reach out?

[45:45] Bobby Offterdinger: I think any signal that you don't do deeper analysis on is a really bad signals. So I'll give you an example. Like I was talking to a business that we're now working with, but before they were a Starbridge customer and they were like, anytime one of our competitors is mentioned at a board meeting, we're reaching out to them. And I'm like, how are you reaching out to them? They're like, we're calling them because they talked about a competitor at the board meeting. Sweet. What did they talk about? And it was literally like a PO that just got approved. It's like, well, that's a little bit late to the game, guys. Or it's like somebody, if somebody brings it up, they're like, hey, have you guys heard of this thing called Blah, blah, blah. Like that would be maybe be a good reason to reach out, but it's when you have a signal and you don't use your own data corpus to then analyze it properly to then decide what action to do. Like there's a missing step there. That's that whole go-to-market engineering piece that turns any good signal into a crappy one if you don't like analyze it properly.

[46:52] Rick Fernandez: What's the biggest time waster?

[47:00] Bobby Offterdinger: I mean, I'll go back to what I said before. It's like, it's marketing teams and sales teams alike spending way too much time on nuanced email copy when you're not even sure if you're gonna land in the primary box for one thing, much less like just nickel and diming little words and things like that. It's not, waste of time. Pick up the phone.

[47:24] Rick Fernandez: Very good. Well, Bobby, last question for you. Where can people connect with you to learn more about TAM to Target? And thank you so much for coming on, boys.

[47:32] Bobby Offterdinger: Yeah, absolutely. I appreciate you guys having me. Super fun. Back anytime you want. TAMtoTarget.com is an easy one. Connect with me on LinkedIn, kind of normal stuff like that. Yeah, like really at the end of the day, we're here to support businesses selling into K-12 with Outreach, and then also with their inbound leads with this AI search initiative too. So yeah, happy to happy to be here. Thanks for having me, guys.

[47:56] Rick Fernandez: Can you can you play us out of here with the guitar?

[47:59] Bobby Offterdinger: No, but next time I'll practice, and then I'll play you a little ditty, Rick. Whatever you send your request.

[48:08] Rick Fernandez: There we go. There we go. Put a little tip jar out as well. Well, Bobby, thanks so much for coming on Boys of EdTech. To all of our listeners, we hope you got some value out of this interview. Please like and follow. On all podcast platforms, and we will see you next time on The Boys of EdTech.