How to Rebuild an SDR Team and 3x Outbound Pipeline

Elric: Smile and dial. Don’t think too hard about who you’re calling, just dial more of them. That’s how most SDR teams still run in 2026. This SDR director took over a team that ran exactly that way. Four reps, no manager, just $200,000 in pipeline after four months. He threw out the playbook, and a month later, the same four reps were bringing in about 600,000 a week.

Elric: His name is Will Rohleder. He runs that team. Now, 14 SDRs at 88% conversion to opportunity pipeline. He works at TeachTown, special education software for school districts. In this episode, Will breaks down the system that replaced smile and dial, how he builds territories, his show-rate playbook, why he pays SDRs to move deals forward instead of just booking the meeting, and who he hires.

Elric: Enjoy the episode.

Elric: Okay, so everyone, thanks for joining. Today I have Will joining us. We are going to have a session on his system. I’m going to give some context around why I have Will specifically. So we are part of a community called the SDR Leaders of USA, and he was asking questions about the show rate that they have at TeachTown, actually.

Elric: It’s above 90%, and he was asking about is it good, can we do more? And then the conversation was really long. I think there are like 30 messages, something like that, so the conversation is really long. And I think Will was talking a lot about different things they are doing, about the metrics they have.

Elric: Will, thank you for joining us. Could you give us a quick intro and then we can start?

Will: Yeah, thanks for having me. So Will Rohleder. I am the SDR director at TeachTown, and I’ve been at TeachTown a little over two years. I started in March of 2024.

Elric: Okay. When we were preparing this, you told me that the numbers you have right now with your team are basically your experience working at four different companies on the SDR leadership team. So it’s experience, obviously, but can you give us some background about how you came up through TeachTown, and what is the stuff you are doing at TeachTown?

Will: I’ll skip a couple probably more boring jobs. I was a full sales cycle rep for a commercial insurance company, so literally ground up of cold calling all the way to closing and managing the book of business.

Will: That was pretty eye-opening in a lot of aspects in terms of what is beneficial outreach, and then how do you find the right prospects and clients and close them, which I think in turn goes with my first job as an SDR, which was at a company called Jellyvision. It was not what I would call a personalized approach or a unique market.

Will: It was selling an add-on to HR systems, so any company over 50 people was a prospect. That’s a lot of companies, so very much was like a smile and dial. Don’t necessarily pay attention to who you’re calling, just call them. After that, I left Jellyvision. I went to a company called Backstop. I was in the SDR role for five months before I became a team lead, and then two months after that, I was the SDR manager.

Will: I was the third SDR ever hired there, so I kind of built it as an SDR. Managed there for a little over a year. Went to a company called InstaWork. That was another smile and dial. Where Backstop was very unique, it was fintech, but it was venture capital hedge funds. Only businesses that managed a billion dollars or more in assets.

Will: There’s not more than 10,000 of those. There was roughly 4 to 5,000 when I was working there, so unique. You had to be very personalized. And then went to a company called Multiplier, another HR software company, smile and dial. Now I’m at TeachTown. What we do is we sell special education software, which includes curriculum, IEP tracking, a lot of other very special education specific things.

Will: But you only have school districts, so again, back to a finite number. Very unique market, very unique ICP, and that’s a high level overview of how I got to TeachTown.

Elric: Okay. So you talk a lot about smile and dial, which I think today we’re not going to talk about that specifically. We’re going to unpack the stuff you’ve been doing with your team.

Elric: Let’s talk about when you joined TeachTown. When you took over the team, how many SDRs did you have on the team? Because right now I think you have 14 SDRs. So what was the state when you joined TeachTown?

Will: When I joined, like I said, it was March of ‘24. They had hired four SDRs without a manager between November and December of ‘23.

Will: From December of ‘23 to March of ‘24, they had only built 200K of pipeline, and no direction, reaching out to multiple states all over the place, not a whole lot of guidance. So I came in and actually introduced a system. The first thing I did was I shrunk everybody’s territory from either one state to three states, depending on what states they were.

Will: I introduced how we’re going to all start to work out of one, well, we use Gong Engage, so one flow or sequence or cadence, whatever you want to call it, but one actual form of outreach where it’s more standardized rather than everybody doing their own thing. We got messaging on track, and I aligned SDRs to AEs, where before they just supported every AE across the organization, which for four SDRs and roughly, I want to say at the time it was 18 AEs, was not very sustainable, and which is why they were really struggling.

Will: So I joined in March. By April, we were now starting to do 600K in pipeline a week, just with those same four SDRs, maybe a month turnaround of the systems I implemented.

Elric: What did you see? So basically they could prospect the full US, and then you start to implement some specific territories, for the best territories basically.

Will: In the education world, there’s certain states where generally they have more money to spend, but not only that, they have a higher student population.

Will: For us in special education, the breakdown is roughly 3 to 5% of your entire enrollment in a school district is the moderate to severe population for disabilities, which is what we service. We looked at the higher densely populated states, your New York, your Texas, your California. Those were our three first targets.

Will: How can I cover those? After we cover those, what states do we generally have a higher win percentage, and how can we throw more fuel on the fire? Your Pennsylvania, Michigan, Illinois sort of states as well. So that’s what we determined, where are our highest need states? Where are we getting the most dollars from?

Will: And we’re going to start there first. As the team grows, we’ll then work our way down that list until we have your priority states covered. No offense to Nebraska, but there’s not a whole lot there other than corn, so just not a priority, which is why we don’t really focus on it.

Elric: You were talking about the four SDRs for 18 AEs.

Elric: So what did you change? Do you have a pairing? Maybe not a pair because with four SDRs and 18 AEs. But did you have one SDR working with four or five AEs? Or what was the ratio?

Will: Yeah, that’s a great question. So when I started with the state approach, it was how many AEs are in that state.

Will: So at the time, we had two AEs in Texas. That one SDR working Texas, because it’s so big, it’s such a massive state for us, one SDR, two AEs. California was three. One SDR, three AEs. And then when I was looking at New York, it was one AE, so I added on Pennsylvania, one other AE. I prefer a one-to-two or one-to-three approach.

Will: I think it limits the one-on-ones that they have to do. I think it also narrows their scope, and they have a very clear path forward. Also, generally the AE in the same territory, like the two in Texas, they’re kind of on the same page of what works, so you’re doing the same thing with those AEs. You’re not doing completely different strategies for two different people.

Elric: Now let’s talk about more numbers. So I know from the thread, to give context for those joining now, we are talking about some metrics. The show rate you have is 92.7%, and you are aiming for 95%, conversion to opportunity 88% and pushing to 90%.

Elric: Could you talk about that specifically? Do you want to start with the show rate?

Will: I think as someone who was a past SDR, I hated it if I booked a meeting and they didn’t show up. I’m sure everyone does. It was personally pissing me off. It felt like a slight against me as a person.

Will: So some of the things that we implement, I’ll start with cold call. I think email is different, but if you’re getting a meeting via cold call, the biggest thing I push on, and it is not about us, the SDR, the organization. It is all about the prospect. So I think what really attributes to our show rate is all we do is we try to talk about them.

Will: We very much try to talk about what is your pain? What is going on? And then how can our solution help to solve that and tie it back. But I like the metric of 70% they’re talking, 30% us. As we’re talking through it and we’re getting them to kind of buy in, in an ideal world they’re going, “Man, it sounds like you could solve our problem. I want a meeting,” and they ask for it. We do get that to happen, which I’m always excited to hear about. But as we’re going through and we’re booking the meeting, we’re always recapping. “Hey, I know we’re going to meet two days from now at this time. I heard that XYZ is a problem. Here’s how this part of our solution will solve for it.

Will: This part, XYZ, is also a problem. This is how we can help with this,” and we’re recapping in that. While they’re on the phone, I always ask my team, “While you’re recapping, I’m going to send you a blank calendar invite, and what I would appreciate is if you could accept it. I will fill it out with the Zoom link.

Will: I’ll fill it out with the agenda. I’ll add on my product specialist, but can you just hit it so I know I hit your inbox?” Nine times out of 10, which goes with our show rate, when they hit accept, they’re always showing up. They’re like, “Yep, I saw it.” Most of the time, if they’re not hitting accept, they’re like, “We don’t have it.”

Will: And then it’s, “Okay, well, did it go to your spam folder?” We’re doing that sort of rhythm and roll. Or they just go, “Nope. I don’t know. I don’t see it. Well, I gotta go,” and they weren’t a real prospect, or they weren’t going to show up to begin with. But via phone call, that’s what we start with.

Will: We use Google. I like the 10 minute before notification. I also like that you can add another notification for a day before. That has been super helpful, where we get people who are like, “Hey, thank you for the reminder. I actually have to reschedule. Can we do that now?” It does help with, if anyone is going to reschedule or no-show, how can we get ahead of that as quick as possible? We do have some reps who will send an email 24 hours before and call. They’ll call and be like, “Hey, just wanted to make sure that you’re still available for this. Cool. You are? Sweet. See you tomorrow.” Pretty quick follow-up there. So it kind of sounds like a lot, I think, but I would rather you put in all the effort to get the right person and have them show up than not.

Will: Part of our show rate, I think as well, is how well we attack our ICP. We’re very, we know exactly who we need to call. If I call a gen ed PE teacher, they’re not going to show up. Why do they care about special education? Like, that’s not going to happen at all. So us knowing we need the special education director, the special education coordinator, assistant superintendent to special education, those are the right people and these are things that we can solve for.

Will: So really getting your ICP correct has been huge as well.

Elric: Yes. That’s a good point, because most of the time when you start checking the quality of the meetings, you can see really quickly if it’s on target, on ICP. Sometimes that’s the reason why the no-show rate is higher for those meetings.

Elric: Something I didn’t ask you, the first meeting, is it on the call, is it the first call with the AE, or what’s the process for you?

Will: The call that they’re setting up next, I like every SDR to be on the call, but they don’t have to be. Generally, it is the AE who is running the show.

Will: I want my SDRs to be in lockstep with their AEs. I want them to hear what AEs are saying on the call and what prospects are saying, especially since it is so regionally based, working with this district. What about the school district literally next door? Are they having similar issues? So I push for SDRs to have a bigger role in it, ask questions as well if the AE is good with it, and be a part of the actual discovery process.

Will: But otherwise, it’s mostly the AEs.

Elric: Do you ever do a handoff, like you said on the phone the intro for the, you said that you are going to put them in touch with a product specialist, but do you send like an email to introduce the account executive?

Will: We’ll do a couple things on the handoff.

Will: If it’s a call, we’ll send the Gong recording to them. We fill out BANT like, “Hey, here’s everything I have. You can also go back and listen to the call.” If it’s an email thread, we don’t just say, “Oh cool, you said yes to a meeting.” We do go back and try to qualify as well, like, “How many students do you have?

Will: What are you currently using?” Stuff like that to really hone in on what is going on via email if they say yes. But we forward that entire thread to the product specialist. But to answer your question, yeah, we do a, “Hey, this is…” I’m going to pick on Melvin because I see his name in the chat. “Hey, this is Melvin, my product specialist, and really looking forward to talking to you about XYZ, XYZ, and how we can solve.” Like, we’ll recap again in that introduction email.

Elric: It’s really interesting here, because recently I shared a newsletter about this topic, show rate specifically, and the first thing I’m seeing mainly on calls, it’s a reason to be on the call for the prospect. Most of the time the SDR pushes for the meeting and the prospect, they don’t have any reason to be on the call.

Elric: So maybe they are curious, but we couldn’t find any problems mentioned by the prospect on the call. And here it sounds like you are really trying to unpack some problems and then if it makes sense, move forward to another conversation, which is, “Oh okay, you are saying that you can help me? So okay, I have this problem and maybe you can help me with that.” So it makes sense for them to be on the call. Every time the first time I’m seeing on calls, they are pushing for the meeting, but they have no reason to be on the call. So I think this specifically, if you think about the buyer journey, it’s a reason for them to be on the call.

Will: We do a ton of research prior to reaching out. Probably one of the biggest things I am a proponent of is you should go into your call with some sort of intent, like, “Hey, I’ve done research on your district,” and maybe even on you as a prospect, depending on your title in the school district.

Will: But I know it’s a very unique market, but for us, every school district has to have a strategic plan. What is your plan for the next three to five years to improve things? We look that up. You do a quick use of AI, Gemini, whatever. You go, “Hey, summarize this and how it relates to special education.” We find that, and then we’ll send emails around it.

Will: We’ll make cold calls around that, and at least that’s a jumping off point for us.

Elric: And you are talking about calls. Do you do something differently for email, or do you use LinkedIn, or maybe not because I don’t think it’s an industry super active on LinkedIn?

Will: Yeah, we use LinkedIn.

Will: Generally the education space isn’t very heavy on LinkedIn. I mean, we still use it. We give it a shot. I have one SDR who recently has had three meetings set over the last month, and that’s three more than we’ve had in the previous two years. I don’t know what she’s doing differently. We’re trying to unpack that just with the fact that she’s gotten three, but hey, I’ll take it.

Will: Our emails are a little bit more scripted, I would say, in terms of, “I found this. Is this still an issue? Is this still a priority?” Where the calls can be a bit more flexible of like, “Hey, I was reading your strategic plan. Is that a top concern for you? Or what is a fire that is going on right now in your department, and what is your plan to solve for it?”

Will: If we can talk about what is the issue right now, nine times out of 10 they’re also more interested in fixing that right now, because that’s the biggest pain point, and their long-term strategic plan is still something we can also solve for.

Elric: Do you see a difference in terms of show rate between emails and calls?

Elric: Is it similar for you?

Will: It’s roughly the same. Emails I would say probably actually a little bit higher generally. We’re probably closer to about 95% and actually showing around 91%, maybe 90% for phone calls. We do set about 95% of all meetings over the phone, so 95 to 60% via phone and then 35 to 40% via email.

Will: So that’s where a little bit of discrepancy comes in too.

Elric: Now I would love to focus more on the conversion rate from first meeting to opportunity. You are talking about BANT. Do you use BANT with your team? Or does the AE team also use BANT or do they use something different like MEDDPICC or MEDDIC?

Elric: Let’s unpack your methodology on this.

Will: Yeah. The biggest thing that we focus on in the SDR team, we do use BANT as an organization. The biggest thing that the SDRs focus on is authority and need. Time is somewhat important, but it isn’t the biggest thing that I have them focus on.

Will: If you can get a, “Hey, we’re really interested in doing this for the next school year,” cool. Our timeframe is pretty short, let’s get to it. If it’s, “Well, maybe we do it for 2027, but we won’t do it for the first semester.” Okay, we have some more time, we’ll get it if we can. Truly the need and the pain is our biggest thing, and then we know our ICP.

Will: We know if we have a SPED director, they do have authority, they will be the person pushing it forward. So we do know the authority before we’re going into the call.

Elric: What do you use from BANT? Do you connect BANT to the compensation plan, or is your compensation plan based on the stage of the opportunity?

Elric: Could you explain what’s your comp plan first, and then how it’s connected to your process?

Will: Yeah. I think a big reason this goes back into the conversion rate, of why our conversion rate is so high, is because 50% of the SDR’s comp plan is tied to the opportunity getting opened, and then that opportunity making it further along into stage three.

Will: If it doesn’t make it to stage three, they’re missing out on 50% of their comp. So with that tied into it, yes, the BANT is obviously important, but if they set up a discovery call, okay, you get paid on a discovery call and someone’s showing up, but you’re missing out on the other half of your comp because there’s no opportunity open.

Will: So they’re very driven to get feedback from the AEs, like, “Okay, I thought I had the SPED director, I thought it was the right person. What do I do from here? How can I help us get pipeline out of it and get an opportunity out of it?” And then they go back. Maybe it’s I need a superintendent.

Will: Maybe we didn’t hone in on what the pain was enough. Maybe they also want coordinators involved, so what is it? Do we go back to the same person or we go back to others? And they still only get paid on the one discovery call, even if they set up a second one. I’m not going to pay them twice on it, but they’re really driven to get an opportunity and to get that opportunity to move forward.

Will: So even after the discovery, they’re trying to set demos. After the demo, they’re trying to do follow-up, like, “Hey, do we need to do another demo? Do we need to set up anything else with anyone else on your team?” What can I as an SDR do to help drive this deal forward for my AE, or is the AE handling it and I just get paid on it moving forward because I set a good meeting.

Elric: Who owns the decision about what moves to an opportunity stage? Is it specific enough to say, okay, is it moving to the opportunity stage, or is it based on the AE saying this is qualified or not qualified, for example? I’m saying that because recently I’ve seen on LinkedIn, an AE talking about why an opportunity is qualified or not qualified for the SDR they’re working with, and I said, “You shouldn’t make the decision. This should be black and white.” It should be, “Okay, we have the right person on the call. They have a specific problem, a specific need,” whatever methodology you are using. So normally it should be black and white. It’s not like, “Oh yeah, I feel this is a good opportunity or a bad opportunity.”

Elric: No, a good opportunity is, and then you have specific criteria. Do you use this for that, or what’s your process?

Will: Yeah. So the AE is the one who owns moving the stages. I don’t allow SDRs to open opportunities. I took that permission away, well, I asked our Salesforce admin to take it away, but I don’t want them having any opportunity to do so. In that qualification though, there are very clear guidelines.

Will: Must have the right person, must have demoed. It’s six different bullet points, and if four are hit, then based off of that, the stage does get moved forward, so the SDR can get paid.

Elric: We have one question from Melvin, actually. He’s asking about compensation on closed/won. Do you have something on closed/won already? I think you told me not yet, but.

Will: No, not yet. I did at my fintech company. They were paid 0.25% on anything that they sourced and went closed/won.

Will: Those deals were in the 300-ish K to 4 million range. So 0.25% was a nice little bump, and the deal cycle was roughly 12 months long. It was a bit of an incentive because I kept losing SDRs to promotion there. So it was like, “Hey, if you do stick around for 12 months to 16,” which is what I wanted everyone to do, good chance that at least something you source goes closed/won and you get a nice little bonus.

Will: I would like to do that at TeachTown. There’s been some conversation around it. Would like to go back to half a percent, maybe a percent at most, but that is something we go back and forth on quite often, but I am pushing for it.

Elric: Thanks, Melvin, for the question. We have another question from Vincent, but it’s another topic, so I’m going to keep this one for the Q&A session at the end.

Elric: Anything else on the comp plan?

Will: Our comp plan, I was able to actually lower it, and it was because we had to set 36 meetings a quarter. I was only able to lower it by three, but I think it goes back to the quality of the meetings that we’re setting. I found that if we go for quality over just the quantity, yeah, there’s some quantity there.

Will: But the more that we focus on quality, the higher op size it is, the bigger deal it is, and the better set it traditionally has been. I would like to get it to 30. I think 30 is a good sweet spot for where we need to be, but 33 was where we landed, so I’ll take a little bit of a win there as well.

Will: I’m just a big proponent of, you don’t need 100 deals a quarter or 100 discos, but if you have 30 high quality ones and our conversion rate stays at 90 or above, then we’ll hit our metrics, especially based off of past performance on the team.

Elric: And when you lower the quota, for example, and that’s what you’re mentioning here, do you change the expectations from your team or is it similar in terms of the quality?

Will: The quality has to stay the same. If the quality goes down, then yeah, you’ve got to set more. That has to go up. I do expectations a bit differently, I think, than I’ve done in other places. I know I mentioned I work at smile and dial places. I think you can tell I’m not the biggest fan of that.

Will: That doesn’t work for me as a person. When I was in SDR, I struggled with it, but when it got personalized, that’s when I found success. If they’re not taking their time finding good quality stuff, then comp’s going to go up. The quota’s going to go up. On top of that, when we shrunk their quota, the payout per meeting and per stage three opportunity, that went up as well, so their OTE didn’t shrink.

Will: Tried to make sure, “Hey, you’re still coming out with roughly the same dollars, but this is how we’re going about making sure that you’re still doing just as well, if not even better, with a smaller quota.”

Elric: Now I want to talk about the SDR-AE relationship. So at the beginning, we were talking about having one SDR for three AEs.

Elric: And with the compensation plan you have, it also sounds like the SDR-AE relationship is, you have a lot of systems in place for them to collaborate. So could you explain a few things they are doing together? You said that for the first call, the SDR doesn’t need to be on the call, but do you have any specific systems for them to help the AE have the first meeting convert to an opportunity?

Will: I mean, depending on their tenure as an SDR, they might be more involved in the disco rather than just being a fly on the wall listening in. I require them to meet in a one-on-one at least once a week. It is very important, especially with how strategic we need to be in these states. You’ve got to meet, and that one-on-one could be 15 minutes.

Will: You determine what it is, but as long as there’s a true path forward and there’s some strategy behind it, that’s what I care about. I do have some SDRs who, and I will say they’re generally my higher performing SDRs, they talk with their AE every day, whether that just be a Slack of, “Hey, got this response. What can I do here?” “Hey, saw this news article around funding. Should we change and maybe pivot to targeting this?” Whatever it may be. The best SDRs that I have had have such a close relationship with their AEs because they are in tune with what is going on in their territory to make sure that they’re setting up good meetings and building quality opportunities.

Will: So from the handoff and the disco, I think this is part of your question, what are they doing to help set up that opportunity? They also go back and like, “Hey, Vincent, this is what I heard on the call that I set up for you. This is their pain, this is their pain. Are we on the same page?

Will: This is what I think the dollar amount will be.” And I want the SDR in the exercise of, if I were to open up an opportunity, what would I put for a dollar amount? And then ideally, the AE is like, “Yep, you’re spot on,” or, “Oh, I also heard this, which tells me maybe they need this part of our solution.”

Will: I want them collaborating afterwards, and they do that, where every once in a while an SDR will catch something, and the AE’s like, “Oh, I didn’t even think of that. I didn’t catch that because I was so busy in the disco doing my job. I’m glad you were listening.” Sweet. Let’s add that to our quote, and let’s come back with a game plan of how to demo that.

Will: So I think that answers your question. That’s kind of how I’m having them be in the disco and be a part of it and not just sit in there listening. Granted, when they’re more tenured, maybe not like, “Oh, this is my first meeting. I’m going to sit in, and I have no idea what to say. I’m just going to be on mute watching my AE do their job.”

Elric: Do you have one decision-maker in the process in your industry, or do you need to multi-thread, and do you have your SDRs helping on this too?

Will: It’s definitely a multi-thread approach. So even if a SPED director is the main point of contact that we go after, and they’re a great person to go to, generally they have their coordinators, and they might even have some teachers at the district join calls as well.

Will: Teachers being in the classroom of like, “Yeah, I would actually use this,” or, “No, this is just another tool. I wouldn’t.” The superintendent and the school board is also a big part. We do need them to sign off on things, so it’s very multi-threading. Basically, where we have it right now for the SDRs is just in the SPED department.

Will: The AEs will multi-thread into the superintendents and school board as well, but mostly the SDRs are the ones focusing just on the SPED department.

Elric: Now let’s talk about hiring. The result of the team is the impact of a lot of things, the system, the right people on the team, how you enable them, et cetera.

Elric: So you mentioned that’s important for you with your team. So what have you done when you joined TeachTown in terms of hiring? Do you have a specific background you’re looking for? Any soft skills that you are looking for for this industry? Tell me more.

Will: TeachTown is definitely different than pretty much every other place I’ve ever hired at.

Will: I almost exclusively only hire teachers. I have one person on my team who’s never been in a classroom, but the other 13 have, and maybe they’ve been in the classroom and left for a couple years, but at least they have that experience, and I think that really comes across in the confidence of what it’s like to have been sitting in it.

Will: So for me right now, one of the major things you have to have is, you’ve got to be a teacher. For the previous places I’ve worked at, like the fintech company, I’d like them to have some sort of financial background, but if they didn’t, I could still coach that up, and we had materials and stuff to be able to speak to what goes on in hedge funds.

Will: But it’s so hard to talk to a special education director as someone who’s never been in a special education classroom, to say, “Yeah, I can really relate to how difficult that is.” No, you can’t. You haven’t been. That’s completely different. You have no idea how to do that. You don’t know what it’s like if a kid is freaking out and trying to stab you with a pencil because they’re having anger management issues.

Will: You can’t relate to that. The biggest thing I look for is I start with teachers. The second thing is, because I’m generally hiring teachers with no sales experience, I do have two that had sales experience, cool. My favorite question to ask in the interview would be, if you could sell me on a passion of yours, what is your passion, and why should it be my new passion?

Will: Because I can’t ask them to sell me their previous company that they worked at if they didn’t sell anything. So if you were to sell me anything, sell me something you care about. I’ve had people sell me on yoga, on matcha lattes. I don’t care what it is. But the main thing for me, and I know you heard me say it before, is ask questions and find pain.

Will: If someone comes in, “I don’t have sales experience, and I need to sell you something,” the first thing I have to do is ask you a question. “Well, what is your interest?” Like if, “Eric, do you like to work out? Oh cool. How often do you do it? Oh, what kind of workout is it? How physical are you?

Will: Well, you know, that’s why you should join this gym that I enjoy going to.” I’ve had people use that exact same methodology of, “Hey, I’m going to ask questions and figure out more about you.” For me, that’s kind of the make or break question that I have found, of what really matters. That’s someone who cares more about their prospect and their needs rather than just pushing something on them, and I think that’s something you don’t need to have a sales background to know.

Will: I think that’s just something that people inherently know, someone who’s inherently curious.

Elric: What’s the behind-the-scene here for this question? So are you trying to see if they’re curious, the way they think about this, or what’s your.

Will: Yeah, I’m trying to really see how much they make it a conversation, not just, oh, I trapped someone in an elevator.

Will: I’m going to talk to them for 30 seconds. I want it to be conversational. I want it to be that they care about what my responses are, not just, “Oh, I’m going to talk to you about how this gym has this or it has that, and oh, we’re open 24/7 and we never close.”

Will: I want it to be, “Oh, well why do you enjoy that kind of workout? Why do you go to the specific gym that you go to? What’s your favorite thing?” I want it to be what I like my cold calls to be, and if I don’t have to coach, my favorite thing to tell my team is sometimes you’ve got to ask a question, then just shut up.

Will: And I think that helps them out, right? Ask your prospect something, and that’s what I want them to inherently come with if they can. Now I’m not expecting them to knock it out of the park by any means, but if they can at least come in with some level of curiosity, some level of questions, I can work with that.

Elric: We have one question from Vincent. So Vincent, if you want to unmute yourself and ask the question.

Vincent: Can you hear me?

Elric: Yep.

Vincent: Yeah.

Elric: Yeah, we can.

Vincent: Perfect. Hey, Will. Thank you first of all for all the insights. So my question is, if you hire new SDRs, what do you advise them to do in the first 30 days to succeed as much as possible?

Vincent: A bit of context, I have some SDR experience, and I’m just changing companies. My perception would be to learn as much about the product and the problem the customers face, but do you have some other insights that I could apply, or other people could apply?

Will: That’s a great question. Part of the onboard plan that I have set up is every SDR is required for the first two weeks to, I have a buddy system, so I already pre-partner them with another more tenured SDR, but they’re required to, for the first two weeks, sit in three different sessions where the SDR is researching accounts and then writing personalized emails.

Will: What is the research process? How are you assigned these accounts? How are you writing these emails? They will sit on Zoom. They might talk the entire time. Maybe they’ll be muted so they can focus. Whatever works for them, but they have to watch the person sharing their screen going through it.

Will: Most of the time they’re not muted. They narrate. “Here’s how I was assigned this account. Here’s how I’m researching. This is why I picked this particular thing to email around.” So that’s the email side of how are we researching, how are we doing that. They’re also required to do three, if you can squeeze in a fourth session, of the same sort of thing, sharing your screen, but it’s on cold calls.

Will: So they’ll sit there and listen because we are a fully remote company. You know, what’s the best way if you were sitting next to someone on the sales floor? How can you listen to their calls? What do they say? How are they going about it?

Will: Is it just, yep, click, call? Or is it call, didn’t connect with anyone, going to take a second, going to read my notes, going to come in with a good intent on my next call? This is how I’m setting myself up. This is what I should do as an SDR because this SDR is very successful. That’s the plan. I would say that’s probably the biggest thing that helps ramp people up in the first 30 days.

Vincent: Thank you very much.

Elric: Let me add also a few things on top of this. You are hiring former teachers, so I think they already have some business acumen about what they are facing.

Elric: So when you do not have this business acumen, one thing that I found interesting to do is to listen to calls with customers and prospects, so you can be more involved in the words they use, the problems they are mentioning, not just the materials that you have internally, because I’m not saying all the materials are bad, but most of the time the material is more like the marketing team built something and it’s more fancy words to explain what the prospects are facing.

Elric: So one thing is to listen to customers or prospects. If you don’t have a lot of recordings, you can look for the podcasts where you have your buyers, where you can listen to these conversations. And same here, the goal is just to listen to what they are saying, what’s the day-to-day of this person, so you can increase this business acumen.

Elric: Because product, I think it’s great to learn about the product, but at the end you need to understand the world of the person, and knowing your product, I don’t think it’s enough to have a conversation with your own prospects.

Will: That’s a huge part. I have an entire folder of sets that we’ve done over the phone from SDRs.

Will: They’re actually required to come in and make a comment on every single one, whether that be like, “I’m going to take this intro of how they approach this prospect, and I’m going to do this in my next call role play and make it work for me.” That’s a, “Here’s a great pain point question I’ve never heard before.

Will: Love how Suzy did this. Going to use this in my next call.” That’s part of it as well. We have about 45 calls in a folder right now that I also require them to listen to. I will say probably after about 30 of them, I get a bit redundant, so they’re like, “Hey, I didn’t have any new notes, but obviously it was a great set.”

Will: That’s fine too. But I think listening to those, to your point, are very beneficial.

Elric: And another thing also, you were talking about top performers earlier. Something you should do is have conversations with top performers, but the other thing is shadow them. You need to see what they do because one thing that I’ve learned working with top performers on the teams I used to lead, they don’t.

Elric: Sometimes they do stuff, but they don’t know why, and you need to shadow them to see the little things they are doing because top performers, they do a lot of little things that they are not able to explain. So you can ask them questions, but also on top of that, shadow them.

Will: That’s the shadowing of the emails and phone calls and stuff. It’s huge. So helpful.

Elric: Anything else on hiring that you want to share?

Will: I think some of it’s probably what other people do in hiring. For me, it’s very important that the person I’m interviewing has questions as well. I’ve had people who don’t ask me anything, and I think if you don’t ask anything, that’s a pretty hard no for me.

Will: I still need them to be curious. But yeah, just how they come in and address themselves, I think that’s pretty important. Just the fact that it is teachers, it’s very unique for where I work, so.

Elric: I imagine. Thanks, Vincent, also for the question. Now let’s talk about AI. So how do you use AI with your team, but also personally?

Will: So we use AI, never as an actual outreach tool, so I don’t have any sort of AI sending emails. I am very against AI making phone calls. I’ve received some of those, and they are by far some of the worst things I’ve ever heard.

Will: We use AI purely in our research and our data. So I know I mentioned we use Gemini. We’ll pull up a strategic plan from a district. We’ll say, “Give us the synopsis.” We’ll pull YouTube videos of board meetings. That one’s been very useful, and we’ll say, “Hey, when do they talk about special education in this?

Will: And how does it pertain to how it can help sell Encore, which is our platform.” And because we fed it what is Encore, what does Encore do, it can go, “Hey, it sounds like this part and this part would be super beneficial.” We pretty much strictly only use it for the research part.

Will: We’ll use it for not only researching specific districts, but which states might have certain legislation that’s coming up, which states are generally doing better and investing more in pre-K or special education and stuff like that. So I know I just keep reiterating the research side, but outside of that, AI isn’t as heavy here as I think it might be in other places.

Will: Mostly because when we did have an AI inbound SDR, we used it for a month. That inbound SDR did things that we’re not supposed to do. We had a lawyer contact us and ask for a demo, so the AI decided to send it a recorded demo. We don’t talk to lawyers. That’s not something we’re going to do.

Will: But because it’s an AI and it was easily tricked, it did that. We had it responding to people of like, “Yep, going to set you up in the meeting,” but doesn’t qualify anything. We just had some issues with it on that side, which is why.

Elric: Okay.

Will: I’m generally against it for those sort of things. But fantastic when it comes to research and cutting down the hours there, especially with as personalized as I require my team to be.

Will: So it’s been fantastic for that.

Elric: I agree with you on that. For me, AI specifically, the biggest lever is on the account research. It’s so good at finding a lot of public information about the company that you can use for your outreach, that before you could do it but it was something super manual.

Elric: It could take, depending on if you don’t set a limit, you could take 15, 20 minutes per account, where here with AI it’s super quick to do that.

Will: We’ll use it to kind of help us rewrite emails, and then we’ll go back and change it a little bit too. But we almost never send out an email that was directly written from Gemini or ChatGPT or anything.

Will: I know Gong Engage has its own AI email writing tool, but even in that we just use it to reword things for the most part.

Elric: Yeah. The issue that I have with tools like this, most of the time it’s what you give to the tool. If the input, if your research is not good, most of the time the output won’t be good.

Will: I don’t have the time to feed it everything it needs to be good. I generally just don’t do it.

Elric: Melvin said that he can’t go live to ask the question, but the question I think is similar. Is the SDR team using AI, and what have you found beneficial in AI workflows, in increasing that win rate, et cetera, if they are using it?

Will: Yeah. I would say this is a limitation of Gong Engage, which in that Slack channel that you found me in, I think you’ve heard me say I don’t like Gong Engage. If you’ve ever seen me comment on anyone, I’m staunchly against Gong Engage, but I’m stuck with it. One thing I wish AI would tell me more of, which again maybe it’s just a Gong thing, is what emails are actually performing better than others.

Will: How can AI decipher that? Is it because it’s a certain time of year and we’re coming up on budgets? Is it because this email mentions this particular pain point? How can AI decipher our own internal data of what’s working? If I could take it a step further, I would love if AI could tell me, “Hey, you set more meetings between the hours of 7:30 AM and 9:00 AM, and then again from 2:30 to 4:00 PM.”

Will: I don’t have that data. Right now I’m going off of my gut feeling, and I’m going, “Well, I see SDRs put in meetings at this time,” so I’m pretty sure that’s when it happens the most. But I want them to be able to see, and this is where I want AI to pick up, is, “You set a majority of your meetings between 9:00 and 10:30.

Will: The rest of the team seems to swap between 7:30 and 9:00. What are you doing differently? Is it a different territory? What’s going on there?” But I would want it to be personalized not just to the team, but to the individual, of here is your best workflow and here’s your best output.

Will: Let’s replicate that. Let’s get that going better. And so far I haven’t seen it. I don’t have a tool that can do that. Maybe there’s one out there and I just don’t know about it, but that would be beneficial.

Elric: Maybe Gong Engage can do it, but I don’t know what’s the, if you are super technical. I’m not technical, but I’m going to explain what you could be doing here.

Elric: You should check the API documentation and see what’s possible to extract from the app. Because I think even though in the analytics of Gong.io, maybe you can see it, but maybe you can extract this information and make your own model about that. I’m saying that because I’ve been doing it right now with some customers, with some tools. We have some limitations, so I found a workaround. That’s what I’m saying.

Will: I think that’s a good way to go about it, and I have a sales enablement guy that maybe can be able to extract that data and we can figure it out. I just haven’t had the time to be able to do it yet.

Will: But also it’d just be nice if it did it for me.

Elric: Actually, Vincent, do you want to come live to ask your second question?

Vincent: Yeah, for sure. Yeah, so my second question was how do you improve the calling quality of your SDRs? So what are tips or recommendations that you can give, especially in the opening, so that the other person you are calling gets that interest, stays on the line, and isn’t annoyed about the cold call?

Will: I have made some controversial, I guess, takes on LinkedIn around openers specifically, where I had some SDR influencers come at me, and then their buddies come at me. I can’t stand the, “Hey Vincent, hope this doesn’t ruin your day, but it’s a cold call. Can you ta…” That is probably one of the worst openers I’ve ever heard in my entire life.

Vincent: Yeah.

Will: I’m not a fan of it. What I prefer is, “Hey Vincent, this is Will from TeachTown. I’m giving you a call. I see you’re the SPED director. Are you the right person?” I want it to be very, “Hey, I have you. This is your title. Am I correct?” Just want to make sure I’m right before I talk to you.

Will: You might go, “Yeah, but what is this about?” Cool. I get straight to it. I am not someone who wants to talk about the weather. I don’t want to use some cheesy line. I want you to get to, “Yeah, Vincent, I’m giving you a call because I researched your district. I looked up what’s going on at the district, and your name is on the strategic plan.

Will: And you know, I think that we can help you achieve those goals.” You can ask, “Do you have three or four minutes to talk about it?” I don’t like putting a timetable on it. I don’t like saying, “Hey, I want to limit myself to three or four minutes.” But does that fall in your purview?

Will: Is that something that you’re actively still working on? And then the conversation flows from there. I think being very direct with people, not trying to bullshit them, not trying to weasel your way into a conversation by some corny pickup line is the best way to get someone to have an actual conversation with you and be a human.

Vincent: Yeah.

Will: That’d be my advice.

Vincent: Great. Thanks a lot.

Elric: To follow up on what you just mentioned, here, really it’s they can’t research, also. It sounds like your reps have done some research to make the call, so they have some context, so the quality of the conversation will be higher than just calling all the contacts they have on the list without any context.

Elric: So if someone picks up, they are more prepared to have this conversation.

Will: Yeah. I probably get about one to two SDR calls a day for me specifically, of someone trying to sell me something. One of my first questions is, “What do you even know about me, and what do you know about my company?” Nine times out of 10 they go, “Well, I know it’s called TeachTown.”

Will: Cool, man. That’s literally no information. You did nothing to do any sort of research. Why do you think you can help me? “Well, we help a lot of companies.” All right, I’m done here. “You can try again later if you do some actual research and find how you can help me. Sure, let’s talk, but I don’t want to just be another number, and that’s how I look at my prospects. They don’t want to just be some other number on a sheet. They want to be treated like a person.

Elric: If you think about the buying experience also, it’s the best, because if you think about all the calls they’re receiving every day, no one does this research, and if you are the only one doing it, obviously some people are going to be pissed about you calling them even if you do some research.

Elric: But that’s the problem with cold outreach in general. Because of the bad outreach that they’re receiving, they don’t like sales people because of that. But being prepared and knowing what they do, for you specifically, you do some research, you know maybe the initiative or the stuff they are doing, the conversation will be better.

Will: Oh, 1000%, yeah.

Elric: If anyone wants to follow you or connect with you, what’s the best way?

Will: LinkedIn is definitely a solid place to start. I know that some people have already requested, which is great. Really appreciate it, and that’s a good way. If anyone’s in the SDR Leaders of USA, I’m in there too.

Will: So really good place to connect, and always happy to talk about anything, or tell me that I’m wrong. I’m always happy to be wrong as well.

Elric: Well, Will, thanks so much for joining us, and if everyone wants to connect with Will, I will send the recording and I will also send the link to Will’s LinkedIn profile.

Elric: And yeah, thanks, Will, for joining us.

Will: Awesome. Thanks for having me.

Elric: Thanks everyone for joining. Thanks, Vincent. Thanks, Melvin, for your questions.