Edited Practical Founders Podcast interview with Christine Rogers, President and COO of Aspireship

Greg Head: And we’re live with my friend Christine of Aspireship. Welcome to the Practical Founders Podcast, Christine. 

Christine Rogers: Thank you. I’m so excited to be here, Greg.

Greg: This isn’t another practical founder interview. This is an expert interview with one of the people I know who’s been doing SaaS sales and leading SaaS sales teams and BDR teams and now has an awesome venture helping new SaaS sales executives in supporting the SaaS companies called Aspireship.

Greg: Today, I’m going to pick your brain about what it takes for practical founders early stage and growing software companies that aren’t huge and aren’t overfunded to be successful with BDRs, business development reps, SDRs, sales development reps, getting those outbound leads and playing that game. Very treacherous for most founders, and there are a lot of questions that come up in my practical founder peer groups about SDRs and I talk to founders all the time. So today I’m going to ask Christine the biggest questions that I hear all the time about how to be successful, in adding BDRs and SDRs to your sales process and your growth channels.

Greg: So, Christine, let’s just start. Tell us a little bit about your background and what you guys are doing at Aspireship. You’re a co-founder and president of Aspire Ship.

Christine: We know each other from back in the day. What was it? It was over 10 years ago that we met at Infusionsoft. I’ve kind of spent my career in sales of some sort, and that was really my first software and tech experience in selling. Through that, I really saw a lot of different things through that high growth. We were right at, when I got hired, about $26 million. I was an individual contributor and moved through that organization. And since then, I have been working with all different sizes of sales orgs, optimizing and creating efficiency and really whatever the outcomes and business outcomes that we were looking for at the time, really driving those, I would say, effective sales engines. And some of those included SDRs, BDRs; some of them didn’t. And it was all very interesting. I did a lot of learning.

Christine: And so from that learning, one of the gentleman named Corey Kossack, his business was acquired by Booker, which was one of the places that I was at. So we had a chance to work together, and at one point he said to me, “I don’t understand why you’re always having a hard time finding talent for these sales roles.” And so that’s really where the idea was born, that there are a lot of amazing people who want to get into selling and want to get into tech sales but don’t know how. And so we created this vehicle called Aspireship, where people can come in and take an online course. And if they can successfully pass it and show competency in this work, then they can get into, I will introduce them essentially to companies that are more interested in their competency than their background in both sales and customer success. So really, we saw a big need in the market and we’re filling it now with people that are great.

Greg: How many people have gone through the Aspireship process and gone on to successful careers in SaaS companies?

Christine: We actually have thousands that are currently in our membership pool. So, a lot of times people come through and they actually get snapped up before we can even get them hired with our companies because they raise their hand and say, “I’m an Aspireship grad.” So yeah, it’s quite a few people here that we’ve helped.

Greg: Great. Well, it’s really awesome. The SaaS business is growing and you’re helping the serious people be successful in the software business. There’s a lot of motivated and capable people out there, and you and I both know the magic of the software industry, how exciting it can be, how fast growth it can be and how challenging it can be.

Greg: So, let’s talk about SDRs and BDRs in the B2B SaaS business. If you’re selling to businesses and you have a high enough price point, if it’s not a $5 app, you’re selling to small business, mid-sized business, enterprise, what is an SDR or a BDR and what do they do? Are the same thing? Are those terms interchangeable?

Christine: You know, whenever someone comes to me and says, “I’m looking for a BDR,” or, “I want an SDR,” the first question I ask them is what exactly do they do during the day? Like, tell me about what they actually are doing, what you would like them to do. So, I clarify because most people in market use those interchangeably. You know, I hear now XDR a lot. So that’s what people are saying, “We’re XDR-ing.”

Greg: I would say that in general there are a couple of different ways that I ask these questions to get clarification. Are we looking for someone that is going completely cold, doing a lot of research, really pumping the top of the funnel in order to make connections and kind of making smart decisions about who to go after? There’s kind of like that outbound model.

Greg: To go get qualified leads for the sales people.

Christine: Yes. And I would say this, to go find suspects first, because we’re not even calling those qualified yet. So we’re kind of… We need some brains around that. Like, who? Who in the companies? What are we doing here? Maybe they are doing a lot of research. That would be more of what I would consider an outbound model. Then we’ve got an inbound model where we have a lot of white papers, a lot of traffic that’s moving people through the top of the funnel that’s getting initial interest, and we’re not sure if those are actually going to be good and qualified and so they take a lot of inbound. And that is getting really good at qualification, so that’s a very different type of skill set. And then there are kind of hybrids, some that do both and that that mix and match. And often what I hear from an earlier stage founder is like, “Well, what do you think I should do? Well, I just need more leads.” So they don’t what to do about it.

Greg: Yes, that’s very common.

Christine: Yeah, “I just need more leads. I just need more tee ups and I need somebody to help me do that.” So, they don’t necessarily know what they need, specifically. So I think there’s a lot of different thoughts around that. But that’s generally what I’m hearing in market as far as “the roles” when people are talking about BDR, SDR. They’re used interchangeably for sure. So for the purposes of this, we could say SDR or whatever.

Greg: Let’s call it SDR for the sake of our conversation today. So SDRs are, “Go find some people to talk to. Go talk to them. Talk to the people that downloaded our white paper that we don’t even know. Get in a conversation and get them interested in what we’re selling and qualify them so you can tee up a qualified lead for a salesperson. Warm up the lead, serve it on a plate to a commissioned salesperson, account executive waiting back there for that qualified lead.” Is that generally what SDRs are doing? It’s just in between whatever, the marketing funnel or whatever is out there or no marketing at all, and sales people waiting for qualified leads.

Christine: Yes, that is generally what I think most people think about when they’re talking about these roles and what they’re hoping for, let me just say that, when they’re talking about these roles.

Greg: Yeah, there’s a lot of hope in here. It’s a little bit like the funding game. There’s a lot of confusion, everybody thinks everybody does it and it always works, and there’s a lot more to it than that. And sometimes, early on of course, the CEO is the chief salesperson. And they just need more conversations, more demos, more conversations. You hear that all the time, more leads, one of the things they’re desperate for.

Greg: When should a start up, a B2B start up, consider hiring an SDR? Either they’ve got some leads coming in or they can identify some people out there in the real world who they should be talking to. Is it as soon as they have a viable product and the CEOs start to selling, or does the CEO and maybe the first salesperson need to get a little traction and get a little experience, a little learning, a little process to get that going? Can BDR be successful in that entrepreneurial mess?

Christine: Generally, no. So, no. What I’ve seen work and when people come to me, I ask a lot of questions. Because if you think about how we… We’re almost like a marketplace. So if my people go into a company that is not a viable opportunity and they go to the market and say, “They placed me in a wack-a-doo situation,” that actually really hurts me. So I’m very careful about who we place with.

Christine: And so a lot of the questions, those early qualification questions that I have when I’m vetting a company for them to move into is I would say, “Talk to me about your process. Like, what’s your sales process look like? How long is it, about? So I understand who’s been doing it. “How long does it take? Do we have a really good bullseye? Do we know what the bullseye is that we’re going after?” This is often what I hear. “Oh, gosh, we can sell to a whole bunch of people. We have a product that hits a lot of different types of industries, so our bullseye is very big.” These are starting to be concerns for me. When I start hearing that, I’m like, they’re thinking that we’re talking about total addressable markets, nice and big and wide and we can go after anybody. And I’m like, “Oh! I’m scared.”

Christine: So I really say, “Well, who is, though, the bullseye? Do we know who that is?” Because here’s the thing. You can put a really savvy, smart, hard working learner into a role that is not ready for them because actually, we need a container. We need a framework, we need to be able to give them, “This is who we’re looking for. This is where they play. These are their titles.” And we need to give them some guidance.

Greg: Here’s what it is and here’s what it’s not.

Christine: That’s right. What is the bullseye? Because when we’re trying to be too much for too many people right away, you put somebody in there that’s supposed to be just sorting through all of that, even if they are super experienced, which most of the time, that is also not what founders were before. So they want somebody that’s like, “I can teach them everything.” Great, and what do you have set up in order for them to be successful? What tools? So I would say we need some sales tools. How are you listening to their calls? Do we have a process? Do you have basic qualification questions that they could walk someone through? These are very foundational pieces that also founders should be doing as well.

Christine: Anybody selling should have a cheat sheet of questions because I have this for myself. When I get a new company on the line, I have my little cheat sheet where I’m like… Because I will forget. “Wait, how much revenue do you make and how many people are there total?” I forget the questions because I get so into the conversation that I forget those as well. Keep in mind, whoever we hire won’t get as into it as you, and you need to guide them through that and give them those tools and resources.

Christine: So it’s really important to have a framework, have an ICP and make it as tight and focused as you can. You need to have a process. I’m not talking about… You know, it doesn’t have to be some convoluted, very big… It’s like, “Okay, we reach out. This is what we say, this is what we do.” Walk me through a touchpoint like series of how this works. And, has it been done more than once? So many times I talk to people and they’re saying, “Oh yeah, we’re ready to go.” I’m like, “How many times have you done this process?” “Oh, you know, we’ve done it a few times.” I’m like, “Okay, you’re literally telling me you want to scale. What we need first is rinse and repeat. Have you done it once? Have you done it twice? Have you done the same thing five times? Have you done it ten times? Don’t even utter the word scale until you have done it enough times that we say for the most part we’ve got this 80% baked. Then we know we’ve got something.”

Greg: Right? Well, thanks for sharing that. That’s very typical. The crazy founder, especially technical founder, doesn’t have experience in repeatable, scalable, the sales factory. And they say, “But if I can talk to them, I can sell them, so I just need more conversations.” And then they hire an SDR or a BDR.

Greg: Our friend Tom Blondi in Phoenix jokes, he has the question, “How many first salespeople did you hire?” to start up founders, because they go through them. And an SDR is generally a junior person, right? This is an entry level job. It’s generally a younger person. They don’t know your industry. They don’t know sophisticated sales. So what you’re saying is for founders, before they hire an SDR to “go get me some leads,” they need to have an ideal customer profile, the center of the bullseye, the ICP. They need to have kind of a process.

Greg: Imagine a junior person showing up at McDonald’s and they say, “Do this, wait 60 seconds, flip the burger.” You know, there’s kind of a process where a 16 year old kid can make a burger anywhere in the world. But it’s more like that. Not as sophisticated as McDonald’s, but like, can you imagine somebody coming in, defining what that target is, here are the steps to do it, here’s how to do it. Let’s start, kid, right? If they don’t have that, it’s going to be a mess and they probably should stop.

Christine: Well, what’s going to happen is they’re going to put somebody in there. They’re going to give them moderate instruction at the beginning. And I say moderate because usually the founder is very busy doing a million other things. And then they get frustrated. Like, salespeople are very needy. It’s like, yeah, they’re trying to learn how to do this. They’re supposed to be doing how many touches a day. They’re going to be doing all this stuff. They need monitoring. They need like, “Am I directionally okay with this? Did that email land? What’s happening?” You will have to manage. And even if you have someone that is extremely experienced…

Greg: An SDR, an experienced career SDR, right?

Christine: Well, here’s why I think most founders ask for SDRs and not full cycle sales reps. They don’t want anybody closing for them. So here’s what they say. So usually they’ll say to me, “Well, here’s the thing. I just need them to tee it up. I don’t want anybody closing. I want to close because I know everything about this and I know how to do it; I’ve closed all the business so far.” So actually, I usually ask the question too, why do we want an SDR?

Greg: Why don’t you go get and an AE, a commissioned salesperson who can go find leads too. Some salespeople actually do that. That’s interesting.

Christine: That’s right. We call that full cycle sales. And if you’re asking me, Greg, if you were to ask me, “Christine, would you prefer to have a sales org, a full cycle or SDRs and AEs,” I would tell you “Full cycle,” because I actually believe that a lot of times we create more friction in the process than is necessary to be there because of our uncomfortable feelings.

Christine: So here’s the thing. If you hired someone… These are the questions you need to ask as the leader who’s sitting here trying to determine. Like, am I just making this decision because I want to not have anybody close right now? You’re going to set your organization up then in a way because you’re being fearful of this like scarcity mindset up front. So I would say to you, in general, it is not a great idea when you are moving people about through a process and you’re introducing them and creating friction. That is about us as…

Greg: The handoffs.

Christine: The handoffs are messy. The handoff is where things go sideways. That is also our problem and that is us. That is our uncomfortable feelings around it. It’s not the prospects, it’s not our customers. So I would ask that question too, “For the sake of what are we doing it this way?”

Greg: Right. And technical founders and founders themselves, a lot of people have uncomfortable feelings about knocking on doors outreach outbound, and they want to delegate that important but very difficult problem to somebody else. And I think another thing is founders think, “Well, I can hire an SDR for $35K plus commissions or $50K plus commissions depending on where they are in the world, but a commission salesperson would be more than $100,000 in total compensation. So I just want to get started cheap. I just need to get some leads and run the experiments.” But a lot of times CEOs have never done the outbound. If you said to a CEO, a founder, “Have you done 500 outreaches on LinkedIn and email and phone and have you done the process?” And almost nobody would say that.

Greg: But what about price points of the solution? If you’re selling to small business a $70 a month kind of software solution, you don’t have any room to almost even talk to anybody in the sales process. You’re selling $1,000,000 annual contract, then the CEO or some very experienced senior salesperson needs to sell that. What is the range in between where SDRs fit in a business model and it’s a lead generation and sales qualification layer?

Christine: Yeah. So I definitely think in the SMB side it can be really messy if you’re trying to do that. Even when you get into mid-market, that mid-market, it can still work, because when you start to think about the multithreading that has to happen in order to get some of these deals across the line, that is actually where an SDR can be very effective.

Christine: When an AE has an SDR and they are going after very specific accounts together, they can do this in a way that feels very comfortable because they’re working as a team. So when I am trying to understand who are the players, I need somebody to kind of help me with some of those research points and doing different things and sending and what are they talking about and how are they engaging on LinkedIn? Or if they’re not on LinkedIn, where are they playing? So we put together kind of that strategy and that can be very effective.

Greg: So an SDR as an assistant to a commissioned salesperson taking the tasks that aren’t the closing and the dealmaking and the negotiating to go find and nurture prospects in the funnel.

Christine: It is really that front end where they are doing much more research, understanding like, “If I send this or we get them in this sequence, I’m starting to see people get “clicky.” This is what I’m doing.” They’re taking ownership of that education before they even try to do much on the reach-out point. So then they’re working in tandem and they’re really warming up and educating those top of funnel to that place where they’re working together to get it into a real conversation with certain people. When you’ve got procurement and a bunch of other people, it is very helpful to have more than one set of eyes on something like that. When the deals are coming over, they’re large.

Greg: Yeah. You said mid-market there, the kind of mid-market B2B SaaS. What is a mid-market price point, like in annual, is that like $10,000 to $100,000 a year and you’ll contract value?

Christine: So yeah, I would say you’re in the tens of thousands of dollars. Some people would even consider mid-market up to a couple of hundred thousand. And true enterprise is, I would say, probably a half million plus, is what we’re looking at.

Greg: What about a $ 300-a-month solution for a serious small business? Infusionsoft was like this, and many others are generally in inbound sales and marketing motion and there is some kind of qualification. Can you do outbound at $300 or $500 a month, customer value?

Christine: I think that the concept of outbound is very interesting because I would actually say that founders and things are like, “I’ve never gone outbound.” Well, maybe you’ve never called through a list of 500 yourself or done that, but you probably have gone outbound in some way. For instance, if you see someone on LinkedIn talking about something interesting and you chime in and you chime in and then you connect with them, and then you’re like, “Yeah, I love that discussion that we had,” and doing those different things, that is a version of outbound. And so a lot of times we have this concept…

Greg: A productive version, as opposed to pestering somebody and trying to get them on the phone or something like that.

Christine: That’s right. For instance, if I see somebody that I’m interested in getting in front of that they are hiring, I can see they’re doing quite a bit of SDR hiring and I want to talk with them, I look and see who they know that I know, and then I literally ask for a favor. Like, “Hey, I need an intro to this person.” I’ll even write it up for them. “Here’s the intro, can you just intro me to this CEO or somebody. I can see you guys are actually…” And people think about that like, “Oh that’s referral, that’s this. Actually, you guys, that’s outbound. That is exactly what I would consider an effective, targeted, thoughtful approach to going cold to someone. You’re using the resources that you have in order to do that.

Greg: I guess the way I think about outbound is that person wasn’t thinking about you before you were thinking about them. So you’re going to go and introduce yourself in some way. And so, if you can be thoughtful about that, maybe I put a thoughtful comment into one of their posts or into something, and then I don’t do anything for a little bit. And then I engage with them another way. Guess what? Guess who starts to get some attention? Me, because I’m being thoughtfully engaging with them. And sometimes I don’t ever say anything. And you know what? A lot of times they come to me when they need hiring, because reciprocity is a thing. It is.

Greg: I get it. SDRs and outbound was not as common; there were full cycle sales reps in the old days. But, you know, about 10 years ago it started. And then the “let’s buy a list of emails,” especially in vertical markets where your customers are known and identifiable, there’s 30,000 physical therapists and we sell to them or something like that. We’re going to download a list, we’re going to pummel them with email, we’re going to follow up with a phone call, we’re going to stalk them on LinkedIn. You know, that connect and sell kind of motion that I hate kind of thing.

Greg: And there’s a lot of people doing it, and hence buyers are moving back. They don’t want to answer their phones, they don’t want to respond to emails. They don’t go on LinkedIn anymore because there’s too much of that. Is there anything useful to that, to the buying a list and outbound that isn’t very savvy and warm like you just described. Can you just cold call and play a game there? Maybe the odds are down and the costs are high, but it can still work? What’s happening in that “buy a list and send a kid on their way to go get some leads?”

Christine: Well, I will say that I think you could try that. I don’t think you’re going to have anybody doing that job for very long. So, it’s very boring. So in this market, if that’s your approach, you will cycle through people over and over and over and over again. Because guess what? There’s not a lot of brain activity that has to do with that. And generally, these individuals, they aren’t looking to be a career SDR. They want to get into selling, they want to get into closing, they want to have to critically think.

Christine: I mean, look, we all get spam emails, and I always think to myself, “Who opens this? Who does anything with this?” But you know what? Obviously somebody does, because if they still do it, they’re still getting some traction here, so someone does at some point. But here’s the thing. In this market, when it’s hard enough to find good people, it’s extremely difficult to find people that are savvy, that are learners, that want to grow with you, and especially for founders who are looking for people to stick around and do not want to be hiring every few months because that can be exhausting, then you need to give them a career, not a pounding the phones.

Greg: Oh my goodness. Yeah.

Christine: Yeah, it’s a career. Help them. Help them learn. Help them be interested in this work. If I were doing a cold, bang the phones, I would go overseas. That’s how I would do it. If that was a market that I wanted to test, I would try something like that where it was cheap, easy, and I didn’t have to actually have a soulless environment for people that I actually care about and want on my team. Because that is what it used to be. Old school telemarketing is old and we’re not doing… it’s just not as effective.

Greg: Can you hire, outsource to an agency, like a lead generation agency? There’s a lot of people out there. Everybody’s having difficulty in leads and B2B SaaS. And so, there’s a lot of, “You know, we can solve your leads problem” type agencies somewhere in between the outsourced, bang the phones, pummel the email list and hire a very savvy internal SDR with a lot of love and care and warm introductions. There’s something in between. Can a founder who’s never done this before hire an agency to get a couple BDRs that have management in some process and some coaching through that, or does that not really work?

Christine: There are entire models, entire business models and that’s what they do. They have an outsourced team. I will tell you, most of the time what I hear when people actually come to me, I’ll give them some advice like, “Hey, these are the things that you need to know.” And then I hear, I’m like, “Hey, how did it go? Did you get the sales process done? Did you get these things?” “Actually, I didn’t want to do any of that. I didn’t want to put it down on paper. I went to an outsourced SDR.” I’m like, “Cool, I’ll talk to you in a few months.” Guaranteed. Because what happens, generally, is if you haven’t put that time, energy and thought into it, but you just kind of like said, “Oh, I just need these,” and gave them kind of -ish…

Greg: Just get me some leads right now.

Christine: …Guess what you’re going to get, -ish, back. Because they’re not going be it great. Generally, they’re not going to be great. They’re going to be -ish. And so you’ll be spending for kind of like, “Hmm, this isn’t quite right. I’m having a lot of conversations that are not awesome. I am paying for these leads.” And so it gets kind of expensive to be doing that.

Christine: Here’s what I know. You’ve got to get the process down. You’ve got to get it down regardless. If you’re going to go outsource, you better have it very clean on the definition of what is a qualified lead, because I promise you, you’re going to pay money for those. And when they don’t do anything, you’re going to be coming back and saying, “I don’t want to be paying for those.” And they’re going to say, “Met the criteria, you’re paying for it.” So regardless, you have to do the work that I’m suggesting that you do one way or the other. It just depends on how you want to get it done.

Greg: Well, this can be very expensive. How much does an SDR cost? How much should you invest? In the old days, it was under $50,000, like entry level sales. Go get on the phones and talk to… Go warm up these old leads or something like that. But what is it these days? Labor is still tight despite layoffs in tech. What should somebody expect to pay?

Christine: So, I don’t typically take a search with a company unless they are paying… They need to be paying about $50K in base. And usually the OTE needs to get us around $70 to $85 is about right. So they are commissioned.

Greg: So OTE is on-target earnings. So it’s a base salary. So they have a salary regardless of their effectiveness or what they do, and then there’s on-target that says you meet these targets and deliver these leads. If you exceed it, it’ll be more than that; if you don’t achieve your goals, it’ll be less than that. But your on-target earnings should be about $75K, plus or minus in SaaS.

Christine: At 100% to goal.

Greg: Does that depend on where they are in the country? Obviously, if you’re an SDR in Southern California, you need more salary than an SDR who’s playing in the SaaS business in Omaha or somewhere else.

Christine: Generally, yeah. So you’re going to pay more in L.A., you’re going to pay more in San Francisco, New York, some of those bigger areas. I have a search right now that’s in Austin and they’re paying $45 for a base, but they have extensive benefits and a lot of other things that are pretty sexy, but that OTE still gets us right up there.

Greg: What should the business goals be about SDRs? If they deliver 50 qualified leads and you close 10 of them and it creates this amount of business, it’s worth that investment. How should founders be thinking about the goals for SDRs?

Christine: Well, it 100% depends on who they’re selling to, what the price point is, all of those things. So, I have some companies that if they get one meeting on the calendar a week, they’re super happy with them because it’s a much larger sale. They’re going to be doing a lot of research to even try to do reach out. So, it really depends. So I would say this. First of all, figure out what you can pay for it. So if we’re talking about $80K, total OTE, back into the numbers on how many deals do we have to have come in from this effort.

Christine: If you’re looking at the total cost of acquisition and you have an SDR, you really need to think about that’s going into your sales CAC. So if I’ve got two people that are selling, that’s another reason why sometimes full cycle is right because you’re only paying for… If LTV to CAC is important to you, which it could be… Maybe it’s not, but it could be, then I would absolutely think about that and say, “Okay, so if I’m willing to pay X amount of dollars and we’re paying this rep over here X, I’ve got to get at least how many deals out of it for that to make sense.” Then work backwards and figure it out.

Christine: You’ll know right away if this is penciling. It’s going to be like, “So I need them to do 52 meetings a month.” That’s actually probably not going to pencil at a $30,000 deal. So, we’ve got to figure something different out. And so I run the numbers a couple of different ways to get to that. How hard has it been for you, the founder, to sell something?

Greg: With all their superpowers, right.

Christine: You know this better than anyone and you love it better than anyone. And you also know where all the piles of dog poop are about this product or service. Then you actually know way more than anybody else will. And how long has it taken you? Maybe you don’t have quite the gumption and the rigor of someone else that was only focused on that, and so that’s what you tell yourself. But I’m going to tell you, you expecting more from somebody coming in than what you’re going to do, that won’t happen right away. It won’t happen for a while. So you really need to make those numbers make sense and create goals that are really, really workable and that they can be excited and enthusiastic about.

Christine: Because if you go three, four months, and if they’re supposed to be getting three to four meetings booked and sat, so they’ve actually happened, and that’s how they get paid and they’re only doing one, they’re going to look at you and go, “Have you ever done three or four a week or did you just give that to me?” And then you’re going to be looking for a new SDR real quick because they’re going to leave. You know, they’ll stay as long as they can, then they’ll find something else and they’ll leave.

Greg: Another thing I hear about the first salesperson, the first SDR is never hire just one. You’ve got to have two so they can support each other, so they can compete with each other and there’s a little accountability in there. Is that true, or can you hire a remote SDR somewhere with this very difficult job and expect that to work?

Christine: Isn’t this interesting? We have a lot of expectations of people, don’t we? No, you need to higher two, a hundred percent. Hire two. We don’t know if this is a process problem, if they’re not selling. We don’t know if this is a people problem. We don’t know if this is a management problem, which most of the time it is because you’ve got a leader…

Greg: In the early stages, right, yeah.

Christine: And I have said, “Hey, did anybody look at this activity report? They’ve done like eight calls all week.” And they were like, “Oh, it’s because we’re too busy.”

Greg: Right.

Christine: So, if I were a founder right now, most of the time this is what I say. If you were looking for your first salesperson, what I would actually find is somebody who would be a sales manager. That’s what I would do. I would not hire an SDR, I would not hire an AE. I would hire somebody that had been like a team lead that was looking to get into leadership. Not a head of sales, not somebody that’s up here. I need a person that can do and learn and figure out and be able to digest some of that. So I would literally be looking for someone who has been a team lead or has been in sales for a little bit.

Christine: You’re not going to pay top dollar for then a head of salesperson, you are going to pay manager dollar. I would not make it super heavy commission. This is just how I would do it. So I’m just giving you… This is how I would do it. I would make it more heavy on base and I would say, “You’re going to do this a few times so we can figure out what actually works.” So I’m going to tell you, “We’re going to do the process. I have the process documented, but I’m not sure if it’s exactly right, and then, I’m going to hire people under you. And that will be where we can put a little less experienced people, because now we have a management layer there.”

Christine: Now, where that doesn’t work is if you’ve got somebody who is acting like an IC, an individual contributor. So they’re super focused on their commission clawbacks and every other thing. That’s why I say give them a higher base, give them some commission, but also what you’re trying to do is… I need someone to thought partner with me to get this sucker rolling. And you’re going to pay a little bit more for that. That’s typically what I would say if we’re talking about this, because you don’t have as much time to manage as what you actually will need when you start hiring true SDRs, BDRs, even full cycle junior AEs. Anything like that, you need that. You need that management.

Greg: Right. So it is a misconception. It doesn’t work very often for a non-sales oriented tech founder to imagine, “We’re going to buy some leads and we’re going to hire some junior SDR and they’re going to be pretty independent. We haven’t done it before,” and imagine that’s going to work at all. Even if leads are kind of inbound and so forth, they need to be supported. And having a sales manager who can sell, but somebody who’s building the factory 1.0, the MVP of the sales factory, as opposed to just focusing on day to day sales, making their commission number to set a foundation where SDRs is part of the solution and account executives or full cycle sales people who can do both could be appropriate in either way.

Christine: Yes.

Greg: Is there a difference between an outbound SDR and an inbound SDR? The hunters and the farmers analogy that’s always been there. Those that can go knock on anybody’s door and warm somebody up and those that wait for somebody to knock on their door before they have a qualified conversation.

Christine: There are. Yeah, those are different. That’s how I always think about it. What is this person doing all day long? Are they researching, trying to figure out certain things? So, outbound people have to have a little bit of a different perspective and a different persona, in my mind. They have to be really, really curious, trying to dig, trying to find the interesting nuggets that they can get someone’s attention on. And certain personalities really love this because they like this creativity that sometimes has to be there. It’s a different perspective than the old school way of just hammering the phones.

Christine: Now inbound, very different. So generally, their personas are figuring out things. Moving quickly, because certainly when inbound leads are coming in, you’re trying to sort through and figure out, do some quick research, get them on the phone as fast as possible. That speed to lead is really critical. And so it’s a little bit of a different thing. I can tell you when we talk to candidates and it’s like, “Okay, this is an outbound motion,” you can tell right away people are like, “Ugh, I don’t really want to do that.” Or it’s like, “Oh yeah, that sounds fun.” So generally, they kind of have that feeling.

Christine: I’ve had some people that have said to us, “I really do well on the outbound, I don’t really want to do inbound.” Like, just having people call me saying, “But what’s it cost? But what’s it cost?” And that’s all they care about. Versus like, I get to kind of play with this communication style and figure out what’s going to work. Those are a little different in personality.

Greg: If you’ve got a free trial or a freemium experience in your B2B SaaS software, the new product led growth we call it these days, or you have a content strategy where people are downloading things which is different than somebody reaching for your product, they’re reaching for a whitepaper, which isn’t, “I’m ready to buy yet,” I would imagine inbound leads, people trying your software and all over your website and they’re knocking on your door, if you have some leads like that, that’s easier to create a process around to support for an SDR to train then, let’s say, the wild West of the outbound. I don’t know, I’d imagine that would be easier. Is that any easier?

Christine: Yeah, it’s definitely easier because the testing is going to be easier. So when you’re doing that, you’re like, “All right, here’s where it came from. With this one, we’re going to bump up these questions because this is really important. Because this is the piece of content they downloaded. So we know already what they’re already kind of thinking about. We already know some things about that.” So that to me is an easier kind of AB test. So we have just more knowledge around it, right? The old leads work, right? Putting the critical thinking behind it different.

Christine: Now on the outbound, especially if we think we’ve got the bullseye, we’re going to focus on these certain ones initially, we may not know what’s going to work, what’s going to get their attention, what are the pain points that we’re talking about and the market shifts. All of a sudden we need to hit something else very differently. So yeah, I think that testing is a little bit trickier. I think about the level of critical thinking that has to go into it is pretty high as far as you need some strategy around it. And usually if you just let somebody do it, they’re not necessarily going to come up with that themselves.

Christine: That is a little bit of a different mindset and thinking, and usually you need some some kind of leadership thinking there, and that can be a little different because we’re totally shifting on, “How would you get my attention?” And that could be talking to a bunch of people that are in the role currently and saying like, “Hey, what would get your attention? Anything? Want me to send you a clean board? What do you want? What does it look like?” So trying to do that is a little different.

Greg: If you search for job openings for SaaS, SDRs, BDRs in tech, there are tons of job descriptions, tons of companies hiring teams of these, the big software companies. How would a smaller B2B software company find SDRs and BDRs, either part of their team or as they’re growing up? Do they just go to the same LinkedIn and job posting boards, websites, as everybody else? How does a smaller software company compete to hire quality folks?

Christine: I mean, that’s partially why we created our business because it is unfair. It’s very unfair. Here’s what I would do if I were still going to put an ad up on Indeed or put up a LinkedIn post. I would embrace that you are a smaller company. I would embrace the fact that you are intentionally only adding one to two or two to four. It’s like highlighting what could be seen as a weakness as a strength for your organization. And I don’t think that will be that hard now.

Christine: Now, I can tell you that this is because so many bigger companies have laid off people and because you do have people like me in market saying, “Hey, sustainable growth is the key. Why are you hiring 20? You know you’re going to cycle through all 15 of those 20 and you’ll have 5 left by the end of 5 months. Come on.” And so when I say to my candidates, “Look, you’re going to get hit up by a bunch of big companies. I’m going to introduce you to some that you’ve never heard of. And you know why? Because they have strong leadership, because they’re only going to add a few. You will have some influence and a seat at the table, and if you actually care about impact, this would be a better place for you. And it might not be sexy, sexy.” And guess what? That works; they get it. A lot of people get like the shiny object, “Oh, that’s a pretty pink logo. And they’re talking about all this. They have 77,000 rounds of funding.”

Greg: And it’s a big company that people know about.

Christine: And I’m like, “Yeah. And you are going to be the first to go.” When we have that pretty honest conversation with the candidates coming through, they actually… And we call them kind of boomerangers. We’ll have some that go, and then three months later, like, “Christine, you were right. I don’t want to do that. I want to actually come to a company that cares.” I would really highlight those things as leverage points to find great people.

Christine: Then you’re going to have to vet, and that also makes it challenging. Because the vetting, you’re going to get like 500 applicants. That also is very difficult. I mean, that’s why we created our program the way we have.

Greg: So I can imagine when a CEO founder says, “I sold our first 10 deals and now I need a BDR or an SDR to get me some more leads so I can sell more deals,” that without enough of that foundational structure in the process for somebody to be successful and, I don’t know, hours a day to help run the experiments and coach them through it and see what worked and see what didn’t, that they’re probably not going to be very successful with hiring just one or two SDRs without a lot of supervision and care and feeding of that engine.

Greg: It’s common for startups to… Speaking of shiny objects, to hire people that have worked at bigger companies where they’re well known and they have big responsibilities and have grown and were successful there. But should these early stage SaaS founders and sales leaders be hiring people who work for big companies who are part of a big factory where it’s all worked out and all the experiments have been run or can those big company people be successful inside a scrappy, still experimenting young startup?

Christine: Yes, and. So, you can hire as long as you are setting expectations right up front around, “We are scrappy. We’re still figuring it out.” I can tell you if you can identify people that have an entrepreneurial spirit that have been frustrated by some of those bigger companies and some of the things… So you’ll find people that have been like, “Man, it just really wasn’t for me. It was a lot of red tape. I couldn’t do anything. I couldn’t change any of my emails. I had to go just the way that it was in the sequence. I couldn’t even go back and forth.” These are the kind of things where usually it can indicate… So I would dig in a lot, but those can indicate where they’re just more well-suited to a smaller company. Generally though, those individuals have a lot more knowledge and baggage that you may have to clear out.

Christine: So for instance, some people that are new… This is why our company exists, because new, fresh, they don’t have a lot of story. They’re just enthusiastic. They also don’t know if you’re like, “Okay, this comp plan is okay,” but if you hire somebody that’s pretty experienced, they’re going to come in and go, “I don’t like this, this, this, this, this about the comp plan. Change it and then talk to me later.” This is different from somebody that’s, “I’m making a base salary. I just want to do this. Seems okay. I’ll give it a try.”

Greg: I’ll give it a try, yeah.

Christine: And there are some differences there. Am I saying that seasoned people are not good? Absolutely not. They are. You just have to have a different mindset and you’re going to need to think about who you want to manage. That is a different level of management. If you want to manage people that are a little greener, they’re going to ask questions that you’re like looking at like, “Really? You’re asking me that question? But they will have different needs and they will likely have a different kind of persona about them versus somebody that’s coming from a bigger company. You’re going to hear things like, “Well, that’s not how we do it there.” And sometimes that can be good because then we learn like, “Oh, okay, these are some great learnings of how not to reinvent the wheel.”

Christine: Also, you’re going to hear, “That’s not how we do it there,” and it’s like, “Yeah, that’s a $100 million company. We’re at $6. That’s very different, and I can’t pay to have 17 pieces of tech stack for you. Sorry. You’re going to have to use the 3 that we have and make it work. You might have to write your own emails here and there.” These are the things where you want to kind of differentiate between how do you want to manage, who do you want to be playing with? As the leader, what do you want to be doing there? And I think that’s a really effective conversation to have with your self and your team.

Greg: So, what you’re doing now at Aspireship is helping solve the talent shortage in the sales and customer success parts of SaaS businesses. Has this talent shortage eased up in the post, let’s call it the tech recession of late 2022 and 2023, with layoffs and maybe reduced hiring. Are there more folks available than last year and is it easier to hire, or is there still a talent shortage that’s still a problem?

Christine: So, there are a lot of people available. I will say there are a lot of people available. And the problem with that is now you have a lot of noise. So when a founder or leader is like, “God, I just need… I want to hire two salespeople.” Now you’ve got to vet and you’re going, “Okay, these people are very low on the experience side. This group, lots of experience but got laid off.” And now you’re trying to figure out who to hire. And so it actually complicates things quite a bit because it muddies it.

Christine: So, if people got laid off, especially because some of them have gotten laid off multiple times, like even in one year, someone might have been laid off twice because they went to a very similar type of company and then boom, that one hit, kind of last in, first out. And so, sometimes that happens. So you’re trying to kind of decipher is it this person or is it the circumstance? Is it both? And so, I think that vetting portion becomes even more important, where you are really clear on competency and character that work really well for your team.

Christine: And I will tell you this. You need to be able to decide on each individual that you’re bringing into your hiring process. And I say this because it just doesn’t work right now where you’re saying, “Okay, I’m going to see these 10 and then I’m going to decide which ones are moving forward. Then I’m going to move 6 of them forward.” You will lose everybody in market. It is moving quickly enough that you will lose them. So, you need to be able to say, “All right, I got Kelly and we’re all interviewing Kelly. Kelly came out on the scorecard at an 87%. Kelly moves forward because anybody over 85% on our scorecard for the competency…”

Greg: So you don’t do them as a group. We’re going to wait until we get all 10 and then see who are the best 5. You’ve got to move them forward.

Christine: You look at them as individuals. And really, Greg, this is how we always should have been looking at it. Look at each person individually. What do they bring to the table? But this also requires you pre-thinking about… Every question needs to be measuring something. We’re not just going in there and just shooting the shit. Like, we’re going in there with, “Hey, Greg is going to be looking for these three things, so these are the questions,” and creating as much of an unbiased environment as you can so you can see the differences as people come through.

Christine: Man, you will see that your team has to get clearer. Usually that’s what happens right away. You’re like, “Okay, we were really divided on this.” Great, you guys get clearer. You guys get clearer. And I can tell you, Greg, you saw me do hiring when we worked together. Man, I was pushing through people all the time, but I did have the flexibility to be able to say, “Actually, I want to see those two before I make my decision. They’re coming up tomorrow.” And right now, it’s just not the way it is. We just have to be able to look at people and say, “Are we good enough on this?” That’s why I set a scorecard, really simple. If we get to these things, then we are moving forward. And if we get to the next step, then we are moving forward. And at any point, if anybody is like, “Yeah, this is like a veto,” then we stop and we talk, but we take them individually. And that is really what I’m seeing work.

Greg: You’re talking to a lot of sales leaders and a lot of folks getting into the sales game as their careers and developing those and matching them up. Do you have any resources at aspireship.com? How can early-stage founders learn more about the SDR, AE, customer success? Do you have resources that would be useful to them?

Christine: Yeah, we do. So, we actually have a couple of different things. So number one, I would say, any of the people on my team, we talk a lot on LinkedIn about what we’re seeing, what we’re hearing, what the market is looking like. So I would say follow first.

Greg: Yeah, I do see that. I love that.

Christine: Secondly, at aspireship.com, we have an interesting offering as well. Because we are actually placing people into organizations, and then the organizations were saying, “Hey, so the other two that we just hired from you are better than the other four that we have. Could we get people going through your stuff? Can I put my team through your stuff just so they get all up to speed?” So we do have some learning components that are there as well for teams. And we do it very simply, just a flat fee per team. So we’re not trying to get crazy. Because what we know is when teams are learning together and growing together, they actually continue to grow the company. We will get more hires out of those companies.

Christine: So, we created a video library that has over 100 hours of training in there. I also created a sales management course in there. So, for those individuals that are on the team that are like, “Hey, I’d like to get into sales leadership,” that’s in there as well. So we’ve tried to become kind of a stop.

Christine: It’s kind of like the gap. If you don’t have a full enablement and training team, but you need to consistently get training. We do live training every two weeks. So, anybody can come to those; you don’t have to pay at all. And the video library is completely free. So, if anybody wants to go sign up for aspireship.com, just go into the video library and do a bunch of learning, that’s free too.

Christine: So we’re trying to help as much as we can, knowing that I think good begets good. And even if when companies hire and they’re not a partner and they hire one of my people and I don’t get any revenue for it, it’s still good. It’s still good. This person who did not have a vehicle now has a new job. They’re happy. And at the end of the day, a lot of those people are doing so well, they’re now coming back to me like, “Hey, I’m going to be a manager. I’ve been there for a year. Christine, I need to hire from you.” We’re just trying to help as many people as we can.

Greg: Well, I see that on LinkedIn, and I know both you and Corey and other members of your team. You guys are great contributors and you’re helping thousands and thousands of people and hundreds of software companies to grow and be more successful. Christine, thanks for answering my questions and the questions I’m channeling for practical founders out there about BDRs and SDRs in the modern B2B SaaS world. Thanks for sharing your insights. I really appreciate it.

Christine: Yeah, it was really fun. Thank you.