How to scale revenue operations, with Dan Englander

January 19, 2022


Dan Englander, Founder & CEO of Sales Schema, joins the show to share his perspective on how companies with longer lead-to-sale cycles can scale revenue operations. In this episode, we cover:

  • biggest challenges aligning sales and marketing teams
  • how to find the right balance between personalization and scale
  • going outside of personal networks and referrals to win new business
  • building an effective revenue team in the right order

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John Tyreman:  Hi gang. Welcome to the Digital Marketing Podcast where we go in the trenches to help you learn more about digital marketing topics and trends. I’m your host John Tyerman. And I am joined today by Dan Englander, host of the Digital Agency Growth podcast and CEO and Founder of Sales Schema, a fractional business team for marketing agencies and B2B companies. And we’re here to talk about systems for scaling revenue operations for agencies and B2B companies. Dan, how are you doing today? 

Dan Englander:  I’m well. I can’t complain. It’s getting colder here in New York. So I’ve managed to stay in my apartment all day working. But I probably need to get outside at some point.

John Tyreman:  Some fresh air always does us some good. Well, Dan, I have to ask, I saw in your bio that you’re into Brazilian Jiu Jitsu and I worked with a marketing friend of mine a few years ago who also did this and he would come into the office with all sorts of bruises, battle scars, and have you had a similar experience? 

Dan Englander:  Yeah, it’s kind of just par for the course at this point. So I have been training for about five, six years now. So I’m lucky that I haven’t had any horrible injuries but there’s always just kind of like pain and soreness, that kind of thing. I don’t think we get as many of the really prominent bruises like you would if you were like a boxer or something but they come up sometimes. Yeah.

John Tyreman: xactly. Well, let’s dive into our topic at hand today. So we’re here to talk about systems for scaling revenue operations. And let’s start here. So what are some of the challenges that you found with organizations in first aligning sales and marketing functions? 

Dan Englander:  Yeah, for sure. So just for a little context, kind of like our main realm of expertise is doing B2B sales and specifically outreach, basically getting meetings for people among skeptical decision makers and, you know, mid to large companies in high places and that kind of thing. So, to answer that question, I think it’s a really good one. And I think it’s changed over the years. And I think my perspective is kind of largely influenced by a guy named Robert Rose, who we’ve had on the show recently. He’s a great, great marketing thinker. And he kind of like observed the same thing that we do, but he put it really well which is that, you know, we always hear that, you know, all the battles done on the marketing front and just people kind of know what they want before they ever reach out to a salesperson. But I think what’s not exactly true and what’s kind of like underappreciated about that dynamic is that most people, rather most prospects don’t necessarily want to have to do a ton of research before they have that sales call. So to answer your question, I think one of the toughest things is finding out what that minimum viable level of information is before somebody is going to agree to have a call, right? And if you go too far with it, then you’re spinning your wheels and if you don’t do enough, then you are not getting enough activity and enough calls, right? So I think that that’s the most important thing because for the products that we’re talking about, and that I think your audience deals with, everyone’s going to need to get on the phone with a salesperson. We’re not selling anything, we’re not doing ecommerce here, etc. So I think it’s really about finding what that like minimum threshold is. And there’s not one way to do that. So I think that’s probably the biggest challenge.

John Tyreman:  That’s really interesting. I like the way that you’re viewing that problem, so that minimum viable information that your average prospect would need before they reach out to have a sales conversation. Can you unpack that a little bit? Like, what are some examples of some information that a prospect might need? And like, can you give us a little color to that?

Dan Englander:  Yeah, totally. So again, our context or our background is doing outreach to get meetings and I think that you just saw I don’t have as much experience building full on marketing plans in a while, you know, I worked in the agency space years ago, but you know, at Silverback, you guys might be doing more of that. For us, to answer your question, the way that we’re thinking about it is basically like, what does it take to de-risk a conversation in terms of outreach? And what we tend to find is that it’s often, it’s less about case studies and materials and funnels and all these sorts of things. For us, it’s more about, you know, mutual relationships and things like that. And we actually have our own process that we call relationship sales at scale, which is about you know, really doing the sorts of things that a lot of companies I think, do initially to build their businesses, i.e. working the rolodexes and getting referrals and all that stuff. But then going a layer beyond that, right? So you have your kind of like immediate circles of influences, which might be your clients, people that refer you business partners, etc. What if you were to just go, you know, one more layer outside of that? So to answer your question, de-risking that conversation might not always be a funnel, it might be like, well, what if I were to take everybody that attended this trade show, or was likely to have attended this trade show that I went to a month ago and then focus my efforts on them, as opposed to let me just find this golden list of prospects that is like our clients and contact those people. I’m not saying you shouldn’t sell or market to those people, but for the purposes of getting conversations now instead of later, focusing on the people that are closer to your circles of influence. So there’s a lot more I can unpack there, but I’ll kind of leave it at that for now.

John Tyreman:  Sure. Yeah. No, that’s really great. Thank you, Dan. It sounds like that road could lead to having a very personalized outreach outreach plan, but that’s sometimes not scalable, right? So how can companies find the right balance between personalization and scale and sales and marketing?

Dan Englander:  Yeah, it’s a great question. And there’s not one way to do that. You know, we’ve heard people trying all sorts of different strategies that could work but I think just to kind of like highlight the challenge and the sort of place that you’re riding between right? Between personalization and scale. On one hand, if you have too much scale, you’re probably bothering people or at least not breaking through. That can play out in a lot of ways like low open rates, because your messages are just going to spam or whatever. Then on the other hand, if you have way too much personalization, then you’re not getting enough activity to actually get a meaningful number of meetings. And we’ve heard this from agencies we partner with. We specialize in working with agencies, and they tell us hey, we tried to do this. We did all this research on a prospect and we said hey, you’re tweeting this or you’re in this situation, and the problem is, that falls apart as soon as you get busy because you can only get so much out. So to answer your question, there’s not one way to do it, but to kind of like shed light on what we’re doing for our clients and like one of our most common strategies is us saying okay, like instead of going in cold, what if we were to identify the people you already know, that know somebody that’s in an account in which you want to do business, right? So we have a client now, we launched the last campaign like just a month ago. They’re an agency. They are selling to hospital groups and bio, life sciences organizations and pharma and that kind of thing. So first, you know, we’re identifying that list of whatever several 1000, maybe 10,000, organizations that they want to do business with and get on the same page about that. Then we say, (making up the name or client – Bob.) “Bob, can you here’s what we need you to do. Go into LinkedIn. export your contacts, highlight everybody that you would feel comfortable asking for an intro from”. Right? And that might be for some people, a few dozen, for other people rather, a few hundred. But everyone that least knows you, that you feel comfortable asking for an intro from right? And so that’s a lot of people. And then from there, what we’re able to do is find everybody that those people know in those organizations in certain handful of titles that they want to talk to. And then we’re sending everybody in that first group, a message that says “Hey, you know, so and so… Hey, Lisa, saw, you know, hope you’re doing well. We haven’t connected in a while. By the way, I saw you’re connected to these 1 to 3 people in these organizations that you know, and we’re doing some business development initiatives. Can you help me out? You know these people. Would you be willing to make an intro?” Sometimes that plays out in a conversation and so on. So what’s really cool about this approach is it’s basically designed to generate referrals at scale, right? And designed to get into specific accounts. So I think what’s annoying about people like me on these shows is like, “Great, so the only answer is to hire you”. No, no, if you were to do… so if you DIY this, there’s lots of ways you can still take your efforts in this way, even if you never hire us. And I think one way is to start thinking about things in terms of your circles of influence, right? So maybe even if you don’t have the capability to do what we do, yeah, we have all the secret sauce, etc. To find those people and that data, you might start thinking about okay, well, I have this list of accounts. So starting on an account based level, and then thinking about what would it take to identify the people among these accounts that I share a strong commonality with? Emphasis on strong, right? So thinking about things in terms of, well out of these accounts, which are the accounts that attended the same trade show I did? Out of these accounts, who have C-level people that went to the same college as me? Or even simpler, if you want to just… if that’s too sophisticated to you, which are the accounts that have people that are in my hometown or in the city where I am at right now? So those are all areas of personalization, where you can be contacting 50 to 100-something people a day without having to write custom love letters to each one, and it’s a strong enough level of personalization that is almost timeless, right? I’m in the same place as you, we know people in common, we’re from the same place. Now is  that always going to work perfectly? Maybe not, but it… to me, in my opinion, in my experience, it’s a lot more timeless than, “Hey, I saw you tweeted this thing earlier”. Great. You know, so that’s, that’s kind of how we think about things. So hopefully that’s useful.

John Tyreman: Have you found it a pain to make the ask of the down to export the CSV from LinkedIn and highlight the folks that they would feel comfortable reaching out to? Because that seems like it could be kind of a time consuming task.

Dan Englander:  Totally Yeah, it is time consuming. It is like eating vegetables. But I think it’s worth it. Because that’s not even the hardest part about it. I’ll set all the right expectations. The hardest part isn’t just the manual work. That takes about a half hour, I’d say. The hard part is actually getting on those calls and asking for what you want, right? But it’s worth it because you’re going into these situations in a deliberate way. And you know who they’re connected to in the account in which you want to be doing business. And you’re asking for a specific thing from your Rolodex. So what you’re doing is you’re essentially condensing like five years of networking into a campaign that might last a few weeks to get referred intros where you have trust built into the right organization. So in our experience, like we set all those expectations before anybody buys from us, but in our experience, like we were totally remiss not to recommend it because it works better than anything else you can think of. But yeah, the cost is time. You know, the cost is, you know, talking to your network, but what’s the alternative? Right?

John Tyreman: Yeah, you know, it’s funny. I’ve worked for about five years helping professional services companies come up with marketing strategies to attract new clients. And I’ve seen a fair amount of businesses who have leaned on referrals to grow their business, and then when that well dries up, they just don’t know how to keep growing. So like, I guess that kind of leads me into my next question, like, what’s the best strategy for going outside of referrals and personal networks to win new business?

Dan Englander:  Yeah, it’s a great question.And I think that ideally, like you have, at least in my experience, you have like one big inbound marketing project. Like, I’m getting on a podcast now. We have a podcast. We also are doing ads and stuff to ticket business and some of our better clients are doing that too. Whether you do a podcast or you have a really great blog, or really great newsletter, I think, and maybe you have more experience in the marketing side or have have a different opinion, but my experience has been, you want one really good channel that you’re just building up like building steam with a grain of salt kind of over time. I think beyond that, you know, our experience has been that doing outreach in the right way is the best way to get beyond referrals and personal networks, contingent on you being in a B2B situation where your client lifetime value is high enough and the numbers work for you to actually get on calls with people enough times. If you’re selling to small and medium sized businesses, you have a low, you know, low ticket product, or something, that could change and may not be the best way and you might have to just go painting by numbers, right, to get business? But I think that if your client lifetime value is at least, you know, 20,000 a year up to the ceiling of millions or billions or whatever. Getting appointments with an account based way I think is the best way and I think you know, the way to get beyond referrals and personal networks isn’t to go from like your orbit of referrals to like cold, it’s to go to the next orbit out, right? Which might be, “Okay, here are the people I already know. Who are the people that know those people that would talk to me?” And then contacting them in a way that gets you into the right account. Or even going direct. I mean, some of our campaigns aren’t necessarily just using referrals. We have other campaigns where we say, “Hey, I’m from the same hometown as you, went to the same college, we’ve done a lot of business in your space. Can we have a conversation?” When somebody gets that email, what they’re thinking is, “Oh, wow, this person actually did a lot of research on me and I’m at least going to talk to them. They’ve de-risked the conversation”. So I might have lost your question, but hopefully that’s helpful. 

John Tyreman:  No, that is. And I’m curious, like you mentioned that you’ve got the podcast. And I like the way that you’re blending, having a solid inbound marketing channel with outbound activities. So there’s some give and take there. I’m curious, like, how has your podcast impacted sales conversations or your pipeline in any way? Like, I know that that’s kind of like a pain point specific to podcasts, like, what’s the impact on revenue, but… and sometimes it’s hard to show that on an attribution report. I’m curious, what’s been your perspective? 

Dan Englander:  Yeah, I think you mentioned it. Like, it is really tough to attribute and so on, a lot of it’s kind of just like qualitative and anecdotal but it’s been you know, really a game changer, just anecdotally. In terms of leads actually coming from it, “Hey, I listened to your podcast” and maybe that will happen from this but I don’t want to just be that, you know. But beyond that, you know, just basically the authority building, just being able to reference episodes to people and like one thing that really helped us and I think people that are listening to this  can do the same thing, if you’re in the client services business is like getting your clients on the podcast. Not just to do like a live case study, but to actually talk about things that they’re working through and so on and so forth from there. That’s been really useful. But I think there is a surround sound effect and this is bigger than just what we’ve observed where, you know, yeah, these things do start to tie together, especially in small worlds where if you’re doing outreach and somebody’s, you know, heard of you, heard of your podcast or even if it’s just in the back of their head, that’s going to have effects that are really hard to measure, but are very real at the same time. So I’ve definitely seen that play out and play out for our clients as well. Yep.

John Tyreman:  Dan, I’d like to shift gears a little bit. And I’d like to talk about how to like, assemble the right team. So like, we talked about having an inbound channel, complemented with outbound activities. But how can companies build an effective sales team, even if it’s like a small operation?

Dan Englander:  Yeah, it’s a really good question. And I think that you know, there’s not one way to do it. We finally hired our first like, full stack, kind of, you know, talented salesperson, a closer role, let’s say. I think what’s easier is to first identify the ways in which not to do it, right? And I think the most common trap we see, especially in the agency world, is hiring that person too early – that closer. And you know, you’re like, I need a salesperson, I need somebody really good. So I’m going to go out and interview a bunch of salespeople, you know, pay a market rate salary, which usually means they’re making roughly six figures combination base, commission, whatever, and then you hire that person and then that person doesn’t work. And you know, we talk to a bunch of companies every week, and probably like, at least a few times a month we hear a story like that. And it’s always a situation where the company said, “Okay, great. I hired this person. I gave them case studies. I gave them collateral. I said, ‘Here’s who we’re going after. Good luck.’ And then they came back with nothing”. And the issue is like those people are… that closer role is successful in an existing infrastructure when they’re plugged into an environment in which there are systems for getting leads, there’s processes for getting prospects, those prospects are already coming in, and so on. So I think the big mistake is doing that too early before you have a repeatable sales process. And I think a lot of the time, some people are cognizant of this problem and they’re working to fix it. Other people have an overinflated sense of the repeatability of their sales process. And that happens because they’re getting most of their business from referrals and personal networks. And I’m not beating anyone up. If you’re doing that, it means you’re doing great work. And it doesn’t mean you know nothing about sales, but it means that there’s still lots of kinks that you’ll need to work out from talking to gen pop, right? From talking to people that don’t have any connection to you at all. And being able to take them on that journey, take them from, I don’t know you, but this is kind of interesting, to buying. Right? And that doesn’t happen overnight. And that takes a process and so on. So I think the first thing is knowing that that challenge is there. And then the second thing is, you know, building those systems, like we’ve talked about, it could be through outreach, or something else depending on your situation, but you have something that’s at least bringing in prospects, and so on. It doesn’t mean that closer can’t be involved in prospecting at all, but they at least… you have something to give them to show them how to do it. And ideally you’re just feeding them calls. That’s the ideal situation. From there, though, there’s a lot more. So in terms of building the prospecting team, I could talk about that. I just wanna make sure I didn’t lose your question.

John Tyreman:  No, this is all really great stuff, Dan. Thank you. Yeah, let’s… we can talk about building the prospecting team. Sure.

Dan Englander:  Yeah. So that’s the foundation, right? It is kind of thinking about first getting a system for getting the top of that funnel built, right? So yeah, let’s say that you don’t have a big team, you don’t have a ton of resources. Maybe you’re an owner or an executive and you are the sales team right now. That’s common. Even in relatively big organizations, like 10, 20 employee companies, sometimes that’s still kind of the case, right? So I think the first thing is to divide up duties, right? Like we’re offering everything I’m going to talk about kind of in a fractional way, but even if you ever hire us and you do this in house, this is kind of how you might think about things. We kind of think of it as like three hats, right? Where strategy, operations and hustle. So for that first hat, that strategy, that’s higher level stuff. That’s thinking about, who are we contacting? Like, who is our ideal client? What accounts are those specifically? What are those handful of titles? And this is tactical, but I’d say don’t get glued to any one title. Get to like, as many, you know, more as better, of people that you’d be happy to talk to within those organizations, right? And also, like, how are we going to contact them? Like, what’s going to de-risk that conversation? Like I was talking about earlier. Maybe it’s a connection, maybe it’s something else, the personalization, the scale, those things mixed together. So that might be a hat that you’re wearing, you know, when you have energy, early in the morning or whenever works for you. That’s the high level stuff. The operation side is the next thing and that’s actually putting rubber to the road, right? That might mean hiring a list builder on Upwork. It might mean, you know, finding a process for getting a list. It might be buying a niche list somewhere, figuring out your software and the CRMs and all these things, right? And getting those things ready to launch. We could have a whole episode about that probably. And then there’s hustle. And sometimes we do this, other times our clients do it depending on the situation. But that’s actually… then you’ve launched campaigns, the hustle is actually getting those people to stick to the calendar and then actually doing the things you need to get them to convert, right? So that might mean follow up. It means when you get interest, you get a response, you get somebody opening the message a lot, being able to call them, being able to actually invest that real time sort of like, you know, that the real time on the ball activity to getting people to stick to the calendar and so on and so forth from there. So I think that if it’s just you doing all those three things that might seem overwhelming, but the way you do it is you divide up your time into those three tasks and you prioritize it. And I think that if you are in that situation where you’re like, “Oh crap, I’ve got to do sales and client service”, get the client service stuff off your plate first and not the other way around, right? Because if you get… because the sales stuff, you’re not going to be able to hire anybody that’s just going to be able to build that for you. I mean, a company like ours is good at getting meetings and that sort of thing, but in terms of going further into that process and closing business, and that sort of thing, the deeper in the funnel sort of stuff, you’re not going to be able to do that right away, right? You’re gonna need that top of funnel situation filled first. So that means clearing off space with the client side. So anyway, there’s a lot there and hopefully, that’s helpful.

John Tyreman:  It really is, yeah. And I like… there’s one thing that really stood out to me, it was that folks have an overinflated sense of the repeatable sales process. So if you’re leaning on referrals, and that’s the main driver of new business, those have a higher probability to close because you have some sort of a relationship with those people, whereas it’s not the same as cold sales. 

Dan Englander:  Yeah. Just to add to that, though. We’ve built our entire sales process around doing outreach for ourselves, you know, to agencies and other B2B service companies. And I’ve been the main person in the sales seat for years now. And we’ve recently hired somebody to kind of step into that closer seat, and we’ve sort of realized, like, how many gaps and how much of this… like how much looseness there is in the process, just because it’s all kind of been in my head for so long. So even us, like, you know, this stuff takes constant kind of like optimization and coaching. A great sales coach of ours, Mike Ganzel, has been helping us a lot and just really tightened up that process and like, you don’t realize like how much is missing until you have to plug another human into it, right? So I think that’s a really useful exercise.

John Tyreman:  Yeah, so… and I really like the three hats and how you bucketed those into strategy, operations and hustle. So I’m curious, like, I think you dabbled in this a little bit, but I just want to just kind of ask you a pointless question around it. Like, what’s the right order of operations for hiring and training salespeople?

Dan Englander:  Yeah, I think it’s sort of like in line with the funnel, right? So focus on top of funnel first. That could be a combination of sales and outreach. I think if you’re early on, you know, we’re biased. It’s our domain expertise. So grain of salt, but I think emphasize more outreach, because that’s going to be more revenue generating than the longer term marketing projects, although long term stuff can be way bigger in the long run. So you want to do a little of both. And so that means, you know, focusing, whether you’re hiring, prospecting, like working with a company like ours, or hiring in house or just assigning your time that way, like focusing on top of funnel. Once you get that figured out and you have a good amount of repeatability that might, depending on your situation, that could take months or even years, then looking to hire that full stack sales closer role. Now that role in my experience, like, I think that I have personally messed up trying to hire that role too early. I’ve seen lots and lots of people mess up trying to hire that role too early. I have also messed up and seen people make similar mistakes under paying for that role. So that’s, you know, that’s essentially a six figure role, whether you want to break it down by you know, commission or base. So you want to, you know, and also you have to… even if that person is really good, they’re going to take a long time to ramp up. Their sales cycle’s gonna probably take longer, their close rate may eventually be better than yours, but it won’t be probably in the first year. So you’ve got to just plan for that and be able to sit tight for that process, but it’s very lucrative at the end of the day. So then beyond there, you know, then that’s all about scale from there. And then that becomes the service business, which is our expertise. It’s a little different than things that are infinitely scalable, right? But if you’re infinitely scalable, if you’re selling a software product, you could just keep putting fuel on the fire and keep hiring salespeople and so on, so. But there’s a lot that goes into that and that’s probably a whole other episode.

John Tyreman:  Sure, yeah. Well, this is all really great stuff, Dan. I’m just over here, taking a bunch of notes myself because these are things that I know that we’re constantly working on and iterating and evolving our own sales process, as I’m sure so are many other businesses out there. 

Dan Englander:  Yeah, so are we. 

John Tyreman:  Exactly yeah, it’s a process of continuous improvement and it never ends. Well, Dan, I know we’re running short on our time here. If folks want to connect with you and learn more, where can they find you?

Dan Englander:  Yeah, so I’ll go ahead and hawk our on demand video training, which is Plural. So that goes into a lot of this and gets a little more tactical. So if you want to DIY some stuff, or hit us up, you know, always happy to talk to people casually. That’s just My email is

John Tyreman:  Thank you so much for taking the time to come on our show today.

Dan Englander:  John, this was great, really good questions. And would love to do it again.