Episode 37 – Jason Dorfman – building versus buying in outsourced sales development, the science behind recruiting the right sales people to your growing company, and getting clear on a process

Jason Dorfman, CEO at Orum joins The Talent, Sales & Scale Podcast for Episode 37. Host Bryan Whittington and Jason dive into Jason’s vast experience as a sales leader, business owner, and authority in all things sales development.

-using technology as a complement to a solid sales development process

-finding the right type of new hires to scale your sales team the right way

-building a training culture

-predictions on the future of sales development

Jason’s Linkedin:

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Bryan: Hey, everyone. This is Bryan Whittington with The Talent, Sales and Scale Show. Today we have Jason Dorfman from Orum on the line with us. And the reason I reached out to Jason is that he had a really good article where he wrote about CEOs and the requirement to really get the sales development program up and rolling—what you should outsource, what you should automate, and really the pitfalls behind it. So I’m really excited to have you on the show, Jason. Thanks for joining us.
Jason: Thanks for having me, Bryan. I appreciate you reading the article.
Bryan: Yeah, absolutely. And the reason I wanted to have you on is because it really spoke to me. And so you go through it, and we’ll link it in the podcast here whenever we push this out.
But you really laid out the fact. And one of the reasons that I started up this company, Jason, is that I saw so many good entrepreneurs, really good programmers, really good engineers. You know software engineers; they have a really good viable product. And they found that, oh my goodness, this sales thing isn’t quite as easy. It hasn’t built a better mouse trap and they’ll come kind of thing. It’s competitive, it’s loud out there. And so they would hire really bad sales people, really bad VPs of sales. And then they would just destroy the company burning money, burning runway, and an otherwise viable business goes under. And it just frustrated me to no end. So that’s one of the reasons that we started up our company.
So I really appreciated the article. But I guess one of the top questions we always ask, Jason, is what makes you an expert in this? And why should we listen to you, because there are lots of people out there saying, “Hey, do this, do that! This is the secret sauce, the magic bullet. If you do this you’ll be successful.” So why should we listen to you on this topic?
Jason: Yes. So I think I’ve built up a unique perspective over the years, just having worked in sales development. I started my career in 2010 as a sales development rep. I was an account executive at a company called Right Scale.
I ended up leaving there to move to Silicon Valley to start my own company. I ended up in a small Apple hire that was not particularly successful. And in the aftermath of that I was kind of figuring out if I should go back to my sales career full force, or should I go back into the entrepreneurial world? And I really got the best of both worlds. And I got hired as the first sales/business hire at Rubric. I was the twelfth employee there as myself, the CEO of the Fally and Jerry Team, and then stayed there for about six years until we were 1700 employees.
Bryan: Wow!
Jason: And that company built out a worldwide inside sales team, and then later a corporate sales team. And through that I just got to observe just a lot of different things and learned a lot of hard lessons. I did some things right. And then, you know, starting Orum which is a company in the sales development space. We make it easier for reps to get into instant live conversations with their target prospects.
That gave me a whole other perspective, because I started to see all of the different sales development organizations outside of my own. And so I think that all of those experiences put together have given me some viewpoints I think that are contrarian and just ways that I think about sales development in general. And I think that there’s a ton of room for improvement here and a lot of opportunity as well.
Bryan: Well I love contrarian, so let’s hit on the contrarian. So you’ve built it ground up, you know, from employee 12 to a massive-sized company. You’re now building out Net New in a sales enablement tool, and that space is getting pretty loud as well. Whether it’s Out Match, whether it’s Sales Loft,--or you name it; there’s a bunch of them out there,--from an email approach to a dialing approach. So talk to me a little bit about how you created Orum. And what was the idea behind it?
Jason: Yes. So I think it’s important to remember that five or six years ago, especially when I was managing a large get sales women team, the whole sales acceleration space was really a collection of widgets. And now you’re seeing these billion-dollar companies emerge, like Outreach and Gong, and hopefully Orum in the near future, because I think technology has gotten to the point where we’re looking at all these repetitive tasks that we’re doing in the workplace. And we’re automating them with AI machine learning and other tools. And that’s a really big opportunity for digital transformation, because humans are incredibly expensive. And if you look at the amount of money that’s going into sales marketing, how much of it is really spent having quality interactions with your customer base? And how much of it is grunt work that we can use software to solve?
So I think that’s been the driving under-current behind all these companies, including Orum. With Orum specifically the idea really sprang from when I was managing an SDR team at Rubric.
You know, I was trying these kids out as reps. You know, some of them might have been rowers from Princeton, or these really smart high-quality people who were right out of college. And then I would have them sit there and make a hundred calls that three or four people would pick up. One would grudgingly take a meeting. And it just seemed like an incredible waste of time.
And in the meanwhile I was checking out all these next generation tools. And it seemed like they were solving everything except for that core problem. And so when I looked at the companies that were trying to solve this, a lot of them were very old school. They were very expensive. They were really just outsourced services. There was no technology company that was taking this head-on.
So that was really the original inspiration for Orum. And I think that later on we realized this opportunity to partner with the rest of the ecosystem—people like Gong and Outreach—and really build this next generation stack, which is what people are looking for to drive more efficiency and speed to their SDR organizations.
Bryan: So who does this really work for? I mean, is there a typical type of company that we have to do? Do you have to have a huge target market? I mean, what’s the ideal user of this type of platform, because you’re talking about a lot of outreach in a short period of time?
Jason: Yes. So our initial segment is about 100 to 1,000 employees, specifically if they’re an Outreach or a Sales Loft customer—just some evidence that they’re starting to adopt these next-generation tools. We are moving up market rapidly. And some of our best trials are with bigger companies because they tend to have much better data. Obviously, being a small start-up, going through the regenerative process, those longer-deal cycles are harder for us. But that’s absolutely where the product is moving to.
We do have some smaller customers, some one-man bands that want to, that have very little resources and want to do a lot. But I think that the real benefit is for someone that maybe has a 5% SDR organization on up.
You know, the other requirement too is that they have to have pretty good data to call. They have to have a culture of cold calling. They have to look at the phone as a main tool for outbound. And I think that some customers are doing that better than others, and that’s something that we’re kind of coaching them on. I think the market is really evolving there.
So I think that those are the main things. And we have to have a champion in that organization that really believes what we believe, which is that live conversation is really the cornerstone of sales and sales development. And you really need to build your training and your outreach around that concept if you want to get the most out of your people.
Bryan: Yes. So let’s dig down on that. So all right; I’m outbound demand generation. This makes perfect sense, right? How about if I’m heavily digital—inbound lead conversion? Does this make sense for me as well? Does having a tool like this work? Or should I just be doing emails and social?
Jason: Yes. So speed and timed first touch is really important. I mean, if someone comes inbound to your service that’s a prime time to try and get them on the phone as quickly as possible. People get so many emails these days, most of which are just templates or LinkedIn messages. And it’s really hard to stamp out when you’re doing a syncretistic communication like that. It’s much harder to build a relationship. It’s much harder to handle objections in detail, and really for both sides to qualify each other quickly to ensure that it’s a good fit.
So some of our customers are just like that, right? They have a lot of inbound leads. They’re having trouble touching them all in a timely fashion. And so the phone is a very effective tool for doing that.
Bryan: Yeah. And that’s one piece in your article that I found interesting, right?, because one of the things that we look for from our marketing is a good return on investment. And you constantly hear the back and forth between marketing and sales, and sales and marketing, about marketing pushing these opportunities over. And then sales #1. Don’t follow up with them in a timely fashion, or #2., won’t even call them, right? And they just get colder and colder and colder, and leads are like produce; they sit on the shelf and they’re going bad and rotting quickly.
So talk to me maybe a little bit about that ideal technology stack, because I know that you’re partnered with Outreach and Sales Loft. I mean, what does that ideal sales stack look like as I’m building out this sales development program?
Jason: Yes. So I think that the basics are right. Every company has to have some type of system of records. Typically that’s going to be Sales Force because they integrate with the rest of the broader ecosystem. I think at this stage of the game it’s having some kind of Keynes management platform, like an Outreach or a Sales Loft. It’s really important just to be able to manage and schedule the reps, and make sure that they’re putting in the appropriate amount of touches.
And you know, in addition to calls I believe in a multi-channel outreach. So you should be doing LinkedIn; you should be doing email. But you should also be doing calls. And I think the way a lot of these cadences are designed is that they might have fifteen emails and two calls, because the calls are the bottleneck.
Bryan: Right.
Jason: And the reality is that you should be calling people multiple times, but maybe only sending them a few awful hard messages so you don’t end up in the spam folder. So I think it’s better just to try to get them on the phone with most of those touches.
And you know, I think that doing conversational analysis is a good cherry on top to understand the content of the conversations. That really depends on the size of your team too, and whether you’re able to arm them directly. So I think that’s really the basic stack. And of course having data, whether it’s Zoom Info or Sales Intel. Those are companies that obviously have very advanced marketing, so they’re generating a lot of their own leads. But you need to have great accurate data in order to make these tools effective.
What I really think it comes down to philosophically is that you want to hire world-class people to be in your sales development organization. And you want to make sure that their time is spent having quality interactions with customers, and converting people that might otherwise not convert. What you don’t want them doing is grunt work—listening to the phone ring, dropping voice mails, manually writing things out. So in so far as you can use this evolving technology to take that off your plate, their plate, you’re going to have better retainment of your SDRs. They’re going to become much better sales people and quicker. You’re not going to need as many SDRs potentially, so you can be more thoughtful in who you’re hiring, rather than just constantly adding people just to stack up your activity volume.
So I think that’s the lens in which people should look at this. And all of the tools and technology are cool. And as my article alludes to, leadership and sales management and the way that you recruit, that’s all really in a separate bucket. And no tool or technology is going to save you if you don’t have that side of the equation really dialed in.
So I think that there are a lot of these sales development nerds—myself included—that like to nerd out on the tools. But success really comes from the leadership and the process that you put in place as a manager.
Bryan: Yeah, and it’s funny you should say that. It’s the reason for the name of our podcast: “Talent, Sales and Scale,” because if you don’t have the right talent, you know, all your technology stack is going to do is a really bad job, amplified and much more quickly. So yeah, talent is a key piece.
Now one of the things that you said is that in this sales development program it’s developing a sales strategy. So if I don’t over-simplify this, the sales strategy that you’re recommending is the omni-channel approach—whatever it takes to have as many conversations as quickly as possible. And make sure that the list is good. I mean, is it that straightforward?
Jason: Yeah, I think it’s that straightforward. But the caveat is that you have to make sure that the person that customer is connecting with is excellent, that he’s really a product expert, that he knows how to handle sales objections, because that’s ultimately going to determine the quality of your sales development. The tools are just enabling them to get that interaction.
Bryan: Yeah. And then one thing that you had mentioned in the article is really creating, and this is long-term play here. So if you’re looking for short-term solutions, to use the Queen’s English, they’re ain’t one ever. So really what you’re talking about is creating strategic partnerships with local universities or different universities before you can get top talent coming off of it.
And so we all know hey, hire the collegiate athletes. We all know those good things. However, coming out of a university, they’re really challenged with sales acumen, because what I’ve found is that you can get people into a conversation quickly. But then that conversation will quickly end if you’re not able to hang in there from a sales acumen standpoint. So talk to me a little bit about how you were finding best practices of helping these young folks right out of school, right out of the university, to get that sales acumen—to hang in there, to have those good conversations.
Jason: Yeah. So it really does start with the recruiting. Actually I have another article coming out about this; I can speak to this a little bit. So yeah, I think there’s a stereotype. Yeah, you can hire a college athlete, and it does make sense. I’ve hired a lot of athletes before they tend to spend less time in college partying and more time working their butts off and trying to manage their scores. And all these things lend themselves well to the grind that is being an SDR.
But I think that there really is an art to interviewing and recruiting. I guess that starting off with just maybe the science side of it is that I’m a big believer in using external recruiters, people like Bad Score alliance, and making sure that you’re doing twenty, thirty phone screens a week. And that way you have a good sense of what good actually sounds like. And then you can start to be really, really picky about who you’re hiring.
And I think the second piece is having the interview skills to really pick out who is going to end up being a great sales rep. So when you’re hiring AE it’s different. You look at the last company that they worked at. You asked people who worked for them if they crushed it and if they hit their quota. If that’s the case they’re probably going to work out for your company, assuming that it’s a similar market.
With an SDR it’s like buying an early stage stock. You don’t know how they’re going to turn out in two or three years. So there’s some guess work to do.
So the way I like to start off an interview is to talk. You know, have them give me their life story. And then sit back and really just listen to how they describe themselves.
And I usually ask myself at the end of their life story, were they the heroes in that life story? You know, were they hitting obstacles and then overcoming them? And is that the type of person that they view themselves as?
So when they come into that role as an SDR, are they the type of persons where things start to get really hard and they’re going to figure it out, and really try to be the number one person in the organization. Another question to always ask is this. Give me an example of a time that you’ve done something that is really, really hard or challenging where you came out on top, or as number one?
And all the exceptional candidates that I’ve hired have a really great answer for that. I mean, one person that comes to mind is a field rep now at a big company, but when I hired him he was entry level. He wanted to be a professional race car driver when he was sixteen. His parents were like no, you can’t do that.
He was going door to door to raise money for it. He ended up figuring it out and became a race car driver and won a championship. Now he has to figure out what he’s going to do next.
And so this is the type of person that when he wants to do something, he’ll figure it out. They’re going to do it. So I know that’s a long rant, but you need to have a person in the seat that is highly motivated for his own success, and has that social acumen to be a great sales person with that aggressiveness.
And then, you know, from there you need to build a training culture. And training doesn’t mean that this is how you use all these different tools. Training is constantly going through objections, doing mock cold calls, listening to their calls, breaking them down—really training them on the fundamentals of sales, not just on how to sales development grunt work.
And I think that’s where a lot of companies go wrong, because this is how you use the tools. Here’s this script; this is what you say. But they don’t really have a culture where they’re constantly training on just the fundamentals of sales. They need to do that.
Bryan: Yes, so let’s hit on that. So from the hiring perspective it seems that what you’re suggesting is having a highly organized, highly systematic programmatic approach to be able to vet these folks, because we always joke around that, you know, you think that you have Rambo on Friday and the Pee-Wee Herman Show is up on Monday, because people who like people don’t necessarily make good sales people. They make professional visitors and lots of friends, but they don’t close anything. So you really have to know the difference between people who are extroverts—good with others—as opposed to good sales people. There’s a difference there.
I also heard you say that you need to find those with grit—college athletes that have the grit of the daily grind of getting it done. That can be very disciplined on their time management, because if you come to an SDR role you have to really know your time blocks, be effective in those time blocks, and hold those no matter what—having that discipline equals freedom mindset. So I heard that as well.
You don’t say this. But it also seems that I gather, based on what you said, constantly be recruiting; never relent there. So is that a good summary of the hiring side?
Jason: Yeah, absolutely. One more point on that is that I think there is something here that sounds obvious: hire the best people. Well duh! Of course I was going to hire the best people. (Laughter)
But what do people actually do? They don’t put a system in place to have enough candidates come in the door. They get desperate because they use the pipeline as empty. And they go, “Whatever; he’s an SDR. He’s just hitting the phones and sending out emails. Just hire him. You know, if it doesn’t work out, we’ll hire someone else.”
And they have that sort of lazy mindset. And when they have the wrong person in the chair, there’s just nothing you can do to fix that. And I think you would be surprised at how they rationalize these bad hires in their minds, because they didn’t prepare or really take the position as seriously as they should have.
Bryan: Which goes to the second point that I want to amp on, which is that what you’re talking about is more a strategic thinking SDR, right? Because you’re not talking about BANT here. You’re not talking about just smiling and dialing. And it seems to me that what you’re suggesting is finding people that can have a strategic conversation to drive deeper into the sales pipeline, because if we have good strategic opening conversations then we can have more effective exploratory discovery calls. From those exploratory discovery calls we can have more effective pipeline management whenever the demo comes in. And we’re problem solving the whole entire way which allows a shorter sales cycle, which really starts off at the very top. It’s an effective initial conversation.
Believe it or not, my belief (and you can tell me if I’m wrong here), allows for a shorter cycle time to close or at least get a no. But if it’s going to be a no—an n-o—then at least I k-n-o-w, I know pretty darn quickly. Is that kind of what you’re suggesting here?
Jason: Yeah. It’s also about the long term. Companies aren’t built in two years; they’re built in ten years, twenty years. And in so far that you’re hiring someone with the idea that he’s going to stay at your company for five or ten years, they have to go beyond the SDR position. They have to be that top field rep. They might be those SDR leaders. They might go into another department in your company.
So, you know, you want to hire people. This isn’t like you have your company where you have a bunch of smart Google engineers, and then there’s this call center that’s an offshoot of it, where those people don’t really matter. They’re employees at the company and you need to hire people that are talented enough to just scale with it, even beyond the SDR position.
You know, it’s just really looking at the same bar that you would have for any other position. I just find this when it comes to SDRs, because it’s an entry level role that’s not technical. I think especially of the technical CEOs. They kind of put it aside as well, it doesn’t really matter because it’s a grunt work job. And then they bring low quality people into their organization. In other places they wouldn’t do that, or they wouldn’t have permission to do that.
Bryan: What do we say to them? How do we catch their attention? Because my goodness, this knowledge is ubiquitous out there. But they seem to keep making the same mistake. How do we speak to that other founder, that other technical CEO, that CFO? Because they’re the ones that will either make or break this structure. Giving that VP a sale and the time to develop this, this is not overnight. People want instantaneous results and oftentimes, to your point, it can’t happen.
Now does it sometimes? Yes, you can get lucky. So let’s not discount that. But for the most part there’s some heavy lifting involved. So what do we say to them, Jason?
Jason: Yeah, I think it’s interesting. And you know, in the ‘90s it was very common to have an MBA or business founder, and then engineers were in the back room coding the product. And you have these things like AWS and Cloud Computing. And you have Y-Commonator where a couple engineers can start hacking together a product and scaling out a business. And you have people like Andreessen Horowitz, where they are specifically focused on investing in a really talented technical role as co-founder, and then teaching them the business stuff later.
So you have a lot of companies that are run by technical engineers. And sometimes with Facebook that can work out really, really well. At Rubric we had a business CEO. And I think that there were a lot of advantages to that. And I think people are coming around to that idea of hey, it’s not just building a great technical product. Distribution is just as important.
So a lot of technical CEOs (and I’m giving training for a D.C. firm in the near future), and just kind of on this they really struggle with all right, I have this product and a little bit of traction. How do I build out the business side of things?
And even before you get to that SDR team you have to think about who’s going to be my first sales hire as an SDR, as a sales leader? You know, what type of VPS sales should I hire? Should I hire this worldwide person from Sysco or Microsoft? Or should I hire someone who is just a rep?
So you have to make all of those decisions first. And even after they’ve gone through all those hoops building a sales organization, you have this sales development thing which is a subsection of sales in most cases. And that just seems like a detail that they’re just going to pass off to the sales leader that they hired. And they’re not really thinking about it as a fundamental engine of their company.
But as the company scales out, all of a sudden they’re like holy cow! There are millions of dollars being spent on this segment of my business. And by the way, as we’re going public, this is going to turn whether I hit my number or not.
Bryan: Right, right.
Jason: I think it‘s just one of those things where they just don’t know what it is. They’re just learning the company.
Bryan: So can you give them this? What’s that stepping stone? Because you’ve seen this a couple of times firsthand through Rubric, now with Orum. How would you suggest that? What does that pathway look like? I’m just starting off. It’s me, the technical founder. I’m guessing that I get funding, right? So that’s going to look a little bit different than if I’m just boot-strapping. So can you maybe lay out if I’m boot-strapping versus funded?
Jason: Yes. So it’s not one size fits all. But I think that for your typically funded VC-backed company I think that there’s some sense in hiring sort of like an inside sales rep that’s maybe a little bit more expensive than what you would hire when you were a more built-out company. Maybe someone was in a position for a couple years. And he got promoted and wants a shot at getting on the ground floor of the start-up.
That can start getting you into a whole bunch of new things. It may even close a couple small deals and then ultimately even build up that team, because the problem is that if you don’t have any sales yet, and you’re just starting to build your product, what great VP of sales or account executive who wants to be a leader is going to join your company when he’s not sure if he’s going to make money or not?
Bryan: That’s right.
Jason: I’m not in a great position to hire that person. But if you can build up a whole bunch of pipelines and have the CEO acting as the AE with an SDR by his side, I think that’s a way to build them on a pipeline. And then you’re like “Hey, Mr. VP of sales who I heard is super talented, we have thirty sales campaigns. I’m not a sales person; I’m not even managing these. Can you come in and take over this process?”
So I think that’s a good way to kind of get the ball rolling, as opposed to “We don’t have many sales. Our VC knows this worldwide VP at big company XYZ.” They’re super process oriented. They’re going to come in and they’re going to do this. But what they really need is an executive for the next eight months that’s going to close their first twenty customers.
Bryan: Right.
Jason: So I think you need to hire for the people that you need six months or a year in front of you, not the people you think you need five years from now. And I think that an inside sales rep who has probably somewhat more of a limited experience than average is what I think is a good business hire for a technical founder. And they can do more than just cold call. They can set up some of these business systems and start tracking things. They’ll usually have the skills to do some of that at a basic level.
Bryan: Okay, so we have that; we’re now working it. So from there what’s the next step? What happens next?
Jason: So I think you’re saying that once I have your initial SDR and then you have your VP or AE that’s acting as the leader, so—
Bryan: Right.
Jason: I think from there it really comes down to obviously getting more first sales down. But, you know, hopefully those two people are the seeds of an organization who will go out and recruit. So I think what you’re looking for in that first VP of sales in a seed stage start-up is maybe someone who is a front line manager that was recently closing but has some experience managing people, but really wants a shot at running it all themselves, or someone that’s a very high-level individual contributor who maybe has been in the field for six or seven years that has a really strong network and the respect of his peers, so he can start to bring in people that are really good, because, you know, the great thing at Orum is that I’ve trained and recruited over a hundred sales reps in my career at this point. And they’re not all from the companies I used to work at. They’re spread out all over the industry.
And so I know who’s good. I can call a few of their friends and say “Hey, is that person still good? Where are they in their lives?” And then I can bring them on board rapidly. And when I do they have respect for me. They know how I manage.
And so you want to bring on someone like that who can go out and close this image of a contributor, but has enough umph to also get people to follow him.
Bryan: So really what you’re looking for there then is that as you look for this VP of sales, it’s not necessarily only the technical ability from a sales perspective; it’s not only the management perspective, but also their network. How have they led others? Do they still have that network of people that they can tap to grow a little bit more quickly? So that’s a pretty interesting point.
Jason: Yeah. You can’t raise the sales number unless you add people. And if you don’t have someone that has the ability to rapidly add really great sales reps, you’re never going to get the kind of trajectory that a Series A. or a Series B. investor really wants, which is a rapid revenue growth. You can’t do that if you just have one or two reps. You need to have a plan to scale it out.
Bryan: Yes, 100%. Okay, so how much should these people know about how to build this thing from whole cloth? Are you counting on this inside sales person, this seasoned inside sales person, to really build out the systems and the processes, and then the VP to kind of tweak it? Or are these people just really good at sales and management and leadership, and you’re bringing other people in? I mean, what’s your sense of the best approach there?
Jason: So it’s absolutely that this VP of sales is an architect that is going to start up. You want him to be a great natural leader. But as I mentioned in the article, almost fundamentally they’re likely disconnected from modern sales development and inside sales. If they’ve been in the field carrying a bag for the past six years, or they’re front-line managers for a bunch of AEs, they’re not really thinking. The SDRs have not been on their minds for a long time. And in so far as they’re not stopping in together, or dropping into a top-line leader, look! They’re not just responsible for an AE team; they’re responsible for an entire revenue team.
And so I think it’s important for this CEO to really look at this prominent VP of sales and go, “How do we think of a sales development team from first principles? How do we align this with the goals of our organization and our company?”
And with the same kind of thought that we put into hiring great AEs or hiring great engineers, and in building out this great SDR program, do we want it to be a bench to recruit from for the rest of the company? And—
Bryan: Oh, I’m sorry; go ahead and finish that thought.
Jason: Yeah. I was just saying that I think the CEO figures that because my VP of sales is a sales expert he must already have a plan for that. And I have enough things to think about, so just take care of that side of the business.
Bryan: Yeah. And the curious thing is, a lot of times sales people, these VPs of sales, (this is a stereotype, so don’t take this as the gospel or anything like that), but a lot of times good sales people aren’t very good technically. They aren’t very good with details. They’re very big picture; they’re quick decision makers, high risk takers; let’s just go. Where does a Rev Ops person come into play? Because of how important this technology stack is, do we maybe not have that VP of sales and have a Rev Ops person in this new technology environment in which we find ourselves? I mean, can you talk to me a little bit about that?
Jason: Yeah. I think the job of a VP of sales isn’t to be an ops, an operational kind of nerd, so to speak.
Bryan: Right.
Jason: But I think that’s a different job. I think that being a VP of sales you’re not going to have charisma. You want them to be great up-front customers. You want them to be the people that are inspiring other people to join your company.
I think that a very common argument that happens early on in companies is that people start to go, “Hey, we need an Ops person. This is going to be a mess; we need an Ops person.” And it’s very hard to justify that in an early stage company, because for every account executive I add I can add another chunk of quota and project my revenue going up. And an operations person is an overlay.
Bryan: Right.
Jason: It’s just another expense for the business. So I think that taking a guide and hiring those types of people early can really help to allay a lot of problems later on. I think that it’s a hard thing to justify. But we did it at our company, and we were kind of blown away by how much was taken off of everyone’s plate.
But I don’t think you should play it light, because there are all these tools and technology. Therefore I have to hire this very technical VP of sales. Someone can only be good at so many things. And I don’t think that’s fundamental to that role.
I think that when you’re a really, really large company I think that ahead of worldwide sales they need to have a certain operational skill set, because the problems you’re facing at that stage are much different than recruiting and getting your first skills. It’s really about territory planning—you know, cost-efficiency models, those types of things that they have to have a sense of and be familiar with. But the job of VP of sales isn’t to optimize Sales Force. And you’re most likely not going to get someone who is great at both of those things.
Bryan: Yeah. And that’s what kind of made me think of it, because especially when you’re looking at an Orum or an Outmatch, or whatever the case may be, your list management, the cleanliness of that list, (Laughter), it is insane how a lot of that can be. And that’s what I was thinking. And you can probably even outsource that; I know of a couple of different outsource sales revs. Now is there ever, ever a time when you outsource that sales rev, or do a fractional VP of sales kind of thing? Have you ever seen that work out well?
Jason: Yes. We have an ADR service. We’re doing a chunk of that for our customers. And on the operational side I think early on that we were hiring some contractors. It’s not a bad thing; it doesn’t necessarily have to be a full time person. You know, getting the right data in your system, especially when you’re moving with automation tools, is always a challenge. I think that’s a part of the tools stack that’s still evolving. It’s something that our product helps a little bit with, at least one side of it. But I think there are a lot of companies that are making that easier to use. But if you have perfect data, that’s really the holy grail; that’s what everyone is working towards.
Bryan: Yeah. Perfect data with a perfect sales team, with the perfect sales leader and the perfect recruiting. If you’ve got that, that’s easy, right?
Jason: Exactly. (Laughter)
Bryan: So let’s kind of keep moving on here. And you know, with all of that said, unfortunately there’s nothing new under the sun. It’s just gaining some additional perspectives about how we can do these things, because the blocking and tackling is that—it’s blocking and tackling. We need the right talent with the right systems implemented well, executed well by the sales team on a consistent basis. I mean, there’s nothing new under the sun.
You know, I’d check out Orum. It’s fairly easy to use, and it’s effective. So check it out. But in addition to that, give us some insights here, Jason. We’re starting off whether I’m in sales, whether I’m a founder, you pick. What is one business challenge that you face that you’d like to share with us, ways that we can avoid that same pain and frustration that you’ve had?
Jason: Hmm! I have to think about that, maybe more specifically just the challenge in terms of building a start-up or a sales team?
Bryan: Yeah. How about we go at it from a sales team perspective? Let’s narrow it down there. So the biggest challenge from an early stage—and you’re still Series A., right?
Jason: C.
Bryan: Oh, you’re C.
Jason: Yes.
Bryan: Okay. So from a C. stage, maybe a lesson learned from building up your sales team, whether here or at the last place as #12 on the hired list.
Jason: Hmm. Yeah. I mean, I think—I’m trying to think here!—I think that one of the challenges with an early stage sales team is that things are moving extremely quickly, and it’s really hard to balance. Do I invest my time in building more process and more guide rails? Or do I just spend my time getting after it, and trying to be in front of customers?
And I think that you want to use time. When things are slow that’s when you need to take a step back and really put some of those processes and other things in place, because I think that what happens to a lot of early sales leaders is that they’re so caught up in the drama of the deals that they really can’t land that next phase of what things are going to look like. I think that’s one of the really hard things to balance.
And also I think that any early employees that you hire are very much going to be doers. And very quickly as you grow they have to become delegators, because it’s not your job to close every deal, like looking after counters. Is it going to look like an individual contributor counter, or does it look like a manager’s counter?
Bryan: Right.
Jason: And there’s a gray area that I think every employee has to cross as they’re seating their teams. And I think that’s something that they have to help their employees manage through, because it’s really difficult to do that.
And I think that sometimes it’s a letting go process, too. You know, you become the only person in the bottleneck to be trusted with a certain task. But there’s no way that you can free up your time to do the recruiting and managing that you need to do if you’re doing all that yourself. So I think that’s one of the big things.
And I think there’s a parallel to that with start-ups as a whole. It’s that when you’re growing really quickly, your earliest employees every six months to a year, their role almost has to be a different role. They’re going to grow out of what they’re doing. And you have to figure out how to take your early employees, who are arguably the most valuable people in your business, and make sure that they’re positioned to be really successful. And I think that a lot of start-ups have growing pains with that, where they’re trying to hire executives to solve their problems. They’re not sure what to do with early employees in the business. And sort of figuring out that puzzle so you can bring those new talented people in, and the people that look forward to your business in the beginning, to get them to work together in a productive way, I think those are the things that ultimately determine your culture and your success.
Bryan: So it seems that what you’re suggesting then is that much like you bring a strategy to your sales development efforts, bring a strategy to your talent development efforts.
Jason: Yeah, absolutely, in the way that you are structuring your business over time, communicating to your employees that things are going to change, because start-ups are not a steady state business, where hey, you’re a sales manager and you’re running a 16-person team for five years. And things are going to be different every few months.
It sounds silly, but it can be very difficult and emotional for people to adapt to. And so making sure that everyone is in the right position at the right time, that they’re refreshing their goals, that they’re not doing the same things that they were doing when there were ten employees, when there were thirty employees.
Bryan: Right.
Jason: I think that those are some of the hard things that you have to figure out as a leader.
Bryan: Yeah. And I think this goes a lot to what you were saying before, where you’re thinking six months or a year in advance. What are the roles and responsibilities that they’re going to be doing six months or years from now. And what’s generic now—those six things that they’re doing, those four to six things that they’re doing now—might branch off into a more specialized four to six things. And those might branch off into a more specialized four to six things. And we need people to back fill, to take over those other roles and responsibilities. So if we can forecast that and think that ahead, whenever I was flying airplanes it was called being ahead of the aircraft, right? If you’re hanging on by the tail of the aircraft you’re going to die. So you always have to be ahead of the airplane. You always have to be ahead of the business is what it seems that you’re saying.
Jason: Yeah. What percentage of my day could be done by other people? And what percentage of my day needs to be done by me? And I think that the early people in a start-up—the CEO included—they forget to re-visit that question.
Bryan: Yeah.
Jason: And they end up becoming a bottleneck in various processes in the business. So I think that’s one of the things that you always have to be on top of.
Bryan: Any business hack or suggestion around that topic that you might suggest? I mean, have you learned from the school of hard knocks, or have you figured this one out yet?
Jason: Yeah. I mean, a common one, and one I was guilty of, was that I was really focused on managing down.
Bryan: Okay.
Jason: Because, you knows, it was myself and the CEO and then just my team under me. And as time went on I didn’t realize how much managing I had to do up. I mean, if I wanted an employee I needed to be thinking about how I would justify that to the business. If I want extra men on the job I have to think about how I would justify that to the business. If I need to rearrange people’s quotas I need to figure out how to navigate that within an organization. So I think that with the top line leaders, it’s their job to be coaching their front-line managers on how to think about that and navigate that and spend their time, because that’s something that could very quickly change for an individual who has a bunch of people under him and feels like they’re killing it. And then all of a sudden it’s like they don’t have their act together in this other area that just emerged.
Bryan: Yeah. And so that’s the difference between, to your point, being a doer and an executive, really stepping up to the plate. Got it. Okay. Any resources that you might recommend, whether books or podcasts or different guides? I’ve been reading your blog post on how to do all of this stuff.
Jason: Yeah. Everyone asks me. “What sales books do you like that are out?” I mean, I’ve read all the typical ones like Challenger Sale, and a lot of the stuff that’s out there. I mean, for me I’m always reading something. I like to read stuff about history and about economics and broader things that help me identify different types of people, and just understand leadership more generally.
You know, I think that if you’ve been in sales for a while you tend to learn all the kinds of different tricks that pop up there. And I have folks on my team—Paul and Terry—that are really sales experts. And I’m always learning from them what some of the latest stuff is.
So that’s the way I think about this. It’s just the self-education in the sales space. There’s a lot of stuff on LinkedIn that people are posting. Some of it I agree with; some of it I don’t. But I think that in sales you learn from really good mentors, and you learn by doing it. I think that those are the primary sources of most of my knowledge as I’ve gone throughout my career.
Bryan: So what’s your history? What’s your economic source?
Jason: I like the one that the CEO at Rubric recommended to me a long time ago which I love—Genghis Khan by Jack Rutherford.
Bryan: Okay.
Jason: It’s about how Genghis Khan basically came from complete obscurity in the middle of the desert as a bastard child and then ended up conquering the entire world, and sort of all of the lessons and things that he did differently from other leaders to get him to where he was. I mean, stuff like that isn’t directly relatable to sales. But it’s just an interesting take on human behavior and the way people interact with each other.
Bryan: Well, you bring up a good point. I mean, for people to be well-rounded, for them to keep moving up, you can’t just look at one discipline; you have to look at all of them. And it’s so funny how that once you learn one discipline really well, my sense is that you’re probably seeing business ideas out of the book. You’re seeing sales ideas out of the books. You’re seeing operational ideas out of the book. I mean, you can start to pull all these pieces together. So I think that’s really sound advice.
Jason: Absolutely. It makes life more fun too, rather than reading about sales development for ten years. (Laughter) You can have a lot of fun, right?
Bryan: Exactly. So hey, pull out your magic 8-ball if you wouldn’t mind, Jason. What does the future hold? What’s going to bite us in the butt if we’re not paying attention to it?
Jason: Yeah. I mean, when it comes to sales development in particular, in sales there really is a revolution going on around additional transformation. I mean, you have big public companies that are worth $5 billion plus. They’re spending half of their revenue on sales and marketing. And as I mentioned earlier, that money is not being spent on quality interactions with their customers. It’s spent on process, grunt work, things that can be automated by machines. And so that’s really the market opportunity for these next generation tools.
So I think that technology is going to be replacing some things that people may not have thought were totally replaceable. And you know, people are going to be able to do a lot more with less resources.
And on the flip side I think you’re going to start to see the real art of sales coming back, because the people that are going to be valuable in the future from a sales perspective are going to be the really authentic leaders, and the people that are really trustworthy and great in front of customers. And I think that will be valued higher than someone that’s just all into the technology. So I think this stuff is going to be turnkey at some point.
So that’s where I see it going. It’s becoming more human in a certain way. But it seems that I think there’s going to be software in the background that’s going to get rid of this farm of people doing repetitive tasks. It’s like people putting caps on tubes of toothpaste in an assembly line or something like that. I think that’s the industrial revolution that’s happening for knowledge workers.
Bryan: Yeah. And how many times do we need to hear about this? I mean, you yourself are a case in point—up from the ranks of an SDR, running the show at your own start-up. I mean, that’s pretty impressive. I mean, if we look at it whether it’s from Malcom Gladwell, or we look at Daniel Pink’s To Sell is Human, these human relationship skills—the ability to communicate quickly—are vital. And where else can you get better practice at this than having hundreds of conversations per week with people that don’t want to talk to you? And you learn quickly how to engage them, have conversations with them, lead with influence because you can’t lead with title. You can use that anywhere along the lines. And there are some pretty smart people that are doing this. This is not just if you’re good with people. So I really like that, Jason.
So hey, I can’t thank you enough for your time here, Jason. So let’s wind it down? Who should reach out to you, Jason? Why should they do it and how should they reach out to you?
Jason: Yes. So you should reach out to me if you’re a leader of a sales organization, a sales development organization or a company, and you’re really looking to automate your sales process and get advice on how to take things to the next level. You know, pretty much all of the executives on my team on the business side, we’ve all built and scaled sales development teams before. And we have a brilliant engineering team that’s building software to solve all of the hardest problems in sales. I mean, the thing that makes us different is that we’re not being a rigid platform to manage your employees. We’re building technology that actually does the hard parts of sales development for you. And thereby we’re saving you tremendous amount of money that you would put into hiring people to do this grunt work. So I think the best reason to reach out to me is for us to show you how we’ve helped customers do that in the past.
Bryan: Nice. Well hey, Jason, I can’t thank you enough for what you’re doing out there and your insights that you shared with us today. So happy Thanksgiving; it’s just about coming up here. So by the time this releases you’ll have woken up from your Thanksgiving slumber and you might even be in the new year. So happy 2021 to you all.
So hey, this is Bryan Whittington with this episode of The Talent, Sales and Scale Show. Get after it! See you.

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