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How Automation is Reshaping Sales Strategy: A Tech Talk with LeadMD

After years of suffering through counterproductive technology, sales teams are now celebrating big wins by leveraging the latest generation of automation tools.

Join Anati Zubia, Director of Marketing at AppointmentPlus scheduling software, as she chats up Justin Gray, Founder and CEO of marketing automation powerhouse LeadMD, for a candid conversation about what’s next in the world of sales and marketing automation, and why you should care.

In this episode of AppointmentPlus Talks Tech, you’ll learn:

  • Technology trends for sales automation, and how it’s being influenced by marketing tools
  • Whether or not sales automation tools are a good fit for every business
  • How to fine-tune your sales technology to meet your needs and pain points
  • Why Sales teams can no longer work in a vacuum, and the importance of a symbiotic relationship with Marketing, Big Data, and Artificial Intelligence

Click below to catch Justin and Anati’s lively discussion at Scottsdale, Arizona’s Morning Squeeze restaurant! A full transcription follows.


ANATI ZUBIA: Hello, welcome! I’m Anati Zubia from AppointmentPlus here at Morning Squeeze in beautiful Scottsdale, Arizona. Joining me is Justin Gray. He’s the CEO of LeadMD, a marketing and sales automation firm based out of Scottsdale, Arizona.

JUSTIN GRAY: Beautiful Scottsdale, Arizona!

AZ: Absolutely. Justin, tell the viewers a little about your story, and a little bit about LeadMD and what you guys do.

JG: Sure. I started LeadMD about eight years ago, by accident, by helping marketers really leverage marketing technology. And we’re still doing that eight years later. What we say is that we’ve bridged the gap between strategy and tactics, which tends to be a big disconnect in most marketing orgs. So, we’re helping organizations really triangulate people, process, and technology for success. And we love what we do.

AZ: Beautiful. So, Justin’s joining me today to talk about how marketing automation can be leveraged to empower your sales organization. Let’s talk a little bit about what automation really is, and put a definition out there for our viewers.

JG: You know, marketing automation is a little bit different for everyone. Sales, marketing, Ops—it depends on your focus. But I would describe marketing automation as really a means to automate those highly operational, but often skipped over, areas of the marketing and sales process and really empower a conversation with the buyer. It’s not a replacement of it, it’s an empowerment of that process.

AZ: And through this journey, and all the work that LeadMD does in the area of marketing automation, what’s something that you guys have learned along the path that’s really a key challenge, or something that businesses should key into when they’re looking at implementing a solution like this?

JG: Really all of those fundamentals just continue to ring true. There’s no replacement for quality. Quantity is not going to drive success. You know, just stringing together the best automation campaigns is not going to drive success. You have to implement that personal touch and engage with the buyer throughout that journey, and plug in automation where it really makes sense. Again, those areas that are difficult to conduct, they’re a pain, people are skipping over them—we can remove those friction points with marketing automation.

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AZ: We’re talking a lot about those friction points. That kind of takes us into that question of how do we take those friction points that sales is experiencing on a daily basis, and take some of those key learnings from marketing automation and bring that into our sales organization?

JG: I truly believe that marketing and sales have the same friction points, they just kind of manifest themselves differently. Whereas marketing is worried about driving qualified individuals, sales is worried about receiving and having those great conversations that are going to lead to a sale. I think there’s a lot of overlap when it comes to marketing pains and sales pains. Traditionally they’ve just been looking for a different outcome. Marketing is going to be looking for that hand raise or form fill, sales is looking for revenue. Those lines are starting to bleed together and really become more aligned than ever before, at least from the executive level. And so now your practitioners and your operational level layers are starting to catch up to that norm.

AZ: Yeah, absolutely, and I’ve seeing that more and more in new sales technologies that are coming into the market. And what was some of that lag in sales technology? I mean we’ve kind of been behind the game in sales for a long time, whereas marketing was racing ahead. What do you see coming up into the limelight for sales in the technology space?

JG: I think there’s a couple reasons for that kind of lag in sales technology that you described. Number one being a true misconception that sales doesn’t have the creative or operational ability to offer some of these tools, right? Like, marketing gets to play with all the cool tinker toys and sales just needs to be smiling and dialing and closing deals. But marketing and sales, again, are really starting to blend more than ever before. So, marketing is starting to adopt more of those sales methodologies and tactics, and likewise, sales is adopting more of that marketing mindset. They need to be concerned with content, and be concerned with what if that buyer is not ready to purchase right at that moment. So, a lot of those traits are starting to co-mingle, and you’re starting to see more technology being adopted by the sales team and empowered by the marketing team.

AZ: It’s definitely a trend that’s on the rise. It’s interesting, and I hear from a lot of companies of various sizes, and the smaller ones usually say, “Hey, this technology is not for me, this is for bigger organizations.” Is that a myth, or should smaller organizations be looking at these technologies?

JG: You know, I’d really say that any organization needs to experience a little bit of the pain before they start buying into technologies. If you’re an enterprise organization, and we’re talking about the messaging and playbooks that sales puts together, what we’re running into is the question of “Should I buy this technology?” And our question is, do you have a repeatable process? Do you have a playbook that you’re following? If not, that’s going to be your question day one. Similar to what we’re running into with marketing automation around content, and people are realizing they don’t really have the content to empower that tool. Same thing on the sales side. So, if you’re not experiencing any pain, and you’re not saying “hey, I’ve got this playbook but I can only execute it five or six times a day, realistically,” then you’re not really ready for technology, whether you’re big or small. I think even a small organization can embrace those repeatable elements, get the playbook together, get the messaging together, and then, once they’ve reached that pain point, bringing technology in.

AZ: Excellent. So, if you have a company that’s reached that point and they’re starting this journey to integrate technology, that’s one of the biggest challenges out there for the sales organization. Adopting that technology. I can imagine what a sales rep goes through— “I have to update the CRM again, I have to log this—”

JG: There are all these fields!

AZ: Right? It’s all these different things they have to throw into the mix now. How do you really fine-tune what is valuable from a technology space, and how do you evangelize that in an organization to help the sales team with technology and get that adoption that you really need?

JG: First things first, if you’re in a marketing role or an ops role, or even if you’re an executive and you’re looking at the performance of your sales team, I would invite yourself, some of your Ops leaders, some of your team, and look at the process that sales really needs to go through. I would say most people would be floored at the amount of, just tactical little tweets and fields and updates that sales has to go through. We did an audit for one org and found 22 different literal clicks just to set a meeting with a new prospect. That’s a lot of time. So, how can we cut that down? I think that question will help us get a little bit away from that whole notion of “Marketing’s got this new fad it wants sales to do” and the sense that it’s not rooted in actual production. First things first: take a look at the landscape, see what you can do to enable that everyday process. And secondarily, you’ll be able to understand what are those friction points, what are those pains that they’re experiencing that you can scale with technology. And then you can understand again, at that point, what technology aligns to solving that best. So, I would say a little bit of an audit there goes a long way.

AZ: That’s wonderful advice, Justin. I think that’s going to help a lot of organizations that are trying to implement these technologies see a clear path for what they need to do.

JG: A lot of times they think—sales is there to sell, they work as long as they need to. But when you start adding that time up, in terms of the cost of that rep and what they could be selling, and the opportunity cost, that’s a huge expense.

AZ: It definitely is. There’s a lot on the table there when it comes to empowering them. I know I’ve looked at a lot of different tools and technologies in play. What are some of the technologies that you’ve seen in working with LeadMD and your clients that you think are just great technologies that can be integrated and will have an impact on your bottom line?

JG: I would say that data is absolutely a shared resource from both the marketing and the sales perspective. So, if you’re not looking at data in terms of hygiene, in terms of being clean and keeping it up to date, I’d say that’s a foundational element that can benefit both marketing and sales. Any sort of reporting or analytics you’re going to try to look at from a 30,000-foot view is going to be completely dependent on that data. If you don’t have a good strategy for waterfalling it, validating it, and keeping it clean over time, that’s always my first recommendation. And also—is the sales team and the marketing team keeping it clean with their in-head knowledge? That in-head data—is it easy to get that in the CRM? Is it easy to understand what they’ve consumed in the past? With so much turnover today in both marketing and sales, it’s so important to have that shared resource that’s reliable for everyone.

Secondarily, are you empowering those reps to consume what’s actually going on? Just from a day-to-day perspective, there’s so much we’re putting on social media and out within the world. What’s important to that organization that marketing can empower through content? Even simple things like Google Alerts and LinkedIn Sales Navigator that can be some really quick wins that are under a few hundred bucks per rep, per month. Those are some absolute ROI points that any org can focus on. And once you’ve got those elements put away, then you can focus on a little bit more sizzle, a little bit “sexier” items that include those outreach solutions, those engagement solutions that we hear so much about, where someone can execute all those playbooks. Focus first on the foundation and the essentials, and then you can move into those really “nice to haves.”

AZ: I pulled some really key points out of this that I just want to highlight for everyone who is watching. Definitely data. Data across the funnel is key in this sense so that you can lifetime decisions based on what’s really happening in your market.

JG: Absolutely.

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AZ: Another key point that I pulled out of this is that you’re looking at this 24/7 engagement now. Where sales reps are not in an 8 to 5 job. They need to have that type of engagement on social media and those other channels coming into them as a tool, and those need to be aggregated in a source that they can actually do something with.

JG: Right, like even on their LinkedIn page, they’re putting out content which you can then use to understand how that org thinks, what’s important to them, what are their goals for that year. So, a lot of the times we’re just overlooking some of these really obvious elements, which are great resources.

AZ: Yeah, that’s excellent advice. I know it’s a pain point for a lot of sales leaders I’ve talked to, you know, “what do I do with these different channels, and how do I pull them into a place where they’re valuable?”

I wanted to touch briefly on another technology. So, AppointmentPlus provides online scheduling, and what we’ve done from our aspect is that we’ve implemented our own solution into our funnel at the point of the journey where somebody can get in and schedule a demo at their own convenience, at their own device, at any time. I know there’s a lot of opportunities with utilizing that. Where else would you see that having a benefit in the marketing and the sales funnel as a tool?

JG: I think what’s interesting there is, again, if you were to take the life of a sales rep—and everyone’s got a good data point to base this on, like we all know how much of a pain in the ass it is to just to book a meeting: “oh, I’ve got to shift that, do you have 8:00 or 4:00 tomorrow?” I just went through this process with a panel that I’m hosting. I’m trying to coordinate 5 people, and it’s unbelievable the amount of logistics that goes into that process.

From a sales perspective, again, if we’re valuing the time of those reps and we understand the pain points in scheduling those types of meetings, how can we apply a layer of obligation in there that, number one, is going to create efficiency for them, but overall create a better experience for the prospect or individual whose time we’re already blessed to have? We don’t want to make things harder for them to adjust those appointments. There’s a lot of potential there, I think, in just smoothing out any of those operational elements that we all struggle with.

AZ: Excellent. Yeah, it’s one of those tools that you’re looking at that [gets at the question of] “How do I continue to serve the needs of the consumer?”

JG: We all live in our email every single day.

AZ: We all do—absolutely!

JG: It’s one of those elements where, strangely, there haven’t been a lot of innovations in that regard. Its still very much one to one. We get that one to many, but it’s still this big glossy area. So, I think there’s huge potential.

AZ: Exactly. And I’m sure you’ve been asked this million-dollar question about automation: how do you keep automation personal? Right? That’s the myth—that I’ll lose all the personal factors. So, what is your advice for someone thinking that?

JG: I think first, you have to understand what personal is. These playbooks and these nurture streams that we hear so much about, a lot of this technology has started that process within the organization. No one had a nurture strategy before or a playbook before, but now we bought something and it has these blanks that we need to fill in, so let’s develop it. If you take the time to understand what that successful buy-in journey looks like, you’ll look at what does that buyer really need at each step of the journey?

For example, in the early stage, how are they researching and talking to other people? How are they gathering information and data? And then, at the late stage, what are they concerned about? How are they going to implement their solution, are they concerned with training and adoption? We can take all of those elements of that buyer journey and build them into more automated frames, whether that’s lead nurturing, or sales engagement, or even customer journey once they’re actually onboarded. By mapping out what that successful journey looks like, now we can start to automate at a later date, rather than just saying, “it’s gonna be great, I’m going to automate these drip campaigns and people are just going to miraculously buy.” You as a consumer are trained to recognize that now. So, you need to take a customer-centered approach, understand what the buyer needs. Do that at the manual process, and then really understand what elements really are painful that can be repeated and build that into automation. And eventually, you’ll get that higher degrees of automation, but, day one, you’re still going to be doing a lot of that conversation or interaction manually.

AZ: It sounds like that’s where data becomes more and more important, and that’s why it was the number one issue. You can’t do any of that without being able to see that data.

JG: That’s right.

AZ: It also really highlights the fact that, more and more, it sounds like this mythical divide between sales and marketing that we’ve always seen, that can’t be in place, right? So, do you see sales and marketing merging in the future as these technologies begin to converge on one another?

JG: Yeah, so we call that “threading.” When you look at that buyer journey that I described, there’s no natural baton pass there. Like there’s no “Okay, I’ve told marketing everything, now I’m gonna go have a separate conversation with sales.” When you look at that from a buyer perspective, it literally makes no sense. Normally we’re dealing with larger B2B purchases, considered purchases, but you can think about it in terms of buying a car. What if you walked onto a lot and had an entire conversation with one individual, and they said “Okay, I wrote down most of what you said, and most of it’s inaccurate, so I’m going to hand you to this guy, and now he’s going to pick up where I left off.” It makes zero sense.

You have to thread that approach. You have to continue to empower that buyer with items that marketing is best at, which is those big concepts, creating educational content, and serving that up to the buyer, but also having those one on one interactions that sales is great at. So, that needs to be a threaded approach really from the beginning, all the way through the customer life cycle.

AZ: Excellent. That’s definitely wonderful advice for organizations. It’s important to focus on those things and really make that part of your strategy at a much higher level.

JG: It’s difficult. I think that’s the most important item to keep in mind. Sales and marketing alignment is not just a knob you turn and it happens.

AZ: Exactly.

JG: It’s those little degrees of improvement. So, expectation setting, I’d say, is huge there as well.

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AZ: What are some of those technologies that are emerging that you see in the next ten years that sales teams should really be paying attention to, and looking at how does this fit into our strategy?

JG: Sales, marketing, really any discipline within the organization, has to be looking at data science and AI, and I know that sounds a little bit futuristic and Utopian. The reason that I bring it up is that any sort of AI model where we understand someone at a deeper level, it’s rooted in really simple, really unflashy items, and that’s data. How are we understanding who that buyer is, what they want, and how can we move forward people and process based on that? So, we don’t have to go out and all take an AI class or whatever, you just have to focus on the basics.

Are we recording what our customers care about within our systems of record so we don’t have to have a manual conversation with someone else in our org every time we need that? For example, “So and so called in and they have a problem, and here’s what it is.” You want to be able to put that in the system, and we want to be able to predict their next problem or their next need. That’s where I think AI is important and really valuable, but it starts with some really basic stuff that we can all do today.

AZ: That’s a great technology to stay focused on. I see it being used more and more.

JG: Everyone’s an AI company now!

AZ: Right?

JG: There’s a great quote that says just because you use AI, you’re not an AI company. But, I do think it will enable what sales reps are inherently trying to do, and that is understand the buyer, and have a first conversation that builds trust. In sales, there’s nothing better than that goal.

AZ: Absolutely right. So earlier on we were talking about LeadMD and you said you kind of stumbled on to this. I’d love for you to elaborate and tell us the story of what that stumble was, and any learnings that someone out there who is an entrepreneur and passionate about this industry could learn from that.

JG: The beginnings of LeadMD were super humble, and involved me taking an exit from an organization I was a part of, and kind of not knowing what I wanted to do next. Some folks reached out to me and asked if I could build that engine that I’d built at my previous organization—which was a company called Billing Tree—they asked can you build that engine for us? I said yes, I’m happy to do that in a consulting capacity, and you need to bring on these types of technologies to empower that process. I would do a lot of training, sales rep training as we’re talking about here, marketing training, and then I added marketing automation to that mix.

What I really found was this big disconnect between these PowerPoint presentations of best practices, and the people who actually make the rubber meet the road, and pull the levers and push the buttons. That was kind of the impetus for LeadMD, which addresses the question of how do we understand that best practice, and then how do we turn around and implement it and make something better each day? 120% is always our goal. How do we make everything we touch 120% better? That’s how the organization got started, and again, we’re doing that same core concept 8 years later.

AZ: It’s exciting. You found a need and a niche in the market space that wasn’t being served.

JG: The fortunate niche was that marketing automation was really taking off and we were fortunate enough to ride that wave.

AZ: And it’s interesting, you came in on the wave of marketing automation, and I see so much opportunity in sales automation that just hasn’t been realized. Do you see that same kind of opportunity in the space for individuals to come in and find those gaps and continue to grow as they both begin to collide with one another?

JG: First and foremost, there’s still a huge amount of opportunity for marketing automation. When you look at that marketplace, in comparison to CRM, any venture capitalist will tell you that marketing automation is extremely underserved in terms of organizations that are actually using that technology. And I think sales automation and sales enablement is in that same kind of maturity curve. The early adopters bought the SKU because Google was using it or other companies in the Bay were using it. We’ve gone through that initial tick, and now you see organizations really wanting to know what is the return? What are the keys to realizing those gains, and how can we plan for that? That’s what we’re in. We’re in the little bit of that secondary step where people want to put planning first. They want to enable their teams, they want to train them for success, they want to foster those skill sets that are really necessary. And I think that’s a much better way, frankly, to go about it than those early “Hey, let’s buy it just because it’s cool” approach for the shiny object factor.

We’re really well-positioned now to see a bump in both those areas. On the sales side, again, understanding what that buyer needs throughout the process and having those conversations—seeing what works and being able to scale that—that’s so critical. So, learn from marketing’s mistakes. Don’t buy the tool on day one. Buy the tool on day 180 after you’ve actually had the chance to understand the buyer at a deeper level.

AZ: Wonderful. Its sounds like there’s a lot of education that could take place.

JG: Absolutely.

AZ: What are some recommended sources of information for someone who wants to take that advice and start learning?

JG: I’m laughing, because this is a loaded question. We’ve actually spun off a marketing education start-up from our learnings at LeadMD, so that’s going to be my number one plug. So, go to and you can sign up, it’s free. The impetus for that, and the underlying need is really that marketing has changed drastically, and you know sales is doing the same thing, yet we’re not training those professionals to adopt those new skills sets. It’s very much a learn on-the-job environment. So that’s what Six Bricks was created to do, is to take that on-the-job training and apply it before you’re actually in the seat, in the role.

There’s other great resources out there. Vendors are an awesome resource. You know, EloquaMarketo, HubSpot runs an awesome university. HubSpot has taken content marketing and defined it in a very literal sense. Great resources. Even resources like, you know, online resources like Udemy are great, but the absolute best is to find someone who is doing that job, and shadow them. Spend a day with sales, spend a day with marketing, develop a mentorship, get plugged in to people that are really running best practices in those areas, and that’s always going to be your best exposure.

AZ: Excellent. That’s great advice on being able to build out that educational toolkit and really get the resources to your organization to help you make those right decisions.

Thanks so much to our viewers for tuning in to this session, and I want to thank Morning Squeeze of Scottsdale, Arizona, for letting us host this interview at their beautiful location. I also want to thank Justin of LeadMD for joining is today and offering his expertise for the sales and marketing automation space. Thank you.

AppointmentPlus has put together an eBook for sales teams on how to use automation to power up their organization. You can download that free eBook by clicking the link on the screen. Again, I want to thank everybody for tuning in today, and from AppointmentPlus and LeadMD, we’ll see you next time!