Amplify10 was formerly known as Featurewave Fireside Chat- The State of Sales Enablement

An insightful convo on The State of Sales Enablement with guest Joe Booth, Global Head of GTM Enablement at Lacework.

Sales Enablement Fireside Chat Transcript

Joe Parlett –  Hi, everyone. Thanks for joining. I’m Joe Parlett, co-founder of Featurewave, which is an AI powered sales co-pilot that helps your sales teams navigate every stage of every deal. And today I’m joined by my good friend and colleague, Joe Booth. 

Joe Booth is the current head of go-to-market enablement at Lacework. And today we’re gonna talk about Joe’s perspective on sales enablement. So where it’s come from, where it’s been over the last 10 years, where it’s at today, and where he sees it going and where he thinks it needs to go. He’s got an incredible sales pedigree, sales veteran as far, direct sales, enablement, rev ops, sales operations, go-to-market. And Joe and I worked together for a number of years at Apttus where Joe was responsible for making sure that the sales teams were good at their job. And he did just that, did a great job at that. As I mentioned, Joe’s got an incredible sales pedigree, but he’s also got some other interests and hobbies that I think are very relevant for his role. And a lot of folks, what they do outside of the office, outside of the 09:00 to 05:00 oftentimes has a significant impact on how they approach their professional life. So, Joe, I introduced your sales pedigree. What about your, what do you do outside of the office that maybe translates well and impacts and influences your approach to enablement?

Run Global Sales Enablement Like an Adventure Athlete

Joe Booth – Yeah, thanks for that intro, Joe. I appreciate and it. And it has been great knowing you for so many years and working with you. And I think that you’re right, what we do outside of the office, we bring to work every day, right? There’s your work life and your personal life, but really at the end of the day, it’s all your life. So what things do I do outside of my work life or the office that I think influenced me? 

I am an avid outdoorsman or adventure athlete. I spend a lot of time playing in the mountains. In the winter I’m snowboarding every weekend and in the summer and the spring, I’m kayaking as much as I possibly can, whitewater kayaking. There’s a big difference in paddling around on a lake versus risking it all down waterfalls and class five rapids. And I love putting myself out there. I love putting myself in situations that require absolute focus and getting into a flow state and working with my body. And then frankly during the week when I’m not doing these things, making sure that I’m eating right and getting enough sleep and exercising so then when the weekend comes around, I could perform at a high level. And also that I don’t get injured. As I get older, I’ve realized that, not only do injuries suck, because they take you out of the fun for weeks or months, but also because if they’re hard to recover from physically and often emotionally, depending on how hard you slam or whether you end up in the hospital, which, you know, I’ve done both playing my games and how this influences the office. 

So running a global enablement program is very challenging. Like you are working with high performing individuals, whether it’s your chief executives, heads of sales, or whether it’s your top performing reps, these are people that demand a high level of performance and they also demand a high level of communication and execution. 

And being an adventure athlete for so many years, you have to be able to do these things, whether you’re trying to style yourself down double black diamonds on the mountain, whether you’re riding through the park and trying to put together a nice flowy line that has tricks that you enjoy doing, or whether you’re out in the back country and you’re jumping off cliffs in an avalanche-prone zone, like you have to get your head right. 

And it’s the same thing when you’re whitewater kayaking. Being able to scout a difficult rapid in a section of the river, being able to figure out what the line is that you need to take to get you to your goal, and also to be able to figure out what the obstacles are that you’re gonna have to navigate. And sometimes these can be obstacles that you want to avoid or they could be obstacles that you wanna perform a trick or a maneuver off of that is just gonna provide you with some joy while you’re going down that rapid. 

So there’s a lot of overlap, I think, between what we do in corporate learning and development, sales enablement, and the things that I do outside of the office. And, you know, I was very fortunate to have been a snowboard and ski instructor for 10 years before I made my way into enterprise sales. I was also a whitewater kayaking instructor for many years and a raft guide for many years. So I learned how to communicate, help people understand motivation, help people understand how to get focused, and also understand that there’s a variety of skill sets out there. And people come into sales for different reasons. 

Some people love the technical aspect of selling software. Some people just love working with people. Some people are excellent project managers. So figuring out what somebody’s strengths are and helping them hone that, I think is very important. And I just love how dynamic the enterprise software space is. Just like action sports, it’s constantly changing, constantly progressing, so you have to change and you have have to progress with it. So I think that’s a great question and, you know, I appreciate you bringing in the background and the fact that, you know, there is life outside of the office, but it certainly influences what you do when you come into work every day.

The Evolution of Sales Enablement

Joe Parlett –  Yeah, what you described, there’s absolutely a lot of crossover between what you described as an adventure athlete, how you have to navigate all these obstacles. Same holds true for sales, as you know. Like there are a lot of obstacles that people on the selling team need to be able to navigate or they’re not gonna get the price. So part of your role in the last decade or so included making sure that the sales team can navigate these obstacles and get proficient at traveling down that sales path. It’s not an easy journey as you know. 

How have you seen sales enablement, whether it’s just the approach or technology, how has it changed over the last 10 years or so, 5 to 10 years? Where do you see it now and where do you think it needs to go?

Joe Booth – Sales enablement used to just be sales training. It used to be, and lemme back up a little bit. So when I was 30 years old, I was old to be an SDR. It was my first job in enterprise sales. I was an SDR. I was the oldest guy on my team. And all the enablement that we got was basically a sales trainer coming in and helping us just understand who our buyer persona was that we were selling to at the time and then helping us understand like messaging and the importance of persistence. And this sales trainer was excellent. And I remember the big takeaways that I had from this individual were, it’s about confidence, that was important, and it was about persistence and staying organized. And I was like, those are my big takeaways from my first, you know, enablement session. It was really about motivation, helping my confidence be there and helping me stay focused on the prize, right? That was my introduction to sales enablement. 

Sales Enablement for Enterprise Sellers

Today it’s completely different, completely different. What sales enablement is, it’s helping enterprise sellers navigate an entire ecosystem of tools that they have to be able to become proficient at, content that is gonna be pointed to their personas. So how do they find that content, how to utilize that content? And then there’s the entire sales messaging side of things. How do I get my message across in a crisp way? How do I do excellent discovery? How do I make sure that what I’m selling is going to relate to what the buyer needs to help solve their overarching business problems. So yeah, their motivation, confidence, all of that stuff has to overlay all of that. But there’s these specialized tracks that our sellers are expected to excel at all of them. They have to be excellent communicators, they have to be confident, they have to have the right discovery questions, they have to be able to craft a great demo along with their sales engineer that’s gonna help the customer see the vision that they’re trying to paint to solve those business problems, and they have all these tools that they’re expected to become proficient at. 

So as enablement people, we have to learn how to put together programs that are gonna address every single one of these buckets in a way that’s gonna help move the needle for the entire sales organization. So it can be complicated, there are a lot of obstacles there, but when you get it right and you’re in tune with your sales leadership and the reps are starting to pick up on this stuff and you get a good cadence, it’s awesome, man, because you realize you’re one big team. Yeah, there’s a sales leader and there’s an enablement guy and there’s SDRs and there’s people from marketing involved and there’s sales engineering and there’s product. When all of that stuff starts to gel and you know what this is like, because we did it before, man.

Joe Parlett – Yeah.

Joe Booth – We did it before. And, you know, we grew that company and sold for over a billion dollars. And when you get that combination right and people start working as a team, there is no better feeling. You can’t do this. You can’t win alone, but you can lose alone. And the worst thing you can do in enterprise software is lose alone.

Sales Tech Stacks and Sales Enablement

Joe Parlett – Hear, hear, definitely, yeah. So there’s a lot that goes into making sure that you’re a proficient seller. And to support the sales team, as you mentioned, there’s a lot of sales technology out there today. The sales tech stack is piling up. It is getting high. And to be proficient sellers, you gotta be firing on all those cylinders that you mentioned. How do you work with the selling team to make sure that the stack isn’t, you’re not piling on too much, and that they can navigate those systems, and do it efficiently without a level of frustration that keeps them from even using the systems themselves?

Joe Booth – Yeah, this is a big challenge that every enablement person and every ops team faces today, rev ops or sales ops. We spend so much money, there’s an investment of dollars to buy the licenses for all of these different softwares. And every one of them has an incredible business case associated to ’em, an ROI that’s supposed to help the company reach. its whatever level. And there’s some sophisticated stuff out there. 

But there’s also this huge investment of time to get these systems implemented. So now we’ve spent a ton of time and a ton of money and then the CFO and the leadership is now expecting a payback. They’re wondering is the sales team adopting it? If so, is it moving the needle on deals? Whatever that may be. Is it helping us forecast more accurately? Is it helping us increase our pipeline? Is it helping us sell more deals? Whatever the value prop for that particular tool could be. 

The hard part is that there are so many great tools and there’s so, frankly, there’s so many great salespeople out there and so many great marketing teams that we all feel like we need this large tech stack. So it’s kind of like this problem that we’ve created in the sales industry in enterprise software sales where we are so good at eating our own dog food that we are like, we know, we know what it takes to sell to an enterprise buyer, right? And we’ve become very potent at that. So now we have this proliferation of this tech stack that we expect our sellers to be able to become proficient at, and it’s unrealistic. 

So what happens is we spend a lot of money, we spend a lot of time on this tech stack and reps don’t get the full value out of it. And now that’s not just the sales stack, that’s every bit of enterprise software that’s out there with very few exceptions. There’s great features and functionality out there, but, you know, 20% maybe is what we actually end up using. But the value of what we pay for is 100% of the product, but you can’t just pay for 20% of it. So now we have to get our sales rep to become proficient at it. 

So how do we do that? One, we take stock. What are the primary goals of the sales team this quarter, this year? Do we have the enterprise technology to help them reach those goals? There should be fundamental things that every organization needs, and depending on the size of the organization and their sales process, and that will vary by team to team. So take stock of what you have and then figure out is it aligned to the strategic direction of the company? If it is, awesome. Renew those products. If it’s not, figure out what you don’t have to renew anymore. Are there duplications of technologies? Does one thing do 50% of what the other thing does or can you just consolidate and say, okay, we’re not gonna renew this one, we’re gonna use the functionality over here and this is good enough? 

Smart Admin for Sales Enablement Tech Stacks

So take stock of the inventory that you’re paying for. And then within the stack that you actually want people to use, figure out how you get the most value out of that. Because what you find is that most sellers are using maybe 20% of the functionality. Is that the 20% that you want them to use? Do you need to do more training around those stacks or do you need to say, hey, listen, this team actually doesn’t need a license. It’s only this team over here, so let’s just pay for this thing. So now we’re talking about like the financial side a little bit and we get into the revenue operations piece. But let’s get into a little bit around the tools that a team actually does need. Make it easy for them to use these tools. The admin setup has to be dumbed down to the point that somebody that’s not in it every day, or even every week, can quickly go into and find what they need to find or complete the actions that they need to act on. 

The problem is that a lot of the times these are set up by admins that are great at what they do for their role, but they’ve never lived in the seat before. Maybe they’ve never been sellers before. They’re trying to think like sellers, but really what they’re doing is they’re taking their perspective on what a seller needs to do or what they want their sales team to do. So then they often architect workflows that a seller could be completely turned off by and ignore or the seller’s just gonna bypass stuff to get what they need done. You see this all the time in CRMs when there’s too many opportunity fields and things like this. 

But there are ways to kinda condense down the business process that you want reps to follow and be able to achieve both objectives. I’ll give you a a good example. We have a software, I won’t name any names, that is designed to help reps increase their pipeline. So one of our strategic directions is of course expand our, to grow our renewal rate and increase our cross-sell and upsell. So what we’ve done is we preloaded templates and sequences in this tool that reps can now go in and utilize on their own. Now this is pretty common practice, especially for sales development teams, but when you have enterprise sellers that aren’t used to doing a lot of prospecting, you need to make it even easier for them. So what we did is we preloaded templates for them to use and then we taught them the basic functionality for how to use the tool. And that sounds very fundamental, and that’s my point. It should be fundamental. We’re giving people too much to do and too much to memorize. So we have to dumb it down, everything along the way if you want reps to actually adopt this stuff. I think we’re in a point now where we have proliferation of content, we have proliferation of tools, we’re expecting too much from our sellers. 

We need them to build pipeline, we need them to close deals, we need to manage strategic accounts, all of this stuff. Where can we simplify the process? How do we do that for them?

Joe Parlett – Yeah, it’s almost like AI, it’s kind of been around for a while, but it’s really come to the forefront and it seems like just in the nick of time.

Joe Booth – Yeah. Yeah, yeah, we need it. We need it now more than ever. Like if there’s a way to condense what I just described, if there is an algorithm for that, that’s what I wanna know about, right?

Joe Parlett – Yeah.

Joe Booth – ‘Cause we’re seeing AI, I think we’re gonna get into it a little bit more, right? So you I think, should we jump into the AI stuff now?

The Role of AI in Sales Enablement

Joe Parlett – Yeah, let’s do that. So let’s transition to that. Now it’s ChatGPT this, AI that, it’s everywhere, and impacting everything when it comes to business. And even outside of business. With that in mind, where do you think AI needs to take sales enablement and ensuring that sales teams are effective? How can it help? And what do you think sales enablement 3.0 needs to look like as we move forward?

Joe Booth – Sales enablement 3.0. Yeah, then the AI component of sales enablement 3.0 is going to be a consolidation tool. It’s going to allow people to get what they need faster than they ever had before. It’s going to take just-in-time learning to a whole nother level. It’s going to allow reps to go to one place to find everything that they need. And the content will be curated for that individual when they need it. Without them having to go through a series of clicks or tags or content repositories, things will be surfaced to them when they need it. That’s what AI is gonna do for us. 

AI is going to help sales enablement leaders put together content in places faster than we’ve ever been able to do it before. It’s going to help us build content faster. It’s going to help us build more impactful content. AI is gonna take a lot of the steps out of the process of writing and building curriculums. All of that stuff will be built for us, which means that sales enablement people are going to be more around the execution of programs and less around the content creation. I also think that AI is going to help simplify the process by which sales reps are able to utilize content. 

And what I mean by that is, as a sales rep, I have access to so many systems and so much content that’s helpful for me that I need to know, I need somebody to tell me what I need when I need it and then I’m smart enough that I will go out and execute on it. And hopefully if I have a good training program, I’ll be introduced to these processes around execution and I could focus more on learning around the execution piece as opposed to learning where I go to find stuff and how I use this stuff. 

I think what the promise of AI and machine learning is that it’s gonna make everybody’s lives easier. But what we’ve realized is that it’s not, it’s not smart enough yet. But with tools like ChatGPT, OpenAI, Google Bard, what you’re able to do right now is you’re able to go in and you could say build me a curriculum on pipe generation for a sales rep that sells into this industry. And these tools would be able to write that curriculum for you. That’s the future of sales enablement when it comes to content and curriculum creation. But what I really want is I want a rep to be able to go into one place, wherever that place may be, it needs to exist in all the places that the reps are, and to have that information be accessible to them when they need it, regardless of where they are. 

Here’s an example. You go into the CRM. I have a customer in the pharmaceuticals industry. They’re Fortune 500 company. I’ve had two calls with them. This is an early stage deal. I want the content. I want the recap notes. I want anything that’s gonna help me progress this deal to show up there in the CRM while I’m there. I don’t wanna have to go anywhere else and I don’t wanna have to search for it. I just want it to be presented to me. I want the machine to be smart enough to say, Joe, we see you’re selling to this company. Here’s what they do. Here’s the tools that you need to get this deal done. And here’s a few other resources if you need to brush up on some of your skills. That’s what sales enablement 3.0 is gonna look like and that’s how AI is gonna impact things.

Joe Parlett – Yep, I agree. And it feels like it’s late, because we’ve been conditioned over the last at least five years to expect everything just in time because of our phones. We don’t have patience for anything. You know-

Joe Booth – Nothing.

Joe Parlett – My generation, generation coming up behind me and behind them, like we’ve been conditioned to expect everything right now and that’s what AI is going to enable, because we don’t have the patience nor the fortitude to search all these systems. And as a result, we only use 20% of their great functionality ’cause I don’t have the capacity or the time. I just gotta get a deal done. And if I can get it done by just utilizing 20% of what this great system has to offer, that’s where I’m gonna stop. And we’re not gonna get the return on that investment. So yeah, again, AI is coming just in the nick of time. We need it. We need it in in sales, in sales enablement, the world needs it. But yeah, it’s gonna have a tremendous impact. And it already is. 

All right, so last question here. You’ve been in your role for a few months now at Lacework. You’ve had similar roles and responsibilities though in the past. What guidance can you give someone who’s walking down a path similar to yours where they’ve got to take inventory of the tech stack that they have, the investments that their company has made, and build a plan that’s going to optimize and set the sales team up well for onboarding and ever boarding?

How to Take Inventory of Sales Enablement Tech Stacks

Joe Booth – Well, we talked about the need to take inventory of what you have. And that could be the technology that you purchased or the inventory of content that you have in there. Maybe you have to take a look at the training programs that have already been built, the learning paths, figure out what’s up to date, what needs to get thrown out, what needs to get up, and then what needs to get built, right? Where the gaps are. But none of that matters if you haven’t identified the strategic direction of the company. You really, as a sales enablement leader, you need to know what your CFO wants out of the sales organization. Do we wanna focus on our renewal rate? Are we focusing on selling to the install base? Are we new logo hunting? Like what is it that we want? What is the segment that we’re selling into? If you do understand the strategic direction and the underlying metrics that are going to support that growth, then you can put together sales training programs that are gonna support that growth. 

Otherwise you’re just gonna be putting out fires all the time. You’re gonna be playing Whac-A-Mole for every great enablement idea that every sales leader across the organization wants you to come in and teach their team. If you don’t know what the priorities of the company are, how can you say no to anybody? If you do know what the priorities of the company are, you can build programs out that are gonna address the immediate term, the medium, and the long term. And then you can prioritize whether or not the requests that are coming into you fit within those buckets. If they don’t, then you need to politely say, that sounds like a great idea. I wish we had the bandwidth to do it, but what we’re focused on are these priorities here and here’s how those are gonna help your team. Help redirect back to the value to the leader. 

So you need to understand those strategic directions, the underlying metrics and then you could build your programs around that.

Joe Parlett – Prudent guidance, it sounds like you’re probably in the throes of that right now, being a few months in.

Joe Booth – Yeah, and even during the interview process, I was asking these questions around what their direction goes, ’cause then I, you know, listen, I’ve been selling for many years myself. And during that interview process, some of the first questions I had were, “What are the growth goals? How are we gonna do that? What is the plan?” And then every person I talked to after that, that’s how I crafted my message. Hey, I understand from speaking to so and so that these are the growth goals. Is that right? Yes, okay, great. How is your team gonna support that? Okay, awesome, here’s how I think I could add value to that. So I have the strategic direction of the company and I validated along the path. 

Then I talk to the individual, I wanna know how it’s gonna impact them and their team, and then I explain to that individual how I’m gonna support their growth as it relates to the strategic direction. It’s enterprise selling 101, right? Where it’s high and wide within the account, validate the message along the way, all of that thing. And that’s what a sales enablement leader needs to be able to do. 

They need to be able to sit in the seat of the seller and have empathy for ’em and be able to live that, ’cause I’m telling you, man, enterprise software is a freaking knife fight. It is hard. Not only do you have to be great at all the process internally, the messaging for your company, the demo product knowledge for your industry, all of that, but you’re up against somebody else, two, three, four guys just like you that are working their ass off to beat you, because they don’t wanna come in second place in a software deal. I think people forget that.

Joe Parlett – Yeah.

Joe Booth – I think people think it’s all about like, hey, what support am I getting to be proficient at my job? Dude, guess what? There’s somebody doing pushups and squats down the hall, so when they step in the ring, they can knock you out. Every time you get in front of your customer, you’re not the only vendor talking to them. You have to be better than your competition. And it’s not just about relying on the marketing team to give you what they need. Hone your craft. Google it if you don’t know how to do it. If you’re not getting the support from your sales enablement team, take the initiative to build that out yourself. There’s so many resources out there to get your tools.

Joe Parlett – Yeah.

Joe Booth – So do it, man, because somebody else is. And trust me, they wanna make a million dollars a year just as bad as you do. And maybe even more. They might be hungrier than you. And then if that’s the case, do you have the right job, I don’t know. Maybe it’s time to teach instead of do.

Joe Parlett – Joe, great insights. This has been a fantastic conversation. Appreciate it, you’re a few months in there at Lacework. No doubt in my mind you’re gonna make a massive impact there. So let’s check back in a few months, see how things are going. Maybe record another conversation. And be safe out there kayaking this weekend.

Joe Booth – I will, man. Thanks, Joe.

Joe Parlett – Always a pleasure.

Joe Booth – Right, Joe. Yeah, it is. Thank you, buddy. 

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