March 12

Leading Transformation in a Fast-Paced World


Sale Leadership Awakening
Sale Leadership Awakening
Leading Transformation in a Fast-Paced World

Ryan Thomas, the sales VP of Elastic, Americas, shares his insights on effective leadership, team motivation, and driving business growth. He emphasizes the importance of inspiring and motivating teams, aligning individual success with the company’s vision, and making data-driven decisions. Ryan also discusses the challenges of leading sales teams in a complex and fast-paced industry and provides valuable advice for sales leaders.

“It’s not about just selling them technology. It’s about selling them a solution that they know they’re going to be able to acquire tech, get it implemented, and drive change in their business quickly.” – Ryan Thomas

Key Takeaways:

  • More than just focusing on strategy alone is needed; leaders must prioritize team motivation and clarity around individual success.
  • Understanding the “why” behind each employee’s role and connecting it to the company’s vision is crucial for team engagement.
  • Soft skills like empathy and knowing when to let go of underperforming employees are essential for first-line leaders.
  • Second-line leaders must develop business acumen and make strategic decisions to optimize resources and drive desired outcomes.
  • Failing fast and learning from mistakes shows leadership maturity and fosters a culture of growth and innovation.

Follow Ryan Thomas on LinkedIn

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Follow Steven Rosen on LinkedIn



[00:00:00] Colleen Stanley: Hi, everyone, and welcome to the Sales Leadership Awakening Podcast. My co-host, Steven Rosen, is Colleen Stanley, and I am joining today. Hello, Steven. Hello, Colleen. How are you doing? Good. Once again, we’re tackling the age-old issue of bridging the knowing and doing gap, so we’ve been very fortunate again.

[00:00:24] Colleen Stanley: We’ve got a great guest, so I’ll turn it over to you to make that introduction. 

[00:00:27] Steven Rosen: Well, thank you. I’m very excited today that Ryan Thomas, the VP of Americas for Elastic, a high-flying company, will be our guest on the sales leadership awakening podcast. Ryan, thanks for joining us.

[00:00:42] Steven Rosen: Can you share with our audience a little bit about yourself, a little bit about your team, and, of course, your company, which has been experiencing incredible growth and is a really exciting organization to be part of and to lead?

[00:00:53] Ryan Thomas: Absolutely. Well, first of all, thanks for the opportunity to join you. To start with a little bit about myself, I have a 29-year career in sales, all in technology sales.

[00:01:06] Ryan Thomas: I have spent the last 22 years leading sales teams across many companies like Citrix and Red Hat. Many great technology companies, EMC, and I’ve recently joined Elastic. I say recently, about two and a half years ago. Today, I run the Americas for Elastic, which consists of our teams in the U. S., Canada, and Latin America. We have roughly 400 people on our go-to-market team, including our sales reps, solutions architects, and various other roles within the go-to-market. 

[00:01:41] Ryan Thomas: Pretty big team to lead. 

[00:01:43] Colleen Stanley: Ryan will direct the question to our signature question.

[00:01:47] Colleen Stanley: What was your awakening moment? Your long experience in leadership has made you a more effective leader. When we met before, you emphasized that the awakening moment was really how you inspire a team. Part of our goal here is always to share our wisdom with our guests.

[00:02:03] Colleen Stanley: Can you tell us more about that?

Leadership Maturity: Moving Beyond Transactional Leadership

[00:02:06] Ryan Thomas: I would say it’s a great question. Early in my career as a leader, I focused quite a bit on strategy. How do we attack the market? What are the things we need to do? I realized very quickly that even the best-laid strategy won’t succeed if you don’t have a team of motivated people who have clarity around what the vision is; more importantly, at the individual level, they understand what success looks like, and I think ultimately they’re excited about where you’re going.

[00:02:37] Ryan Thomas: I learned that for a lot of trial and error, right? You can create these great strategies and sit back and say, why are we not executing? And it does boil down to people. 

[00:02:47] Colleen Stanley: Ryan, it’s interesting because you mentioned a couple of things here. I always want to yawn, and I think you’re the same way.

[00:02:54] Colleen Stanley: We all know we’re supposed to envision strategy, but I think the important thing you’ve accomplished is that you were [00:03:00] able to have your people somehow link their actions and outcomes with the vision. Is there something you do specifically there or just teaching and preaching it?

[00:03:12] Ryan Thomas: Well, I wish I could say we were already there, but I think we’re making much progress. I’ll step back a second and say that we use the term accountability extensively across businesses. I understand what that means for your team. Number 1, they’re clear about what they’re accountable to, and number 2, are they excited about that? Is that something that keeps them in the game, and is there a “why” within that for each of your employees? So I think it’s essential to find the why and get people rallied around the why, and then the other side of that coin is making sure they’re clear on what success looks like.

[00:03:55] Ryan Thomas: that has to be apparent from the top to the bottom of the [00:04:00] organization. Your leaders must understand what success looks like, which must be closely tied to the company’s key priorities. We need to ensure those priorities are carried out so that every employee in the business can connect with them.

[00:04:15] Ryan Thomas: Whatever their job is, how do that job and that role connect with the outcomes we’re trying to drive? It is very important. The more work you do to just drive that clarity down to every single employee in the organization, the faster you accelerate growth and the fewer surprises you have along the way.

[00:04:37] Ryan Thomas: That’s something we’re working on. I wouldn’t say we’re there, but we’ve spent much time over the last nine months making sure people understand where we’re going. We’ve focused on why it’s important to them, going in front of a team and saying, well, we need to go to a billion dollars.

[00:04:51] It clarifies how you crystallize that message for each role. With my direct reports, that comes across as a mission to create shareholder value or a publicly traded company, and we’ve got to focus on driving a business that creates shareholder value.

[00:05:06] Ryan Thomas: When you talk about that with your account executives, for example, it’s not about, oh, we need you to do this because it creates shareholder value. We want this for you because it creates generational wealth, career opportunities, and more fun in the environment. When we’re succeeding, everybody has more fun.

[00:05:23] Ryan Thomas: Right? So it’s just being very clear about who you’re communicating to and what will motivate that specific group of employees, which is really important. 

[00:05:33] Steven Rosen: When I first started as a sales manager, I had a coach, and she’d always talk about the WFMs. She drilled that into my head all the time, whether it was what was in it for me or what was in it for them.

[00:05:42] Steven Rosen: What’s the WFM here? So that’s precisely what you’re talking about. I researched Elastic, which I’ve known for the last couple of years. You’ve had over 24 percent growth in 2022 and 18 percent growth the last year, but it’s challenging in your role because you don’t directly lead the sales team; you have first and second-line managers reporting to you.

[00:06:03] Steven Rosen: If you can help other folks in that situation, what soft skills and hard skills have you found to be most effective in helping your sales managers create that highly motivated team? I know some of it exudes from you, but they’ve got to do the work, too, right?

[00:06:19] Steven Rosen: How are you helping them do it? What skills are critical?

The Power of Clarity and Purpose

[00:06:21] Ryan Thomas: We’ll start with the first-line leaders because they are the most important in the company and have the most complicated jobs.

[00:06:29] Ryan Thomas: They’re being put right in the center of your go-to-market strategy and sales, and they have a lot of pressure coming at them from leadership, hitting numbers, and they have pressure to make sure they’ve got a team that’s motivated and connected and is on board with driving the business.

[00:06:48] Ryan Thomas: It is a challenging role. What I look for in terms of soft skills with our first-line leaders is some basic things. Do they exhibit empathy, right? Do they understand that sales are tough? There’s a lot of rejection. There are a lot of challenges that you have to overcome, and it takes a toll on a human.

[00:07:08] Ryan Thomas: So, having the right degree of empathy with your team. The other side of that coin is knowing when you start to care about an employee’s success more than they care about their success, knowing that it’s time to move on and allow that employee to flourish somewhere else, making the hard decision.

[00:07:25] Ryan Thomas: What I find to be the hardest thing with the first-line leaders is helping them understand that the decisions they’re making on a day-to-day basis with their team and the coaching that they give their team around where they’re spending time and what activities they are burning their calories on are going to have an incredibly high impact on how well we either achieve or exceed our target.

[00:07:50] Ryan Thomas: It’s tough to find RVPs, which is our 1st line that has that business acumen that they can say, I’m spending dollars on this role, but I’m not getting the return that I want for that expense. If I move that here, I will get a better expense. I’m covering these accounts.

[00:08:08] Ryan Thomas: I’m not getting the return from those accounts, so I may move that coverage or that expense to coverage on accounts that will have a higher yield in our business. It’s really hard to teach that at the RVP level. I always think about it as RVPs have to keep the plane in flight while they’re changing the engine sometimes, and those two things can be challenging. 

[00:08:31] Ryan Thomas: The second line, and I will say at Elastic, we’re going through a pretty big transformation. We’re growing at such a fast rate. If you think about the RVP role, five years ago at Elastic, they were running much smaller businesses. Those decisions were less important because you could get by, right?

[00:08:52] Ryan Thomas: We must continue growing at a certain rate and driving profitability. Now, how you run your business requires a different lens because those decisions become essential.

[00:09:02] Ryan Thomas: And at the AVP level, our second line, the role is transforming from just running sales teams to running a franchise. It’s being mindful that, you have a cost envelope of XYZ; you’ve got to make the best use of that cost envelope to drive the outcome that the company needs. There is a lot of shifting regarding our requirements for the leadership team.

[00:09:27] Ryan Thomas: We’re recognizing that, and we need to make sure we give the team some training and, to your point, Steven, a lot of soft skills development. 

[00:09:37] Ryan Thomas: That’s what we’re seeing here and what I’ve experienced in some of the other enterprises, great software companies I’ve worked at. You need to see those things happening in your 2nd and 1st lines. We’re seeing the soft skill, and that’s buried in there. We’re seeing that if you don’t make those good decisions and aren’t investing to drive the right outcome, it catches you. You need the pipeline that you need to drive your business. You can’t get to the number because how you’ve invested and deployed that expense in your business isn’t driving the result you need. The leading indicator is where you are deploying investment.

[00:10:12] Ryan Thomas: What is the return? You’re getting the lagging indicators, whether or not you have enough pipeline and can hit your number. 

[00:10:18] Steven Rosen: It is fascinating because as you formalize and move from an entrepreneurial organization. The side question here is how do you measure the return on time?

[00:10:27] Steven Rosen: I speak to that quite a bit with companies I work with, and we call RGAs, Results Generating Activities, but they’re hard to measure. 

[00:10:36] Ryan Thomas: We’re looking at it in a few different ways. The first is we look at our pipeline conversion rate to close very closely across several different metrics.

[00:10:45] Ryan Thomas: We’re also looking at rep productivity. Is our rep productivity improving? Is it declining on a quarter-to-quarter, year-to-year basis? Basic things like that indicate whether we are burning our calories across the organization on the suitable set of activities to drive the desired outcome.

[00:11:01] Ryan Thomas: Digging a little deeper, it’s looking at whether we are covering the right accounts with the right go-to-market strategy and the right cost structure. What I’ve learned. In my career, sometimes, when you invest money and think you’re going to get a faster return or you can accelerate growth, you end up covering or over-covering accounts where the probability of that account growing at a rate that makes sense for the investment is very low. It’s fail fast, right? Get out of that model, move your expense and investment to a part of the market where you’ll see the addressable spending at a much higher level, and be able to attack that and convert it to business.

[00:11:46] Ryan Thomas: That’s one of the things we’re looking at right now. What is the growth rate at an account level, and is that growth rate decelerating or accelerating? If it’s decelerating, we’re starting to ask ourselves, should we continue to cover that similarly? 

[00:12:02] Colleen Stanley: It is, and Steven, I bet this is rolling through your head. It strikes me, but what I’m hearing a lot is critical thinking skills. But the other one, from soft skills and, Ryan, not to put words in your mouth, but in the EQ world, we call it reality testing, and it’s the ability to see things as they are versus how you want them to be.

[00:12:20] Colleen Stanley: If you don’t have that reality testing, you go into denial. I love burning calories. What struck me were the critical thinking skills and the soft skills with it. One of the things that Steven and I grabbed when we met before was that leadership is not transactional, yet I have to tell you what I’m observing in a very busy world, and it keeps getting busier and busier.

[00:12:40] Colleen Stanley: People are transactional, and then they don’t get to the point where, as I’ve heard you say in this interview a couple of times, they’re not inspiring or motivating. One of the things you do well is your Thursday morning meetings, and I’d love for you to share how they came about and what you do in those Thursday morning meetings to support the team in both hard and soft skills.

[00:13:01] Ryan Thomas: We do several things, not just Thursdays. We have several meetings with the team. I implemented a call that we hold with all business leaders every two weeks, and we don’t always hit hard topics in those things. What are the things that we can do as a leadership team to drive the business forward?

[00:13:20] Ryan Thomas: Sometimes we take a topic that might be top of mind for the business, right? We’ve got a market opportunity. We hit it on that call, but we talk about why we try to always boil it down to why this matters. Generally speaking, on Thursday, those conversations are about how we more effectively lead our team through what I think is a transformation that we’re going through as a company and a transformation that we’re going through as a geography within the company. The big thing we’re focused on right now is not losing alone. We’re trying to encourage leaders in the business to embrace the network of leaders around them. So their peers, but also when you are thinking about building your go-to-market, working with the other supporting organizations within Elastic to ensure that you’re looking at every opportunity through the right lens and that we’re doing the right thing for our customers.

[00:14:15] Ryan Thomas: So, there’s a lot of focus on customer first, ensuring that we are doing things that help our customers, and so on. That’s a lot of the focus on the Thursday call. 

[00:14:25] Colleen Stanley: Repeat that. Again. You’re not alone… 

[00:14:27] Ryan Thomas: We don’t want you to lose alone, right? We want you to embrace the power of the team.

[00:14:32] Ryan Thomas: Our technology and go-to-market strategy are complex, right? We’re a cloud solution, and we work with customers to build and create precious solutions that help them drive their business forward through our platform. We compete in three different areas, and search is the preeminent provider of search and observability.

[00:14:57] Ryan Thomas: We’re focused on helping our customers login with metrics, APM, and security. We are out there, driving many new SIEM security solutions with our customers. What’s happening through that is the team’s realizing that all of these sales pursuits are becoming more complex.

[00:15:16] Ryan Thomas: Customers have much bigger demands, and you can’t solve that with just an AE, right? You have to bring a team of people to the customer, and it’s not about just selling them technology. It’s about selling them a solution they know they’ll be able to acquire tech, implement it, and drive change in their business quickly.

[00:15:35] Ryan Thomas: They want to ensure they have a partner, not a vendor. They want a partner there to help them. We’re focusing on the customer-first mindset, which should drive a lot of internal behavior about how we think about working with our customers. That’s a lot of the leadership calls around these things.

[00:15:52] Ryan Thomas: It’s about transforming ourselves as leaders. We should not think about getting a deal done. We should think about running a healthy business. 

[00:15:59] Colleen Stanley: Ryan, it’s interesting because when you say it’s getting more complex, those salespeople will remain employed. We all know this.

[00:16:05] Colleen Stanley: If you’re in a transactional, they can go online, and your job will be gone and with that said, do you ever have any challenges with people calling on the resources, even after you’ve told them, kind of that knowing and doing gap? And if so, what have you guys done to bridge that? Because, again, people know they’re supposed to be calling on the resources, yet I’ve talked to enough sales leaders who need to play better together as a team or using the resources.

[00:16:27] Ryan Thomas: We see that in a few parts of our business, right? We now know that with that complexity comes a responsibility to ensure you’re selling the right services and a transaction to enable customer success. 

[00:16:40] Ryan Thomas: Selling services in a deal reduces the time it takes a customer to get active in our solution, and how the customer deploys our technology will be much more efficient for the customer. It’s ensuring we engage with that services team early enough in the deal cycle that it becomes part of the selling motion with the customer. That’s one example. 

[00:17:04] Ryan Thomas: Another example is when you show up to a customer now and discuss Elastic solutions. Customers don’t just want to know that you get great technology. They want to know that there will be a partner there to help them by migrating their existing technology to Elastic or implementing the Elastic solution for the first time in their business.

[00:17:26] Ryan Thomas: It’s ensuring your customer success team is at your table as you wind down the sales cycle. You want to ensure they have this comfort that we will be there to help them through that next phase. It’s teaching people that having these other parts of our business involved in the sales cycle is incredibly important. They’re also learning that getting deals done in a tech company takes a lot of work. There are legal and revenue implications that you have to talk through. Many things have to happen on the back end of the deal while we’re working through all of these other things.

[00:18:03] Ryan Thomas: It’s making sure that our sales team understands that process because what many of our sales reps learn the hard way is you can only circumvent some of those steps. We have teams of people like our deal desk team who help orchestrate deals, build orders, and ensure all of that stuff gets done according to our revenue requirements. There’s a lot of teamwork that has to happen where you see the AEs that embrace that, understand it, and know the process well; they do incredibly well. We see people stumble when they try to circumvent all of these things and just do it all themselves, and then they end up dropping a deal at the end of the quarter. 

Failing Fast: Embracing Mistakes for Growth

[00:18:42] Steven Rosen: It’s fascinating, and I know you’re in a highly competitive space regarding cloud-based services. It’s fast-paced. You talked about one concept before and also mentioned it today, and I don’t want to let it go because I think the term is very insightful. You talked about failing fast because sometimes we perpetuate bad decisions over and over again. Can you share what you mean with other sales leaders? 

[00:19:06] Ryan Thomas: By failing fast? Yes. I would classify that as leadership maturity.

[00:19:12] Ryan Thomas: You make decisions. We make a lot of decisions. Think about how many decisions we all make in a day. We are going to fail. We’re going to take all the data we have, and we’re going to make the best possible decision with that data, and sometimes we’re going to get that wrong. That can be related to an individual on the team. It could be related to a strategic decision that you made. It could be related to, Hey, we thought this partner was going to be great for us and it was going to help us fill a gap, and it’s not, we’ve made all this investment. You just have to decide that it’s not working and move on.

[00:19:43] Ryan Thomas: Let’s be honest about the things that aren’t working because it’s okay. I try to ensure that my leaders know that making mistakes is part of our job, and living in that uncomfortable space is where we grow. When we’re just comfortable all the time, we’re not growing. It might feel good, but when you make a mistake, you learn to grow, and together as a leadership team, we must realize it’s okay. 

[00:20:08] Ryan Thomas: Even though we made the decision, we felt good about it when we made it. Look, markets change, customer needs change, all kinds of things are changing, and they’re changing fast. If we made a wrong turn, let’s just admit it. Let’s turn around and go in another direction. That mentality drives our ability to grow as fast as we are because no one’s afraid to come to the table. Like I always say to my leaders, my philosophy on leadership is I want to give you all the tools and all the support and be an empathetic leader, but at some point, if you can’t get the job done, then I’m going to make a change.

[00:20:46] People’s understanding that this environment is safe encourages a fail-fast mindset. In many organizations, even some I’ve worked in, you don’t want to fail because it’s like, oh, I failed, and the axe is coming, and you don’t want that. I don’t want people to feel like they can’t fail. We want them to know that it’s okay to fail as long as we recover and do the right thing. 

[00:21:06] Steven Rosen: I think that’s an important part because people are going to fail. There are always going to be issues in businesses. It’s how we respond to them, and the final component that makes that okay is that it’s not that you failed; it’s that you didn’t do anything after you failed to right the ship or to go in a different direction.


[00:21:22] Steven Rosen: I think I could spend another 20 to 50 minutes just asking questions here because I’m learning a lot, and I hope our audience is learning as much or more than I am. Colleen, in terms of takeaways, what are your big takeaways from Ryan that are off the charts?

[00:21:37] Colleen Stanley: I wrote down. I hope I’ve got it right. You don’t have to lose alone. I have to tell you, that is so important because, like it or not, sometimes when you get into the sales profession, you could have lone rangers, and it’s one of the reasons they do well, right? They’re self-motivated and self-directed, and then it becomes their Achilles heel.

[00:21:55] Colleen Stanley: I really like that, especially in this growing, complex sales environment. The second one is leadership maturity, and boy, is it big. I think back to my 30s when I was in my first leadership role, and thank God I didn’t have bosses who fired me because I was well-intended but a bull in a China shop trying to push things through.

[00:22:17] Colleen Stanley: I don’t know if I cared about your why. I’m kind, but my attachment to the goal was greater than sometimes, bringing empathy to that as well. I will stop there because I will take all of yours, Steven. So those were the two that I wrote down.

[00:22:32] Steven Rosen: For me, what’s near and dear to my heart that Ryan shared is something I try to help sales leaders do because coaching on time, not on time, but on the time factors where you spend your time because that’s your one finite asset. You can always hire more reps, and you can always hire more managers, but where we spend our time because we all have the same amount of time is critical of success and coaching people on the understanding that that it’s not chasing every deal, it’s not continuing to beat your head against the wall in something that’s not moving, but spending your time where you’re going to get the biggest ROI and I think that’s a beautiful lesson to teach managers in terms of where they spend their time.

[00:23:11] Steven Rosen: We can also teach our salespeople and everybody that focusing on what’s going to drive results—what’s going to impact the customer—is better than doing all the things that add little value to the business. That’s my takeaway. I’m very passionate about it.

[00:23:28] Steven Rosen: Ryan, thank you for sharing your insights. I know you’re in a complex business with no shortage of challenges, but you’ve got most of them under wraps. So kudos 

[00:23:37] Ryan Thomas: to you. Well, thanks for having me. It was a lot of fun. Absolutely. 

[00:23:41] Colleen Stanley: We’re so fortunate because we just get very smart guests here, but it’s always nice.

[00:23:46] Colleen Stanley: Somehow, Steven, we’re attracting smart and humble people. I appreciate you sharing that you’re on a journey. You’re not quite there. For anyone listening today, if you like what you’re hearing, please subscribe to our podcast. It is our goal to help sales leaders, where sometimes it can be a little lonely at the top.

[00:24:04] Colleen Stanley: We’re bringing in guests in those same positions. They’re either coaching your team or, in your case, like Ryan, you’re coaching sales leaders. Thanks again for your time, especially after the busy weeks of travel you’ve had with your QBRs.

[00:24:16] You’ve got another quarter to go.

[00:24:17] Steven Rosen: Once it’s done, you can focus on the business again, but you are always insightful. Ryan, again, on behalf of Colleen and myself, thank you for sharing. This is one of our great podcasts, so it’s great having you, and I wish you continued success. 

[00:24:30] Ryan Thomas: And to you as well. Thank you very much.


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