About the experts:
Steve De Marco is the Chief Revenue Officer at LeanData, where he leads the company’s global revenue organization including Sales, Partners, Account Management (renewals + upsells), Sales Development and Solutions Consulting and is focused on driving revenue growth across all segments (SMB, Mid Market and Enterprise), achieving quarterly and yearly revenue goals while running a cost efficient organization. Steve’s previous experience includes CRO at Conga, SVP of Global Sales at Malwarebytes and 12 years leading sales at Xactly.
Tim Mann is the VP of Sales at Blueboard, leading the Sales and Sales Development teams, focused on driving new business and revenue growth. As a prior service Marine and with a background in sport and performance psychology, Tim matches years of sales and sales leadership experience with a unique perspective on how to build team culture, set sellers up for success, and inspire high performance.
Sales has always been a high pressure job. But right now, it’s particularly brutal. Teams are navigating constant change, from economic headwinds and turnover, to new tools, products and motions—and 69% of reps agree their jobs are harder now than ever before.
This leaves revenue leaders scrambling to figure out how to drive consistent, high sales team performance in a time of “do more with less”. The question of the day: How?
In a recent virtual session, two seasoned sales leaders—Tim Mann, VP of Sales at Blueboard and Steve De Marco, CRO at LeanData—had a candid conversation about the challenges revenue teams are facing right now, how to build team culture in a time of disconnection, and how to get creative with comp and incentives and blow your goals out of the water.
Here's what you'll learn:
- Top-of-mind trends and challenges for revenue leaders right now—and tips for navigating them
- How to build a motivated sales team and culture that attracts and retains top reps
- How to introduce fresh incentives that get more of your team to stretch in tough times
A VP of Sales and a Chief Revenue Officer walk into a zoom room...
Tim: Hey everyone. My name is Tim, I'm the VP of Sales here at Blueboard. I’ve been at Blueboard, coming up on four years. I was actually at Blueboard for a couple of years, left for a year, and had the opportunity to come back here and lead the account executive and the SDR organization.
We are a reward and recognition platform that focuses exclusively on experiential rewards and incentives. So, we are generally selling into HR organizations as well as sales organizations for a variety of use cases.
Now I've been in sales for a number of years. But Steve, here, has been in the game a little bit longer than me with a ton of experience. So I'm excited about the conversation to learn a lot from Steve and just exchange ideas around what we're seeing. So, Steve, with that, would love a quick introduction to yourself.
Steve: Excellent, Tim. Thanks for inviting me here. It's a topic near and dear to my heart. And I think it’s something that a lot of revenue leaders are thinking about these days, you know, driving behavior and trying to incentivize employees to do more. You know, we're all told to do more with less.
I've been selling technology now for more years than I want to admit—25-ish years. The last four of which I've been here at LeanData. LeanData is a revenue orchestration platform. We work with Salesforce to help companies orchestrate key pieces of data. We're best known for lead to account routing. So, leads routing to the right person, making sure they're getting to the right person immediately so they can be followed up on.
So it’s great—because we sell to revenue operations, marketing operations, sales leadership and marketing leadership, I get to talk about a lot of this stuff, Tim. And to your point, I've been selling technology in and around Silicon Valley, like I said, for 25 years. I've gone through three of these downturns. Some folks may remember in the early 2000s, tech was affected by the dot-We com bubble bursting. And, of course, ‘08, ‘09, and ‘10, were really tough years with the subprime mortgage industry affecting the economy in another downturn.
And now here we are. It seems like it happens every ten years or so. And it's never easy, what we're dealing with, what we're going through. But strong companies and people that have the right mindset and understand how to get through these times can do it really effectively and come out the other end even stronger.
Q: What trends are you seeing today in sales that are shaping your decision-making as a revenue leader?
Tim: Something I've been hearing a lot in conversations is, you know, some people like yourself that have been through a number of these downturns and then, for other people, it's the first time. And they’re used to selling in the “good old days” when it was a little bit easier out there and companies had a lot more money.
Given your experience from SAP to Xactly, Malwarebytes to Conga, now LeanData—you've been at all these companies, these different-sized organizations—and as you look at not only the time in the market, but also just the size of the organization, what trends are you seeing that have shaped your decision-making today in terms of being a CRO in sales leadership and how you’re approaching the way you lead and manage a team?
Steve: There are a lot of great things we can talk about there. It's true, I've worked for various sized organizations. Conga, Malwarebytes were in the $100 million range of revenue, ARR per year. The sales organizations alone were in the hundreds of people. LeanData is a little smaller—I joined when they were about $17 million and we're pushing up towards, you know, $50, $60 now, which is great.
But you know, I loved that stage of growth at Xactly. I was actually there for 12 years, which is a long time. And I started as the 15th employee and the first salesperson. And then I was able to sort of help grow this and scale the team and we evolved and got to the point where we were, you know, hundred million plus, went public and then got acquired by Vista equity partners.
And I was still running the sales organization, which was now 100+ people. And that was a really good learning experience for me because it showed me all the different stages of a company. And as a sales leader, you definitely have to reinvent yourself. Because in the initial stages of a company going from, say, zero to $15 million, you're just trying to get the first hundred customers on board. And you're doing everything you can—you're rolling up your sleeves, you're in the trenches.
But then to get from $15M to $50M, you have to change your scope. You have to bring in really good next level management, you have to start scaling the organization and building really good processes. And then, of course, from $50M to $100M, it's even more of the same.
All along the way, though, the fundamentals still apply. It's just whether or not you're hands on as a sales leader or you're galvanizing your leadership team to make sure that you're pushing the right fundamentals, you're measuring the right things. You know, it becomes a much more metric-focused organization as you scale.
And the metrics are all really just reflecting:
- Is everyone on the team doing the right things, are you focusing on the right things?
- Is the pipeline growing the way it needs to be?
- Is activity the way you want it to be?
And on and on so that you can successfully lead the team and make sure you're breaking down barriers. So, fundamentals still apply no matter how big the organization is—but it's about how you enforce those fundamentals.
Q: How have the metrics you’re using to guide your sales strategy changed (if at all) over the past few years?
Tim: It’s a great point. I'm curious—as you’ve seen shifts and downturns—how has that impacted how you think about zeroing in on the right metrics? Because every sales leader knows there's no shortage of metrics that you can look at, you can get lost in a lot of different metrics. So, have the metrics changed in the last year, two years in terms of where you're dialed in and where you’re focused?
Steve: The fundamental metrics that I zero in are the same. You’re looking at growth, you're looking at pipeline, you’re looking at where pipeline is coming from. You're looking at win rates for your team. We're talking about really sales-focused metrics here. You're also monitoring things like sales cycle time, average deal size, average discount level—this is primarily for new business.
I also have Account Management where we do renewals and upsells for our existing customer base. So there's a different set of metrics, although somewhat similar. You're still looking at your pipeline of potential upsells within your base, but you're also looking at churn. You're looking at renewal and net retention. And you're having to forecast there, you're having to forecast new business—it's a lot. So those metrics really haven't changed.
I think the thing that changes, especially in tougher times, is the level of granularity. If you start seeing anomalies, maybe you need to get down to the rep level. If pipeline is there, for example but—and this is a mistake I see people make—but your win rates are different, you can't apply those old win rates to your current pipeline because you're gonna miss your number. Right?
So you have to constantly adjust based on the reality of the situation and in that regard, yeah, there's change. You know, if you see that it's taking 5x pipeline instead of 3x, you’ve gotta figure out how to get that incremental additional pipeline. It becomes, what do we have to do? We're collaborating with Marketing and partners and everybody else. So those things do change, and you have to be fleet of foot, if you will, able to withstand and deal with those changes.
Q: Given the current economic climate and where you’re at in your fiscal year, what’s keeping you up at night when you think about your sales success?
Tim: Yeah. You’ve gotta be very dynamic. And those are also not always easy conversations to have across the business, to say, this is what we modeled and some things changed and now we’ve gotta change motions, and we have to do some things differently.
So, along those lines, being in this third downturn in the market, being in the fourth quarter at LeanData, staring down a fourth quarter number, looking to next year, what are the things that are keeping you up at night where you're like, man, like, these are the things that I'm worried about right now? We were just talking about sales goals, whether that's a specific type of metric or more at a high level?
And the flip side to that is like, what are you bullish on right now? What are you excited about, in terms of the opportunity you see in the market?
Steve: Well, first, let's talk about the things that keep me up at night. And then that'll lead really well, I think into the things I'm bullish about. But there's a lot keeping me up at night these days, Tim.
You know, for sales leaders right now, these are the probably the toughest times that a lot of you have faced. To your point, unless you were here in ‘08, ‘09, and ‘10 as a sales leader. You're [probably] scratching your head going, man, what else can I do?
For me, it's always going down to these two basic things: 1) It's pipeline development because I know that pipeline is key—nowadays more than ever, because win rates are decreasing. And so you've gotta maintain healthy pipeline because if you don't have opportunities to work on, if your close rate has to be something it's never been before, you're putting a lot of excess pressure on the team that probably won't work very well. So pipeline development is key.
And then 2) sales execution. And you might say, no kidding, Steve. But it's true. And when I say sales execution, I mean, are we doing all the proper things for every single deal to achieve sales success? Because we have to increase that win rate. So, there aren’t any throwaway deals. You know, there's no such thing as, ah, you know, if we just get these five out of seven—you’ve gotta figure out how you can get all seven of those deals to close.
So we're doing a lot of deep dive inspection and this is where the first line managers have to really get on their game.
But it's not something where you’ve gotta drive the team and just you know, bang the table. It's really the opposite of that. It's jumping in with your team and saying I'm going to help you and I'm gonna work with you as sales leadership. We're all in this together: How do we execute? How do we make sure we're executing as best we can?
And if they see you in there with them trying to help them, that's gonna motivate them and that's gonna make them realize that they're not alone in this endeavor. Because that's the worst feeling they could possibly have is wow, I've got this mountain to climb and I'm by myself.
But it is also incumbent upon them to do all the right things so that they can continuously build the pipeline that is needed. And then at the same time, you know, balancing building pipeline and working on opportunities to try and get them closed.
Tim: As a quick follow-up to that before the things that you're excited about: When you say, “jump in there together with them”—what does that look like from your perspective? As a CRO of an organization, how you do that yourself, and how do you work with your leaders underneath you to make sure that they're in the game there with them.
Steve: You know, LeanData is a little smaller than some of the other companies I've worked for. And, I mean, the goal is always to grow the company. But one of the reasons I like working with companies around this size is because I get to dive in and roll my sleeves up with the team, you know. And so as a leader, you know, you can't help work every deal. That doesn't scale.
But what we do is we do a lot of deal reviews where we pick the top, maybe the most complex deals, the largest deals, or the most strategically important deals. And the rep, the manager, the SE, and me, we're all working, and we were brainstorming on what we can do to help this deal along. And and and the reps like that. And they look at that, like, this isn't a gotcha session where I'm gonna, I'm gonna get upset if you haven't figured out who the economic buyer is.
It's the contrary. We use MEDDPICC, by the way, you know, a very specific (sales) process. But it's about them saying Steve, I can't get to the economic buyer—I think I know who it is, but I can't get confirmation and I need to get to this person because it's a risk if we can't. Then it becomes, Ok, let's figure out how to solve that problem. You know, start scouring LinkedIn: Who do we know who knows this person? Can I reach out to them and try to connect? And so I'll get down to that level to try and help them solve these problems.
And that does a world of good. And as the scale of the organization grows, obviously, the head of sales can't get into everyone, but their second level or, you know, managers can. And that's what you have to do, I think, to make sure that the reps know that you're there to help them and support them and try to make them successful.
Tim: A hundred percent—I couldn't agree more. And I think a big part of that is building trust, within the leadership team and at the IC level. We all get bad news every now and then like, hey, this deal died, this thing happened, contract fell apart, but you always want to create an environment where people can come to you and have that conversation. And then it’s like, alright, it’s not great but let's figure out where things went wrong. What did we miss? How do we learn from it? Is there a way to fix it? But if you don't have an environment like that, you find out about things maybe a little too late sometimes.
Steve: That's it. There’s gotta be trust. It can't be leadership through fear. The team has to believe that you're in there with them—when I say “them” I'm talking about the individual contributors, levels of management, that you're all in it together. And and and that's a cultural thing that you have to build throughout your tenure at a company.
Q: What are some of the things you’re excited about as a sales leader heading into 2024?
Tim: I asked two questions at once; I always tell my team to not do that and I did it to you, but what are you excited about?
Steve: You know, 2023 has been very challenging. We all remember back in January when everyone was on pins and needles because we heard there's gonna be a big giant Salesforce layoff, right? And it kinda started there and then, you know, subsequent layoffs happened and everybody was on edge in Q1. So that happened, then Q2, Q3, you know, and here we are in Q4. The good news, and I tell my team this all the time, is that if it goes the way the other downturns went, there's a light at the end of this tunnel. And I think 2024 is gonna start brightening up a bit. And I'm already starting to feel it.
There are still some layoffs that are being reported. I think some companies are still very carefully figuring out how they're going to grow. But going into 2024, companies need to grow. We kind of stepped away from that growth at all costs, let's just spend like drunken sailors and, you know, and then just grow, grow, grow. Well, that's probably not ever gonna come back.
But the requirement for growth is going to be there nonetheless. And this whole notion that companies are going to be asked to do more with less—that's fundamental, you know, all companies should be thinking that way all the time: efficiency.
And so I think that this year was a very good year for salespeople to really learn skills that maybe they didn't have to have before. Really understanding the fundamentals of value-based selling and making sure that your product was not seen as a nice-to-have.
And now, for those who have developed those skills, going into a better economy with a little more freedom to spend and companies coming back and saying, hey, we have to grow, coupled with this new skill set that a lot of salespeople have developed—it’s gonna make them wildly successful in the future.
I think 2024 is definitely going to be better than 2023. And I'm excited for that because I think 2023 forced us to learn a whole bunch of new skills and just be better at our craft.
I tell my team, wait until you get back into an economy that's decent again. With everything you've learned, salespeople, you're going to just be just crushing it, you know, quarter after quarter.
So that's what I'm looking for.
Tim: It's such a great call out. I'm a runner so I'd compare it to running—it never feels good while you're doing it but afterwards, oh, man, was it worth it. And I feel like that's a lot of what I hear right now and see across sales organizations: It’s a lot harder than it has been to be a seller.
Steve: Yeah. It's like when you're getting ready for a race and you're maybe running up hills, and it’s painful but it's gonna make the race better. Right? Well, the race to me is 2024, and you're going through some severe workouts in 2023 that make that race really successful—
Tim: Workouts that maybe you didn't even know that you signed up for. You showed up and you thought you were doing an easy run and somebody walked up and told you we’re gonna sprint.
Steve: That's it. That's the analogy.
Q: It’s harder to be a seller now than it’s been in a long time: How are you creating a high performing sales team culture where reps feel like they can thrive and do hard things?
Tim: I think that’s a lot of the sentiment right now. Along those lines—and I've seen this across my team and I'm talking to sales leaders every day as they think about incentivizing their teams—one of the primary topics is that it is harder to sell right now and trying to keep people motivated, trying to keep sellers excited and able to do these new behaviors that organizations need them to do, it's hard.
So companies are really drilling in on, like, how do I create this high performing sales team culture, a culture where people feel like they can thrive and do hard things. Does that resonate with you? And if so, how are you tackling that? And what are you seeing across other sales organizations? I'm sure you have a deep network of other sales leaders that you're probably talking about these things with on a regular basis.
Steve: It's never easy, you know. And it's and it's probably gotten even harder. You know, we kinda got the double whammy, Tim, because, on one hand, we just came out of the pandemic, which changed everything. And I think the biggest change was a lot of people working from home.
Whereas, I'd say 95% percent of LeanData’s sales team prior to the pandemic was all in the Santa Clara office. And now we're distributed. We still have two days a week for collaboration but it's not like it used to be: five days, everybody in the office.
Now I see the benefits of being able to be hybrid or being able to to work from home and do your thing. But it's also challenging—sometimes sales teams need to be together to do call blitzes or to just collaborate or to keep each other motivated. When one person has something bad happen, you know, having somebody there to kind of pick you up is great. And you don't have that as available as you used to.
So to me, that's the double whammy: People are distributed and now we're in a tough economy. So how do you keep everybody galvanized?
Well, I've always been a big believer in [incentives]. Xactly, where I spent twelve years is an incentive company, they automated commissions. And so I really became a student of incenting employees, particularly salespeople—what drives their behavior and what it motivates them.
So I certainly believe in incentives. On one hand, you can try to drive your team and motivate them negatively, and some people do that. Some people, believe it or not, still do it. It was much more prevalent when I was a young sales person, you know, 25 years ago to have these mythical sales managers that would walk around with a baseball bat in their hand saying, what's your forecast? You know, and it was intimidation and fear. Well, those days, I think, are gone. There still is a little bit of that, you have to do this or else. But that's just a very negative way of trying to enforce or motivate or get people to do what you want them to do.
I find it's much better to talk about how you're in the trenches with them, you're all in it together, these are common sales goals we're trying to achieve. But then reward them for doing the good things. Motivate them by showing them that there is a light at the end of the tunnel. If they develop certain skills, if they engage in these activities or execute the sales process flawlessly, or put that extra time in—whether it's prospecting or getting on the phone with a customer and working through problems. All of that's gonna benefit them somehow, whether it's through rewards, dollar incentives, promotions, and what I just mentioned, which is that they’re developing skills that I guarantee if they stick with this career, they’re gonna benefit from next year and the years after.
All of that can inspire the feeling of maybe I will work a little bit harder in order to to develop these skills or to get those rewards.
It's really about putting something in front of the team that they want to aspire to to gain. And it could be financial, it could be rewards, or it could be just knowledge or a promotion or something like that. The main thing is that they have to see what's going to benefit them because goodness knows they can feel the difficulty and the pain so you’ve gotta counter that.
Tim: I love that and I completely agree. I think it goes down to, you know, everybody is motivated in different ways. Some people are more motivated by moving up in segments and getting larger opportunities. Some people are more motivated by an immediate payday. Some people are more motivated by other things. And that's gonna vary.
And a lot of that comes down to the frontline managers and the leaders to really be able to understand how to work with the team, which can be hard—especially as you get into larger organizations—it can be hard to take the time when you have the CRO banging on your door asking for the forecast.
Steve: Yeah, yeah, that’s it.
