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Growth Partner at Emergence Capital | Former VP of Sales Productivity & Enablement at Box
In today’s SaaS purchasing climate, you are more likely than ever to be dealing with a buying committee… and those committees are getting larger.
What does that mean to a seller? And how does the size of the buying committee make selling against the status quo even more difficult?
In this episode of Closing Time, Doug Landis of Emergence Capital chats with Insightly’s Dave Osborne about tactics for selling to buying committees, the pitfalls to avoid, and the extra work it takes to close a deal.
The B2B tech sales world is seeing some pretty big changes. Remember when just one decision-maker could say “yes,” and that was that? Well, those days are long gone. Now, we’re looking at a team of up to a dozen people just to get through one purchasing decision. And this isn’t just some passing fad; it’s a real sign of the times, reflecting the tricky economic waters businesses are navigating these days.
Doug’s got a sharp eye for why things are shifting towards these bigger buying committees. It boils down to the economy. Everyone’s watching their wallets a bit more closely, aiming for efficient growth and profitability instead of growth at all costs. This big shift means decision-making is a team sport now, with folks from different parts of the company weighing in, especially the CFOs, who are now key players in most purchasing decisions over $10,000.
This move towards larger buying groups isn’t just about changing how decisions are made. It’s about understanding what’s at stake in today’s economy and making sure every purchase or investment really lines up with what the company needs.
For sales reps, this means stepping up their game. They need to be not just persuasive, but also incredibly well-informed and adaptable. They have to understand the unique priorities of each member of the buying committee and tailor their approach accordingly. It’s about building consensus among a diverse group, which requires a mix of patience, strategy, and the ability to communicate the value of their product or service in a way that resonates with everyone involved.
With investors and boards closely questioning every expense, CFOs are under pressure to ensure that every investment is neccessary. The reality is, instead of making numerous decisions throughout the year, they’re narrowing it down to just a few key ones. And naturally, they want a say in these critical choices.
This situation poses a unique challenge for sales reps. The knee-jerk reaction might be to start pitching directly to the CFO. But Doug questions whether that’s the smartest move. It’s not just about getting access to the CFO to mitigate risks; it’s about understanding the right timing and approach. Should sales reps go straight for the CFO, or is it more about keeping them informed rather than selling directly to them?
Doug suggests a subtler strategy might be more effective. Instead of aggressively selling, reps should focus on updating the CFO on the progress and insights gained during the sales process. This approach respects the CFO’s position and the fact that they might not want to get bogged down in details, preferring their team to handle the groundwork. It’s about providing them with a concise analysis and recommendations, allowing them to make informed decisions without the pressure of a direct sales pitch.
In Doug’s view, this strategy aligns more closely with how buying committees actually work. It’s not about forcing a conversation with the CFO but about keeping them in the loop, making them part of the decision-making process in a way that’s respectful and acknowledges their role.
This can be a more effective, less intrusive way of ensuring that when it comes time to make a decision, the CFO has all the information they need without feeling overwhelmed or sidelined by aggressive sales tactics.
Doug dives into the strategic role of sales reps in fostering executive sponsorships during the sales process, using the example of selling a CRM solution like Insightly. He explains that introducing such a system isn’t just another sales deal—it’s a significant change that impacts the entire organization. Given its disruptive potential, Doug emphasizes the importance of involving executive relationships early on, not to sell directly to the CFO but to ensure there’s a strong link across the organization, which he calls “connective tissue.”
Dave adds that sales reps need to rethink their approach to engaging CFOs and other C-level executives. Instead of aiming to have those high-stakes conversations themselves, they should facilitate introductions between their higher-ups and the client’s executives. This tactic, known as executive sponsorship, aligns leaders from both sides—matching a CEO to a CEO, a VP to a VP—to de-risk the deal and lay the groundwork for a fruitful, long-term partnership.
The essence of Doug’s message is that it’s all about collaboration and mutual success. He suggests a talk track for sales reps to communicate value to executive sponsors: “Hey, I just wanted to show you, as a result of our partnership, what you are now able to deliver to your customers or how much more value you’re delivering to your customers. This is a really important point you should probably take to your next board meeting.” This approach not only positions the sales rep as a valuable ally but also reinforces the executive sponsorship by providing actionable insights that can directly benefit the client’s business.
Doug also stresses the importance of maintaining this executive alignment not just during the pre-sales process but throughout the partnership. He shares a crucial piece of advice for sales reps: always bring value to these high-level meetings. It’s not enough to simply check in or run through typical QBR metrics like monthly active users. Instead, reps should offer insights and solutions that make a real difference to the executive’s priorities and challenges. Failure to do so risks losing the engagement and support of these key stakeholders.
Is it a surprise that your biggest competitor isn’t actually your competitor? Instead, it’s the Status Quo aka doing nothing. With over 60% of deals ending in “no decision,” reps are left having to defeat the fact that any change is more risky and less safe than sticking with their current Status Quo.
Doug shares a powerful insight: our job as sales professionals is not just to sell but to guide our prospects through a conscious decision-making process. This means helping them weigh whether the problem they face is significant enough to warrant the investment of time, money, and resources to solve. And if they decide to tackle it, guiding them on the best path forward—whether that’s with us or someone else, or even sticking with their current solution if it truly is the best option for them right now.
He highlights a critical point about addressing the Status Quo head-on, right from the get-go. Doug suggests a straightforward, honest approach for engaging prospects: “Dave, how I view my role in our relationship is, I’m here to partner with you to help you, at the core, make a conscious decision. That decision may be to stick with what you’re currently doing, partner with me, or partner with someone else. Now, let’s dig into why that may or may not make sense.”
This approach is refreshing. It’s about laying all the cards on the table early, acknowledging that changing the Status Quo is a challenge, especially when it requires consensus from multiple stakeholders within an organization. Doug emphasizes the importance of sales reps being prepared to assist prospects in navigating these internal conversations, leveraging their experience to foresee and address potential objections and barriers.
In essence, Doug’s conversation is a masterclass in conducting discovery in a way that’s partnership-oriented, devoid of sales jargon, and grounded in honesty and mutual respect. It’s about showing that we’ve “seen the movie before” and are ready to help our clients look around corners and anticipate the challenges they might face. It sets the stage for a more meaningful engagement and also positions the sales rep as a valuable ally in the decision-making process.
It’s not your imagination. Buying committees are more common and they’re getting bigger. Let’s talk about tactics for selling to buying committees who may really like the status quo in this week’s episode of Closing Time. Hi, I’m Dave. Osborne, chief sales officer at Insightly. Welcome to Closing Time. The show for. Go to Market leaders. Today, I’m joined by the legend Doug. Landis. Doug is a friend of the pod. He’s a friend of Insightly. He’s has many years in B2B sales coaching. Several SaaS businesses. He’s a growth partner at Emergence Capital. He’s the most stylish man in tech. Also, former chief storyteller from Box. Please welcome Mr. Doug Landis. Thanks, Dave. Good to see you, buddy. No longer in Austin. Yeah, it’s been a long time. Yeah, totally a whopping like two weeks. That’s it. So Doug actually was a keynote at our SKO last week. And for those sales leaders looking to bring on a heavy hitter for a keynote, look Doug Landis is your guy, about as good as it gets. Yeah. Good to see you again my man. I would gladly do it. In fact, I’ve been talking to Jen. Allen a lot lately about the two of us doing, like, a two person show. Heck, yeah. Yeah,. I think that’ll be really, really fun. We’ve done it a few times and it’s been wildly successful, so. Yeah. More on that to come. Man, we’ll be looking forward to that. Those are two awesome, awesome speakers and thought leaders in tech sales. But Doug, let’s dive into it. So let’s start with why, so why are buying committees more common today than they were, say, five years ago? I actually say I don’t think anything’s changed in the last five years other than the fact that there are more people involved in the buying decision right now and largely predicated on the fact that we are in an economic situation where CFOs, well look, if you just kind of think and kind of take a step back. Right. So investors, board members, executives, the pressure you feel this like you’re in your executive committee. The reality is it’s like the belts are tightening in terms of financial decisions that we’re going to make for the business. The big shift in focus for our a lot of our companies has been focus on efficient growth, profitability. What is this past profitability? Versus growth at all costs. When it’s the growth at all costs mindset, your job as an executive, as a leader is to empower your teams to help make important strategic decisions, even spend money. Whereas now in this environment it’s like, okay, cool, go do the research, bring it back to me, and then we’re going to discuss how this fits into all of our priorities. We need to get more people involved in this conversation. And typically CFOs get more involved in deals over $10,000. So the truth is, is the buying committee is changed in terms of size, but the process itself hasn’t necessarily changed. You know, people have been buying in committees for ages. 100%. So, I mean, and you brought up before, We’re seeing the CFO get much more involved than we were, say, three years ago in even in like purchases that are 25k, what we normally thought were relatively incremental purchases in past years. So I mean what’s your thought process there is the essence to try to mitigate risk or is that maybe is that pessimistic thinking and paranoid thinking from a sales guy? Well, first of all, I’m so glad you said that. I think every seller should be paranoid.. Period. You should operate from a place of paranoia and knowing that, you know, the deal is never done until actually, you know, till you’re delivering on your promise. And honestly, the deal’s really never even done even after that, because so many things can go sideways. Look, CFOs are getting involved because at the end of the day, they on the hook now. Right. So board investors are like,. Yo, what are you spending your money on? CFO is like, okay, does this really make a whole lot of sense? Is this something that we should be prioritizing? Because instead of making ten decisions throughout the year, I’m only making three. And so as a result,. I want to be involved in the process. I want to basically be the final say. I think the challenge that we all face is so many people think that, you know, since the CFO is going to be involved in a decision, we need to go sell to the CFO. Right. Okay. I need to go prospect. I need to engage. I need to go sell to the CFO and actually,. I’ll throw the question back to you, but I have my take on that. Do you think that’s the right approach for an AE to go try and engage with the CFO? Look,. I think timing is going to be relevant. I’m sure there’s going to be qualifying that moves all the way up. But I think for a lot of these purchasing decisions, if we don’t have access to the CFO, I think that’s just adding risks in to your deal. Sure. Sure.. Because there’s a lot of unknowns, right? That’s right. There’s a ton of unknowns. However, there’s also something else to consider. What if it’s less about selling to the CFO and more about updating the CFO? So think about it. Yeah, kind of responsible vs. informed. Right, Right. So, like, if you’re a CFO or even a CEO, it’s like, look, you hire people to go do the work. So we often talk about like, you got to get the power. Get to power. Get to power. Oftentimes power, CFO, CEO, like,. I don’t want to talk to anybody right now. I got enough stuff to think through, right? Like, I got enough to navigate. I’ve got a board meeting coming up in the next week. I don’t want to talk to anybody. I want my team to talk to, you know, all the different partners or vendors. Evaluate options for solving for some of the core problems that we’re trying to solve for for this year. And I want them to bring that to me. What was their analysis? What was the process for doing their due diligence, what are their recommendations? And then we’ll discuss as a team. So if that’s the case, and this is kind of how buying committees operate, if that’s the case, then do I need to try and make it awkward and uncomfortable to reach out to the CFO when we know the CFO really doesn’t want to talk to you? Or what if it’s a, Hey,. I want to keep you informed, Because, look, I recognize the fact that in most of my conversations we’re having right now, CFOs typically are going to be involved in this conversation, usually behind the scenes. As a result. I just want to keep you up to date as to what’s been happening. The conversations are happening and kind of the progress that we’re making to help you solve one of your more immediate and what I would consider more, more important problems. Feels like much more of like a benign like offer, right? Like, hey, I just want to keep you in the loop versus just kind of commanding it. I know there’s a lot of we’ll call it aggressive kind of enterprise sales tactics of companies that just kind of force their way right to the decision maker, to the economic buyer, whether they want to or not. And yeah, to their credit, a lot of times it works out pretty well. But sometimes it doesn’t. Sometimes it rubs them the wrong way and kind of ruins your relationship with your point of contact. But I would also, the flip side of this, of course, cause I like to see all sides, is it kind of depends on what problem you’re trying to solve for and the type of solution. So I’m going to use Insightly as an example for a CRM type solution. That’s a really big disruptive problem to solve. Right. And, you know, it touches almost everybody in the entire organization. So given that,. I would suggest if I were out selling Insightly as an example to a prospect, I would suggest getting you or Anthony, your boss, involved as an executive relationship, largely because we know how potentially disruptive a solution, a new CRM can be in an organization. And we want to make sure that there’s a you know, there’s some connective tissue across the entire organization. So in that case, it makes sense for me to try and make an introduction between you and the CFO or Anthony and the CFO versus me reaching out and engaging with the CFO. So I like I’m being a little controversial, against my own point, which is don’t disagree, like don’t not sell to the CFO, just be thoughtful about like, well, why would they want to have a conversation? And if they do want to have a conversation, you can come up with an idea as to why. Then think about who should be having that conversation. That’s it. Oftentimes, I think, as AEs, we think that we are far more important than we actually are. And a lot of times our job is to be that quarterback. And it’s like I don’t necessarily have to be the one that has that conversation with the CFO, but I want to make sure somebody in our organization above me is appropriate title match. That’s it. Yeah. I mean, we call that tactic kind of executive sponsorship, right? Because you may have. Yeah. A champion or a mobilizer, as I know you like to call it. But then there’s also like that executive sponsorship, right. Like it’ll depend on who the sponsor is on their end. Right. If it’s their CEO, then maybe getting your CEO or, you know like but just aligning some like a C level to their C level. a VP to their VP, and if you can line that up, could de-risk the deal considerably and actually create a more successful relationship long term. It’s like, look, we are in the business, we together are in the business of making you successful, of helping you better support your customer’s customers, right? And so like we’re going to do this together. We’re not just selling you a piece of software just to sell you a piece of software to make you more efficient, make you whatever, whatever kind of internal metrics you think are really matter. I think at the end of the day, it’s like we’re in this so that you can go sell more to your customers. And if that’s not happening, if we’re not hitting the mark together, then we need to have a discussion about that. That’s it. And having that executive alignment and relationship allows to your point, it allows for that communication to happen. Like, hey, listen, you know, like this seems to be working well. We want to talk to other people that you’ve worked with about some other little things that we might be able to do, make it even better. So and one last tidbit before we move on to the next topic is when you’re having those kind of executive alignment meetings, right? So there’s going to be a pre sales, probably a few touch points, but then obviously post sales, assuming it’s a, you know, strategic enough deal, you know, I think it’s important to maintain executive sponsorship throughout in that alignment. When you’re having those meetings, make sure you’re bringing value. Like I think I’ve been on both sides of this, right? Yeah, I’ve been on both sides of this where I’m like the sponsor on the sales, like selling to. But I’ve also been the sponsor on the buy side, where I’m buying technology. And I’m kind of the, the budget owner of those items. And I can tell you like. I’ll go to these summaries on the buy side and they’re just like checking in and it’s like almost like a normal QBR and look,. I got a lot of stuff I’m working on. Like this is not a good use of my you know, I got a lot of things. I could be doing with this hour versus you running through my monthly active users or whatever that may be. Yeah. Who cares? So what? Come bringing something that’s going to help me move better, faster, easier like or else you’re going to lose that, like that sponsor was never going to show up again. Yeah. Why? Yeah, what’s the point? Yeah, that’s so, like everybody listening to this, pay attention to what Dave just said because that is so critical. This is why I started with Hey, by the way, most of time, CFO is not going to want to talk to you because what value are you going to bring to them? And they’re like, okay, so what? I trust my team more than I trust you because I don’t know you yet. And so even when you make that executive alignment, you create that executive relationship. There has to be value in that. And what is the value that you’re actually delivering? So let’s say, you know, if I were selling you, Dave would be like,. I’d be like, Hey, Dave, I just wanted to show you. You know, this is a five minute conversation. I want to show you as a result of our partnership, what you are now able to deliver to your customers or how much more value you’re delivering to your customers. This is a really important point. You should probably take to your next board meeting, right? Huge. Imagine that, you’d be like,. Oh, thank you. Make a note of that.. That’s a really good point. Right. Because, you know, getting ready for board meetings is a pain in the ass, we all know that. Huge. Huge. So let’s maybe quickly change gears, Right?. Yeah for sure. So something you and I have talked about. It’s all connected. Yeah. It always is. Something you and I have talked about quite a bit over the past few years that we’ve known each other. Our biggest enemy in a deal cycle is the Status Quo. Right? And I think the stat that you threw out there, it’s it’s a majority of deals. It’s 60 plus percent of deals. Yes. We’re losing due to the status quo. Right. Or do nothing. Yeah. So maybe talk a little bit about like the dynamic there. Right. Like in turn, because I know you’ve talked about like good is good enough. Right. Is being part of the problem. But I’d love to kind of like. I think you have a very strong thesis on why these kinds of things are happening and maybe what we could do about it. Yeah. Yeah. Well, look, I mean, you know, my good friend Jen that I was just telling you about, like she has this whole, you know, narrative around the cost of inaction. I think a lot of people like to get us to the cost of inaction because that’s going to help driving urgency. Right. But before we actually get to the cost of inaction, we just need to unpack why they might actually not want to take action. And one of my core thesis in life, in selling, in period is one of the things that part of our job as sales leaders is to help our prospects make a conscious decision, a conscious, that’s our job is to help. If I’m working with you, Dave, and I’m engaging in a conversation with you, my job is to partner with you so that you can make a conscious decision as to whether or not you want to, if this problem is big enough for you to try and invest some time, money, energy, resources to solve it. And oh, by the way, if you decide that it is, then let’s make a conscious decision as to what direction you want to go together. That may be partnering with us, that may be partnering with somebody else. It also might be, as we uncover sticking with what you’re currently doing, because it’s just way easier or it’s safer or there’s less, you know, there’s less risk of something going sideways because by the way, you’ve got this huge conference coming up in three months. And if something were to go sideways right now, this could potentially derail that. So I just want to be really honest about that. I think oftentimes with the status quo, we don’t first of all, we don’t bring it up early enough in the conversation. Like I’m a believer that right in the beginning, let’s just say this is one of our first calls together. Dave. You know, one of the things how I view my role in our relationship, Dave, is one, I’m here to partner with you to help you at the core, make a conscious decision, right? That decision maybe to stick with what you’re currently doing. Now we want to dig into that. Why that may or may not make sense. Just I want to call that out because at the end of the day, I know there’s a greater than 50% likelihood from all the other conversations that I have that sticking with what you’re currently doing is easier, it’s safer. And oh, by the way, in order for you to actually make a decision, you are going to have to get everybody else in the organization on board. And that’s a lift, I’m here to help. But no matter what,. I just want to make sure that we have everything on the table and we’re talking about it all. And I’m going to help you navigate some of those internal conversations that you’re likely going to have to have, because I’ve done this before. And you’re like, and I know how strongly you feel about the Gestapo like line of questioning that typically happens in Discovery. You know, what Doug just kind of walked through, he actually gave you the talk track. That’s actually, that’s how Discovery should go, how they should feel, it was very natural, it was very partnership oriented. You know, he’s not using fancy buzzwords. He’s more just like, this is us having a conversation, kind of deciding what’s going to be the right next step. Are we a good fit or not? Like, let’s be honest. Well, and it’s also like. I’ve seen the movie before. Dave Yeah, I’ve seen it before. And my job is to help us, like look around corners, anticipate the things we’re likely going to face. Right. Doug, I think you and I could, we could shoot the stuff all day, but maybe just to wrap up really quick. So we talked about committees, committees getting bigger, Like what are the most common pitfalls that you’re seeing that sellers are making when trying to access or work through these larger and larger committees? And how can they maybe, what are the flags they should be seeing? One of the biggest challenges in buying groups that we all have to just be really conscious of is that there’s not alignment on the actual problem. So part of our job as sellers, if I’m working with you, Dave, is like, Hey Dave, one of the things that we’re going to have to do in time is get everybody together that is going to be involved in this decision to some degree or who’s impacted by this and make sure we get alignment on the problem. What problem or we solving? And why does this matter? Why should this be one of the top three priorities that we’re focusing our time, energy, effort and resources on? Because if we can’t get agreement on that, I don’t matter, my solution, what I’m bringing to you, bringing to the table does not matter. If you and all of your executives and everybody that’s involved in your buying decisions can’t agree on what fundamentally the problem is. Then why does it matter woth solving? All right, Doug, appreciate you, man. Great, Great having you. Great seeing you. That’s all the time we have in this episode of Closing Time. Appreciate you joining. Always a pleasure. It’s always good to be here, my man. Remember to subscribe to this channel, like the video, tick the bell for notifications so you don’t miss an episode. We’ll see you next time, everyone. Thanks.