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The Revenue Operations Blog

The Complexity of Sales Leadership, Cliff Dorsey

November 25, 2021

The Interview

Kluster's Take

Tom spoke with Cliff Dorsey, Chief Revenue Officer at Salient Systems. He describes the complexity of sales leadership and forecasting during the pandemic.

Cliff explains how enterprise selling has changed in a virtual world. It’s a world where we don't have the opportunity to dig into deals “over a coffee”. Cliff makes a conscious point to schedule one-on-one time with potential champions.

He believes that this change creates the challenge of uncertainty. CRO’s and sales leaders have many methods to overcome this.


Probably the most important attribute, which is being able to do what you say you're going to do consistently and repeatedly.

It's all about forming a team, forming a vision and creating, um, a sales team that is the best in its respective. Hmm, capable of selling at a level that is as important as the product itself in terms of differentiation and, um, ability to compete so that we, when our unfair share of deals and, and charge a premium.

Um, so that, that means we have some bedrock principles around pipeline, generation, and forecasting process using medic and value based selling. Um, that are, you know, non-negotiables that, um, allow us to achieve, you know, that, that sort of excellence, um, you know, a lot of that is formed for my time. Um, I.

Grew up in technology selling and a company called PTC, which is where things like medic came from. Um, so I was, I was there when that was, um, you know, being come up with, um, and, and kind of that discipline, that process. Um, I was also an army officer, so that, that, that I had a little something to do with it.

Um, you know, carries over into, you know, how, how we execute as a sales team. So I think that's a. A little bit what shaped me and, you know, not, not getting stale from the nineties, I've, I've, uh, picked up things. And I like to challenge myself to, um, learn and add new concepts to this as we go. And this is, you know, some of the things I want to talk about today are, are part and parcel of that.

That's the perfect case. So we drive for having a real high performance team. Now, unusually Claire, you've been CRO welcomed for over five years. It's not what you typically see, you know, 10 years ago, is that an 18 month? Uh, like, uh, life's. Is that clear? Exactly. That's what I wanted to mention. And cause you're talking about processes here.

We've ingrained high level processes and the real high performance team. And I'm interested to hear what journey you've gone on with your team over five years and how that might compare to, you know, like you said, typically it's more like an 18 month tenure. Isn't that right? So w with, with any company.

So I happened to work for, uh, welcome software pre previously news cred. So, you know, that journey we were, uh, we began in content marketing, selling solutions to marketers and content marketers around the power of content. Um, you know, on that journey. Um, growing from low teens to, you know, 45, 40, 40 5 million, um, you know, over, over the course of four years.

Um, you know, I, I would say the reasons why you like, keep your job that long. Um, one, our amazing relationships with. Your boss, right? Like, like my boss of built on trust and respect. And that trust a lot of time comes from probably the most important thing, a sales leader, the most important attribute, which is being able to do what you say you're going to do consistently and repeatably.

Um, and then finally, I would say, um, having a mindset that is. Not always putting sales at the, the front of the line, like the best, the good of the company, thinking of what's needed for the company versus, you know, a sales leader that might always be thinking about their team or them. Um, that's what allows you to stay or the 18.

Yeah. Yeah. Good, good dissection. And that last bit is interesting for me. So I've spoken to a few people about this recently, and they said one of the big jump from being a VP to CRO it's when you're a sales person, like carrying your bag. And when you're a sales leader, you're thinking about closing.

That's like really important CRO you have to think much more strategically and holistically, and I'm really curious about your personal journey. Uh, to learn basically how, how you've taken that more holistic approach. Like how did you approach it? How did you, uh, get ingrained with thinking a bit more broadly than just closing the deal or, well, there, there, um, there's books you can read of course, but there's no, uh, there's no college courses you can take on mass, right.

And it's in multiple dimensions. So you have to take. Bigger picture in terms of the strategy, the organization, um, and you know, like, uh, you know, your, your yes, you, uh, I think a trap for sales leaders is, you know, many of them, all of them typically are very competent at selling. Right. But, um, you have to make that jump from being, yes, I can go in and sell all of these deals just as well as anyone else.

That's actually not my job. My job is to enable the entire team to do that and sell the right kind of opportunities. Um, and why my team is focused on the here and now I actually have to be thinking about the next, you know, to use a military analogy, you know, general has to think about like the next battle and the battle after that.

So I can be prepared. So I have the resources so that I have the, the things to come together together in the right time and sequence to. Make the most impact to the organization. So those are just things that, you know, made a lot of mistakes. So that's how you learn things as well. Um, and, uh, you know, just part of, of maturity and growing into that role.

I appreciate that. Okay. Let's apply that to the topic at hand then, which is complex selling, especially during the time of COVID. And when that turns Birch you're cliff, interested to hear what your experience has been in that as the foregrounds for discussion, right? So that obviously has turned our world upside down, or at least it feels like it has to me, um, where we operate in a.

You know, complex enterprise selling so much time in front of customers and prospects. Um, so to have that gone, um, I mean, there is a reason we spent all the time doing that. So it would be absurd to think that if that's removed you, weren't missing something. So I think in worried about this a lot, um, and as I mentioned, being able to deliver on what you promise.

As a sales leader is oftentimes as important as actually hitting your goal, right? Because you need to be relied on. And, um, a trusted sales leader is one that sees when problems are coming and, and can show that. So for me, one of the biggest challenges has been yes, the selling, but how do we accurately forecast in this environment?

Where a lot of the things that, um, I would normally look at, which I can get into, um, aren't there. So how, how is virtual 100% virtual selling caused by COVID impacting our ability to understand drive and forecast revenue? Yeah. Understood. What is it about virtual selling? That's what you missing then?

What's it taken away from the CRO? Yeah. So, I mean, let's first, let's talk about what it's takes. It takes away from like the selling cycle, right? So, you know, medic is the physics in which I use to like engineered deals and, and thereby forecast them is all about discovering pain and quantifying it with metrics.

And then using that, that power to develop chair. That's the fact that it has to start with those things. Um, it's much more difficult within a pure virtual environment. Um, you know, just to, to retouch on the definition of a champion for, for those who may not be familiar, right? So these are folks with power and influence who are going to sell for you when you're not there, um, and have personal wins.

So. You know, normally you would have, um, you would have coffees, you would have sidebars, you would. You know, one of the biggest recipes for developing champions breaking bread, right? So, you know, having a meal and discover, there are things that people will say, especially when you get into things like personal wins, because then you touch on touch on politics and you touch on.

And just the personal it's right there in the definition. So, um, it's very challenging to do that, um, in a remote environment, not to mention just generally like people buy from people, um, that they, that they trust. So, you know, those things combined to make those characteristics, which an organizations I run, like it's not just finger in the air.

Like we. Put science to that, right? So there are medics scores in Salesforce that are driven by level and definition of champion. And, you know, do we have access to the, to the economic buyer and have we driven our differentiators and what is going on with the competition? And it's caused kind of a fog, um, in many opportunities to be there.

So therefore our medic scores are lower. Um, and. It's more difficult to see the reality. Yeah. Understood. So then what's the, that's the situation then? What's the response? What have you found if you found anything that can be helpful and effective to close that gap? Yeah. So just, just to, to stick on the problem or like the negative implications for that for a moment.

Um, so what that has caused for us is, um, Normally, we would have a process to, to commit an opportunity, um, because of its relative characteristics. Um, and just fewer of those are able to happen because we aren't able to answer these questions that we can normally answer. Export's more difficult to do the question, you know, we have, we have opportunities where it's also, it seems easier to hide for some reason.

Um, so. Clients just go dark for, for long periods. And of course this can happen in a non-virtual world. It just, it just seems higher. Um, as another consequence, it, you just have to have more pipeline, um, which is hard to, in order to, um, to overcome that, you know, if you have three opportunities, you know, you might only be able to suspect, expect one based on the characteristics, whereas.

No, that you can commit two out of three. Um, so it, it, it, it is a big problem. Um, you know, as I, I, I don't have perfect answers on the actions or the solutions, but I, I know some things I've done and some things that I want to continue to do, um, A lot of these are true before COVID right. But working hard and making a conscious point to schedule one-on-one time with your potential champions.

Right? That's a big one. So how many times do we get pulled into a demo with a room full of people? Right. Great. That's that's going to happen. You can't ask. It's tough to ask a lot of qualifying questions in those meetings. Um, why don't we already described, like you should be doing anyway. Pre-code because a lot of selling is done on remote, but, you know, did you schedule the prep session with your champion?

Did you schedule multiple? Do you have a calendar debrief scheduled? Not just, I'm going to send an email to ask how it goes. Um, I think that's just like a tactical best practice that you can. Um, no, again, in that one-on-one you might be able to ask a question. You can't ask in the room, right? Like, geez.

Jane had some really tough questions for me. Do you, do you think potentially Jane, um, is not supportive of the project? Ask that in a room full of people, right. And get an answer to that question. May hinge on whether or not. How does this person answer? Are they a champion? Like who, who is the, you know, do I have enemies that are, that are not there?

So, um, anyway, let me pause there that, that that's, that's one like, um, Best practice that I would say everyone should do anyway, but certainly in this time it's very necessary. Yeah. Okay. We lose a lot of the art. Then we lose the interpersonal relationships. The small nuances we pick up from being in rooms of people.

There's opportunities to ask deep questions, a hundred percent. Yeah, a hundred percent and, um, a really interesting part of visibility in a forecast and the deal and your pipeline, isn't just between the rap and the champions or their prospects. It's also between the sales leader and the rep, right? How do we really know what's going on?

How do we cut through the fluff cut through optimism? How has that been affected by COVID at all and how I think somewhat, I mean, you know, it would be common. Uh, typically pre COVID your more high stakes meetings were in person. Yeah. And it would be natural to, um, have a sales leader go to those meetings.

Um, now typically it, at least for me, I don't jump in and run those meetings. That would be weird. Yeah. I trust my salespeople. They're doing that. So, but my role at an in-person meeting, like that would be. To track down the champion, have a conversation with them to track down the economic buyer while that, while I'm there and develop some level of rapport, um, you know, over a cafeteria lunch or whatever it might be.

When I think about that ability to have higher level connections, um, you know, callbacks to things they said or discussions we had, like a lot of that is gone. Um, so it's, it's trickier to insert yourself as a sales leader. Um, In a deal like that, unless you're, unless you're basically co-selling, which I don't think you should be, but, um, it happens.

Yeah. Yeah. Interesting. So at the beginning of the discussion cliff, you said, um, you know, we're not just bringing some practice from the 97, we're trying to pick up new things. Like, do you think that this might just be an adjustment period? That one day we'll see normal and we'll find ways of finding those that, that information, those nuances, and it won't feel.

As big of an issue. Um, or do you think like this is legitimately something which is, uh, an existential challenge don't surprise the level of selling I'd like to tell you. I just think it's all going back to normal, but I don't think it is. Yeah. Um, I think things are permanently altered in terms of how buying and selling occurs.

To what degree? I don't know. Um, And some of this I welcome, right? Like I probably will not be jumping on a plane for a two day trip for a one hour meeting anymore. Like that's not gonna happen. Um, however, um, things that are missing, um, you know, more, a lot of times we'd have huge success in bringing larger groups of clients together.

And co-mingling them with our current set of prospects that are in the pipe, um, and organically letting that like produce Goodwill. Like it it's cha it produces champions because they see the success. They see other people having success. I think people are going to want to travel and participate in those kinds of sessions.

Um, so I think that that's that sort of organic. Uh, selling is going to be critical. Um, and then we're also just naturally an appoint, especially for complex enterprise sales, where there's just more stakeholders. There's more, um, you know, there's, you know, uh, Challenge your customer tells us that there's, you know, five plus key stakeholders involved in every, you know, large complex opportunity.

So, um, just the days of single threading, a single champion are gone as well. So I think we do have to, um, figure this out for the long haul. Yes, but also when you think about long-term effects, like think of your STR your business development rep, they're not knocking on doors as much anymore, right?

They're in their bedroom making the call. And then it's interesting to think whether their, um, perspective of this would be totally different from someone who started off and the traditional way of selling what, what you've described. Yeah. It's true. That that role has certainly been turned on its head as well.

Um, so yeah, I, I do think there's also the trend. Um, Less desire to engage with sales earlier. So that's why you're seeing a, a lot of product led growth, um, and kind of try before you buy of sales cycles back bar, um, you know, of course then lead mechanisms. Um, but, uh, yeah, I mean, look, being, being an SDR BDR, it's not an easy job anyway.

Um, but, uh, it doesn't make it. No, it doesn't make it easier, but maybe they'll say, oh, I don't want to be in front of a prospect. It might be terrifying. I've only ever spoken to a prospect over the screen. Yeah. Yeah. It's true. That's I mean, that's a good point in terms of me. That's your, um, that is your place where you, one of the places in which you develop talent and, um, It's true.

There'll be a whole crop of sellers that, um, didn't have that experience of going door to door or really interacting, uh, with a lot of people. So that'll be, that'll be interesting. Yeah. One of the final questions I've asked you collect, but one thing I really respect in a sincere way, CRA's forwards their ability to pay.

To think on their feet to change things. So always stay like confident, optimistic despite the challenges where other people might Mount. Um, so this is something CRS and sales leaders have been doing for a while. What natural skills and inherent abilities can we draw on to use or to use against this challenge that we might have done before in parts of our lives and parts of deals or processes that have gone wrong?

What, what can we draw on here to get this right? Right. So, um, specifically around this topic, or just get, getting, getting through everything we're in right now, getting through everything we're in right now, or however you want it to focus that. Um, so you know, this has been going on for a long time. Um, uh, are you familiar with, uh, the Stockdale syndrome?

So this was a gentleman that was in a Vietnamese prisoner of war camp, Hanoi, Hilton shot down. And basically the paradox is the more optimistic you are about your going to be led out of this prison. All those people died because they're like, oh, I'll be out by Christmas. And Christmas came and they weren't.

I'll be out in a year or two years. So, and they didn't make it because they were broken. So this man, his point of view was, I know I'm getting out of here. I'm just going to do everything I can to live in the here and now and, and, and take it a day at a time. So focusing on the task at hand, um, and. Never losing hope for the long-term, but not just, you know, don't letting the, um, the tough, tough reality that might be staring you in the face right now.

Cause you to lose your faith. Yeah. It's inspiring clef. But last question for you then if you're in a room full of CRS, like the best CRA's in history, what would you ask them? Um, what do they learn? Like, what are the things that new that they've applied? We tend to, uh, pick up things from our past, um, which is great.

Um, but certainly I'm keen to, because I think, I think every, I think things are changing. I think the world is changing. So, um, I'd want to know the new things that they're learning.