The Role of Chief Revenue Officer and how to resist the pull of Sales with Duane DuFault

The CRO Spotlight Podcast, powered by the Growth Firm Production. Hi, I'm Warren Zenna, founder and CEO of the CRO Collective, and welcome to the CRO Spotlight Podcast. This show is focused exclusively on the success of Chief Revenue Officers. Each week we have an open, frank and freeform conversation with top experts in the revenue space about the CRO role and its critical impact on B2B businesses. This podcast is the place to be for CROs, sales and marketing leaders who aspire to become CROs and founders who are looking to appoint a CRO or want to support their CRO to succeed. Thanks for listening. Now let's go mix it up. Okay. Welcome to this episode of the CRO Spotlight Podcast. I'm Warren Zenna. I am the founder and CEO of the CRO Collective and kind of popped out a bunch of episodes over the last couple of weeks. Some of them have been really amazing. Coming out, I think this week with a very close friend of mine and mentor of mine and colleague of mine whom I named Jim Wexler, who hired me to do my first job. And we still talk, we're still very close. So it's a really interesting conversation about sales and relationships and, you know, the, I hate to say it, but, you know, reminiscing a bit about the old days, you know, the way that we used to go to market when we didn't have computers and cell phones and stuff. But a lot of the ways in which some of that stuff resonates really closely today and how it should and how some of that stuff is lost and I believe is coming back. Because some of the automation that we're seeing right now is stripping away the relationship and the customer centric focus that we need to have. And I think the old school sales relationship skills are much needed. And I think, you know, unfortunately, I think that people like me probably aren't good people to train people to do that. But also wanted to talk a bit about. I was at a conference in San Francisco, the Chief Revenue Officer Summit, and it was just terrific. You know, we had this great event and I spent the entire day cheering the event. And you know, one of the things that's coming up a lot, this has been really interesting. I'm actually going to do an entire episode on this is the role of marketing in the revenue operation and the, say, the conflict, but the inherent conflict that could occur between a Chief Revenue Officer and a Chief Marketing officer if in fact the CEO wants the Chief Revenue Officer to run the entire revenue operation. Hard to do if you have a chief Marketing officer and how do you rectify that or navigate that? And it's, I don't want to get into it here but it's one that we're going to talk about. But I'd be interested in thoughts if anyone has and you can certainly just blast them to me on LinkedIn. How does that work in today's world? If in fact the focus is going to be more on revenue, which I believe it is, it's moving towards that. And if you have a revenue leader, how does the CMO and the CRO navigate that relationship effectively and still create enough cohesion between those two fact those two groups without creating conflict? So anyway, today I'm excited about my guest today. Today we're going to be welcoming a gentleman by the name of Dwayne Default who is a CRO coach and a go to market advisor. And Duane and I talk a lot on LinkedIn all the time and he's really smart and he's got some really great perspectives on things that are very much in line with me. And we just started rattling on a couple days, couple weeks ago and I said, you know, you should come on my show. But anyways, so Dwayne has his own business and for, you know, a long time now he's been a contract CRO, a leadership coach and he's been doing this for quite some time, mostly in the SaaS business. And he's really smart. He's got some great perspectives. This is an amazing conversation. We talk about a lot of things that resonate with people who are either hiring CROs or CROs who are about to get the job. So I'm going to welcome Dwayne and listen to this episode. Was a really terrific conversation and again, as always, thanks for tuning in and stay tuned for the next episode. Why is this sort of a new. And two, what's the resistance, you know, to this? Like why is it that I even had to start a business that was designed to remind people to focus on the bigger picture instead of just sales, which again, not to knock the importance of it.

Yeah.

But I think you agree that it, it eats everything for lunch to it destroys companies actually. So I'm just curious what your thoughts are, why you think it is. We still sort of need to remind people of something that just seems logical.

I think there's two sides to it. One, there's, I think there's a big part in ego where we've done a really good job of patting people who haven't done a lot of work on the back by Giving them a bunch of money for a good idea and then they think it's, then they act like it's the field of dreams. And I think that we've created an ecosystem in our environment. And don't get me wrong, I love working with VCs, all boards, there's some great ones out there. But I really think that there's just been this over focus on creating an amazing product and then doing some marketing and the production itself itself, even if they're selling it for a thousand dollars a month. Right. High MRR ticket type of product led growth, but the, the need to have a holistic approach to revenue. I feel like it's just been gone the last 10 years and I. And the whole growth at all costs issue during the pandemic, they just exacerbated it where we were constantly moving away from sales because you know, the stigma that movies brought to the table over the last 10, 15 years as movies got bigger and bigger and more and more detail about stuff and people's past lives and whatnot, it just continued to put a bad reputation over a sales rep regardless. I mean even myself the first few years when I was in sales 15 years ago, I would try to create a name or a title because I felt bad for having to be in sales where I thought it was like a failure in career that I had to go into a sales role. And that kind of stuck around for a long time. And then as you know, like product led growth came about and started to become a thing. I think it was more of an excuse for people to lean in that direction instead of worrying about the holistic customer journey and thinking that since they bought for a reason initially, that that's how they're going to continue to stay. And so there wasn't any patience or interest to be curious in the customer themselves to understand that hey, just because they bought. Today most, most decisions are emotional purchase. And so that's going to be different when they're a logical beast six months later and you realize your product can't actually do the thing your marketing page said it could. And then they realize like, oh wait, salespeople are really good at creating relationships when you hire the right ones. And so I think there's just this misconception of the field of dreams mentality where it's like you build it and they will come. We don't need salespeople and it's a necessary evil if we do. So I think that's one of the, like one of the primary frictions or, or or reasons why companies are against not only just sales, but then thinking of the revenue aspect of the customer journey. Hopefully that answers your question.

No, it's interesting. I'm, I'm chewing on it because it's, it's a bit of a different take than I've heard and I want to unpack that. It's interesting. So, but I'm hearing it just. I'm succinctly going to reiterate. I heard back from you. Yeah, go ahead. In a very succinct way, it sounds like you're saying that this sort of reason we got away from, let's say full operational revenue focused businesses is because of product led growth and that the technology sector created this delusion that a product itself could be the salesperson. And it sort of, sort of like removed some of the critical value that sales motions bring to organizations by letting technologies and products do it themselves. And there's been a bit of a frenzy and also a lot of money that's flown in the, thrown into that space that sort of supported the notion that this is possible. And there's been enough successes that people think it's true. So people want to play the lottery, so to speak, and they'll come up winners. And so, you know, it's no different than why it is that any snook, including myself, will go buy lottery ticket when it says it's a billion dollars, but I won't buy when it says it's 10. You know, and I think that you're saying, and I'm going to say first, just yes or no. Am I correct? Is that what you're saying? Is that correct and accurate?

Like yeah, yeah, that's very, very close. And there's another, think there's another level to that as well. Because then I think when, when people hear product led growth, they instantly think SMB. And then if they sell an enterprise, then they get to tune out. It's like, well, no, they're, they're not out of, they're not out of a race either because we, we've gone down a different rabbit hole. It's almost like we've had this divide happen where okay, if you're not selling into SMB, then you're selling to enterprise and you know, enterprise traditional sales process, 8, 9, 12 months, let's speed that up. Let's add three people into the prospect's journey to hopefully get them to buy sooner. And then we've taken out the relationship, we've taken out the connection, we've taken out the understanding and Cur curiosity that, you know, quote unquote, Renaissance reps seem to have. And we're just trying to optimize the living hell out of the entire customer journey. And, and I think that's doing a disservice in sales too. And so then people don't, more people aren't buying like they used to because they're not having that connection, that trust building, that relationship through the acquisition process. And so there's not buying. And so they're like, oh well, we need to optimize and we need to move more towards product because that's less expensive of a cost of acquisition by moving towards product led. And so then you have even more companies that are against emphasizing the sales rep and the sales process. And so they try to optimize for that side of things. And so I, I fear that our eagerness to over optimize everything has actually pushed the human element away, which is where the salesperson thrives.

Okay, all clear. All clear. So I would say that I certainly couldn't, I don't, I don't disagree with anything you're saying at all. I'd say that the part that I think is interesting, I don't say I disagree, that's interesting. It's different is the, the product led part of it, which I, I, I like what you're saying. I haven't really heard this before, but as you're saying it, it makes perfect sense that there has become without question within a sector. And I think the sector has a lot of sex to it, attached to it, has a lot of focus on products. Right. And you know, it's probably more apt than I think I think about it because I talk a lot about the rise of the Chief Revenue officer role, which we'll get into in a second, and how it came about and it came out for the same reason. Right. So back in the, the first boom, like in 1998, 1999, you know, before that one crashed and all that money flowed into the Internet. Right? Yeah, it was the same thing. What happened was, I don't know, I'm older than you, so you know, I remember this, but I was working at the time in sales and what happened was we saw this money floating into. But what we call products today are different because, you know, you couldn't build products like that then. But they were products in a sense. They were, they were digital, let's say, you know, Internet based experiences, let's say, I don't know if it's a better word to say, but, but what Happened was, you see these bigwigs, which Silicon Valley sort of started back then, it was when like the first seeds started planting of people with a lot of money that could invest in technologies. And people saw that, you know, Navigator and you know, all these other platforms could become a channel for, for businesses. A lot of these guys, if not all of them like today, were engineers, right? They were just guys that built products. They weren't really business people so much. They were just really smart. They knew how to figure out how to create things in a really unique way. And they can engineer products that made a big difference. And so the CRO was first sort of discovered as this executive revenue leader who could bring commercial expertise to an organization that needed an infusion of commercial growth that the founder couldn't provide. And back then there's a lot of money and you know, there was still a lot of fanfare around this and this, this Chief Revenue Officer role. Probably my research, I've dug into this a lot. You know, I went to Egypt and I dug into the tombs and I found bones of CROs, you know, there it's around 2013, 2012, maybe, maybe even 14. There's a first big article came out in 2015 called the Rise of the Chief Revenue Officer. It's really funny. And you know, they talk about it in two ways, right? So it was one on one hand it was a, without question a sort of a sales focused big shot who had all this executive experience closing big deals and creating partnerships that could sort of accelerate the growth of a company. And they came in with a lot of fanfare and they brought like Rolodexes and connections. And when you hired this person, it was a signifier that you sort of were serious. You know, we got Bob Stevenson. Holy crap, that means something, you know, and it was big news, you know, and you know, these guys were, were sort of, they had almost like a, like a gravitational pull. Like business came to them when they were brought to a company. That's why they were hired. You know, and I think you're correct in that there, there still were the service layer businesses that I'm more used to selling. You know, people businesses. You know, you're delivering long term outcomes to people through the delivery of ideas and, and thought not to say I have a problem with products, because I don't. But after a while, all of a sudden it became really cool to like scale a product and create software and just sell it over and over and over again. And I do agree with you, this PLG thing, which I want to talk to you about, because it's funny how many people talk about this product led growth. Is there really such a thing? Is it true or is it just a term? Because the reality is my opinion, you still need everything else. A product is never, it never really is true. Product doesn't just sell itself. We all know that. What happens is, it seems that way because it gets to a point where it can sell itself. But initially you still needed initial salespeople. You needed marketing, you needed a message, you needed some awareness that all other products do so that you could arrive to a place where the product could sell itself. So I'm just curious what your thoughts are on that because we digressed a bit, but I want to stay on it because it's something that people are asking me about a lot and I think your perspective on it would be really great.

Well, what's interesting is you're talking about, I'd say an old school way of selling and building business which is based on relationships and then your presence in your market. It's transferable. It means something. Nowadays, not so much in the tech world. I mean, you could potentially have some pull in terms of getting jobs. But honestly, if the sales leaders come in the organization and he's trying to flaunt his Rolodex. And for those of you listening, a Rolodex is an old flip book of contact cards that executives have on their desk.

Right, right. I found one in that Egyptian tomb I talked about, by the way. It's covered in, you know, old, you know, those things are great.

Or even like a little, like one of these guys, little, little black notebook.

I had one, I had one. Although different types of phone numbers were in it, but still.

Yeah, right, right. But it's, you touched on something here that I feel like a lot of, a lot of companies seem to think they can skip over and that's that early days of building anything, like you're, you're, you're building something for someone to give you money to solve a problem. And if you don't have somebody talking to your ideal customer, having those conversations, being curious, creating that relationship, then you're just building your product in the silo. And so we, we had a ton of that happen over the last four or five years. We're like, oh, well I've, I've experienced this one problem. I'm going to go build it over here and then I'm going to go hopefully find product, market fit and then bring a salesperson in to go and scale that. And if there was any inkling of a potential revenue stream from that, then investors would just, you know, throw money at it. Which again, that's a model that works in certain environments. But what's happened is we have companies that lean very heavily on this product led growth thing that is supposed to make it to where the product sells itself. But then there's no relationship experience, there's no relationship building experience on the teams. So that doesn't have to necessarily mean you sell, but you lack the skills. There's no skills on the teams to dial the phone, have a conversation, do a real discovery and then translate that into the product development. And then we have all these companies that just kind of fall apart because they never really built something that people care enough about to separate themselves from their money.

Well, at what point does it fall apart like this? You're right, but I'm really interested in talking about stages. Right. So you got a company that's got this cadence and stuff. What happens in your view that the company, then it stops working. What occurs, that is this shift that doesn't work anymore.

I think product market fit can be assumed to a certain degree. It's when they go and try to scale in the ad, and I use the word scale very loosely right now because that can mean something different from anything, many different companies. But it's when they, when they feel like they have product market fit their own definition and then they go out and hire this CRO or VP of sales person to come in and build a team and then they. If the numbers don't translate, if the conversion rates, if the cost of acquisition, if the, the profit margins for the customer do not translate even remotely close to what's being brought in from this new team, that's an early sign of things that are not going to end very well. Yes, you can over index in a certain direction and you treat it as a loss leader and then the money is recouped from SaaS and over time and all that stuff. But if you're not converting at similar rates, if you're not, if your churn isn't going down, like there's specific numbers to look at early on, even if it's a SaaS company that your lifetime value is 14, 16 months or whatever, there's things you need to pay attention to early on, if you're scaling the team from a sales perspective that are going to be early signs of things that aren't going to end very well at all. And that's, that's where I feel like a lot of companies that kind of follow that path are ignoring because they feel like they're in SaaS. That's part of the game. They need a front load on this side and they're, and then the money on the back end from being a SaaS product is going to catch up to them and then they don't do the foundational aspects of building a profitable business, a solid team that enables that back end revenue to happen. And I think that's where a CRO's perspective really helps, especially one that's not overly indexed towards sales. Because if they're not paying attention to customer success and keep an eye on retention and expansion, understanding what land and expand actually means, they're not keeping an eye on marketing to understand how the product they're selling is being positioned on the front end so they can have a level of congruency through the customer cycle from when they first hit a landing page and see some information about the company all the way until 12 months when they hit their first renewal. If we're only assigning CROs to just do sales, which happens more and more, then you, you're, you're overindexing on one side of the business that if they're not paying attention to the back half, which is where like 94% of the customer life cycle is, then you're, you're, you're just, you're digging a big, you're digging your hole faster with a bigger shovel and then you're giving it to more people.

Yeah. No, 100% agree. You just sort of walked everybody through my sort of great treatise around operational complexity, the danger of operational complexity. Because you're right, I mean what happens is most companies start in a way where their business model at the stage that they're in is sustainable. Yeah. I think they get sort of, in a way, I say there's two kind of people. There's the teenager that's unaware that what they're doing is going to hurt them until they get into a car accident. Yeah. And then there's the teenager that knows they're going to get into a car accident. And I think a teenager that's sort of reckless is just going to get to a car accident and they're either going to, they're going to shut the business down or they're going to have to like recollect themselves and figure it out. Then there's the teenager that knows it and they're the ones who are sort of trying to figure out how to stop this adolescent behavior and build a more mature model. And I do believe it's because of the stage. You made a great point, which is there's a point of unsustainability where the sales that you get aren't enough. You need nurturing and you need customer care and you need customer value. And that has to be a focus. I would submit, I suspect you agree that you should start that from day one so that you don't have that problem. But that's a tough thing to do when you're just starting out because really what you need is just you need to get customers to get revenue in the door. And I get it. You know, it's, it's an understandable conundrum. How soon, in your view do you think a founder should be thinking about what we're talking about? Like at 1 million, at 10 million? What's the point at which this stuff needs to be operationalized to make it effective? And how, how do they do that?

That is such a wide question, especially from the revenue perspective. Because if their ACV is lower than someone else's, they can get wrong. They can get advice to steer them in the wrong direction. So I, I will start with a big caveat just to understand like if, if anyone listening to this, if I say a number, make sure you do the work. So that way it equates to your business.

Right. So that's fine, we can qualify for a scenario. Because you're right. I know there's no one brush to stroke.

Yeah.

Let's say, let's just say for the sake of the conversation, it's a really good point. It's a SaaS company. It's a, you know, like you said, it's an SMB based product. Let's say it's a productivity tool, okay. In the sort of Dropbox type of range, like that type of thing, right. Solves some sort of productivity problem. It can be sold to me, right? A solopreneur for X number of bucks a month or it can be sold to, you know, salesforce across their entire enterprise for, you know, whatever. Right. At what point? And given that sort of business, I know there's not probably a lot more detail there, but what's your thought? You're the guy, you're in charge. You've been given the role of advising a company as a CRO and giving you knowledge. What's the way to mitigate these inevitable problems that a company like this is going to run into?

If your product can sell across multiple segments, and when I mean multiple segments, SME, mid market enterprise Just as a general rule of thumb measuring that first thing you got to do, you have to figure out how does each one of your segments convert and buy what is your like you really have to dig into segmentation inside of your customer base. I don't, I don't, I'm not concerned about your Persona and your ICP anything just yet because they're all going to be different across the different segments. But you have to dial in what is your conversion, what is your interaction per the primary potential ROI for each of your customers? And from there once you understand the bulk of your customers in each one of those segments, then you can really start dialing in. What is your cost to acquire any customer inside of that segment and then what is how many become a lead, your definition of a lead and then to a customer and start measuring that. Just start measuring your conversion to customer. And from there you want to make sure you understand the impact of a salesperson can have on your upper level customer segments. If you have, if you have a sales team and you're and Your product is $20 a month and you can sell across all these different segments that $20 a month customer, you better be bringing on like 200 of those a month per salesperson because you have to have high volume and high velocity to make up the cost to acquire that customer based on any marketing spend and any salesperson commissions and comps and all that stuff. Which is why after you segment you want to make sure that you have a product led process to where they can self onboard, they can sell themselves, they can go to your website, they can click, they can buy, they can do the whole thing without ever having to talk to someone. And then you assign and reallocate the focus of your team to the upper segments, the higher potential roi. Just because there's more complexity, there's more conversations and relationship, there's more trust that needs to be built because everyone's business is unique to their own situation. And so that's first few things that I would do. I know it's not one thing, but it was like just sum it up, it's just segment, segment your traffic and your customers coming in. Understand the basic metrics of who converts to a customer and the ROI or ACV in each one of those segments and then assign a salesperson to the highest potential ACV and have them work that channel so that we can convert more of those customers and just paying attention to your metrics across the board.

Got it. So you're sort of, let's say prescription is Here. First, identify the customers who fit into, let's say more of a complex, maybe we can use the word enterprise, but more moving towards a complex, more complex engagement that needs a little bit more talking to. They may represent a certain number of seats, certain number of users, which is obviously going to translate into a certain amount of revenue. But is it going to offer other, other types of complexities that come with that? Right. They got multiple people in the same company, they're going to bump into other systems. There might be some, you know, technology issues that need to be dealt with. There may be some customization that might be required. Right. There may be some bespoke components to which we focus on those things. And that's where you want to deploy salespeople who talk about those particular issues and manage people around those problems, those challenges to grow those customers. And the other segments are really more, you know, that you're, if you're doing your job, you can sort of count on those signups to kind of help feed the foundational, you know, revenue of your business while the upper funnel is being, being managed.

Yeah, 100%. And to get more complex with that is understanding why more people in either one of those segments aren't buying from you, especially in the mid market and upper segments. So a little bit more complex and, and that's where. Now let me back up a sec. That depends on where you want the company to go. Like if your goal is to grow revenue scale, grow big teams and go down that path, or if you want to do like lifestyle business and have something that keeps lights on, you want a five, six person team over time, that's fine. You don't have to take the path of, of scaling and increasing conversions and product improvements, that type of stuff. You can be a life cycle. This, that's totally fine. I know a few bootstrap founders that love that. They're, they're digital nomads. They go, they travel across the world and that's possible. But if you're wanting to increase revenue, build teams and do all stuff, you have to optimize for what's working. You have to optimize for what brings in the best revenue per customer. You have to optimize for conversion. You have to decrease the friction throughout the sales process. And even then on the back end, if you can't keep them, there's nothing you can do on the front end. Like, forgive my French, but one of the things I always say is like shit in, shit out. If you can't fix the holes in the customer Life cycle, not just the front end, if you can sell them really well, but if they cancel on the back end because of whatever reason, it doesn't make sense to dump more money into paid campaigns to increase conversions, to just continue to lose them up.

Right.

And so it's, it's when people ask me like, hey, what do we need to focus on? Focus on first. I'm like, well, it doesn't matter if you're a VC backed or bootstrapped company. Go talk to your existing customers right now. They know, love and trust you. And then that's going to feed into the top of the funnel. How you speak to those ones, how you move up market, how you can, how you talk to more customers and then making sure that you're paying attention to the people who are already paying you money. Because that's, that's a stronger indicator of the, the ability to grow long term than it is. What's your cost per lead on Google?

Right. Yep, I completely agree. So, yeah, good. We're on, we're sort, we're obviously aligned here in that we agree that the CRO is the sort of, let's say, operational, strategic, operational conscience of the business. Right. That brings to the fore a focus on customer centricity. Right. Yeah. And growth from relationship based sales and marketing that not just gets leads, but educates customers so they come smarter. Right. Yeah. So how does the Chief Revenue Officer community? Because what I'm trying to solve here, and maybe you can weigh in on this is, you know, CROs are, they're not hired, Right. Yeah. Most, Most of the CEOs I talk to, even though they may articulate this, they still have their CROs run sales. Yeah. Despite the fact that they probably would probably say differently if they were just having coffee with you or something. And that's interesting to me that they know that. But yet the triggers of the business force the CRO to be in deals all the time. How does a industry like the ones that we're in, which is, let's say call them like, you know, it's not tech so much, but it's, you know, the B2B space, let's say the general B2B space, make the, make the shift so that Chief Revenue Officers are deployed effectively to bring the outcomes that you and I are articulating as opposed to being shoved into a sales channel where they get lost there forever and never get the chance to actually bring the value of that sort of operational expertise. What's the, what's your thought on that one?

I fear for the future perception that those CROs have and then the uphill battle that they're going to face because of that. And but to answer, answer your question, it's what problem are you solving from a, from a CEO's perspective? And you're looking to hire someone to come and write the ship in terms of revenue. Like what? Let's make it very simple. What problem are you trying to solve? Are you trying to solve top line? Are you trying to solve churn? Are you trying to solve conversions at the top of the funnel? Because if it's only one of those, don't hire CRO. Like if, if you struggle from a CEO's perspective, if you struggle to articulate what the simple problem you're trying to solve is, then, then maybe it is time to bring in someone from the outside to help kind of right the ship in that area. But it's, I think the, I think the number one thing that I see right now is CEOs just kind of need to get out of their own way. I feel like there's some ego involved. And don't get me wrong, I was born in sales and ego is everywhere. But I think we tend to think as business leaders we need to do more than we should and that we need to have control over so many things and then forget that we succeed operating within our strengths. Yes, we grow slightly by stepping outside of our comfort zone and doing things we're uncomfortable with and whatnot. But the way we scale our own successes as individuals and is by leaning twice as hard into our strengths. And so if you're a product based founder, if you're a technical founder and you're still trying to figure out customer success and retention and marketing and sales while your product is struggling at the same time, like just understand what your strengths are and realize that you need to bring someone in earlier than you may real than you may think you should have. But I think there's, there's again bringing it all the way back. Like what problem are we solving if it's not all three of those or around all three of those? Don't bring in a CRO if it's just one of them and you're only trying to solve top of funnel, if you're trying to solve the closing more customers, then maybe you need to bring a marketing person or maybe you need to bring an actual VP of sales or a sales director in. Right? And same thing for customer success. But if you're not, if you're not trying to holistically solve the customer Life cycle. Don't bring in a CRO, because then you're just going to bottleneck them and then they're only going to have a certain level of experience with that title, and then they're going to go to their next role only thinking it's going to be sales or only thing it's going to be marketing. And then maybe they do get to a company that requires a CR DO to do all three of these things, and they're without two massive skill sets that they need in order to function as a successful CRO.

Yeah, I agree. And I think that you pointed up probably one of the critical things, which is ego. I do agree that founders, they. At some point, I'm generalizing. We're generalizing. But yes, I see it a lot where founders are loathe to admit that they need that kind of help. And so, you know, they want to figure it out themselves. Yeah. It's also really risky to bring on a CRO. They're expensive. But if they fail, I'm not sure I want to go to the board or the investors at this early in stage and say, I need an expert. They'd say, what are you the CEO for? There's a lot of this nonsense that goes on with this sort of stuff. And I hear this a lot too. And then the other part of it too, is. Is on the other side of it is also, they're sort of mandated to do it this way because I speak to CEOs almost primarily now. Yeah. This is the challenge they have. Right. So, okay, so I started a company. We went through this already. You and I went through this life cycle, life cycle of the company. You know, I built a product, it's going well. I got customers. People are buying it. It's a pretty good product. People are showing its value, growing. I got, you know, 10 million ARR. And then I get some money. I get some money from some, I don't know, PE or va, whatever it is, vc.

True.

And now there's another consciousness that's been kind of entered into the game that comes in with not just funds, but also, you know, resources. Right. They have advisors and they have board and all this other stuff. And, you know, they have a weird objective, which understandably is they're spreading money across a whole bunch of different companies, and they sort of know that there's a percentage of which one of them are going to hit which one are not. So there's a degree of acceptable loss. Right. Yeah. But they do want all of them to win. Right. So they're going to give whatever support they can in the hopes that they can improve those odds. But they know, right, that there's some degree to which only couples are going to hit and they may not. So that's a different context than the engineer who found the company has. It's not the same. And then the second part of it is, okay, so our model, our model is, you know, we give our. When you give our clients money and they follow this model, we find it's working and it may be, see that they've got a really good system in place. But, you know, and I know that, you know, I take the same medicine and I apply it to four different people, it's going to be received four different ways. It's four different bodies, you know. Yeah. Science is, you know, we know this from recent events that, that figured out. Right. And so they're trying their best to be as bespoke as possible, but also be as general as possible to manage complex bunch of different businesses. And you got the CEO who's sitting there going, all right, so now my original higher purpose was making a great product for customers and solving this particular problem. That's why I started this. But now my, my secondary purpose is to satisfy my investors. And they don't care about my customers. They care about their return. Right? Now they probably would logically know that if my customers are happy, that they'll get their return. But that's just typically not how it works, Right. It's more like just show me evidence of revenue, of, of deals. Right? So now you got a CEO who's stuck between two masters, right? Make my customers happy, make a great product, or make sure that the investors that want to continue to give me money are happy. And I don't know which one to listen to. So I find that the CEOs are caught in this conundrum, which is not necessarily ego in my, in this particular case, it's more indecision. It's like I don't know which master to serve here, you know, and honestly, money tends to win in those decisions, Right?

It does.

So, you know, this is, I think one of the factors that impacts the role of the Chief Revenue Officer is it's very easy for the organization to degrade the role down into a sales role when the VC says, look, dude, you had your experiment, he's a good guy, he's been here for three months with a half a million dollar investment. You got to get him into deals quickly or else this isn't going to really work out. For us anymore because, you know, we, we're just not seeing the return. When you and I know, you and I know that it'll take six months or so before the CEO make the real significant and more dramatic returns that they can do, because that's how long it takes for that to happen. So how does a CRO, let's talk about them, manage that situation where they're being forced between making decisions that they know are not in the interest of the long term health of the company, but they have to keep their job and make short term decisions? What's the sort of way in which you help people navigate that problem?

He said one thing in there that changes my answer. Keep their jobs.

Well, you know, some of them want.

To, you know, I know my, my, my big thing with this stuff is, is do a really good job at understanding the situation. First and foremost. Don't hesitate to ask for another interview, don't hesitate to speak to the board, don't hesitate to ask for data. The answers to those questions should indicate whether or not you should go there in the first place. Like if you're getting pushback to understand the data and the lifecycle and the revenue and the cost of acquisition, the conversion, like all of that stuff, if you're getting friction on that, if they won't present or if they can't present to you certain pieces of crucial data points in the customer lifecycle, which is probably a red flag. So that's first and foremost. Now if you're in it for three or four months and something like a pandemic happens, do you get the job in January and then March happens, you know, what do you do? I think having a hard conversation and understanding expectations going in. But I think there's, there's a level set conversation that needs to be had and for lack of a better term, being adults about the situation, right? Like what is the reality that needs to happen? What are the priorities? What problem are we solving? If this, has the situation changed, has it not? Do members of the board or the executive team feel deceived? But I think in that situation you have to make that decision on what is, from a CRO's perspective, what is your long term goal from this engagement? And I say this engagement because it's not going to be your last.

It's not going to be your last for sure.

Like there's, there's a blue ocean out there, there's a red ocean filled with the products that you're apparently in, you know, and it's like you have to Understand that it's not your last engagement, it's not your last company, it's not every, it's not your end all, be all, hopefully. But it's, it's going into that conversation and this was a mistake that I've made before where don't take the deals you have to take. Don't put yourself in a situation to where you have to take that offer because you've been hunt, you've been jobless or you've been a consultant for so many times, so many years and now you're in a weird situation and you're just biting at anything that gives you money. And so it's, it's a, it's not an answer to give for someone needing to make a decision based on an immediate change. Because I would hope that if someone is in that CRO type of situation, scenario and mindset that they're of the type of person that is preparing for, you know, six 12 months out of nothing. Yeah. But. And if you're not, if you're not of that mindset and you want to be a CRO. Well, you know what it takes to be a successful CRO? An immense amount of patience to understand what it's going to take to do that 6, 912 month run without making the board happy.

Yeah. I totally get it. It's amazing. It's like we're, we're like reading from the same playbook. I love it. So I tr. I coach CROs on getting jobs. It's a big part of my what I do.

Yeah.

And I almost verbatim tell them the same thing. I'm like, first thing is do your homework. But what I like what you said. There is an important part of it and I can't solve every problem. Sometimes, like you said, you just got to embrace reality. Yeah. Like there may be limitations in what this job can provide you given what you want out of it. And you have to make tough choices. Right. It could be you do the job as they prescribe and you, you accept that way. So in other words, your expectations are modulated to accommodate what's real about this job. So you don't come home every day pissed off because you know that that's what this job is. It's a sales job. Yeah. And you know, you understand that you have mortgages and you have other things that understandable. You know, we have, and we have to take care of our families and feed our kids and those are noble things. Sometimes maybe you might have to take a hit in your mission for six months until you find the right situation. But what I'm trying to do in that situation is remove the frustration and the anger and the feeling of compromise that comes with mismatched expectations against what's really going on in the situation. That's because, like you said, the, the person I'm speaking to failed to do the right upfront homework on the job before they took it. And they were really, really excited about the role, the title. They wanted a Chief Revenue Officer job because they wanted it on their LinkedIn profile. And I know this happens, okay, we all want that C suite role because, you know, there's this kind of attainment that we look forward, we're men, and we like to climb things and it's fine. But the reality is that it comes with a price if you don't do your homework. And I think we see a lot of people rushing into these roles and finding out too late that it didn't work out. I have a lot of clients that talk to me about this, and so there's a method and a process to, to doing that. Due diligence. And you're 100. Correct. You have to know, you know, I kind of say to, it's like, find out who you're marrying. Yeah. Like, have the tough conversations on the third date because, you know, we all know we've all been in situations where we wish we did. Right. And so, you know, I think it's really important that you do that. And I think that CEOs need to do the same thing. I think that, you know, that's what I'm doing with them is I'm having them have those tough conversations. Like you said. What do you really want here? What are you looking for? Really? Yeah. What, what's, what's the business outcome that this hire is going to have for you? Really? And what does that translate to in terms of the remit? Is it really what you want, or do you really want that? And if that's the case, well, then just go get that.

Yeah, it, there's so much to be said about the side of conversations about expectations from the CEO side. I, I, so when I first got into consulting, you know, I was actually, I went into consulting based on building channel partnerships. That was like my weird silver bullet for scaling into large companies or large, large segments. And when I started getting into consulting, it was just more and more up, leveling into in terms of who I needed to talk to in order to make change happen. And then it was like, okay, I'll go back to what I was doing six months prior in my, my W2 role as, let's just say my title didn't match the responsibilities, which is why I think titles are ridiculous. But from, from setting expectations and understanding from the CR's perspective, I started with the mention of the consulting because CEOs don't matter how long you've been in the role. You have to understand that you're hiring someone that's going to do something differently than you would have done it. And so you have to know and understand the expectations that come in and almost ask yourself how much level of discomfort are you willing to go through in order to get to that number? Because if you hire a CRO and they come in and they're doing exactly what you want them to do, don't plan on hitting the number. Because if they're doing exactly what you would do and you didn't hit that number before, then how is that any different? So you shouldn't hire people to give you a pat on the back for building a cool product that someone purchased once. Like you should almost expect to have some tension between you and your sales leader, specifically your sales leader, because they're going to do things that you couldn't do and you have to be okay with that.

Yep. From.

And that's not just cr, not just CEO. But if you're a CRO, hiring a.

VP of sales, same thing.

And you came from a sales background, you're hiring someone to come in like you. You, you have to remove yourself from that environment to know that you're going to bring someone in to hopefully crush it where you couldn't before. And I feel like that's a, there's a big gap there. And I think that takes a lot of business leaders, not just CEOs and CROs, business leaders in general of inward thinking of like, what's actually the issue? Am I, am I the issue? Am I in the way of, of the potential growth of this organization and how, how do I translate that to the board? Especially right. Like you are a CEO or if you are a co founder or whatever and you're like, I feel like I'm the bottleneck and being okay with potentially being removed if that's the worst case scenario. Most of the time it's not because boards tend to respect people that have that level of intuition and self awareness. But I think there's, there's that level of understanding what the expectations are, bringing in someone who knows what they're doing because they're going to do it differently than you would Have.

Yeah, completely. But it's great. I love it. So thanks for this, like, this particular dialogue. It's important. I want to now ask a bit about you. It's what you're doing, like what you're telling about your, what you're doing now, the way you service clients. And you know, I know you mentioned to me some developments in what you're doing, so I'd love to hear a little more about you and how you serve people.

Yeah, no, I really appreciate it. I feel like the topic we were on is, is a very interesting one and it can go on for a long time and it ends up being a therapy session for people more than it does tactical session, which. Okay, yeah, I was gonna say in my, in my role at being in leadership, you get that. But so on. On my end, I, you know, 20, 20, 21 helped the company, the bootstrap company, scale and get acquired for $350 million. It was great. Bootstrap company did it in three and a half years. Took them from, you know, 2 million up to 11 and a half million during COVID the whole thing. And it was awesome. And then so I took that experience and rolled it into coaching and consulting. And so I mentioned, you know, getting into partnerships. And that was a kind of a silver bullet for a lot of things, which it is, if those of you are listening who are hesitant about going up market into hesitant about trying to go up market, partnerships is usually a really great way to start that and do it for a long time. But so over the last couple years it's evolved into basically a CRO coach, where I'm having that conversation with CEOs and getting companies to the point to where they can scale, to where they understand what are the SaaS metrics and what does RevOps mean to their organization and how does that support enable your revenue teams in order to do the right things in data, in the infrastructure and the process and executing. And so fast forward a few years, things like two and a half years. I'm actually stepping back in the game. I working with a client of mine last few months. And it's one of those situations where all the boxes are checked, the stars aligned and you know, we came to an agreement to where it's like, I'm officially a CRO now or now and officially CRO again. Sorry. And it's, it's exciting because a lot of mixed feelings about what my goals are because I, I feel like the creator economy has, has put a really bad name on consultants and coaches. There's a lot of people that came into the industry that read too many things on social media and are just selling their little bit of experience and then people are buying into it, not having the results and then they don't want to work with another coaching consultant before because they've done that before. And it's, it's, it's muddying the waters around people that actually know what they're doing. Like yourself. Like you've been, gosh, you've been in business for eight, nine years.

Like this company. You mean Sierra Collective?

Yeah, yeah.

It's been actually a little bit over four, but it seems like a longer period of time. But I've been business for almost 30 years myself. Wow.

I got dates wrong on that one. Can't do math, so I hired people to do math for you. But it's, it's, I feel like there, there's a, there's a gap in experience.

I agree there is. And I brought experience to this role like you did brought experience to yours. And I, I, I'm, there's a lot of psychophants out there and also charlatans out there. Yes. And I, I do agree that as a result, that it can result in, in people getting bad results. And you know, I feel, I feel that. But, but I follow you. So anyway, continue more about how you kind of got into this situation.

Yeah. And so now, now it's like, you know, even with that being the way it is and being in the situation and all that stuff, like I, I wanna, I've been having the feeling to just focus and execute on one thing. Like, you know, there is the own business, the consultancy and all that stuff, but it's, it's getting into a company and really, really taking it to the next level. Getting it, getting a, getting a bootstrap company to 50 to $100 million.

Right.

And really taking that to the nth degree and proving out and executing on the CRO model all the way through those different stages. And so I now the CRO for a company called Time doctor And so they're in HR tech. They are an HR platform specifically for remote employees, remote companies, to help time track, to do project management, to really help optimize the way they work with their entire team, regardless of if they're in office, if they're hybrid, if they're at home, like all that stuff. And so it's, it's a, I think it's a very important tool for the way the world is working right now as well as a situation and all the skill sets and things that we talk about because there's a combination of product led that's involved. There's a. And then there's sales led, there's partner acquisition in there, and there's also the marketing side, too. So it's one of those situations where, like I said, checking all the boxes, it allows me to literally execute on all the things I absolutely love doing. And from a consultant perspective, it's. It's hard to kind of get into that environment where when you get a client, there's, you know, there's always like, you know, two out of the four or, you know, four out of whatever.

Right.

And so this one's one of those situations. I'm like, this. This is going to be amazing. It's going to be so much fun to get in and do that stuff. And, you know, I don't. I don't feel like I'm walking away from anything. I don't feel like I. Like I mentioned earlier, having to take the deal that you have to take, like, that doesn't. That's not at all. And it's like, it's been great because they were a client, too.

Yep. It sounds like you had the kind of afforded yourself the ability to evaluate situations to know that this one checks all the boxes for you. So you're going into it with your eyes open, you know exactly how it's going to work for you. And that's. That's a great situation to be in for sure. Yeah.

Yeah. And it goes back to the part of the conversation where it's like, hey, if you're a CRO, if you're interviewing for a CRO position, like doing your due diligence and doing the research and meeting with the team and getting the data. And I feel like there's. I've been, you know, from the consultant coach side, there's so many things I was. I got access to that I wouldn't have been. Maybe I did, maybe I didn't. I wouldn't have been as a candidate interviewing for the role. So it's, It's. I felt like I've gotten unfetterated access to certain things where people maybe normally wouldn't have been. So there's, you know, lots of things coming together to make this possible, but it's, it's going to be. I'm really excited for this and the type of product it is and the market the way it is and the approach and the team that's in place and really getting to apply a lot of things that we've kind of been talking about and coming at it from that perspective and being able to do it in one area and then coach, teach for a while, and then, okay, let's do it at the next stage. And then, who knows, maybe three or four years from now, I'm back at it, spreading the word and helping companies get to that stage, too. But now it's like, really doubling down and dialing in the focus on, you know, what does the CRO actually do, and then making sure that that's something that people can follow.

Very cool. Well, exciting. And congratulations. That's great.

Appreciate it.

It's really great. So, but you. You starting, like, you already. You're ready to go? I mean, did you sign up and you're gonna start? What's the time?

Yeah, yeah, yeah. So I think by the time this comes out, I will officially be, like, in the role. Supposed to start October 2nd or something like that. Beginning of Q4, right in the beginning of it. And so, sure, by the time this is live, I'll be, oh, great.

Well, congratulations on that. That's really cool. And. And look, like I said, this has been really great. Like, we're very aligned. And, you know, I just, I don't talk about this a lot, but a lot of the times I get people. Guests on here because of people I engage with on LinkedIn, you know. You know, that's where I'm pretty active there. And some people just write me and we just sort of connect, and I'm like, okay, I probably should talk to this person. And you're one of them. So it's amazing because as I said before, it's funny, I'm kind of smirking while you're answering my questions. It's like, you know, this guy, he's like, I say all the same exact things. And that's good. That means that we're on the same page. And I'm glad to hear it because this is. The messages that you and I are communicating here. Need to be heard more. Yeah. And so I'm really glad that you're out there doing that, and I think it's great that you're going to be helping some company be an actual Chief Revenue Officer. I like to maybe revisit this conversation in six months when you're in the job, then we can talk about some things you're doing to implement these things, because that's where it gets really interesting. Right? Like, how these things become real, you know? Yeah.

Like, I. I want to, you know, I want to get back into that One of the things I'm excited for is, is seeing that gap. Is seeing, is being able to sit in that gap of like, why do companies struggle to implement the things that we teach them and come from that, come from a different perspective, you know, and, and like, get into that and see it through the lens of the people that we've been working with for the last few years.

Right.

And really work through those struggles and those challenges and all that stuff and put rubber to the road. And I know a lot of people will probably be freaking out about trying to get back into it, but it's like I'm, I'm. I'm excited to, you know, quote unquote, get hands dirty in the situation and really see things through the end. It's going to be, it's going to be a blast.

Cool. Great. Well, congrats and look, thanks. It was really great talking to you and you know, we probably go on for another hour, but like I said, I would like to keep, keep talking because I think it's neat now that you've now with what, you know, and now you've got this job to see, like, what happens because, you know, that's where the rubber hits the road. Right? Yeah. And look, again, I appreciate this and thanks for connecting with me and all the advocacy. Let's keep tethered. And you know, I know we're different coasts, but we find ourselves in each other's part of the world. Let's get stuck together.

Yeah, well, you've got your, the, the con, the, the. I don't want to call them conferences.

But you've got the CRO summits. Yeah, sharing. I just had one in Oakland and then now there's gonna be one in Chicago, which is on. Thanks for asking for. On November 15th in Chicago, the Chief Revenue Officer summit. And I'm excited about those. They're great platforms. So it's been fun.

No, I think it's going to be exciting. Actually. I have an email thread going on with one of your partners to potentially speak at something future. And so it was, it was interesting when I reached out, it was before the decision had been made. And then I went to Saster and did a whole thing and came back and the email was sitting in mine. I'm like, hey, by the way, it's changed a little bit.

Yeah, exactly. Hey, look. Still. But anyway, look, thank you. And let's, let's keep, let's keep the dialogue going.

Yeah, I appreciate it. I love what you're sharing. I'll be, I'll continue to engage. Bye.

Bye bye.