The Three Pillars of Developing Confidence in Your Pipeline

MATT DURAZZANI: Hello everyone, and a special welcome to Doug Ricketts. We are very excited to have you, Doug. You're a great addition to our Revenue Maverick program. I'm Matt Durazzani. I'm your host and I am a Revenue Maverick advisor. For the audience, we have the privilege to listen to Doug. I would love to introduce him to you for just a moment. He is the senior global operations consultant to executives.

That career in particular, is filled with an array of senior leadership positions in global operations. And he is, um, established and lived through several times that close partnership between a chief revenue officer and understands how important that CRO and operators partnership is crucial to the success of a business, especially when it's heavily driven around revenue goals. Um, he so , defines themselves as an accidental revenue operation person. he enjoys collaboration and enjoys being with people, and but, kind of sort of fell into the revenue operation space during his career and, has had the opportunity to kind of develop those processes that boost up the productivity of the people that are supposed to be on the front line and also behind his team. So, Doug, we we are very, very intrigued to have you on the program today, and we would love to hear for you for just a moment. Can introduce yourself if there's anything else to kind of stand out about your background and then kind of turn the time over to you to kind of present to us the things that you would like to share with the audience today. 

DOUG RICKETTS: Thank you. Matt. I think your introduction was great. Um, yeah. I've I've been I would divide my career into two pieces. the first piece was as I entered the business, I was in sales and product marketing and product management. and I thought that would be where I would stay. but I was introduced by, senior executive at one point to an operations role that at first I refused, but over time took it. And it actually became the basis for the for the second half of my career. I absolutely have enjoyed, you know, working to, working to, to collaborate with people, first of all, but with people to define and improve processes and where processes get good, at technology to it. I've truly enjoyed that. I watch I enjoy watching people succeed. in part, because we've got to build a process for them. 

MATT DURAZZANI: I think it's very interesting that you start out with that statement. I think there's a lot of operators on the slide today that, are probably going to relate to the fact that at a certain point in their career, they developed some skills and, and expertise, and then someone, sold them the opportunity for them to be the catalyst to actually take over, um, and, an operational portion of the business. And so, maybe later on the call, let's come back to this one. We'd love to hear some of the advice that you have, to those people early in their careers to discuss this. But, let's go ahead and turn into your content today. 

DOUG RICKETTS: Great. Well, the question that I was asked to address is, can you develop confidence in your pipeline? And I guess the short answer is yes, you can. but I'm here to say that it's a brick by brick collaboration. it's a collaboration that tests your skills to find the best in your sales managers, your leaders and your salespeople. to define the measurable activities, that are both insightful for the customer. and compliment with the way they want to buy. And so, I'd put it into 3 or 4 major components. One is creating a const or a consistent set of cell stages, that each that, that your business can manage towards a consistent set of activities within each sales stage that are creative and insightful, for both the salespeople as well as for the customer.   a few things, we that I call still's, sell stage exit criteria that are consistent, so that as opportunities progress through a sales process,   can be relied upon. And then finally, a sales management review cadence, that pays attention to these things. Um, and, uh. And rounds out the exceptions because there's definitely going to be exceptions. The primary point to this, though, is you can develop confidence in your pipeline by making yourself consistent. You can't control what the customer will do. The customer will react and perceive as they will, and there's as many different customers as each customer will be different. But what you can do to create confidence in your pipeline is to become consistent on how you approach the customer. Hopefully it's consistent, but also it's accretive. It's insightful. and it follows again the way the customer wants to buy. This doesn't come just from you as a sales operations leader. it's the best of your organization. it's the best of best practices. and that's why I say it's a brick by brick collaboration that never stops. Um. Uh. It's important only if your organization is a part of the creation of it. in and and actually sees value in, in performing it. One of the really pieces of good news is that, many of the technology barriers, and actually it wasn't technology in the past. It was just simply time and effort barriers, have been removed. technology has removed a lot of the drag that could have been associated with measuring and monitoring some of these things. and, and these things are possible. So this is a great time to be in revenue operations. at this point, it's about. It's about collaborating with your teams and finding the steps, the stages, the activities, the exits and the kit, and the sales management cadences that make most, most sense for your business and for your company. 

MATT DURAZZANI: I think there's two things that kind of stand out to me that I think, early operators, may, may struggle with sometimes in is this concept of creating that consistency. You know, I think, a lot of people may have heard the saying, there's a lot of strategies out there, but none of them work unless you do. Right? And so I think there's a lot of truth in what you're saying, that as you create the right process, the right consistent, the exit criteria, the stages. Right. Um, you know, the more you do consistently, that's where you get the confidence. Because now everybody's starting to sound like one, one band, one sound, right? So a question to you. And this one is, um, some of the operators on the line may wonder what is the best way to, to really start developing. And maybe practice is on how to enforce that early consistency is when people are learning a new process or maybe, a new way of doing things that is more consistent. 

DOUG RICKETTS: In my case, I suppose there's many. It's like any it's like any buyer that's buying something. When do you know that you need or want to work on something like this? it might be going to a vet. I mean, it could be that, you know, a sales organization has missed their forecast 2 or 3 quarters in a row. Or it could be that revenue was just simply not growing fast enough. Um, but, but those are the kinds of, you know, base level indicators that might cause the desire to spend time on this. in our case,   I was involved in a private equity purchase, and the private equity company wanted to understand the process. They wanted to see a little bit more consistency in the process because we were delivering inconsistent results. Uh what's the first step in our case? we defined a Tiger team that was composed of some of the most successful senior managers and some of the most successful senior sales reps. and we and we stuck together through, probably a 3 or 4 month process to kick this off. Those same people helped us roll it out. Those same people helped us tune it over time. 

MATT DURAZZANI: That's a great example. Thanks for sharing that. Appreciate it. Okay. Let's go ahead and then start having a little bit deeper here. 

DOUG RICKETTS: The three basic KPIs I'm going to talk about in three slides here is one is how do you allow an opportunity to enter the pipeline. What kind of criterias for that? Um, I say enter the pipeline, enter the active pipeline. the second one is how do you really feel comfortable that it's well qualified. And the third is, as it moves along the sales stage process, how can you pay attention and try to understand if it's stalled for some reason, and add additional resources to install it, or to hopefully make it proceed. Those are the three I'm going to talk about. First one, it's sort of the first step, right. Success starts with the successful, first stage and a first step. we focused quite a bit on the idea of identifying a champion. Now, the champion may or may not be the person that called you. originally. It may or may not be the person that was at first assigned to you, to introduce you.   this is a person that that truly, understands the business, understands the problems, can help articulate, the reasons they want to change. Change his heart. so the first point is, truly identifying a champion, and proceeding only when you have a well qualified champion. Um, again, somebody that, understands the costs and the negative aspects of the current solution, someone that is able to affect effectively contribute, to creating the requirements statements. and someone that's it that will share to the full buying team later in the process, which I'm not going to be too much later, but later in the process. One of the ways to test this, that I truly have a champion is, is what we called the "Why's" document. Um, first of all, why do we have why did we have a "Why's" document? Well, we found that most deals that we were involved with, 60, approximately 60% of them, they weren't lost to competition. they were lost to inaction. So the primary first thing that that we did is we identified somebody that we could call the champion. We qualified them as a champion, and we created a document. Pretty simple document, in structure, but pretty. But it's significant in its impact, which is why change? Why would the company want to change right now? Is it a revenue reason? Is it a cost reason? Is it a risk reason? Why would they change right now? Why would they? Why would they buy from me? In other words, my company is it my product is better? Is it, you know, our solutions better? Is it is there something else? And why would they make a change now? And so, in short, we allowed opportunities to enter the pipeline only as we were comfortable that we had, a qualified champion and, and were able to put together a pretty clear, "Why's" document. 

MATT DURAZZANI: So I like what you're saying about the "Why's" document. one question that comes to my mind as I'm thinking, as an operator is where would you have this document? Is that within the CRM? Is it just in some type of Google Drive type of document? And, how how can that be tied to the pipeline. 

DOUG RICKETTS: For each sale stage? we actually built, forms and, and, and, and deliverables that could be easily accessed in the CRM, referenced in the CRM, used in the CRM, by the sales manager, by the salespeople. these were all tools that, that we built into the system. Again, that's going back to one of my points up front. Many of these things were very difficult, 3 or 4 years ago, both to execute as well as to,   actually accomplish. Um, but technology has really come along. It's pretty. It's relatively easy. I at least we have found that it was relatively easy to, to build a step by step process. People could easily see, use, criticize, improve, over time. And we put it all in the CRM so that it was where they did business every day. 

MATT DURAZZANI: I think it's very wise to make sure that that's included within the actual CRM, right where the dealer lives. Um, one of the thoughts that comes to my mind in all of your opinion, this one is, um, um, a lot of operators, a lot of crows, they kind of, um, often see a pattern that usually the top reps, the most effective reps are the, um, maybe the worst, and keeping hygiene and filling out information and maybe reps that are junior or not as experienced. They'll be great note takers. No, have a great hygiene in their pipeline, but they will struggle with progressing the deals, right? Um, what have you found in your in the year to to find the right balance of not asking too much, but at the same time allowing across the board to get this type of insight? 

DOUG RICKETTS: Yeah, there's 2 or 3 levels to that. Um, I mean, there's no question that that, uh. That the the most experienced rep sometimes could be the most resistant. Resistant. But that goes back, I think, to. You know what are what do you request of your sales teams? What are the activities within each sales team? Stay self stage. And do they. And do they have value? Um, we found that the "Why's" document was really important. Um, and it actually helped sales managers, um, qualify their deals as they put together their forecast. And so it was something that was pulled. It wasn't pushed. It was pulled. Um, that was one point. Second point is kind of what I'm showing here in the, in the graphic, which is, which is, you you can't expect 100% compliance because there are going to be those over experienced reps. Sometimes they won't do some of these things. and so we had ranges for what percent of compliance did we expect at certain stages. So that's kind of the second question. We don't expect 100%.   as a matter of fact, some of the stuff is particularly useful for training and for the new reps. Uh uh and then the third step is we could also develop parameters for sales managers. should this deal follow the sales process exactly or not? in which case the rules that we talked about would apply or not apply. So, you know, sales is not completely black and white. It's not completely cookie cutter, you know. 

MATT DURAZZANI: Right. 

DOUG RICKETTS: You can't expect 100% compliance. On the other hand, to the extent people aren't following a process that's helpful. you need to,   discount their deals to some extent because, history would say that they just won't be as successful. So all the all in all the above or at play, it's this is where that brick by brick collaboration point comes in. These things are helpful if they're truly or they improve the deals if they truly are accretive. are closely related to where the customer wants to buy, and actually precedes the deal. And, and the true operator pay very close attention to how these ideas, or the ideas that you create are adopted and modifies them over time. 

MATT DURAZZANI: That's right. I think it also ties to what you were saying earlier. Um, with regards to the exit criteria. Um, when I look at this chart, it kind of makes me wonder, you know, probably you have more expectations of filling out those "Why's" documents the further you progress the deals. Right. This is you know, you may not know a lot of information early on, but as you progress it, you are required to really check all the boxes so that when we go into forecasting, we have a pretty vetted out deal to know whether or not it has the right availability to close. Yep. Okay. Awesome. Thank you. 

DOUG RICKETTS: So this was about the entry into the pipeline. Uh. But we actually found that there was a need for a two stage qualification process. Um, the first was the creation of the "Why's" document with us, with the champion, with a single person. The second was the identification by the champion of the full buying team. all of my all the companies I've been involved with are were enterprise software companies. And, and we came to the realization that you could not be single threaded dealing with a single person, and have any consistency in progressing a deal or closing a deal. And so we we came to the conclusion that it was really important to, to meet those, to meet the rest of the buying team. a buying team is identified. and B, to meet the people, at least in an introductory session, and begin to review those, Y's with them up front and capturing their input. So the second activity that that was a part of our process was identify the rest of the buying team. And this is another good example where technology has made this quite a bit easier. It's not like a sales rep has to go back and enter in a bunch of information into the CRM. we had systems that would capture, email information that went back and forth between, the company and,   and our prospect, and it would automatically create contacts for them in the CRM. So this wasn't about, you know, having to type a bunch of information, but it was about associating, um, the perceived personas of this particular application or solution,   with the names. And so we asked sales reps to associate, the buying personas of this particular solution. our use case, in the CRM.   but that, that was the CRM component. But the but but the sales component was meet with each one of the buying team members. and, and, and do a cursory review of that "Why's" document. And we just found that when this happened early in the process, um, that, sales processes were much smoother from there. I. 

MATT DURAZZANI: I think you're just touching a bone. Probably one of the biggest, core nerves, if you're going to call it that way, of doing deals the right way. Um, yes. You're absolutely right about the multithreading. I like what you said about meat. The keyboard is the action of. You got a meeting? It's it's one thing identifying in an org chart or in LinkedIn or zoom in for some other places, or even asking who who needs to be a dog man needs to be part of this. But the fact that you put in the stress, so you got to meet them, right? That's key. And then once you meet them, you don't just say, hey, hi, nice to meet you. And it's over. You talked about the important stuff. You get to capture their input too. So you kind of re constantly rediscover you. You go more into discovery mode with anybody else. That is part of the process. So you can depend whether there's a Y, whether the potential risks. Right. And then I like the you ended by saying in this needs to happen early. If you do it early you get into this habit the will be smoother. 

DOUG RICKETTS: Yeah. In in the in one of the situations where I was involved, we actually had two stages. There was sort of the entry stage, which is the last slide. And then we had truly the qualification stage. So this these were two separate qualification stages that we just found that if, if the deals really weren't qualified until you at least, you know, had an introductory meeting with each one of the buying team members, again, a lot of assumptions and saying that, you know, you got to identify them. You got to find some way to meet with them, you know, and then have a conversation about the first draft of the document. but if that was done up front, we just found that there was a lot more success. 

MATT DURAZZANI: How did that process this expectation to have an interaction meeting with each one of those blind people? impact the velocity of the deal, that it slowed down significantly. What what did you notice? 

DOUG RICKETTS: Well, there was just more. There was a better understanding. The deal was right sized. Uh uh I mean, the to the extent that the "Why's" document is impactful and meaningful, and the company is motivated to change, um, then the deal moves fast. If, if, if the "Why's" document was not so strong, I mean, that in the end was an indicator of the company was not going to move quite so fast. They're not quite so galvanized,   and motivated to move fast. But by meeting the buying team members early, you could gauge that a lot more accurately. 

MATT DURAZZANI: Okay, so maybe it's fair to say that in some situations I may have thrown it down. But to your point, it was properly sized in the end of the deal, but in other situations it could actually accelerate because now more people are bought into it. And and there's more a propensity or a sense of urgency to to take action. 

DOUG RICKETTS: Exactly. 

MATT DURAZZANI: Okay. Awesome. Thank you. 

DOUG RICKETTS: Great. Okay, then a third KPI or measure. it was one, I would say a positive way to say it was. We really want a vibrant pipeline. We want a pipeline proceeds quickly. of course, that's the target. but having said that, what we also found is that sometimes,   opportunities would reach that qualification, those two qualification stages we talked about, but they would stall.   nobody could figure out why. and they were hard to find. and so sales managers came to, to actually came to me and said, how can we develop a measure that identifies these,   because if if we can identify them, we can begin to take action. So the objective was to always have a vibrant pipeline. the metric we affectionately called stuck deals.   and the idea was, how can we let's how can we systematize and find and locate this relatively small portion of opportunities that proceeded through the qualification stages, but for whatever reason? Stopped. yeah. And, I mean, we we were finding, you know, the things, you know, opportunities could be listed on the last day of the month or the last day of the quarter. And, you know, guess what? A week before the last day of the month of the quarter, they'd moved to the next quarter. And so that was the problem situation that we were in. So we, we, we, dealt a relatively simple criteria that we could systematize and create reports and, and, and and alerts around, um, and to allow sales managers to notice, um, to spend their time is pretty straightforward. If the opportunity had not changed the upper stage and not change for 60 days, and if there were no activities, entered on the opportunity, in 30 days, it was a candidate to be classified a stuck deals as a stock deal. that was a To-Do list for a sales manager. I mean, it could be the deals. Perfect. It could be that for some reason, it's just that's just as true. But, but, but but the but the numbers and the way we calibrated it was such that it wasn't a huge number. It was a it was a size, a size, it was a number. And, it was a quantity of opportunities that was of the size sales managers could follow up. And, and they found that this was a great indicator, and a subject of their one on ones,   to review. The numbers could change based upon, you know, an individual sales process, the kind of product you're selling. All these things, of course, could change. These were just some numbers that made sense in our case. but but the criteria is, you know, what's the right number of these kinds of deals. You can't overload sales managers. You're really trying to find the exceptions. and the sales managers are are truly they're helping where, where these opportunities show up, helping either revitalize them, change expectations or, in worst case, closing them out. And again, this is another example where technology makes something like this easier. I mean. You know, if sales reps needed to go back to their office after every meeting and enter activities, frankly, they wouldn't do it. it would be too administration focused. But to the extent that, you know, email messages, email summary messages, uh uh web conference, audio sessions can be summarized through, some of the leading tools these days. Um, this can be automated. so activities actually, can be analyzed, through machine learning AI. And, and so this is a perfect example where this is the administer area of this is not really so much an issue anymore. you can truly create good data and insights, and provide a tool for sales managers to spend time helping where the sales rep may need help. 

MATT DURAZZANI: I like this. Um. I think everybody's always challenged with, you know, pushing the pipeline that is stuck. Um, two things that come to my mind. I want to ask you, um, you mentioned, you know, in the sentence you said the right number of deals. Um, I think most sales leaders understand in most operators, I have seen in data that there's a certain threshold where a person, Iraq, has too many deals and they cannot effectively manage them all. Um, how did this metric help you? Or maybe he has not yet identified? Maybe what is the right threshold average profit for number of deals? 

DOUG RICKETTS: Well, I think it can change quite a bit based upon the solution you're selling, the velocity of the deal, the complexity of the sale. Um, but certainly in this case, you're, you're you're analyzing opportunities. You're looking at the total, the total pipeline of both a sales rep as well as a sales manager. and you're, and you're weeding out those that are problems. In our case, you know, we found, by playing with this information, you can begin to understand what the averages are, and where the exceptions are. Um, and you will, you will find you'll you'll find all kinds of, all kinds of, use cases, within a single sales team. I mean, one sales rep might find, you know, might be one of those people that are working on 2 or 3 deals on a given quarter. and that's all, but not that that's too low, but but by contrast, you might find another rep that, is got 20 or 30 and therefore pipeline in there proceeding none of them. And, so this is this is an adjacent measure to the question you just asked, which is what is the right average for my company? Very important metric as well. 

MATT DURAZZANI: I love it, I love it. Um, I think, um, I think if for anybody that is listening here, a great takeaway is by looking at stock deals. You know, you can start identifying even more specific metrics that otherwise you couldn't get. Um, one of them being, of course, of what is the right amount of volume of pipeline to rent by the type of market that ran the type of product that they're selling. Right. that can then be used later on to determine the type of territories, the number of accounts for patches that can be determined, the type of teams that there are necessary to achieve a certain number of quota. it helps with pipeline velocity. I mean, looking at stock deals, it's not just a single metric. It impacts all sorts of areas of the entire pipeline. So, I'm very glad that you kind of talked about this, this, this specific metric. Um, anything else you want to say about the pipeline vibrancy? 

DOUG RICKETTS: No, I think that that tells the story on, um, on pipeline vibrancy. It was interesting, though. I guess there is one other thing. this was a metric that sales managers asked for. They had seen for too long. They had seen deals that would be listed on the pipeline, as a current quarter open opportunity with as a candidate to close. at the end of a month, at the end of the quarter, many times, and then all of a sudden it's gone. And, and so this was something that they wanted to use as a tool to identify, the, the, the opportunities that are candidates to be described stuck. and so, this is a perfect example of dig deep, work closely with your sales leaders and your salespeople to find things that, that they that they need to do their business. again, the numbers we the exact figures we used here, were based upon, desire for a certain number of opportunities, which would be a maximum number of opportunities a sales manager could work on in this fashion, against, you know, number of deals that were actually moving up. 

MATT DURAZZANI: As we were talking earlier in the call, you mentioned that early in your career, you had a leader that, um, saw a new a potential to take over an operational role for the organization. And, of course, it was a career shift that not only has been enjoyable for you, but you've been very successful at it. You've been able to help in a lot of different areas. So I'm, I'm, I'm kind of a reverse engineer a little bit. I'm thinking, okay, um, what maybe is, a little bit of that story that can illustrate for people that are early in their career, that there may be some particular positions or maybe should expose themselves to some specific type of experiences or roles, so that one day they could be seen as that valuable contributor to say, hey, why don't we bring that person into this role? Because they have X, Y, and Z that can help us maybe expand a little bit on that. 

DOUG RICKETTS: Well, you know, if you're going to be in the sales organization, I would definitely recommend, put yourself in a sales role at some point, and develop your skills at listening and your skills at empathy. I think, those are going to be critical, to any operations position, be the people. I say that first because I think typically people will go to the second piece of it, which is you definitely need to be a left brain person with an analytical style person, that is able to look at information and help gain insights. um, and, and, and you also need the skill of, of of being a servant, and, and working to improve people's, activities and processes. I say those other pieces. Second, because I think this the idea of empathy, um, and collaboration is the key. It's anything that you can do that will give you those skills as a baseline. I think will aid you in operations roles. 

MATT DURAZZANI: I think it's a great point. I think it's important. A lot of people, um, ask the people to come on this, podcast to, you know, where should we start? And, you know, I think it's it's a lot of places. But if you have a chance, like you said, to be in some type of sales role where you get to practice some of those skill set every day, they will create a great foundation to have the right mindset to do the right type of operations. So, so Doug, one of the one of the other thoughts is that now, as we think of people that are, maybe mid-level in their career or, um, they're trying to get to that senior level, whether it's maybe a vice president role or maybe even more serious than that in, you know, operational side. Um, what type of advice do you have and how they can go and achieve that? They may maybe be maybe a sales, operation director or they could be, maybe on the marketing side or on the finance side, or even the customer success side. Revenue really is across the journey of the, of the customer. Right. And so what advice do you give them to to make that advanced level, push. 

DOUG RICKETTS: Well, you know, I, I would try I would try as many of those as you have an opportunity to do, I mean, sales operations, marketing operations, product operations, um, they're all interconnected in, in terms of many of the day to day aspects of the job. So from an experiential point of view, I would try them all if you can, if you have an opportunity to do so, um, and you might find that you want to specialize in that area. but outside of the experiences as to, to really achieve the higher, higher level positions, what's really important and and I and again, I understand each of you will probably be very analytical, and   and you'll then you'll begin to build your, your ability to create processes that's fundamental to achieve the higher level positions. It is to get into the, into the, into the shoes, or at least the mind of the shoes of the senior level person,   which are. Oh, and make sure that you that as you, as you work in these roles, that you slowly develop the idea of the end. What is the end goal? What is the business leader trying to accomplish? What's most important for the business? these kinds of roles, it can be very easy to get into the day to day details, which are highly analytical, highly detailed,   and very important. But as you progressed through your career, you have to spend more and more time on sort of the strategy. What's the end goal? what will make this the CRO, or the leaders of the company, succeed? and that's that's the transition that as you go, as you get higher in your career, that you'll need to spend more time thinking through. 

MATT DURAZZANI: Very well said. Great advice. Doug. This was an absolute treat. Thank you so much for we wanted to share these, great side with regards to the metrics and also from a career advice perspective. I know that if any of you that are listening would love to connect with Doug. You can find him on LinkedIn and he'll be happy to, you know, answer all the questions and maybe, um, become an advisor to you as well. But, we thank you for being on the program. We thank you all for listening in. And we wish you all a great day.