Mastering Modern Selling
At Mastering Modern Selling, our mission is to equip you with the insights, strategies, and tools necessary to excel in the ever-evolving landscape of sales. Traditional sales approaches, marketing tactics, and lead-generation methods are becoming obsolete. In today's market, buyers dictate the buying process and have little patience for cold calls, email blasts, or aggressive sales tactics.
In this new era of sales and marketing, success hinges on building meaningful relationships with prospects and buyers. We believe in leveraging the power of modern strategies, techniques, and technologies to foster these connections. This approach, often referred to as Modern Selling, encompasses leveraging digital and social channels to create demand and cultivate strong relationships with prospects, partners, and customers.
By mastering Modern Selling, you and your team can enhance your visibility in the marketplace, establish yourselves as trusted advisors, accelerate pipeline growth and revenue, and position yourselves as the employer of choice in your industry.
Join us on Mastering Modern Selling as we explore the principles, practices, and innovations driving success in today's sales landscape.
Mastering Modern Selling
MMS #134 - Redefining the PIP: A New Playbook for Sales Growth with JD Miller
In this powerhouse episode of Mastering Modern Selling, Brandon Lee, Tom Burton, and Carson Heady are joined by JD Miller, a seasoned sales executive turned private equity advisor.
With six successful exits under his belt, JD brings a rare blend of operational insight and boardroom savvy.
The discussion centers on how private equity firms evaluate and scale their portfolio companies—especially in the sales and marketing domains—and what sales leaders can do today to thrive in that high-expectation environment.
- Repeatability Is the Foundation of Scale
JD highlights that scaling isn’t just about hiring more reps, it’s about implementing repeatable, measurable systems.
When transitioning from a founder-led sales model to a broader team, companies need to get critical knowledge out of leaders’ heads and into structured playbooks.
This is essential when growing from five sellers to two hundred. Without repeatable processes, scale isn’t sustainable.
- Sales Leadership Must Be Fluent in Data
Today’s top CROs are expected to lead with data.
Whether through deep CRM analysis, conversation intelligence, or funnel metrics, modern sales leaders need to understand how to break down growth targets into tactical, trackable levers.
JD emphasized the need for CROs to either personally embrace analytics or work closely with RevOps to translate insights into strategy.
- “SMarketing”: Sales and Marketing as a Single Engine
JD introduced the concept of "SMarketing", a true merger of sales and marketing into one go-to-market function.
He shared real-world examples of aligning revenue goals with both teams’ activities and discussed how metrics like sales velocity can guide joint decision-making.
Bi-weekly check-ins and shared accountability are critical to keeping both teams rowing in the same direction.
- Messaging for the Modern Buyer
Buyers today expect a well-informed, highly personalized approach. JD stressed the importance of showing up with a point of view rooted in research, data, and empathy.
In a volatile economy, messaging must pivot from “growth at all costs” to helping buyers reduce risk and improve efficiency.
Sales and marketing alignment ensures these themes are consistent across every touchpoint.
- Performance Plans: Tools for Growth, Not Punishment
In JD’s view, performance improvement plans should be part of every employee's journey, not a disciplinary action.
He advocates for quarterly development conversations that blend short-term performance goals with long-term career aspirations.
JD Miller’s episode is a masterclass in bridging strategy and execution in modern selling. Whether you’re a CRO in a high-growth startup, a founder looking for investment, or a marketer working closely with sales, the principles JD shares can redefine how you scale.
By focusing on repeatable systems, cross-functional alignment, and buyer-centric messaging, you can transform your sales motion into an engine that attracts not only customers, but also investors.
Don't miss out—your next big idea could be just one episode away!
This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.
Check out our Live Show Events here: Mastering Modern Selling Live Show
Subscribe to our Newsletter: Mastering Modern Selling Newsletter
I
SPEAKER_02:got it. We'll go. I'll let you leave.
SPEAKER_03:Here we are. Every single time, we just start dancing.
SPEAKER_00:Amazing. I love it. It's very cool. You just get rolling, and then it stops, though. I need the whole
SPEAKER_01:song. I need
SPEAKER_00:the whole song. We need the whole song. I don't know if anybody would
SPEAKER_01:stay for the whole song. I propose we leverage AI to go back and pull all of our old episodes and write an actual song with lyrics for that.
SPEAKER_03:There
SPEAKER_00:you go. We could have a special episode where we introduce that, and then we do the video with it, the music. I think that could be a hit. Man,
SPEAKER_03:rock stars. Rock stars, here we come.
SPEAKER_00:That's right. All right. Now we can get back to the real world. Speaking of rock stars. That's right. Speaking of rock stars, welcome to episode number 134. We have Tom and Brandon and Carson all back at the same time. And yes, a rock star guest with JD Miller. So JD, welcome. Thanks for having me. It's great to be here. So we're going to talk about, with JD today, a bit about kind of the sales and marketing, modern sales and marketing strategies from the viewpoint of how kind of private equity and acquirers look at things. And as your company evolves, what are some best practices that we're seeing and strategies that we're seeing? I think it's gonna be a really interesting episode kind of looking at it from that vantage point.
SPEAKER_03:Well, and I would say, why don't we start by telling everybody that JD is six for six. in uh in his startups and companies that he's that he's built you're grown and exited i mean come on back in the thousands that's like unfortunate
SPEAKER_01:to be in the right place like the goat michael jordan of uh venture capital he has he has a lot of rings
SPEAKER_02:yeah I would say I would rather be lucky than good sometimes. But yeah, my first job out of college, I worked at a small.com that had done$750,000 of sales their first year. That seemed like a lot of money to me as a college graduate. I didn't do the math of there were 26 employees. But six years later, we went public with a$9 billion valuation and we're the largest tech IPO until Google. And so that set me down the path of How can you repeat that? And it's always been increasingly responsible sales jobs in B2B tech companies. JD, what was that first company's name? What was it? Vignette. And so the late 90s, our sales pitch was calling
SPEAKER_00:from the internet, do you need a website? Vignette was quite the hot company in the day. It was. Yeah. I remember them well.
SPEAKER_02:And then curiously, I actually started at a company that was acquired by Vignette and the founder, Introspect, and the founder of Introspect then went on to found another small startup called Siri and hit it again, talking to his computer and ultimately sold that one to Apple.
SPEAKER_00:Wow. And Apple still hasn't figured that one out yet. All right. Well, hey, before we get into this, as always, we want to thank Fistbump for the sponsorship. Brandon, any upcoming... webinars, shows, anything that we should be talking about?
SPEAKER_03:You know, we don't. The only thing is I've started another show. It's called Revenue Through Reputation and we get a bit more granular outside of just the sales part, but we talk more about the using content to grow reputation for individuals, but also for the brand. So that one, yeah, come join me on that one. It's Tuesdays at 11 a.m. Eastern. You can do a search for Revenue Through Reputation. It has its own LinkedIn page and all that as well, or on the podcast. It's got its own channel.
SPEAKER_00:Awesome. All right. Well, you had a couple of webinars last week, I think, with Mark Hunter, or was that already? That was like
SPEAKER_03:two weeks ago. Yeah. We've got another one coming up in May. I don't think we're ready to promote it yet, but we've got another one coming up on that one hour a week LinkedIn playbook for busy CEOs.
SPEAKER_00:Okay. All right. Well, then let's get into it. So JD, tell us kind of a little bit about what you do now and your background, and then we'll get into some of these questions or kind of taking us through some of these strategies.
SPEAKER_02:Yeah, fantastic. Yeah, so following that vignette experience, I have spent the last 25 years in B2B tech sales. I began as a sales engineer, quota carrier, and then ultimately CRO a bunch of times, CMO, and country president for the US, but always backed by private equity firms. So six times, I've been involved in the sale of a company through private equity. And today, I work for PE firms themselves as what we call an operating advisor. So I'm the guy who sits on the board who knows something about sales and marketing. And I get to work with portfolios of companies, coaching and mentoring their sales leadership team and lending a hand when that's needed too.
SPEAKER_00:What do you, and we may get into this, but at a high level, do you think that there's any sort of special approach strategies or whatever that you need to be thinking about when you're working with private equity companies? in terms of, you know, I know obviously every private equity is different. They have different strategies on how they purchase and so forth. But generally, private equity is not venture capital, right? So they're looking to bring in something that has some profitability, has some growth and profits and so forth. They're not looking for the startup that's earning$10 million a month going through the process. So therefore, you have to kind of look at the world through a little bit of a different lens, I would suspect, as a real estate student. to capture it.
SPEAKER_02:Yeah, that's exactly right. And I think one of the things that I really like about private equity is, you know, we always have an eye on an exit, getting out of the investment in four to five years. So it creates a lot of urgency for, you know, you've bought a company that's got something going really well. How can we implement a playbook to double down on that and, you know, make it go faster? And so what I've done is I've collected kind of the best practices from the PE firms I've worked with and consolidated them into a book that's called RO's Guide to Winning in Private Equity, where we talk about those specific unique things to the ownership structure.
SPEAKER_00:So where do we want to start, Brian? Should we start with the kind of... Go ahead, Carson. Go ahead.
SPEAKER_01:Yeah, I'd say, I mean, you've got me intrigued right out of the gate. I'm always interested in the common themes that you're seeing in the successes, but also the practical application. How can people today make pivots in their business model that will be advantageous for them? Like what should people be thinking about today, the CROs?
SPEAKER_02:So for me, it's about repeatability of process. Most of the companies that I see in the PE firms I'm working with are doing maybe$30 million in ARR. They've just graduated from that kind of founder-based VC backed. And they have between 30 million and maybe$300 million of revenue. And the biggest pivot for that is how do you take what you did really well as a small startup company and implement a repeatability a repeatable process. And so a lot of the work that I do with my CROs is to say, how do we get the intelligence out of your head? How do we implement a repeatable sales process? How do we identify your ideal customer profile, your ideal buyer. What are the sales stages you go through? Because usually in our time together, you're going to go from a team of maybe five or six sellers to maybe 200 sellers. And so it's implementing a lot of repeatable systems and management structures that make sure all 200 of us are doing the same thing in the same ways.
SPEAKER_01:What do you think are the common missteps that CROs are taking today?
SPEAKER_02:I think a lot of the early You know, the early kind of stage of that smaller revenue, a lot of those CROs struggle with graduating to be the leader and the enforcer instead of the super salesman themselves. A lot of people get in that seat in a small startup because they were the person who could sell it on their own. And a lot of the work that I do is talking about how do you now let someone else do what you're comfortable in and have you do the thing that only you can do, which is strategic. And then I think the second big challenge that we see a a lot of CROs is signing up for a number without a plan. You hear from private equity, you've got to grow 20% this year. And I think a lot of CROs get into trouble where they go to a board meeting and they say, yep, I'll sign up for 20% more number, and they don't know how they're going to do it. And so we really need to break down what's going to be new logo, what's going to be sale of your new product, what's cross-selling to your install base, what's happening with customer satisfaction in turn, because if I'm a$100 million company, I don't have to just sell$20 million more if I've got 10% churn. So kind of understanding all of those puts and takes in the annual plan is another really big piece that I spend a lot of time with CROs on.
SPEAKER_03:There's a lot of moving parts there. I mean, especially when you go from a transition from being like the main producer with a small team, there's a lot of behavior that we need to put down and new behaviors that we have to pick up. And then on top of that, you've got this pressure of a 20% growth and managing new systems and new people. That just seems like a real challenging environment. It can be.
SPEAKER_02:I think the biggest skill to... to kind of develop there is getting really comfortable with data and data analysis. Or if you're fortunate, hiring a revenue operations person who could sit by your side and produce data. I was a social scientist in training. I have a PhD in communication. And so I believe everything about a sales process is persuasion that you can measure. And it's a science that if I say this to you in this way, I'm going to get this result. Really great CROs, really great RevOps leaders are able to help unpack the call recordings, all the things that we see happening in emails, everything in your CRM system, and understand when I do this, what's the result? How do I tweak what my input was? to get a better result. And so kind of data facility is a really core key skill.
SPEAKER_00:So what would be the smallest company generally right now that you're getting involved with? Is it a$10 million company would be on the small end or?
SPEAKER_02:Yeah, I have one right now. They're in Austria. They're about 15 million in ARR. But yeah, we'd start talking to those folks, you know, at the eight and 10 million. And then, you know, once we see that there's a great product or a great message, or you're kind of onto something and how you can sell it, we'll go ahead and buy that and put a lot of effort behind, you know, replicating it at bigger scale.
SPEAKER_00:So how
SPEAKER_01:would you go ahead, John?
SPEAKER_00:I'm just going to ask part two to that is, As you then acquire these companies, and it's, I mean, I have a small company, it's not quite that size yet, but we're investing a lot in process and repeatability and metrics, even at a small company. Are you seeing that these companies that are coming in at 8, 10, 12 million ARR are really lacking a lot of that? And they're really just kind of operating by the founder and basically letting the product or their technology carry them?
SPEAKER_02:I see that a lot. Now, that may be a function of the PE firms that I work with. Everyone's got sort of a different investment thesis. So there are some PE firms that are great at saying, let me teach you how to sell really well. And having someone on the bench who's a CRO advisor, that's one of the things we do really, really well. So we tend to have a lot of great products that need a sales engine. There are other PE firms that say you may have a great sales engine and I've got to really double down on helping you differentiate your product and they'll put money into product development and understanding product market too. So it kind of depends on your board and your investors.
SPEAKER_00:Okay. Makes sense. Go ahead, Carson. Sorry.
SPEAKER_01:Yeah. With your wealth of experience, JD, how has the game changed? Obviously, what technology and AI and data can do and point us to now. I would have to think that the savvy CROs are looking at where they can get an edge. What are you seeing in that space? How are the smart CROs adopting technology?
SPEAKER_02:I think a lot of it right now is about knowing your customer so much better. When I started selling 20, 25 years ago, we used to get grace from prospects who would say, I can show up and have a blank sheet of paper and say, tell me about your problems and what would be ideal for your aircraft solutions. Today, Everything that you can know about someone is available online. And so prospects expect you to show up with a point of view. I've done my research. I've seen your website. I have this thesis that this is broken and I'm going to come fix it for you. And then I also think on the coaching side, when we talk about performance management of sellers, AI gives us access to so much more than we ever used to have before. So it used to be, as CRO, I could get in the car and maybe go on two sales calls with a seller and a quarter. Now, when literally every call is recorded, AI has transcribed it, I can really quickly, at the end of every day, see what did all of my sellers talk about, where are the pitfalls they've had. I use a medic-based sales process. So which of those medic questions are we consistently failing to answer? are well, and you can have a lot more real-time coaching. So it's really just kind of raised the game and raised the stakes for sellers to be much better than they ever used to be.
SPEAKER_01:It's
SPEAKER_00:incredible. So let's go down the road. And Brandon, I want to get you to kind of drive this a little bit. I know this is an area that you've had a lot of experience with is this marketing concept, right? Which is the idea of combining sales and marketing tighter together and working closely together. Brandon, where should we start on that? Because I think there's a lot of things that we can unpack here. Yeah, I
SPEAKER_03:think let's start, JD. I'd love for you to kind of define what does that concept of smart marketing really mean and why is the marketing motion and the sales motion being more integrated so important now, especially?
UNKNOWN:Yeah.
SPEAKER_02:So I first learned about marketing actually from a chief marketing officer named Andrea Brody. It's about 10 years ago. And I was hired to lead the global sales motion at this company. And the PE firm was well down the path on their hold period. And we had about a year left before we needed to get the company sold. And we were really looking for the right results. And I got into the conversation by saying, well, where do the BDRs report? And I want them reporting to me. And she said to me, let's stop thinking about sales and marketing and really let me talk to you about the combined organization, the marketing org. We're both leaders of it. It doesn't matter what reporting structures are. It doesn't ultimately matter. other than the two of us together have got to get to this number. And it really led to this tight collaboration that said, OK, if the business's goal is to grow 20% this year, what's our average deal size? How many deals do we need to do? And then all of the kind of predicting behaviors. What's our win rate? So how many opportunities did I need to have? What's my sales cycle look like? How many meetings did I have to have? How many cold calls did I have to have? All of that sort of stuff that's precursors to getting to the number. And I think what was really exciting about that is in a lot of organizations, sales and marketing are pointing fingers at each other saying, oh, if sales would win more, the world would be easier. Oh, if marketing would be giving me better quality leads or more of those leads, my life would be easier. And when we think about marketing, we can have those conversations that, yes, I need to improve the skill of my sellers, but the fact of the matter is this is how good they are today. So what are we collectively going to have to do with the team, with the resources we we've got today to get to the results that we're trying to get to. And so then ever since then, whether it's a sales leader and a marketing leader who hold hands or increasingly, I think people aren't spending as much money on executives because we're landing on a single CRO who owns both sales and marketing teams. It's really aligning all the resources on our common vision and all of the inputs that are going to get us there.
SPEAKER_03:And when you talk about alignment of that in a tactical way, I mean, what does that look like week to week and month to month and getting these marketing motions and these sales motions aligned? And I'm assuming the goal, of course, is more conversations, more at bats. What does that practically look like, though?
SPEAKER_02:Yeah. So for me, it all kind of lands in what are the metrics and what is the process we're going through? And I focus a lot on a sales velocity metric, which is basically measuring all of the activities and how much revenue do we produce every day. So it looks at total number of opportunities times conversion rate times deal size divided by the number of days in our sales cycle. And that's how we get to sales velocity. But then my marketing leader me, my sales leaders are looking at least every two weeks at each of those inputs. So together we'd say, we're trying to get to this$20 million growth number this year. If things keep running the same way they are, how many opportunities do I need to have? What's my win rate? What does that deal size need to look like? How fast does that cycle need to flow? And then every two weeks we're checking in, are we hitting those expectations? And if we're not, what do we need to tweak? And sometimes I don't have as many opportunities and maybe I need to invest more marketing dollars there, but maybe I'm overperforming somewhere else. And so it's kind of constantly adapting what the total equation looks like to get to the very new goal.
SPEAKER_03:And when you're looking at, so I'm going to lean in more on the marketing side or the content side, because I find now that content is so important for creating initial reputation, creating brand, creating that awareness. So you get into the data and some of that content, like where the clicks are coming from, where the conversions are taking place, making adjustment in messaging, or what does that look like where you've got sales and marketing working together? Because the opposite is sales and marketing are And the only communication they do is usually giving each other the finger because they're upset with each other. But you know, you're not giving me enough leads while you're not converting my leads. What does that look like when there is proper alignment and working together to solve the problem instead of working apart?
SPEAKER_02:Well, I think you're exactly right. Content-based marketing is such a ubiquitous thing, and it's become so inexpensive for me to blast off a couple hundred emails and do different things. And so the data that we're seeing today is that it takes about 17 touches to turn someone from a totally cold prospect to someone who's going to take a sales call with you. So part of what we're doing with marketing is to align on what are those 17 touches. Some of them is going to be consumer becoming a blog post. Some of those is going to be a banner ad retargeting that comes from marketing. Some is going to be a BDR cold call, a seller call, a connection on LinkedIn. And so part of what we're doing is, you know, it's almost like account based marketing that we're looking at our prospect list Have we made all the 17 touches in a short amount of time? Is everyone doing their piece? And then the second piece is, you know, which of those is the most effective? Because I would like to shave 17 down to 15 to 13 and get it faster. And so instead of marketing on one side, talking about whatever they talk about in sales, talking about something else is how do we actually align the message that we're talking about? So we look like a unified company to everyone who's engaging us in all the different channels.
SPEAKER_03:Yeah, that's what I was hoping you were going to say and to get to. And I think so often, even smaller teams, You know, marketing's got their plan. They've got their goggles on and this is what they're looking at and sales looking this way. And without that alignment, it just seems like maybe instead of 17, it becomes 30 because they just keep missing. And what sales is talking about, what marketing is producing are not in alignment and really creating more confusion across buyers. Right.
SPEAKER_02:We've all had the experience of sales is doing whatever they're doing with their prospects. And all of a sudden marketing calls up a seller and says, we have a trade show in two weeks and I need you to drive more registrations to the booth. And the seller is kind of scratching their head saying, it's two weeks out. I had no idea it was coming. And that's not at all what I've been talking to my prospects about. So how do we get kind of a content calendar and a messaging calendar that every time we're talking to the market we're saying some of the same basic things and then you know the other part of that is knowing that the message that works today is not necessarily the message that's going to work tomorrow Really early on, I had a sales mentor tell me, every product you're going to sell has one of three pitches. You either have to buy my product because it helps you comply with the law. You'll go to jail if you don't do it. You're going to buy my product because you're going to sell more and make more money with it. Or you're going to buy my product because you're going to cut costs with it. Now, it used to be a couple of years ago, we were talking all about growth and all of these exciting new AI tools that are going to make your sellers more effective. Now, all of a sudden in the US, we're looking at the economy and we're saying, are we in a recession? Are we not? What's the stock market doing? And a lot of people are pulling back. And so those messages about cost cutting, risk reduction are way more relevant. And so really good sales and marketing leaders are kind of taking that pulse and figuring out, yep, sellers, I used to talk to you about buy this thing for 15% growth. Now you're going to shift your messaging. You're going to talk about buy this thing and you can reduce three heads out of your organization with
SPEAKER_00:it. I like Dominique's comment, maybe 17 cold calls is all we need to do to get those 17 touches that are there. Well,
SPEAKER_02:and hopefully it's not all cold calls, right? I mean, in the best organizations, it's all that other stuff.
SPEAKER_00:No, we've got to do something right that actually creates the demand and builds the trust versus just the cold call of the day. Where do you think this marketing strategy should start? to evolve? Do you think that that should be happening right from day one in a company? You know, we have startups and other, we have really all size companies, I think, to listen to the show. And, you know, where would you say, is that something you should be building in the DNA from day one? Brandon, it sounds like you're on a golf course with all your birds and everything. I've got birds out
SPEAKER_03:there. These are good. These are good AirPods, aren't they?
SPEAKER_02:You know, I think it's something that does start from day one. But I remember those early days at Vignette when we were 26 people, it naturally happened because we had a single leader and we had two salespeople. And so they naturally knew all of the marketing messages and all the sales pitches and the events we were going to. And there was a lot of unification there. I actually think marketing becomes more important once you've expanded beyond a single office and you've got You know, now some of your team is co-located in this place and some might be down the street or across the world. And now you've got to start really being intentional about communicating what we're doing and lining that up. And it's really important to do in the annual planning process. And then it's really important to keep refreshing and staying on top of week by week and month by month.
SPEAKER_00:So I have a selfish question for you, and then we'll go on to the next one on the agenda. But my software company sells predominantly to manufacturers and wholesale distributors that are private equity owned. The majority of them are a large percentage of them. Are you seeing that private equity owned companies are slowing down on their growth plans or saying, Hey, you don't, don't worry about growing 20% this year, but it's okay to slow down or, you know, kind of cut some expenses and shore up or what are you seeing as it relates to the private equity? I guess that's a very personal. Yeah,
SPEAKER_02:no, that's a great question. Um, so private equity ultimately tries to drive to what we call a rule of 40 company and so rule of 40 is you're adding your profitability and your growth and those percentages together need to add up to 40. so you know are we slowing down on growth i mean if you're going to get there on profitability yes you can take your foot off the gas on growth if you're not a super profitable company and there's not a lot of obvious stuff to do there then growth is still really very important to you and so i think you know when your company was bought we bought it with some investment thesis of what the next three or four years was going to look like and we really need to make do make make good on that but i do think as the economy goes up and down you know we're constantly re-evaluating those levers of you know which one is sort of in the lead today
SPEAKER_00:got it so which which how do we adjust that 40 it still stays at 40 but are we putting more emphasis on the growth side of the equation or the or the net income side of the equation or the profitability side of the equation.
SPEAKER_02:Great. And I think it's very dependent on the company that you're holding. A manufacturing company, we hear a lot about tariffs today with them, where their raw goods are coming from. There's probably not a lot of profitability motion to happen there. We're going to have to make up for it on growth. Other industries may have different kind of levers that they can pull there.
SPEAKER_00:Makes total sense. So Carson, one of the things we wanted to talk about today was, and I think maybe you cover this in your book, JD, is performance improvement plans as kind of a management tool or so forth. And I know, JD, you have some some suggestions or strategies with that. But Carson, I know you do a lot with this at Microsoft. So be interested in both of your takes on these and kind of what you're seeing in this area about how you use these performance improvement plans as kind of tools for growth versus, I think, as you said, JD, punishment as an alternative to punishment.
SPEAKER_02:I mean, it's sometimes controversial because I believe that everyone should be on a performance improvement plan all the time. But the reason that that's controversial is that there are so many companies that aren't having performance conversations until things are going really badly. And then the performance improvement plan really is just some HR paperwork we're gonna go through so that you don't sue us when we fire you. And I think instead, if we can turn that on its head and say, Every employee, every 90 days, we're going to sit down, we're going to talk about what's going well, we're going to talk about what's not going well, and we're going to come up with ideas about what are you going to do in the next 90 days to continue to become better, building skills and grow your performance. That's a great performance improvement plan that helps all the boats rise. Carson, what's your experience with this?
SPEAKER_01:Yeah, JD, and look, I know you have a lot of great experience coming in and really helping define and set culture for selling. I think the problem with the PIP, as it were, is that it has a negative connotation by default because of how it's been used historically in a lot of scenarios and organizations. I agree with your sentiment. I think, you know, I've been tasked a few times in my career to coming into new organizations or new teams or new situations or failing teams or pre-existing teams to build sales culture or to redefine the team. And one of the things that has been a very valuable resource and tool has been the improvement plan, or at least the thematic element that maybe we didn't call it an improvement plan, but the reality is it is. And what we're doing is we're assessing the current state, right? We're looking at what's working, what's not. What are the strengths? What are the areas of opportunity doing kind of that SWOT analysis on your team and also on your people? You know, I believe everybody. has earned the right by and large to be in the seat that they're in at the time that they get that seat. Sometimes the seat changes, sometimes the dues to be in that seat shift. It's up to us to make sure that we and everybody that works for us is bringing that day one energy, being the person that we promised to be on interview day while the company gives us the tools, the resources, the training to be successful. Now, with an improvement plan, It's important to kind of draw that line and say, okay, this is where we are. This is where we've been. What we've discussed previously as far as the areas where we need to be improving, the steps and the action plan that we agreed upon in order to see that improvement. And it all comes down to process, right? Because if you have the right people, Doing the right process, your probability of success is very high. Now, the people change and variables around the people shift. The outcomes that we're driving with process shift. And so it sometimes will cause the need for new process or pivoting in process. But I think that's why the improvement plan is so paramount. We're going to look at where we've been, where we are, where we need and want to go. And we're going to agree on a plan to get here. Now, when we get to this place in time, we've got to look back at the sum of the parts and we've got to realize, did we take those steps? We either have or we haven't seen improvement. If we haven't seen the actions that we agreed upon, we have a new challenge and we have a new problem. And I think that's where that write up or that performance plan can take a different connotation and tone. But frankly, JD, back to your point, everybody should be on a trajectory of improvement every single day. I love the idea of knocking down the negative connotation of a performance improvement plan because we should all be working on the ways that we can improve every day because we're going to need to be able to be invaluable now and into the future i read an article on linkedin the other day that was about just that i have zero fear about ai replacing me because everything i do is try to be as valuable as i can be to the people in my sphere the people i serve my colleagues my leadership my customers and by doing that I'm working to be valuable, but I've also got to take on these tools. I read a study a couple months ago where individual contributors using a legion of AI agents will be more productive and efficient and impactful and driving more outcomes than full existing human teams that we have today. Now, that isn't the reality today, but it's where I believe the work world is going to go. And so we need to right now be challenging ourselves to improve, to be invaluable, to unlock success.
SPEAKER_02:Right. And it's how do we develop those skills? I think a big piece about the performance improvement plan template, and we probably should rebrand it something else, is, you know, yes, what's going to happen for the next 90 days, but also long term, what's your future career? And what are the skills that we need to be thinking about a year from now, three years from now, because maybe you don't want to be a mid market seller forever? What are the things to get promoted to enterprise or very different to manage a team? What are those skills supposed to look like? And so whether we call it a pip or we call it something else, it's having a really clear conversation about the constant development. I saw a couple of weeks ago, Clary published their state of sales 2025 report, and they looked across all of the, I don't know who their organizations were, but hundreds of organization sales teams, and they found two things. One was that there are about 10% of sellers who were doing 62% of their company's business. we're used to that you've always got some top performers and maybe you've got an enterprise team but what i found was really astonishing is the bottom 50 of sellers collectively were only selling seven and a half percent of the revenue of the companies they worked for and so that told me you know it got me really thinking about this notion of performance improvement You didn't hire half of your sales team of just terrible sellers. Something has shifted in the environment. That just means what they used to do when you hired them is no longer what you need them to do. And so the solution doesn't have to be go fire half of your team and replace them with new folks. It's how do we talk about improving the performance? How do we talk about, oh, the economy's shifted. Here's a different message you need to deliver and training people in developing that skill.
SPEAKER_00:So am I hearing you say that really everybody on the team and maybe even on the marketing team as well, if you take this marketing approach, should have some sort of PIP that you're, and how frequently would you review those? Is that a quarterly effort every six months or how frequently would that happen?
SPEAKER_02:I like to do it quarterly. Now, I hope that everyone, every individual contributor is having a weekly one-on-one with their manager where they're talking about all sorts of things and hopefully having some development. But at least quarterly, that conversation with the manager should be a little bit more structured where we do a retrospective on the last 90 days, a forward look on the next 90 days, and we identify what are the skills we're going to develop together and how are we going to get there. And when I've done that, I've had higher performing teams. It also makes writing annual reviews really easy for me. You take all the quarterly ones and you staple them together and it's conversation. I think the worst organizations,
SPEAKER_00:go ahead. No, I was going to say you could, so you could, you could have a top seller, right? That's killing it from the numbers perspective, but it doesn't mean that they still shouldn't be thinking about how are they improving their relates to their use of ai or there's certainly areas that they can continue to improve on or prepare for even if they're killing it with their numbers right so it's not exactly lower half that's getting the pip that's there
SPEAKER_02:right yeah and that you know that the pip is or the performance improvement discussion is not a punishment so yes a top seller should have an improvement plan how how are you going to continue to refine your skills and become even better how do you you're a top individual contributor today What do you want to do in your career five years from now? How do we improve your skills to set you up for that next step?
SPEAKER_00:So here's a question I
SPEAKER_02:have.
SPEAKER_03:Well, as I said, when, when we, when I looked at the topic around PIP, I mean, this sounds to me much more like a personal development plan. It's not so much the improvement side because it's, it's like, Hey, we can acknowledge generally. I think that the thought is PIP means you're, you're, you're sucking it up and you're going to get fired. What we're talking about though, is, is a, is a better culture of, Hey, we, we're, we want to personally, we want to partner with you and align with you for personal development. Like where, where do you see yourself going? What are the skills that we need to create in you? And then it's that combination of, I think, from a good culture standpoint, what the employee, what the person wants, but then also what the company is going to need in the future and aligning that as more of a training and personal development plan. Is that what I'm hearing?
SPEAKER_02:That's right. And I really got religion on this, you know, maybe 15 years ago when I was fired by surprise. I had been in a job I thought was going really, really well. It was a stretch role for me. My manager didn't talk to me very much. He traveled a lot. So maybe every two weeks I saw him briefly. And I was there a couple of years and I think things are going great. And the head of HR took me aside one day and said, JD, how do you think things are going for you? I said, I think it's going great. And the head of HR said, no one else does. And here's your pin. we're firing you and, you know, you've got 30 days, but really, you know, start interviewing. You're going to find something else. And, you know, I thought about that for a second and I realized if we had had that conversation six months before, a year before, you know, maybe I could have developed the skills that they were looking for. and had a better result and not gotten fired. Now it was bad for me, losing the job. It was bad for them too, because if they didn't have a development plan with the next person who came in, they're gonna be in the same cycle. And so it costs them a lot of money in severance with me. It costs them a lot of money on the recruiter to find the next person. lost time of ramping the person into the role. And if you, if you miss that coaching opportunity, you're just going to be on this cycle. And so, you know, that was kind of the spark of me saying, we really need to have development conversations much more frequently
SPEAKER_00:because it's good for everybody. Hey, AJD, when you got that PIP unexpectedly, or that, when you looked at it, did you see things on there that when you looked at it go, oh, wow, maybe there's, they're right about some of these things. And had I known this... six months or a year ago, I would have worked on these. I just didn't know that this was important for what they were looking for. Absolutely.
SPEAKER_02:I mean, absolutely. I was in my 20s and had never even heard of this kind of stuff. But a lot of times when people are producing these documents, it has built up so far and gotten so bad that the decision's already made. We're moving on from you. You're terrible for the culture. You're terrible at this, whatever. And the kinds of hurdles that we put in those documents, you've got 30 days to get to 200% of quota. Well, that's never going to happen. Where if, on a monthly basis, we were talking about, hey, you kind of missed your quota a little bit there. Over the next 90 days, let's work on prospecting so you have a bigger pipeline. You can start to course correct early on, and you're not pulling this huge rip cord.
SPEAKER_03:So stupid question here, but in that situation, I'm assuming you weren't having the weekly one-on-ones and you weren't having the quarterly development conversations. You didn't get any of that. Correct. Yeah, correct.
SPEAKER_02:And I think a lot of times that can happen with growing companies too, where we take a good seller and we promote them to be head of sales, but they don't think about management. And so they're out talking to the biggest customers and closing deals on their own. And oh yes, I have five or six or eight people reporting to me and they'll call me if they need something. And that's a development skill for that manager that someone needs to
SPEAKER_04:teach.
SPEAKER_02:Here's some new process that you need to learn to be an effective leader of people.
SPEAKER_01:I remember years ago when I was a second line and I had a general manager who would come to me and it's like he would always say, look at where the management problems lie in this. Don't always look directly at the sellers because it is so critical that good sales culture requires sales managers to understand the why and how of the process. And frankly, A great seller does not a great manager make. In fact, look at sports, look at athletics, look at baseball. Some of the greatest managers and coaches were good or maybe even mediocre players at best, but they understood the fundamentals and the why behind the process. I think that's the key. We've got to spend more time as organizations and, you know, thinking it from a CRO lens even, we've got to think about the importance of building that sales culture. How do we do it and why do we do it? Helping ensure that our teams understand the why behind what we're doing. There needs to be a level of transparency. JD, to your earlier point, like signing up for a big growth number. We need to understand how we're going to get there. We need to understand the importance of making that growth number for sustainable business success. We've also got to understand, OK, what are going to be the inputs that are going to be a vital criticality in order to drive the outcomes that we're wanting to drive? I mean, if I know that I need to get more, you know, more revenue, What ultimately is going to lead to revenue? Let me double down on some of the things that I know work. Let me jettison or tweak some of the things that don't work. And sales managers and improvement plans or whatever you want to call them, we've got to be spending time every week, two weeks with every member of our team. We need to be hands-on in the field, inspecting and helping them improve. We've got to be willing to do the things that we're asking them to do. Otherwise, we're not going to take them to the next level. And JD, you hit on something else really important as well. The things that are working today may not work three months down the road. So we've got to also be very agile and able to pivot now more than ever, because the conversations with customers are changing, the data and what they have at their fingertips is changing, and what AI is capable of doing is going to continue to change too. That's why we can't get married to any expectation right now. I work in an industry that is making big shifts. And fortunately, I'm just an old grizzled sales veteran And I'm going to roll with the punches and I'm going to go wherever I can be valuable and I'm going to do what I know to do, which is survive. But, you know, not everybody has had that experience or knows the importance of kind of leaning into these moments and really listening. What are my customers saying? What are the leaders saying? How can I be the problem solver in this day and time?
SPEAKER_02:That's right. You know, a lot of times when I work with a CRO, first time who's working in this environment, they're surprised that the board deck isn't just about the number, but it's about all these other things. And it's, you know, it's really important for me as a leader. Yes, I hope I'm delivering the number and we want to do that pretty consistently, but I don't want to be delivering the number just because I have one super seller who's saving the day for me. I really do want to be running an organization where 80% of the team is getting at least to 80% of the quota, 80% of the time. Because if you're hitting your number, but you've got all this huge churn, am I running a terrible culture that my sellers hate working for me? Am I turning over a lot of people because I'm not developing them? We know that there's always going to be someone who has to leave. Maybe I did make a bad hire. I do need to fire somebody. people are gonna leave and have babies and do stuff like that. But if it's more than 10% of the organization is turning over, that's on me as a leader by not creating an environment that I'm spending money on all of these salaries, we should be getting some return on all of them too.
SPEAKER_01:That's why you got to stay at the pulse of your team and your org. You've got to understand what makes these folks tick. How do I turn this into a destination team? How do I turn this into a destination organization? Survey your people, know what they care about, and actually make changes and make decisions based on their feedback when you can. You're not always going to be able to, but if they can see that they are a part of what you're doing and that they matter and their voice matters, and you're working as an executive to build a bench roster and attract new talent in the plethora of ways that you can do that now with social media and with doing proactive outreach with recruiting. There's so many ways that you can make your organization and your team a destination.
SPEAKER_02:And the social scientist in me and the communication PhD in me says, at the end of the day, the solution to a lot of problems is more communication. When you have a cultural challenge going on, and it's happened to me too. I've seen my name on Glassdoor reviews saying, this is a terrible company to work for because JD does this thing. probably I stand behind what I did. It's the right thing to do, but I didn't communicate it well enough to you and explain why are we doing this unpleasant thing or this unpleasant change? And so more communication, more engagement is really going to win the hearts and minds of your team and then have them, you know, follow to greatness.
SPEAKER_00:So what would you JD is you, if you were, and you are, if you're talking to salespeople right now, probably in any size range company, And to your point, Carson, about the future of AI and everything that's kind of coming, what do you coach them on or tell them on, especially related to AI, on how they need to change or develop different skills? And it's interesting, I did a workshop with a team of salespeople at a wholesale distributor, I don't know, a month or so ago, and we were talking about AI, and there was a lot of nervousness about AI. Like, I don't want it in this building. It's going to replace me. It's going to do my job. Why do they need me? And our whole workshop was, no, no, no, no. That's not really the way that it's going to be. But how do you coach people and help them develop and embrace AI versus be in fear of it? I really think it is about being
SPEAKER_02:comfortable getting uncomfortable. I remember back in the 90s when I was part of the dot-com boom, and we were selling a lot of software to people saying, hey, you're a call center agent right now, and we're building this website that's going to be self-serve. Did we put call centers out of business? No, you can still pick a phone and talk to somebody. But are there significantly fewer call center professionals than there used to be? Absolutely. And so I think back then, there were folks that had a fork in the road of saying, I'm not going to get on board with this new internet thing. And I think they're the ones who are left behind. And then there were folks that said, you know, there's always going to be some kind of profession for me, but I better learn how I play with these technologies. And I think that's what we're finding with AI today too, is I don't think we should be sticking our head in the sand, pretending it's going to go away. It's also, we're going to make a lot of mistakes with it. And we're gonna make a lot of missteps with it. So I don't know exactly where I'm gonna use it well in my job and where it's gonna be a mistake, but I should get comfortable being uncertain about that and trying things out because eventually something is gonna rise to the top as the new way of doing business. And I wanna be someone who knows how to do it.
SPEAKER_00:And should you welcome the opportunity for AI to help enable you and to do that better job, right? And I think that's a key part as well, is knowing that, hey, you could get better through the use of AI, no matter how good you are right now. That's right.
SPEAKER_02:I've been really fortunate in my career. We talked about six exits. The reason I am in the place that I am today is at every step of the game, I've said yes to a new opportunity that I was uncertain about. And so I could have been a great sales seller and said, I'm just going to continue to be the top seller in my next job. I want to be the top seller. Someone offered me an opportunity to lead a team. I said, I've never done that before, but let's give it a try. And then someone offered me an opportunity to be a CMO. And I said, I've never done that before, but I'll give it a try. And sometimes I've done well with that. And sometimes I've completely failed at that. But being open to saying yes, trying something new is how we evolve our skills and we stay current in the world.
SPEAKER_01:Yeah, what's that phenomenal quote from Richard Branson? If someone offers you an amazing opportunity, but you're not sure you can do it, say yes, and then learn how to do it later. I think it's all about the experiences. I've been recruited to come do different things multiple times in my career, and I could stay over here in the comfortable sleepwalking, hit my number, phone it in, or I can go over here and do something brand new, get the experience, maybe fall flat on my face. But fortunately, I never have. I love that mentality, JD. And Tom, when you're talking about AI and sales, what is it from our good old fabled story, Moneyball, adapt or die?
SPEAKER_00:That's
SPEAKER_02:right. That's right. I remember being a student at the University of Illinois in the 90s, and we had a convocation speaker, who's the person who speaks at freshman orientation. And they told us, 75% of you are going to graduate into jobs that don't exist today. And it was true. It was the late 90s. The internet came along and, boy, we had a whole lot of new things. I really believe AI is that same forefront that so many students who are freshmen right now, four years from now, are going to be doing these jobs that didn't exist or look completely different because of the use of AI. And so learning to be comfortable in saying, I'm going to jump in with it. I'm going to figure it out. I'm going to give it my best shot. And then hopefully I'm going to have conversations with my manager regularly about what's going well, what's not, and we can keep course correcting and getting better at it. And they'll have great, phenomenal careers too.
SPEAKER_00:So as we wrap up here, I'd love to get a few tips from you from your book. The book is called The CRO's Guide to Winning in Private Equity. Is that right? That's right. Okay. What would be, I don't know, maybe two or three, if you were to pull out a couple of two or three good tips from the book that people could take away from to really be thinking about, obviously not just in private equity, but to winning in general in this sort of modern sales age?
SPEAKER_02:Thanks for asking. So the book is structured as a year in the life of a CRO, and it's got about a dozen downloadable templates for all the things you need to do to go through your year. So there is a performance improvement plan, coaching conversation template that you can grab today and implement with your team today. The biggest things for me for success I spend a lot of time talking about the annual plan and really helping people sign up for a number that's not just a pie in the sky number, but where they've written on a single sheet of paper. These are the ways I think I'm going to get there through customer churn, retention, cross sell, upsell, new logo sales, and all of that sort of stuff. So tip number one is have a plan that you can measure against through the year because it's going to help you stay kind of course corrected. And then the second big thing, I talk a lot about board communication. It's really leveraging your board members and people like me on the board who are there to help you. I think a lot of folks, we're used to winning and we don't want to disappoint people. CROs tend to have pretty short tenures. 18 months is the average tenure of a CRO before they lose their job. And a lot of times it's not because they missed their number, it's because they didn't communicate that they were going to miss their number. And so in the same way we should be managing down and talking to our sellers every month about what's going well and what's not, CROs need to be talking up to their board on at least a monthly basis. I actually like a weekly email, and you can get a template out of the book on that too, that just keeps them in tune on here's what's happening with the number, here's what's happening with my headcount, here's what's going well, here's what's not, so that you're not showing up on a quarterly board meeting and dropping a terrible bomb that results in you getting fired. You're showing up at that meeting maybe with the same news with a board that says, we knew it was coming and how do I collaborate with you and continue to improve your performance down the line.
SPEAKER_00:That's great. And your book is on, I assume on Amazon or? You'll find it everywhere.
SPEAKER_02:So it's globally, all of the Amazons, your local bookstore has it, and you can find it through my website at jdmillerphd.com.
SPEAKER_00:I am going to get a copy. There sounds like there's some really good stuff. Excellent. Carson, any final questions before we wrap up here?
SPEAKER_01:No, this was a, I love this episode because it was very unique in, you know, kind of the annals of mastering modern selling, but a lot of nuggets that any executive or any sales leader or frankly, any individual contributor can kind of pick up and run along with. JD, was there anything else that you were hoping to impart on our audience today that you didn't get the opportunity to yet?
SPEAKER_02:You know, I could talk to you guys forever, but I've really enjoyed our conversation so far and know keep learning and keep developing
SPEAKER_01:yeah no thank you so much i i think you gave us a lot of really good food for thought um you know and how we can reframe the improvement process um all the way to some of the really eye-opening statistics around uh cro uh tenure and things of that stature and the things that we can do to really own that process. The thing that you said that I love the most, JD, was when you talked about what you learned from even Glassdoor reviews and how you acknowledge that When I think about improvement plans and the connotation that they get, there is a stark difference between giving people feedback that's fluff or giving them feedback that's negative because you're being given pressure to write somebody up from leadership to giving people tangible, real, constructive feedback that they can absorb. And while it might sting in the moment, believe me, I mean, I've been blessed with managers that are willing to shoot me straight. might sting in the moment, but that you can take and turn into something very constructive and be a better leader and communicator as a result. And I love that you called out like reading something on Glassdoor that, hey, you acknowledge they had this perception and I could do something different or better as a result. That's my biggest takeaway. So thank you for sharing that.
SPEAKER_02:And that's what I love about private equity is we're always on a time clock of this company is going to get sold in four years, three years, two years. So we don't have a lot of time to screw around with feeling bad and hurt feelings. It's just about how do I make tomorrow better than today because I have one fewer day to get this company value bigger. And so let's just figure out how to keep doing that and evolving and we'll all wind up in a great place.
SPEAKER_01:Well said.
SPEAKER_00:All right. Well, thanks again, JD. Like I said, we'll check out the book. Carson, wrap us up.
SPEAKER_01:Yeah, hope everybody in Atlanta is safe with the weather.
SPEAKER_00:Yeah, what's going on there? Is there a storm there or something?
SPEAKER_01:Brandon needed to step away. Maybe Butch knows as well. I'm thinking about everybody in Hotlanta. And thanks for everybody for joining. Dominique, thanks for the commentary. Charles had some great comments today and Butch. And until next time, happy modern selling. Thanks, everyone. Bye.
