JD MIller on this episode
JD Miller is an advisor and former chief revenue officer at Kantata with over 25 years of experience scaling B2B tech companies from early-stage to multibillion-dollar valuations. He has served as CRO, CMO, and country president at organizations backed by private equity, and now sits on boards and advises portfolio companies as an operating advisor. His expertise spans sales leadership, revenue operations, and strategic scaling.
Data-driven strategy and transparent communication with leadership are the core differences between CROs who survive and those who get fired within 18 months. The average CRO tenure is just 18 months, and Miller attributes much of this turnover to leaders who either fail to align the board on realistic numbers or hide bad news instead of surfacing it early with a plan to fix it.
Miller's key reframe: most companies don't have a sales problem—they have an ICP problem. His signature approach is diagnosing root causes through metrics like MQL-to-SQL conversion, sales velocity (opportunities × win rate × deal size ÷ days), and territory equity. Rather than assuming leaders need new talent, he looks at the data to uncover whether marketing is chasing the wrong personas, deal sizes have shifted due to market conditions, or territories are unfairly stacked. Once the real lever is identified, strategy shifts follow naturally.
The episode covers annual planning best practices, including building contingency layers (board sees 100%, execs work to 105%, field reps carry 110-120% quota), weekly flash reporting to catch drift early, territory rebalancing for fairness, and how to have hard conversations with boards about realistic expectations. Miller also shares how to keep top performers: set attainable quotas (80% of reps hitting 80% of goal creates a winning culture), structure the year with easier early quarters, celebrate wins publicly, and defer rewards (announcing trip winners in January, executing in May) to retain talent through the year.
What we cover in this episode
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0:26
Career Journey to CRO From White House intern to 25-year progression through sales engineering, leadership, and C-suite roles in VC and PE-backed tech.
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3:46
PE Creates Urgency and Discipline Private equity ownership forces focus on metrics, leading indicators, and credible paths to exit within 3-5 year windows.
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5:11
Data Reveals True Problems Example: high win rate + low MQLs-to-SQLs pointed to ICP misalignment, not sales talent. Data uncovers strategy, not gut feel.
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8:40
Scaling Beyond $20M ARR Transition requires documenting founder playbooks into repeatable processes, freeing early team to solve bigger problems.
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10:47
Annual Planning and Transparency Break revenue into streams (new logo, renewal, expansion), set monthly targets, and report weekly vs plan to spot drift early.
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15:00
Why CROs Get Fired Average tenure 18 months: CROs fail by hiding bad news or committing to unrealistic numbers they cannot deliver.
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23:10
Weekly Reporting and Contingencies Flash reports align team on plan vs actuals, surface issues before board meetings, and invite collaborative problem-solving.
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32:52
Territory and Comp Design Equitable territory setup reveals true talent; quota structure (80% of reps at 80% of goal) and early-year wins build culture.
The lines worth sharing
The things that you had to do to succeed to get where you are today are the opposite of the things you will do to succeed to get to the next level.
JD Miller · 20:33
We win together, but we lose alone. When things aren't going well, you've got to be vulnerable and bring everyone into the conversation.
JD Miller · 24:17
You might not like the news I'm delivering, but you can count on it. If I cave to pressure and commit to a number I don't believe in, in six months I'll be fired.
JD Miller · 31:15
About 80% of sellers hitting 80% of quota creates a happy organization. They feel close enough, and top performers at 110-120% inspire the rest.
JD Miller · 32:52
Common questions from this episode
What causes CROs to get fired?
CROs get fired when they hide bad news or commit to unrealistic numbers they cannot deliver. The 18-month average tenure reflects leaders who fail to surface problems early with a corrective plan, then get blindsided at the board meeting.
How do you set an annual plan that doesn't get missed?
Break revenue into streams (new logo, renewals, expansion, upsells), assign monthly targets, factor in churn and turnover, layer quotas (board sees 100%, execs 105%, field 110-120%), and review weekly vs plan to course-correct early.
What is sales velocity and why does it matter?
Sales velocity = opportunities × win rate × average deal size ÷ days. It isolates what's failing: conversion, pipeline size, deal size, or sales cycle. Miller used it to diagnose that market downturns had shrunk deal size, not talent.
How do you keep top reps from leaving?
Set equitable territories, make quotas attainable (80% of team at 80% of goal builds culture), celebrate early-quarter wins, offer sales club trips, and defer rewards. Announce winners in January, execute trips in May to retain talent.
How should you communicate bad news to the board?
Report weekly, show your work, admit shortfalls with data-backed root causes, and present a credible corrective plan. Boards respect transparency over surprise; missing a number is acceptable if you explain why and how you'll fix it.
What is an ICP problem vs a sales problem?
Miller discovered high win rates but low MQL-to-SQL conversion (22%), revealing marketing was chasing wrong personas, not that sales lacked skill. Fixing ICP and targeting improved both efficiency and revenue.
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JD Miller, former CRO at Kantata, shares how data-driven strategy and transparent board communication separate CROs who survive from those fired in 18 months.
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The CRO's Guide to Winning in Private Equity
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Read the full transcript · 51 KB · JD MIller
RACHAEL BUECKERTWelcome back to CRO Stories, a RevOps Corner segment where we interview brilliant chief revenue officers to see how the best in the biz are helping B2B SaaS companies grow. I'm Rachel Buchert. I'm the marketing manager here at Union Square Consulting, and joining me today is J.D. Miller, the advisor and former chief revenue officer at Quintata, as well as operating advisor for Rothschild & Co.
RACHAEL BUECKERTThank you, J.D., for joining me.
JD MILLERThanks for having me, Rachel. It's great to be here. Yeah. So how about you start us off with a little bit of your background? Absolutely. So I went to college thinking I was going to be a lawyer. I had an undergrad in communication, philosophy, and literature, which is a great pre-law curriculum. But after I interned in the White House and realized that I didn't want to be an attorney, I looked at those degrees and I thought, you're not going to be a professional philosopher. You're not going to be a professional literature comparer, so it must leave your communication degree as the thing to get into. It was the late 90s, and so I wound up working on a master's in how social networks form online and then began a career working for a dot-com. Over the next 25 years, it's been a series of progression from being a sales engineer to an individual contributor to sales leadership, CRO, CMO, country, president, all in B2B tech companies, generally always owned by private equity.
JD MILLERAnd hugely an integration of a U.K. and a U.S. company coming together for the first time.
SPEAKER_04Awesome. That internship in the White House sounds really interesting.
JD MILLERYes. I was not the most famous of the Bill Clinton White House interns, but it was an important experience for me nonetheless.
RACHAEL BUECKERTYeah, that's awesome. So, what made you realize you wanted to journey into the chief revenue officer role?
JD MILLERYeah. So, you know, it was just the natural progression. The first company that I worked for, we were 26 employees, and six years later, we were 6,000 employees with a $9 billion valuation. And so, that first experience, you know, kind of going from very small dot-com to very large publicly traded companies, is one that, you know, had a lot of lessons to be learned. And early on, I said, you know, there's a lot that's repeatable here. And so, as I then looked for the next jobs, it was constantly, you know, where do we find a company that's, you know, maybe not 26 people, but maybe 20 million, 30 million in revenue on that growth journey.
JD MILLERAnd I constantly found that as I got there, there were things that I had seen in the past and could replicate and repeat, which would help us get to the next level. And that's actually what private equity is about, too. I sort of say it's like house flipping.
JD MILLERYou know, they start with a company that's got good, strong bones, and then you do the things you know how to do, and suddenly it's worth more later on. And so, you know, looking at that experience over and over again, it just naturally progressed into sales leadership, and then ultimately the CRO seed a couple of times.
RACHAEL BUECKERTAwesome. And that's really great, because I feel like you can just learn these skills and learn this blueprint. And I mean, every business is going to be different, of course, but once you have, you know, the blueprint down, you can go almost anywhere, I feel, and be able to make a real impact in that company.
JD MILLERAbsolutely. So much of my job has been, you know, stepping into a company, leading it for two or three years, helping do, you know, a couple of good things. It's often, you know, building on the data that they have and getting some better kind of strategic leadership in place, and then leaving it better than you found it and moving to the next.
JD MILLERAnd that actually is why I wound up writing the book, The CRO's Guide to Women in Private Equity, is sort of the collection of those blueprints, best practices, and experiences to speed the journey for other folks.
RACHAEL BUECKERTYeah. And that's coming out in January, I believe?
JD MILLERJanuary 14th. Yes. January 14th. It's available for pre-order today on Amazon and everywhere good books are sold.
RACHAEL BUECKERTAwesome. Cool. So is it that different doing this stuff for private equity company or their portfolio companies and companies that aren't backed by private equity?
JD MILLERSo I think private equity creates a lot of urgency. As investors, there is usually a timeframe that they want to be involved in the business and see results. And usually it's, you know, somewhere between three and five years.
JD MILLERAnd so I think the skills are exactly the same, whether you're owned by private equity or not, but that PE ownership definitely gets everyone's attention on what are the metrics of the business today? What are the metrics of the business we want to see at the end of the journey? And how can we really quickly get there?
JD MILLERRight. The good news is, you know, it's all the basic stuff that everyone benefits from. So CROs, you know, not just chasing a number and every week forecasting, am I going to hit the number or not?
JD MILLERBut looking at all of those underpinnings of what are the leading indicators of conversions from marketing? What does our sales velocity look like? And how can we inspect it, improve it, report on it, and continue to measure it ultimately gets us to a better place in a short amount of time?
RACHAEL BUECKERTYeah, because it's not, I mean, when you're working with private equities and stakeholders, it's not just about, you know, how are we hitting our numbers?
RACHAEL BUECKERTIt's they want to know all of the little details in between and how are you getting there? And, like, what are the, like, the evaluations of certain things and the profitability of the company?
RACHAEL BUECKERTBecause that all rolls into there's going to be an exit or, you know, there's going to be a merger. That's stuff that they need to know.
JD MILLERYou're exactly right. And I think that data can really inform what your strategy needs to be.
JD MILLERYou know, a couple of jobs ago, I was hired into a role where the company thought that they had a sales problem.
JD MILLERAnd, of course, that's usually why they wind up hiring a new Sarah Rowe. It's, you know, it's not good. They're not getting the results that they want.
JD MILLERAnd so, as they interviewed and recruited me, they said, you know, you're going to have to come in and turn over the talent to the sales team and really teach the sales team some new stuff. When I got on board and I started digging in, I looked at the talent of the sellers and I looked at their data and I saw that our sellers were actually winning 33, 35% of the time. That's a really great win rate. So I was like, hmm, if we're not getting the results we're looking for and the win rate is up, what else is happening? And I started to look at marketing conversion rates and their MQL to SQL conversion was like 22%. And all of a sudden the light went on. It was like, hey, you know, you're spending all of this money in marketing. They're creating a ton of marketing qualified opportunities. And they were going to board meetings month after month saying, here's another thousand opportunities I created. But 80% of them were getting rejected by the sellers immediately. And so, you know, when you look at that data point, it said, okay, this isn't a sales problem. This is an ICP problem. How do we align sales and marketing on what does a good lead look like? What's the right industry or what's the right persona? And so, you know, as the CRO at that company, I was actually running both sales and marketing. So they both landed on my plate. It wasn't a finger pointing game. It was like, okay, I thought I was going to come in and teach new sales processes and upgrade the sales team. Instead, we're going to do a whole marketing map and we're going to really talk about ICP and we're going to really design, you know, persona targeting. Because if we can get those MQL to SQL conversions up by targeting the right people, the revenue is going to flow from the end.
RACHAEL BUECKERTYeah. And then also that comes down to go to market efficiency as well, because the more money you're spending on marketing that you're just like throwing into a hole, you know, getting leads.
RACHAEL BUECKERTThese people that aren't ever going to convert sales isn't even going to talk to them because they're terrible leads. You're wasting all of that money. So shifting that focus, you're not only selling more, but you're putting your budget to better use and getting more ROI from all the marketing dollars that you're spending.
JD MILLERYou're exactly right. You know, today I get to sit on boards and serve as a board advisor to a variety of companies that are owned by different private equity firms.
JD MILLERAnd I was talking to one of their marketing leaders today about that efficiency metric, and they have a product that only applies in certain geographies of the world.
JD MILLERBut we were starting to look at their web traffic and organic SEO was generating the biggest percentage of their organic SEO was coming from geographies that their product can't support. And so, you know, it's this exact discussion about what's the money we're spending, what are the things that we're doing that's generating this traffic, what's the money we're spending on that, and how do we reallocate it to a market that we play better in, because that's where you're going to get results. But I think a lot of times, you know, the companies that I work with are usually, you know, maybe 20, maybe 50 million in ARR, and then they're growing to 200, 300 million.
JD MILLERA lot of times that's a transition point where you've had a founder run your company for a while, you get to 20 or 30 million, and then all of a sudden you have to become this, you know, big global player with all of the processes and all of the, you know, all of the structure that's going to help you scale globally. And suddenly that means that you're looking at a lot of data and you have access to a lot of data that you just never did before. So it's really kind of, you know, skills and tools and techniques to help grow your company beyond what one person can personally do.
RACHAEL BUECKERTYeah. And so when you walk into an organization like this, they're 20 million, 50 million in ARR, what is kind of like the first thing that you do or you have done in the past to get them to a place where their operational maturity is at a level that they can withstand that level of scale? Yeah. So first of all, it's a lot of listening and it's a lot of asking.
JD MILLERYou know, it's a very rare company actually that goes from startup to 20 million. You know, most, most startups fail before they've even gotten a million dollars in the revenue. So the fact that you've gotten to be 20 million already means you're a huge success.
JD MILLERAnd so a lot of my first work is understanding what did you do to get there and who are the key players and what are the things that they're doing? Because a lot of times a company will top out at that level because it's the maximum number of customers that I can personally manage. And, you know, suddenly I've got to hire a second, a third or a 10th salesperson and have everyone doing things exactly the same way that I did or the founder did. And so one of the first things that I'm doing is really understanding what success looks like and documenting it into a playbook that then we can go off and hire and teach people to do the same things that the earliest founders and the most successful people did. And the good news then is it frees up those those early folks to move on to solve the next big problem that only they know how to do.
RACHAEL BUECKERTRight. Yeah. And those problems get even bigger as you scale as well. So absolutely.
JD MILLERYou know, we just finished the presidential election in the States. You know, a previous president said, you know, by definition, the only problems that end up on my desk are the problems that no one else could solve because it's kind of worked its way up.
JD MILLERAnd same thing with, you know, company CEOs and company heads of sales is, you know, if you've done a good job of teaching your front front line teams how to do the routine stuff, the exceptions are going to come to you.
JD MILLERBut the better you are at teaching your team to solve those problems, the exceptions that are making it there are going to be increasingly more complicated.
SPEAKER_34Yeah. Yeah. And that's why you get paid the big bucks.
SPEAKER_41We hope.
RACHAEL BUECKERTWe hope. Yes, that's the hope. All right. And so in terms of annual planning, I really wanted to dig into annual planning with you because I know you have a lot of information on this.
RACHAEL BUECKERTAnd we recently published our own framework on annual planning and like how we tackle creating annual plans with our clients and executive communication and, you know, creating scenarios and assumptions and all these things. So I wanted to get your perspective on it as a CRO, your experience coming into companies and, you know, seeing where they're at with the current way that they're tracking their metrics, the metrics, like what metrics they are tracking and how you went from there to helping them create annual plans that are driven by data and real, real data that comes from the truth of what's happening in your business. And not just, you know, inaccuracies or hopes and dreams or assumptions.
JD MILLERThis is one of my favorite topics. It's actually it's the first chapter of the book is probably also the longest chapter of the book, because when I was an individual contributor, I had no idea where my quota came from.
JD MILLERI knew that I had a quota. I thought someone plucked it out of the sky and the next year I had a bigger quota and I had no idea how they got there. And, you know, the annual plan is the core thing that's in a well-run company is going to is going to sign those with sanity. And so it's one thing for a CRO to know I've got to go sell $50 million of revenue next year. The annual plan really helps them align everyone on how are we going to get to that $50 million? Because it's not just show up to work tomorrow, make some calls, sell something and tick a little bit closer and hope that we get there. You actually have to start by breaking down what are all the revenue streams. So chief revenue officer, you know, they're in charge of every kind of revenue to the company. So there's new logo sales. You're going to go win a bunch of new customers. You have a bunch of existing customers that you need to renew. You have a bunch of existing customers you're going to sell more to. And then maybe you've got some other streams going on. So how do we break that $50 million down into a certain target for new logo, a certain number for renewals and price increases, and a certain number for cross-sell and up-sell? And then you've got to go the next step and start breaking down how do you get to each of those individual goals. So just because you entered the year with $100 million of customer contracts, they're not all going to renew. And you already know from your data. You've got some satisfaction data. You know the people who are calling your help desk all the time or complaining or maybe not using the product. So you can predict some churn. You've also got data on their contracts that say, what's the price increase that they're already signed up for? And then when does that renewal happen? Because not every customer comes up equally across. It's not 12 equal months of renewals. You've got some times where a ton come in and some, but none come in. So you can sit down with an annual plan and assign a number, in this case, on just renewal and price increase month by month and know what should happen, what your target is, and how you're going to get there. And then you can do the same process for what's my new logo going to look like, and maybe I'm doing new product launches, and what's the seasonality and what's the timing of that new product launch. And then publish in one piece of paper that everyone can see, every source of revenue month by month, what's the target, why did we get there? And then once you've set the annual plan, I think the next big thing about being a great CRO is being able to then look back at that month by month and be reporting to your team. Are we hitting it? Are we not? What's failing? Why? And how do we course correct?
RACHAEL BUECKERTAbsolutely. And I think that is a really big missing piece for a lot of companies.
RACHAEL BUECKERTYou know, they set the plan, usually just based on hopes or, you know, stakeholders are asking for a number. So they're like, okay, that's the number we got to hit. And then it's kind of set it and forget. And they don't think to like look back on it, you know, either week by week or quarter by quarter and see, okay, like what is happening inside our entire go-to-market funnel? Where do the numbers not match up? You know, are we on goal for our targets? And if we're not, what is happening within our organization that's making it like that? And what dials do we need? To turn.
JD MILLERThat's exactly right. And I think that the better you can lead that conversation, the more longevity you're going to have this CRO. There was a Harvard Business Review study came out that said the average tenure of a CRO is 18 months. So by definition, you know, if I'm only going to sit in that seat for a year and a half and then I'm going to get fired, you know, by definition, a lot of that time I'm running a plan that wasn't my own.
JD MILLERAnd I really think that we're not firing those CROs because they're not firing those CROs because they're not able to tell you why we're missing and what's going to change about it. And so in my own career, you know, I've been fortunate to have many long tenures and get all the way to the exit. It doesn't mean that I've gone to board meetings every month and said, congratulations, our team is doing so well. We beat our plan. But what I have been able to do almost every time is show up to the board meeting and say, this is the number we're hitting. This is where we're going to do next month or next quarter. And here's why. And so it may not be the number you want, but here's where the shortfall is.
JD MILLERHere's what we're collectively going to do to fix it. And can I enroll you that that's the metric we're going to be watching over the next couple of months? Because if we agree that this is the problem and the root cause, and if we agree that my strategy to fixing it is right, then our board meeting is just about reporting how am I doing on implementing that change and the revenue is going to come.
JD MILLERAnd I think that's what differentiates a CRO who keeps their job for a long, long time and one who gets shown the door pretty quickly.
SPEAKER_37Yeah, absolutely. And the only way to be able to get to that point and be able to do that is to know how do you set up your organization to be tracking accurate metrics?
RACHAEL BUECKERTAnd, you know, do you know how to look at those numbers and take insights from them? Do you know what those numbers mean when they come in? So let's say you created an annual plan and, you know, things, maybe they're not going the way that they should be. Do you have a story or like some experience that you've had when you've discovered this and insights that you've gleaned from it and how you came to those conclusions and how you fix the situation?
JD MILLERYep. So a couple of them. We talked earlier about the difference between MQLs and SQLs and seller skill. But, you know, another place where that metric of sales velocity has been really meaningful to me is to break down, you know, what's going on in a business.
JD MILLERNow, sales velocity is it's the number of opportunities you have times your win rate times your average deal size divided by the number of days. And so if you do that math, it kind of breaks you down into, like, how many dollars are you bringing in every day? And I was sitting in a business that, you know, we weren't hitting the goals that we looked for. And I finally said, okay, let's look back at our sales velocity metric and let's look at how many opportunities are we creating?
JD MILLERThe market is creating all the opportunities that they signed up for. What's our conversion rate? Well, we're converting as many as well, right? So that's going really well. How's the skill of our seller? How's our average deal length? That's going really well, too. It's, you know, 45 days or less. It was deal size had suddenly changed year over year.
JD MILLERAnd we had built an annual plan that expected a deal of, like, $90,000 of ARR. And something had happened in the market that all of a sudden our deals were only $70,000 of ARR. So collectively, we were missing the goal by, we'll do the math faster than I, 20% or something. But doing that next level of data analysis said, okay, it's deal size. That's our problem. What happened? You know, let's look at the industry. Okay, all of a sudden, the industry that we served was going through a downturn. And so they weren't hiring as many people. They weren't, you know, signing up for as many licenses. And our existing accounts weren't calling as frequently saying, I just hired 10 more people, get me more licenses. So all of that was just depressing our deal size and, you know, ultimately depressing our outcome. So with that in mind, then we could have a really strategic conversation about what are the things we can do to get bigger deals? Okay, maybe we should start targeting our sales and marketing engine further upmarket than we ever did before. Because here's a whole set of players that we might have thought were too big for us to serve us, that all of a sudden in this downturn, they're the right size for us. And so kind of tweaking that, you know, marketing focus, ICP, sales focus is what got us there.
JD MILLERNow, a CRO in a big company, there's tons of data available to you, but you can't possibly
JD MILLERknow it yourself. And so the other big thing for me is having a really good revenue ops leader or rev ops team for a partner, like an organization like yours, it can help me really diagnose that. You know, a lot of times with private equity, we come in, we've got to collect all of this stuff really, really quickly. And the organization is often sitting on the data, but they don't know what they've got. And so it's often really helpful for me to bring in a partner agency, a consulting agency that says like, let's do a quick deep dive. And in four weeks or six weeks, we can get a ton of really good insights that are going
SPEAKER_29to inform our strategy for the next two, three, four years.
RACHAEL BUECKERTAbsolutely. And you know, like that's pretty much exactly what we do at Union Square Consulting is just, it's just about having, you know, a third party set of eyes that can look at that data and
RACHAEL BUECKERTanalyze it without any prior bias, like no sales bias, no marketing or no internal bias, you know, and give you that truth of what's going on in the business and the visibility of what's happening. So you can make those decisions and make those calls because something like that. Yeah. Like if you're, if the problem is at an ICP level, that's a huge domino effect, right? Like that just knocks down everything.
RACHAEL BUECKERTLike you said, it was affecting new business sales. It was affecting churn, expansion, like everything. And of course, that's going to make a huge difference to your revenue at the end of the year.
JD MILLERYep. And I love that you talk about a fresh pair of eyes too, because, you know, the thing about growing companies is the company is always changing.
JD MILLERAnd I work with a leader who talks a lot about the ages and stages of a company and the kind of summary of his message is the things that you had to do to succeed, to get where you are today are the opposite of the things that you're going to do to succeed, to get to the next level.
JD MILLERYeah. And it kind of makes sense.
JD MILLERYou know, when you're a small startup and you're doing all this scrappy stuff, like here's where I focused my engine. Here's the kind of calls I made. Here's the kind of metrics that I did. And all of a sudden it buys you a seat at the table now to play in a bigger pool or a different pond or different industry. Now, as humans, we look at what was our success skill. And we said, oh, what did I do for the last three years? I got me all the accolades. I'm going to keep on doing that. And all of a sudden you find the wall of like, geez, I keep doing the same thing, but I'm not getting the same result. It's a great sign that someone from the outside who doesn't have that bias may be able to really quickly tell you, okay, look, look at the bigger picture. Yes. What you were doing was right for the time that you were doing it. And now all of a sudden you're, you're operating in a different context that you didn't even realize the waters changed around you and here's a way to shift. And, you know, it's often easy, small tweaks that'll then unlock a whole nother layer of growth and potential for you.
RACHAEL BUECKERTYeah, absolutely. Like the saying, what got you here won't get you there. I think it is.
JD MILLERExactly right.
SPEAKER_53Yeah. Yeah.
RACHAEL BUECKERTAnd yeah. And like having that, that other set of eyes, somebody who has gone through those growing pains also that, that you're currently experiencing. So a whole different set of experience of, of like going through these changes and like knowing
RACHAEL BUECKERTwhat it takes to get to the level that you were trying to get to.
JD MILLERAbsolutely. And that's what I love about the work that I get to do today, but also, you know, having been a CRO in private equity is the PE firms, you know, there's a whole portfolio of companies
JD MILLERthat look just like you. And so today at five arrows, we've got 35 or 36 companies, you know, I have the luxury. I get to go see all of them, but also all of our CROs have a network that, you know, I guarantee there's someone else in the portfolio that's having the same challenge around structuring commission or, you know, how do I plan my sales kickoff or whatever it is that you can look to your peers or you can look to your board or your advisors and get connected with someone who says, I've been here before. I've walked this road. Let me tell you the mistakes that I made. So at least you're not going to make that one again and we can make new ones together.
RACHAEL BUECKERTYeah. Yeah, absolutely. And so once you have this, this annual plan created and everything's, you know, tracked out, how do you continue?
RACHAEL BUECKERTHow do you build on from that throughout the year and make sure that you're moving towards that success?
JD MILLERYep. So, you know, again, I keep thinking about this military leader that I've worked with who also had this little pithy phrase about, you know, no plan survives its first contact
JD MILLERwith the enemy, right? And I also think no annual plan survives its first contact with the field in the real world. But I think it's really important to always have that front and center for us and then implement with our RevOps partners, hopefully, or someone in finance, a cadence that every week we can analyze what did we expect to have happen, what's really happening and how do we move that forward? So I have a little flash report that I use and there's a template in my book that people can download too, but it's just a weekly email that goes to me, all of my sales leaders, every member of my executive team and part of the board of directors that says, here's a look at the quarter. Here's what our annual plan said was supposed to happen. You know, so far. And now as of week two or week three or week four in the quarter, here's what's happened so far. And just kind of realign us all again. What were we trying to accomplish? Are we close or are we way far off? And then, you know, when we start veering off course, it can then stimulate, what are we going to do about it next? And I think a lot of leaders and a lot of first-time sales managers don't want to report that bad news. And they're like, oh, it's not going really well. I'm going to keep it a secret. Well, that's no good for you because then you get to the end of the quarter and you're finally going to that board meeting and you've got this huge bad news. And that's the recipe for becoming a leader who gets exited from the business. If I can communicate with you on a weekly basis, you know, we're starting to tell you the story. You know, one, it eliminates surprise. But two, it also starts to bring some of the best minds to the table to work with you on, okay, so what are we going to do about it? What might we try doing differently that's going to get us to a different result?
RACHAEL BUECKERTYeah, and like you said, it doesn't always have to be good news, but there has to be news.
RACHAEL BUECKERTYou know, if things aren't going the right way, it's worse in the long run trying to hide it and trying to, you know, oh, maybe I'll just like fix this on my own and no one will ever know, you know, and, you know, it doesn't really work that way most of the time.
JD MILLERRight. Yeah, it's that, like, we win together, but we lose alone. And, you know, truthfully, you know, the time you need your team the most is when things aren't going well. And so you've got to be vulnerable. You've got to be open and honest.
JD MILLERLike, here's what's happening. I'm not sure what the answer is. Let's bring everyone into the conversation and hopefully we can figure it out together.
SPEAKER_34Yeah. And again, like I said, that third party unbiased opinion, right?
RACHAEL BUECKERTThey're not really worried about, you know, bringing bad news to the table usually because
RACHAEL BUECKERTit's just the truth of what's happening, right?
SPEAKER_60Right.
RACHAEL BUECKERTYeah. And you can't grow as an organization without knowing what's happening with your organization.
SPEAKER_22And it's okay. You know, it's raining today. That's fine.
SPEAKER_61Yeah.
SPEAKER_22Let's go get an umbrella. Let's figure out how big our umbrella needs to be.
SPEAKER_09Let's not pretend it's not wet outside.
RACHAEL BUECKERTExactly. Exactly. And in terms of like contingencies and preparing for, you know, unexpected things to happen
RACHAEL BUECKERTin the year, or maybe some of them are expected or you should expect them, like things like employee turnover, you know, internal churn. How do you build that into your annual plan? Like these things that might completely throw a wrench in the gears?
JD MILLERYeah. So this is a huge part of my annual planning template as well. It's actually, if you go download it, it's this really big, long Excel spreadsheet. But, you know, first of all, you've got to start by thinking, what are the risks? You know, you shouldn't build an annual plan that assumes every seller is going to be in
JD MILLERthe seat for your whole year. So let's work with our HR partners and say, what does turnover look like in our business historically? You know, how long do people tend to stay? What time of year do they tend to leave? And when I build my plan, you know, I'll assign quota out, but let's go plan on, I don't know who they're going to be, but let's take out three senior sellers in February because that usually seems to happen. And then the next piece is, you know, once that person leaves, how long does it take our charge to recruit the next replacement? What's the ramping period? So I might take out, you know, 100% quota performer in February and not expect their replacement to have any revenue at all until September, October, November. So kind of building all of that in is a really important thing. I think the other thing is once you've set up your annual plan, you've broken down your number and your goal, you know, it never adds up to what the executive team or the board wants. I've got an annual plan to do 20 million and they're like, great, but I really want 30. When you get to that point, let's talk about the bets and let's talk about the guesses. Let me look at my annual plan and show you how I get to 20. And then we can start to add additional lines into our plan that says, okay, we think we're going to get another million dollars because we're going to do this sales training process and that should start impacting our conversion rates in June. We are going to launch this new product and we think we're going to sell, you know, one in the first quarter and three in the second quarter and whatever. But again, all of those assumptions become things that when we're looking at that monthly cadence, we're saying, where have we gotten to? You know, it's not just you're missing the number. It's you got the new logo you wanted. You got the upsell you wanted. Oh, that product didn't even launch yet. So there's a half a million dollars of revenue that, you know, we planned for that isn't here and the product's not even going to be here for three more months. Getting all the voices at the table to understand the why of the mess and what the hopes are for the corrections is a big, big part of the job.
SPEAKER_04And so how much like buffer room do you try to build into your annual plans to account
RACHAEL BUECKERTfor these contingencies and things that you're not expecting?
JD MILLERYeah. So this is the big secret of leadership, right? You know, when I was an individual contributor, I just thought the company's goal was, you know, my quota times the number of sellers out there. So actually I put out, once we've built our plan for what we need in the year, I assign 120%
JD MILLERof quota to people in the field. So, you know, I have extra selling bodies and I have slightly bigger quotas so that we've got about a 20% quota for people to miss their number or turnover or things like that. Now my managers, they're working to 110% of the goal. And then the executive team is working to 105% of the goal. So usually it's that executive plan, that 105% performance that we're talking about every day. And then the board is seeing just the board plan, which is that, you know, 100% number. So you've sort of built all of these layers and backstops of, you go to the board meeting, you're talking about a hundred. You go to work every day, you're talking about 105. You're managing, you're managing your managers and you're managing your sellers to 110 to 120. And, you know, those kinds of conversations have worked really well for me to actually deliver what the company must have.
RACHAEL BUECKERTOkay. Yeah. Cause I, I've heard that it can be difficult defending that buffer room from the board because,
RACHAEL BUECKERTyou know, they see like, oh, we could be making like 10 million more here. Like, why don't we push for that? And in the back of your head, you're just like, well, that's like my contingency plan.
SPEAKER_61So yeah, you're a sandbagger.
SPEAKER_56You know, for me, it's being bold to the board and showing your work and saying, you know,
JD MILLERhere's the plan and here's the rollup of how I got here. And that's the number that I'm delivering.
JD MILLERWhere do you think 10 million is going to come from? And let's have a really serious discussion about it.
JD MILLERYou know, I worked with a company that spent a nice chunk of change on sales training. Like, oh yeah, you're going to go to sales kickoff and you're going to go hire this sales trainer who's going to do this thing.
JD MILLERIt's okay. That's, that's great. And that, and it's important and we should do it. But don't expect me to sell $10 million as a result of that training the next month. So let's just like realistically say, if you think there's another 10 million, where's
JD MILLERit coming from and why? And then where we began, you know, let's go back to the data.
JD MILLERThe best predictor of future performance is past performance. So what does the data say is most likely to happen? And then any of the bets that we're making on increasing, you know, why do we think it's, it's worth the volume or the size that, that you're hoping for?
RACHAEL BUECKERTYeah. And in terms of having those, you know, probably sometimes hard conversations with the board and
RACHAEL BUECKERTother executives, do you have any like tips or advice on how to approach the board with something like that? When, when they're pushing for more and more and you have to like, you know, temper their
SPEAKER_13expectations down?
SPEAKER_30You've just got to be bold and brave and say it, you know, because for me, I wind up telling my
JD MILLERboards a lot, like, you might not like the news that I'm delivering to you, but you can count on it. And, you know, we might have a really heated exchange about you should do more. And I say, I can't do more. And that might be really tough. But the tougher conversation is if I cave to your pressure and sign up for a number that I don't believe in, and I can't deliver, because then four or five, six months from now, you're going to say, you signed up for this number. Why aren't you doing it? It's time for me to go find someone else.
JD MILLERAnd that I think is again, why, you know, that average CRO tenure is often a year and a half
JD MILLERbecause the CRO hasn't done a good job managing the board's expectations on, you know, what's realistic, what you can count on and what you want. And then from a forecasting perspective, I also love to, you know, forecast a couple of numbers. So I manage my teams and I talk to my boards about, here's our commitment.
JD MILLERHere's our best case. And then here's our real forecast. So as we think about the business, I can commit, we're going to sell this much this month. I know that we're going to do that in our sleep. If we closed everything that's in the pipeline, the very best we possibly could do is in this number. And, you know, guess what? All those stars aren't going to align either. So our forecast is going to be somewhere between those two. And that's what we should manage the business on.
RACHAEL BUECKERTAnd I wanted to go back really quick on the topic of, you know, employees turning out and employee morale and all that stuff.
RACHAEL BUECKERTHow, in your experience, how have you managed to keep top performers around and try to limit as much employee turnover as you possibly can, you know, in terms of, let's say, comp planning, territory planning, the way that you set their quotas so that it's, you know,
SPEAKER_61attainable and not making them feel like, oh man, I'll never be at my job.
JD MILLERYeah. Hugely important question. You know, I think you've got to start by, again, looking at your past performance and having a pretty realistic expectation of what's possible.
JD MILLERNow, my experience as a leader is you've got a happy organization if about 80% of your sellers are hitting about 80% of their quota.
JD MILLERYou know, most aren't going to be 100%. If you can get them to at least 80, they feel like they're close enough. And there's always going to be, you know, a handful of sellers who have that giant deal that there are enough walking around that are at 110 or 120% for that one seller who,
JD MILLERoh my gosh, this year I just got a half million dollar commission check, that the culture becomes sellers thinking, okay, well, I'm at 80% and that's not that far off of where they are. And look at all the money that they got. So I think, you know, from a quota setting perspective, that's one thing we could do. From an expectation setting perspective, I also like to kind of manage the year's expectations
JD MILLERthat it's really easy in the beginning of the year.
JD MILLERNow, most companies, you know, if we've got a hundred million dollar goal, they're not, most companies aren't going to do 25, 25, 25, 25. It's just not the nature of the business. And so I'd like to set an annual plan that whatever history says we're going to do in the first quarter, like to take it down even a little bit further so that, you know, we shape
JD MILLERthe year with an easy to hit number in Q1, January, February, March, we're saying we hit our goal, we beat our goal because that's so good for culture.
JD MILLEREven if I artificially deflated the goal a little bit, and I know Q3 or Q4 is going to be a little bit harder than it should be, it's way better to come out the gates in a culture of winning and celebrating your first two months and going to the first two months of board meeting saying 103% of plan, so much better than, oh, January, we were close, but we were only 95% of plan. And everyone's like, oh, you're kind of losers. And, you know, how did, how did we just sign off on this plan and you're missing it already? You know, that's when people start getting scared and cutting costs. So that really helps culture. And then of course in tech sales, you know, I love a good sales club and I know that there are a lot of, a lot of other organizations don't have them, but in tech sales, you make a hundred percent of your quota and you and your partner are going to go on a vacation somewhere and make a really big deal about that. I also like to plan it where we announce the winners in January, but the trip itself is in like May or June. So those very top performers are going to celebrate you. You and your partner are going to go to Hawaii or Bali or some fabulous, you know, four letter island vacation, but you're going to have to wait around until May. So to do it and that top performer will stay for that trip.
SPEAKER_09And suddenly they're halfway through the year and they're ready to move up. You know, they're ready to keep on going.
RACHAEL BUECKERTYeah. And who doesn't want to stay at a company where like, if you just do your job well, you get to go on a free, awesome vacation.
SPEAKER_56Oh my God. That's amazing. Right. Yeah.
RACHAEL BUECKERTYeah. And so in terms of like helping your reps, you know, reach their potential and succeed and feel good about their jobs and stick around, how do you work comp plans and like territory plans into that and making sure that things are fair and equitable and, and they're set
RACHAEL BUECKERTup for success?
Oh yeah.
JD MILLERI think territory planning is really critical to that. I worked at an organization that sold to a pretty niche industry and there were 10 big players in the industry.
JD MILLERAnd the day I walked in, the territories were set up that eight of those 10 big players were in one seller's territory. And, you know, there was all of this perverse stuff going on where the manager thought that
JD MILLERthat seller was like the smartest seller in the business and all the other sellers were terrible. And actually when I dove into it and I met the seller, I was like, actually, you're not very talented. You know, I went on to sales calls. I was like, you're, you're winning in spite of yourself when we rebalanced that territory
JD MILLERand he only had one of those big 10, but everybody else had one of those big 10 too. Suddenly everyone was performing really well. And we, you know, we've won a ton of those. So I do think when you start the year, you know, sellers don't want to see their territories shift, but, you know, I think you get once a year or maybe once, you know, during the PE ownership, an opportunity to say, we're going to re-level the playing field and give everyone a fair chance to compete. Because if I give everyone a fair opportunity, you know, you start to see actually performance
SPEAKER_29differences between people instead of territory differences between people.
JD MILLERAnd then the second thing is just like we talked about with annual plans, the same way I tell my board, you know, here's how I'm going to build up to our annual number.
JD MILLERWhen I give you your territory and your comp and your quota for the year, I need to give you that plan too. And show you, I call it sort of a wind creation waterfall in the book. You know, your quote is a million dollars. Our average deal size is a hundred thousand dollars. And so the way for you to make your number is you got to do 10 deals or, you know, maybe
JD MILLERwe've got a skew that you're going to make your number by doing one slightly larger deal,
JD MILLERyou know, seven regular deals and four small deals, whatever that is. And then also what are all the precursors to that? You know, so based on your previous metrics, you won one out of every four deals. So you need to have 40 opportunities in your pipeline all the time. And how did you get 40 opportunities? You had to have this many discovery calls or this many cold calls or, you know, work with your BDR on that. And so it's showing people a credible plan that says, here's your territory. Here's the opportunity that, you know, here are the number of companies that exist in it. Here's how many you have to get to different stage. And, you know, now let's just start working week by week on, are we putting in the things
JD MILLERin the early stages that are going to lead to the result? And generally you get a successful team as a result.
SPEAKER_37Yeah. And going back to what you said, or your story about the sales rep who, you know, things
RACHAEL BUECKERTare probably going very good for him. He wasn't the best seller. And then, you know, these things changed around and he kind of got called out, you know, like on, on. He probably wasn't so happy in that story.
SPEAKER_83He probably wasn't so happy.
RACHAEL BUECKERTSo like, that's the thing about making these changes that are for the, for the betterment
RACHAEL BUECKERTof the business at large, right? Like it's not always going to make everybody happy because there are, sometimes people are
RACHAEL BUECKERTwriting off of inaccurate data or, or misconceptions and stuff like that. And I think that's another big hurdle that we face at Union Square Consulting is, you know, getting everybody on board because maybe, maybe there is a decision maker.
RACHAEL BUECKERTMaybe there's somebody and a part of the team, the leadership team, or even, you know, the smaller teams, the sales team marketing who don't want to be on board because they're, they're worried about what that might mean.
RACHAEL BUECKERTLike what these process changes might mean for them and their, their targets and stuff like that, like a big one, if we're, if we're changing our ICP criteria and the marketing team is judged on their MQL attainment, right? We, we change ICPs around and suddenly MQLs go way, way, way down because now our ICP, like we're focusing on a much smaller group of people, but these people were converting way more of them. We're making way more revenue from them, but marketing doesn't benefit from that because they're just judged by MQLs.
RACHAEL BUECKERTSo for them, it's like, what do I do?
JD MILLERRight. Yeah. Yeah.
JD MILLERI mean, I think these are the hard cultural questions, but I think we get through them by always remembering it's the company first. It's not the individual. The company's context changes all the time. And can we all align on what are the company's values that we're a company that is fair, we're a company that's trying to, to drive results. And then what is the company's strategy to get there? And then I think all the individuals can have a very candid and clear conversation about, do you align with the company's values and do you align with the company's goals? And if we have a conversation about that and not about how do we make the company adapt to you, you get to a great result. And sometimes that might be like, Rachel, when the company's values and goals were this
JD MILLERway, you loved it and you thrived in it. And now we're moving on to a new phase that you might not like so much. And that's okay. And if you don't want to continue on that journey, that is fine. And I am happy to go help you find another company that looks like what we used to be, where you can thrive and keep doing that. Converse is true too. If you can let go of the past and you can say, it's still the same values. We still are driving for excellence. And I understand the new strategy and I'm going to be a little uncomfortable.
JD MILLERYou might have a very long career through the next couple of phases of it too. Yeah. And that's great. Absolutely. So we get in problems when we have that one seller that, you know, I used to be the top
JD MILLERseller because all the deals were mine. We can't handicap the whole organization to continue to make sure you're always the top
SPEAKER_47seller. Yeah.
RACHAEL BUECKERTAnd like, sometimes I like, it's the CRO's job to, to convince the other executive team that, you know, with certain process changes, there should probably be different quota and
RACHAEL BUECKERTtarget changes as well. So like for, for my example, with the marketing team, they should be a part of their, what they're judged on should be revenue. They should be accountable to revenue rather than just MQLs. And, you know, once things change where, where we have less MQLs, but those, those leads we are getting, they're creating so much more revenue than marketing now is focused on revenue instead of, you know, they're focused on the thing that's better for the business as a whole.
JD MILLERThat's right. You know, the, the reward structure has to reward the things we want to have happen in the business. And that means that the levers of my comp plan are going to change. And it does mean that, you know, structurally you might shift from, you know, we might've been a small company that I did everything. And now all of a sudden we've got a hunting team and a farming team, or we have an enterprise sales team and a mid market and SMB team that all have different goals. That's fine. The hard thing, but the important thing is that we can clearly communicate it. To everyone in the company, they all understand the company picture.
JD MILLERThey all understand their piece and how it ties together.
RACHAEL BUECKERTExactly. And I think that's like the heart of alignment. I think with sales, marketing, customer success, everybody aligned, communicating between each
RACHAEL BUECKERTother for the betterment of the company. Everyone's aligned to the same goals that are for the betterment of the company.
RACHAEL BUECKERTAnd it's not just siloed operations that are driving their own goals.
SPEAKER_12It's just that it is just that simple or it's just that hard.
SPEAKER_04Awesome. Well, I believe you are coming up on time here, but this is really great. I really enjoyed this chat with you, JD.
RACHAEL BUECKERTYeah. And so your book, The Ciaro's Guide to Winning in Private Equity, where can people find that or order that?
JD MILLERYeah. Best place is on my website, jdmillerphd.com. It has a link that'll take you to all of the places.
JD MILLERIt's available on Amazon. It's available on Barnes and Noble. It's all over the place. But if you want to start at my webpage, jdmillerphd.com, I'll point you off to everywhere else.
JD MILLERYou'll be able to find it.
SPEAKER_92Awesome. And is there anywhere else people can find you on LinkedIn or do you have a newsletter or anything like that?
JD MILLERYep. So my personal website, again, is a great place, but you can also find me on LinkedIn. I'm on Facebook and Twitter as well. Always jdmillerphd is the handle. You'll find me in all of those spots.
SPEAKER_92Awesome. - Well, thank you so much, JD.
JD MILLER- Thank you, it's good to chat.
