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Episode 24

The Five Components of a Successful CEO: Focus, Communication, People, Values, and Results

Episode details

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Joelle Kaufman, a seasoned B2B SaaS expert. Together, they delve into the intricacies of what makes CEOs successful, the importance of executive team dynamics, and strategies for driving company growth in challenging markets. Joelle Kaufman shares her five foundational components for CEO success, exploring themes like organizational focus, effective communication, driving team motivation, empowering teams through growth opportunities, and the embodiment of company values by leaders. Randy and Joelle also discuss the essential aspects of creating a high-functioning revenue engine and the nuances of handling business curveballs, providing actionable insights into executive decision-making and strategic alignment.


Randy Wootton
Randy Wootton
CEO, Maxio
Joelle Kaufman
Joelle Kaufman
Strategy & Revenue Catalyst (aka CEO), GTM Flow

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Video transcript

Randy Wootton (00:04):

Well, hello, everybody. This is Randy Wootton, CEO of Maxio, and your host of SaaS Expert Voices, where we bring experts in and around the SaaS world to talk about what's happening today and what is on the horizon. With me, I am very excited to welcome Joelle Kaufman, who's been in B2B SaaS since 1996. She's had roles in product marketing and sales, has been both a CMO and CRO, and over the last three years has been running her revenue catalyst consultancy called Go-to-Market Flow. Her focus is on helping companies make and recognize more revenue. Joelle, welcome.

Joelle Kaufman (00:41):

Thank you, Randy. I'm so glad to be here.

Randy Wootton (00:44):

Yeah, it's been a lot of fun getting to know you over the last couple of months as we've been talking about this, and then trading notes. It seems like where we would like to spend our time today is really actually not talking about the office of the CFO, but instead based on your background experiences, really focusing on the CEO and what makes CEOs successful. We were chatting a little bit about this series that I've been writing on LinkedIn called The Seven Secrets of Success for SaaS CEOs, a lot of alliteration there. You have your own model which has five components, which seems very consistent.


Just as a reminder for people who want to see what I've written, you can go to my LinkedIn and the seven Secrets are tied to overall results, establishing a winning strategy, shaping the values and standards that will guide your company, building an effective executive team, managing your board and investors, allocating capital to balance the yield today with investments for tomorrow and investing in your tribe, mentor coach, peer group, et cetera. Those were seven that I had, and Joelle, you had five that were sort of similar, but would you mind talking us through your five and then I think we're going to deep dive on two.

Joelle Kaufman (01:54):

Sure. I do want to say, Randy, I think it's important that the CFO and the CEO are partners and aligned, and so everything we're going to cover, which is important for the CEO, the CFO has a critical role to play. I am a huge believer in metrics and a real believer in avoiding surprises. That usually means the CFO knows what's coming and knows how to make adjustments at the company level. For the CEO, number one, you must focus the organization with clarity, clarity of vision, of purpose. That will lead to clear missions that support that vision, prioritization, and most importantly, exclusion of what you are not going to do.


You must see this all the time. There are infinitely more things you want to do and you could do and people have good ideas about. If you do that, you have no focus and you will burn through the precious capital resources and human resources of the company. Number one, know how to focus. Number two, clear and consistent communication that is understood by the listeners. It is not enough that you say it, Randy, it matters what they hear, and learning how to communicate so that people can hear you is one of the key learning opportunities for the vast majority of CEOs. Number three, Daniel Pink has a phenomenal book called Drive, and it says, what motivates people? It's an interesting question. Do you know what the answer is?

Randy Wootton (03:41):

Well, I've read the book a while ago.

Joelle Kaufman (03:44):


Randy Wootton (03:44):

What I think of in general is people want to be able to make an impact. I do think that comes into having clarity about what they're trying to do, understand how it ladders up to the overall mission, and then have autonomy to make decisions within their context.

Joelle Kaufman (04:01):

That is why you are a good CEO, because autonomy is the thing. Now, here's the trick, you want people to have autonomy, but you need transparency. You have to balance those things. We don't like surprises, but autonomy is the only way people will be motivated, which brings me to number four. You have to hire, empower and continuously improve people. There's a saying in Silicon Valley, "Oh, we're going to just upgrade people," and they mean we're going to fire people and hire new ones. Let's be clear, that sometimes is needed. That is an extremely expensive and damaging thing for the organization. Every time you fire, you lose institutional knowledge. Every time you hire, it costs money and there's onboarding and there's risk. Now, if someone's not performing, if someone's not the right person, of course, as a CEO, as an executive, we make those decisions.


What if upgrading the organization actually meant upgrading the people themselves and giving them the opportunity to grow and learn and demonstrate that they can perform at a higher level? That's a fantastic thing to do. I think higher empowering improved people is the fourth of my five. Then finally, CEOs are the embodiment of the values of the company, so they have to articulate them, model them, reinforce them over and over again. If they're inconsistent with their values, nobody will believe the values and they will undermine the credibility of the CEO. I'm not saying what the right values are, I'm saying know what your values are and live them, articulate them and model them.

Randy Wootton (05:47):

Well, this is great. It's lots of stuff I would put in the category of how you do your job versus what is that you're actually doing in terms of thinking about leadership capabilities. You got to get your results done, but then how are you doing it in terms of communicating effective, articulating a set of values, living those values, investing in your people? A couple other things popped for me just hearing you talk through it again, is very similar to what Marc Benioff did at Salesforce with his V2MOM, where you have the visions, the values, and I think he describes it as methods, obstacles and metrics, I think, which is having one sheet that is able to articulate where you're going, very important to articulate values and to live those values so they don't become a Dilbert exercise. That people actually see how you reward and recognize people. That's a wonderful reminder.


I was thinking about your fourth one about the higher empower and improve people. I'm in the middle of a book, Cultures of Growth, by Mary Murphy. I don't know if you've read her, but she is picking up on that thinking around genius culture versus growth culture. Genius culture being what I was experiencing at Microsoft before Satya came on board, we had geniuses running the organization and what it meant to be the smartest person in the room and how you built political capital, et cetera, versus how do you create a learning environment where people are working together to grow. I think to the point you were making in terms of we call it grow our own, where you're bringing people in early-stage career professionals, well then you have to have both invested time and energy and career ladders to help articulate what success looks like at each stage.


You have to develop and build out a management program. We call it management excellence in terms of what does it mean to when you make that transition. Then we also have another framework on top of that, the great leader framework, which is for people that are moving from directors to VPs and now there's another expectation in transition in their career. What does that look like? A lot of things you were describing in terms of the capabilities of how you get your job is what you're focusing more your energy on as you get more senior. It sounds like that's consistent with how you're thinking. Before we go into the other ones, anything else around that higher empower and improved people in terms of what you've seen companies do successfully or where they make mistakes other than doing the turnover that you were describing?

Joelle Kaufman (08:23):

Sure. I think one of the challenges of leadership is that A, the Peter principle. We promote people who've been very successful at doing a function, at doing a job, and then we put them in leadership. Overwhelmingly, we think, well, they're human, they know how to lead. It's my experience that leadership is a skill just like sales is a skill or finance or what have you. If you don't approach it as a skill that can be learned and actually needs to be practiced, I don't care if you're a genius or whatever, the number of natural-born leaders, I mean, he's controversial, but people will say Bill Clinton was a great communicator.


Bill Clinton trained himself in communication, practiced it, got coaching and feedback constantly in order to be great. The idea that you can be great because you are just a really great human, that's a fallacy. We have to invest in creating great leaders and then helping leaders remain great. We'll talk about that when we talk about curveballs a little later, but I do believe that leadership, leaders, are the leverage of any organization. Carol Dweck's growth mindset, which is very pervasive in education, but it's also critical for organizations. Because if you have a culture that punishes people when something doesn't work, you get a culture where people don't take risks.


Now, there are dumb risks and there are good risks and we have to help people figure that out. You want people to take risks, to push the edge of the envelope to try new things, and it will fail. I often say, "Great. What are we going to learn and do differently next?" Now, to my CFO brethren, let's not spend absurd amount of monies failing. Let's try to fail fast, let's try to learn quickly, but absolutely, let's embrace failure for the learning. Let's embrace what we learn, and that makes us better. That creates an organization that's willing to take risk as opposed to an organization that's practicing cover your S, which is not an organization that's going to be great on any front.

Randy Wootton (10:50):

Great insight. I think that idea of leadership is a skill that can be developed over time, and there are lots of different types of leaders. Those that are lead for the front versus those that are supporting behind. You have to find your own natural leadership style. I think I've seen books like, hey, there's seven different leadership styles. I actually was just rereading Peter Drucker's, Effective Executive, and he talks in that book about what it means to be an effective executive. Now granted, it's a little bit dated, it came out in 1965. He uses he throughout, and the language is a little stilted, but he too makes the point that effectiveness is something that can be learned and you have to focus on, he has five things you need to focus on, very consistent with what you've been describing. The irony for me is here I am writing these the Seven Secrets of Success for SaaS CEOs, and basically, I should've started off and said, just go read Drucker. He already said it.


I thought I was having original ideas, but no, it wasn't. It's all gone back to the master. His point around exactly what you're describing is that you build this effectiveness through deliberate intention and very similar in the idea of how do you drive focus and drive trade-offs. One thing you mentioned in terms of clear communications that's understood by listeners, I totally agree with you. Another book that we were just working on in my marketing group was actually Aristotle's The Art of Rhetoric. It talks about how arguments are built in [ethos], pathos, and logos, and how you need to be thinking about when you're communicating, how are you using all three of those levers to be effective? How have you found people measure and validate whether they are being understood by their listeners? Other than taking a survey after the presentation, what's the way that you really know that you've landed your message or that people are really changing their behavior based on terms of where you're directing?

Joelle Kaufman (12:48):

If I'm going to communicate and the massive amount of resources of bringing everybody together, I should have an outcome that I'm aiming towards, and it needs to be clear. If I'm giving an update, I could send that over Slack, I could send that over Teams, I can do that in writing. Why am I communicating? If I know why I'm communicating, then I have a clear change or a clear action I'm expecting to see. Then the question is, do I see it? If I don't see it, the I think evolved leader says, my message didn't land. There's too much else people are hearing. One of the things I've invested in, and I was very blessed to first be exposed to it in 2003 is something called the Process Communication Model. It is based on psychological research by Kahler, is his name, Taibi Kahler.


Process Communication proves that we all have communication channels through which we hear best and through which we communicate best, and there are styles that work better with some people and better with others. If we understand who we're speaking to and what they need, not what I need, what they need, and I use the appropriate channel and approach perception to address how you need to hear things, the probability that you will get my message goes up 10 X. The proof on this, by the way, is that the system Process Communication was adopted by NASA for the selection of astronauts and for communicating ground control to astronauts. Because if something goes wrong, it actually is life-threatening. We need to communicate so the other person can hear.


This is done worldwide, it accounts for cultural bias, it accounts for just different languages. I find it very useful. I work on it with my clients and I've been using it and I have funny stories about that, but that will derail our whole podcast. Learning how to understand how someone else needs to hear, and this is harder as a CEO. You could be in front of 50 people, you could be in front of 5,000 people. How do you do that? Well, you're basically going to have to, to your Aristotle, rhetoric. You're going to have to deliver your message in each of the channels in the same presentation. Some of them will not be comfortable because they won't be what's most comfortable for you. Who cares? Your comfort isn't what we're trying to accomplish here.

Randy Wootton (15:43):

No, I think it's super interesting. I haven't heard of that. Is it a book, the 2003 book?

Joelle Kaufman (15:49):

No. This was actually developed in the 60s. You and I are going Drucker, Aristotle, Process Communication. You Can Go to to learn more about it.

Randy Wootton (16:00):

I'll check it out.

Joelle Kaufman (16:01):

There are books about it.

Randy Wootton (16:05):

We'll put it in the show notes.

Joelle Kaufman (16:06):

There's a couple of really popular books, I just have to look them up and I can send them to you. It's really a profound simplification of what goes right and what goes wrong in communication. Once you get it and use it, your leadership becomes transformed because what is the single biggest instrument of leadership? Communication, that is what we do as leaders.

Randy Wootton (16:35):

I think that's right. I couldn't have said it better. I think that when I think about what it means to be a leader, which we're going to get to in a second, is ultimately, as a CEO, you're responsible for results, delivering results. How do you get those results as a CEO? I actually do very little. It's more about how do you help people understand where we're going, why it's important, and how they can contribute so you're getting results through others, and the vehicle for that is communication. What does that look like in terms of your all hands? What does that look like I send a note when I'm traveling, I call it view from 30,000 feet, I'm coming back on an airport? I remember when I wasn't CEO, I always wondered, well, what do CEOs do? Because you never actually see them.


I provide an insight into where I was, what I learned, and really try to embrace the pathos part of communication versus the logos part of communication. You think about that type of forum and construct is very different than what we do in our QBRs, which is very much about logos. Then there's the, how often and frequently you're just doing personal outreach? With the leadership cadre, we have about 30 people in our leadership cadre and try to meet those that aren't my direct reports once every six months. There's that personal interaction as well. I think to your point, a lot of time is spent in terms of communicating and thinking about the different forums of communication and overall effectiveness. I would say the way that we measure it at Maxio is through, we do employee engagement surveys every quarter.

Joelle Kaufman (18:15):

Like Culture Amp?

Randy Wootton (18:17):

Culture Amp, right, everybody does. A couple of questions in there about understanding, well, one, do you have confidence in the company? If people don't believe the message of the CEO, they may think the ship is going sideways. Number two is do they really understand the strategy of where the company is going? Then we have, like everybody, I imagine, have questions around leadership effectiveness. That too is part of, hey, is the leader helping me understand what I'm doing? Is the manager helping me define the work and where I need to make an impact? I'll be super interested in taking a look at that and digging in, so thank you for sharing.

Joelle Kaufman (18:53):

Well, and I'll add a couple of metrics that are not survey-based, but if you are having high undesired attrition, you have a problem. If you are consistently not hitting your results targets, you have a problem. Now, by the way, that problem could be you're setting results that are not in the realm of possibility or the problem could be people don't know how to do what should be ambitious, like ambition, but possible. One of the things that always takes my breath away is you can just do a verbal check-in with just your leadership team. Simple question, what are the three most important things for the company? Over 70% of leadership teams will not say the same three things. Let me suggest that if your CEO can't align the first team, the probability that the first team is aligning everybody else is zero, non-existent, and so that's really important.

Randy Wootton (19:56):

Yeah, that's great. We're actually going to have our executive leadership team meeting. We get together once a month, we're doing it tomorrow. I'm going to lead off with that, the three most important things the company needs to overcome. have them write

Joelle Kaufman (20:06):

Have them write it down on a piece of paper. Have them write it like a ballot. Even anonymous ballot. Because the lesson for you is maybe you're in the 20 to 30% that's got it, that would be awesome. Probably you're going to have some things that are off and that could lead to, well, are these the right top three or should we make an adjustment? Because you don't want people just parroting, you want people owning it. Autonomy, they have to believe. Okay, but we should talk about results.

Randy Wootton (20:36):

Let's do it, because I think it's a lead in and just the bridge I would make is, everyone has one-on-ones, we have a one-on-one agenda, as I'm sure most people do. In our one-on-one agenda, the top thing is what are your three priorities? Every week that we meet or bi-weekly, we come back and say, "Okay, so are these still the right three priorities?" Then I think also having the, hey, what are we putting in the parking lot? Which is around your idea of exclusions and trade-offs. You can have these conversations about things that seem to be exciting, the new shining object we need to go work on, but then you're always putting them against the top three priorities.


Does this supplant one of these? If so, why? The other thing that does I think for people, and this may be goes into building the effective executive team muscle that we'll talk a little bit about. It gives people space and control over their lives. If they're feeling overwhelmed, they can always go back to, well, these are the top three things I need to work on this week. It's not changes every week, but over the next month it might putting enough energy and exerting enough time to really address the things that are really the top three. Then as long as we're aligned, they feel like they can be successful. Still feel like they're working super hard, but they're not feeling like they're overwhelmed.

Joelle Kaufman (21:52):

Top three for each individual executive could be very different across everyone on the leadership team, and that's okay.

Randy Wootton (21:58):


Joelle Kaufman (21:59):

The question is, what are the top three for the company?

Randy Wootton (22:02):

Got it. Totally. That was new.

Joelle Kaufman (22:04):

Great. I just wanted to make that distinction.

Randy Wootton (22:05):

That's what I'm going to do.

Joelle Kaufman (22:05):

I just wanted make that distinction.

Randy Wootton (22:08):

You would hope that the two would be connected, that if you're working on the top three for the company that there's some way for each of the executive team to see how they're supporting and driving it.

Joelle Kaufman (22:19):

Well, it can be that one of the top three things is particularly product oriented, and your engineering and product team has all of their top threes focused on that one, but they know what the other two are. If I can add another thing, the number of times I have CEOs say, "Well, the top three is that we make our revenue number." I'm like, "Okay, that is a measure of having done something. It is not the thing. It is the result."

Randy Wootton (22:52):

Well, let's shift there. One of the things we're going to talk about in the Seven Secrets of Success, and it overlaps in terms of the conversation we've just been having around delivering overall results by building a high-function revenue engine.

Joelle Kaufman (23:02):


Randy Wootton (23:03):

Can you talk a little bit about how a team needs to do that and think about it and the four whys and a who, and then we'll just go from there?

Joelle Kaufman (23:11):

Sure. One of the areas that people trip up is when you say, what's your ideal customer profile? They answer with four or five personas. Let's be real. You sell something complicated at Maxio, there isn't a single person who's going to say, "Oh, I'm the buyer." There's buying teams, and those buying teams have multiple stakeholders, and those are multiple personas. I understand how this happens, but who's your ideal customer? Who's the person, the role, the level, the context they're in that's going to champion this? Because entropy is real. People don't like doing something new and different. It doesn't happen because you're a fabulous salesman. It happens because somebody on the inside says, "We need to do this. This problem is so painful, is so urgent." Whatever is happening. Understanding your ideal customer profile, and there are, as I said, four whys and a who.


Why is your solution a top three priority for your ICP? Before you got there, why is this a top three priority for them? It's really hard to make a prospect change their company's priorities. That's a heavy, heavy lift. It is way easier to find the people who've already made this a priority. By the way, I don't mean buying Maxio or buying something else. I mean, I'm going to do consumption billing, I'm going to do subscription billing. I need to offer this in my product. Great, well, then I'm going to need a solution to do it, but the problem is there. Number two, compared to anything else they could do, why are their other solutions, including their existing, unacceptable ways to solve this problem?


It can't be, well, it's not as good, or, oh, it's a little harder. Why is it going to be fundamentally unacceptable? Third why, why is your solution 10 X better than other options? One of my funnier stories is I have a CTO I've worked with for many years, I adore him, and we were having a conversation about differentiators. I said to him, "Based on our market, what do you think are the most important differentiators that will help our customer, our ideal customer, solve that problem 10 X better?" He said, "No. You need to look at what we've got and determine what differentiates it from the competition." I said, "Well, no, that's backwards." It's scary what I'm saying because I'm saying you as a CEO, as a CTO, as a chief product leader, as a sales team, have to say, we know who our ideal customer is. We know the problem that is so painful, it's made their top three, and we know what will be 10 X better for them, and that is what we're going to build for them.


We have to do this all usually before the customer can actually articulate what those things are because they don't know. They haven't used it. They're used to what they've got. We have to take some risk. We have to lay a bet, but our bet has to be we're going to do something that's 10 X better. By the way, if what you're saying is we're going to disrupt an existing technology, well, you're not going to disrupt them by doing everything they do because they're going to do that better. They've been doing it for a while. You're going to disrupt them by doing something that people need desperately, dramatically better than their other solutions. Who, remember we talked about all those stakeholders and all those personas? This is where the personas show up, who must align to select your solution? Who has to say yes? Because each one of them has a veto.


I'm not suggesting you throw out your persona work, I'm suggesting you see the difference between the ICP and a stakeholder. Finally, and my favorite, why does your ICP need you now? My caution to anyone who's watching or listening to this podcast is the answer to this question has nothing to do with you. It has to do with them. It has to do with something happening in their career, in their company, in their market. There is something external to you that has made this go from a nice thing to do, to I'm going to spend this quarter getting this thing done because it is very hard unless you're selling something that's very, very cheap. It's very hard to actually buy things as somebody who's been the buyer inside multiple organizations. Even in smaller organizations, the number of hoops, whether it is the CFO hoop, the privacy and data hoop, the CEO hoop, the aligning my colleagues and sales and marketing hoop, there's lots of hoops.

Randy Wootton (28:34):

Well, those are great. Just as you're ticking through them, I'm thinking about our own challenges. One of the things we would say is playing out is even though the stock market is going up and large tech companies are driving that increase in value, what you find broadly across the B2B SaaS base is there's been a contraction. That is due in part because the VCs and PEs have pulled back their money. What that has led to with the heart rising interest rate, that what has that has led to is CEOs and CFOs saying, "Hey, pull back spend on internal software." We're an internal software vendor selling into the office of the CFO, which is also really hard because the CFO is telling everybody else to stop spending, so it's hard for them to advocate for a technology change at this point. Gosh, feeling what you're describing. I think the number one barrier we have with people buying is status quo, which is easier to stay with what they got.

Joelle Kaufman (29:28):

Of course. Always.

Randy Wootton (29:29):

I think your point around aligning with the top three problems and trying to demonstrate that your solution is 10 times better, and then what's at stake for that specific persona within the ICP? Salespeople talk about the third order of pain, and you're getting to why are they not sleeping at night or why is their wife or partner going to leave them? When they feel that sort of existential crisis, they're willing to take on the challenges of buying a tool. Let me ask you a question, a couple of things that popped from me. One was under, why is your solution 10 X better than what they do today? I've been at a bunch of different software companies. I'm not sure anyone really had a 10 X better solution outside the marketing that you would describe. What do you coach companies that are, they've got some differentiation? I mean, 10 X, that's big.

Joelle Kaufman (30:23):

It is big.

Randy Wootton (30:24):

Clearly, OpenAI is 10 X better.

Joelle Kaufman (30:27):

That's right.

Randy Wootton (30:28):

In general, because if you don't have that, do you just pull up chalks and go home?

Joelle Kaufman (30:33):

No, you find it.

Randy Wootton (30:34):

You focus. Yeah, go ahead.

Joelle Kaufman (30:36):

Look, this is a targeting and qualification problem as much as it is a product problem. You, at Maxio, have sold your product successfully to a bunch of CFOs and companies. The question is, what made that group amenable? Why were you 10 X better to them? Then how does that inform where you're hunting, what signals you're actually looking for? I'll give you an example from a former client of mine. I was brought in to help them accelerate the growth of a managed service version of their offering. I started my work talking to them, large team, good company. I said, "After talking to your customers, your customers change jobs pretty frequently." They said, "Yeah." I said, "They buy you multiple times when they change jobs, you're their play." They're like, “Oh, yeah." I said, "Why don't you track when they're changing jobs and proactively go after them? There are companies that provide that, because that's a growth engine for you, and when they change jobs, you want to reach out to the person who took over where they left."


Keep the other job and get the new one. That's a pretty solid growth strategy, and it's already there because you do a good job. You are 10 X better to these people than an alternative. Now, these people who are smaller companies, they didn't have as much resources. They needed a managed service, but there's a shit ton of them, Randy. It's not the sexy market of, oh, hey, I can go get Salesforce as my customer, but it's going to fuel your growth engine. Look at Spotify, like smaller businesses are a growth engine if you are easy for them to adopt, service them well, and solve their problems. Now, I'm not saying that's what the answer is for you or anyone else. The answer is targeting and discipline about that. Now, the pressure, the pressure is, but we need more growth.


What happens is companies are like, "All right, we're going to pursue this new market or we're going to add more salespeople." Now, that can work if that new market has the same pain and you can hunt for it and your new salespeople can align the buyers and compete. More often than not, it's a money bonfire because you don't even know that market and you have no idea what their pain is. I think there's another book, Go Slow to Go Fast. It's a good philosophy when we're saying, "Okay, we want to grow. What are the growth vectors we can choose?" The model was, before the inflationary period we've been in, the model was growth at any cost. Okay, well, let's go try this market. Let's go try this region, whatever. Now, it's efficient growth.


Well, efficient growth is about, do you know your ICP? Do you know their signals that they're in pain? By the way, and pain can be desire. You were talking about they stay up at night or they're going to lose their job. A lot of people buy something like Maxio or things I've sold because it can make their career. Look at the history of all the people that bought Marketo and became Marketo champions, it made their careers that they did that. You can have an ambitious person. Again, this idea when people change jobs or get promoted, there's a set of opportunities. Which ones fit your company, and how are you organizing your revenue engine to identify, engage, and offer value to those people at that right ideal moment? I guess I have ideal customer profiles and ideal moments.

Randy Wootton (34:47):

I think that's great. In fact, so we recently became customers of User Gem to address the exact-

Joelle Kaufman (34:54):

That's what I recommended. That's why I recommended to my client.

Randy Wootton (34:57):

Exactly, to address that point. Because what we found was once Maxio was in a company, you would have Maxionauts who would know how to use it, but if they left, a new CFO or a new finance person would come in and say, "Hey, I'm super comfortable with Excel. Why are we spending money on Maxio?" We needed two things to happen. One was to be alerted when there was a job change so that we could reach out with our customer success team, welcome the new person and say, "Hey, let's introduce you to Maxio, how you been using it to date, and how can we get you trained and learn if you're not familiar with it?" That prevent churn, and then number two, to your point, most our best customers are those that have used this before. Heck, I was a customer of Maxio Legacy SaaSOptics at Percolate where I was CEO. Part of the reason I took this job was because it had changed my life.


I knew that 10 X value prop, but it's super hard to articulate it unless you've experienced it on the other side. I was like, "Oh, gosh." User Gem allows us as well in our outreach is to go track people to see where they landed, because they're probably going to stay in the same function. You go find them and say, "Hey, remember us?" We send those Maxio swag and see if they can advocate for us in their new organization. I think it's a great call out. We were going to talk a little bit more under delivering results. I would though, because the way this conversation is unfolding, I think I'd like to shift to the other secret of success around building an effective executive team specifically about the curveball versus fastball.

Joelle Kaufman (36:24):

Thank you.

Randy Wootton (36:25):

Because I think this is one of these really interesting dynamics where an executive team, that first team, has to build muscle collectively, and it's tied into how do you establish trust, build trust, and how do you react to the inevitable changes that are coming down the pipe. Can you talk a little bit about your curveball versus fastball metaphor and how you see that play out?

Joelle Kaufman (36:46):

Sure. It's interesting, I believe in the curveball method, it's actually how I live personally as well as professionally. I think I've mentioned to you that I've had a 40-year journey with breast cancer in my family, including my own experience with it. Cancer and health crises are a complete curveball, they rock your world. In the professional realm, the SVB crisis was a massive curveball. It rocked people's worlds. When you step back a moment, I would posit, Randy, that 80 to 90% of what your leadership team talks about or deals with day-to-day are curveballs because you have other people in the company that are handling the fastballs. It's an unhappy customer, something in the product isn't working the way it's expected or it's delayed. We're having capital constraints. What are we going to do with our resources? These are curveballs, and how we deal with them isn't something we want to make up each time a new or really on the fly.


Any baseball player, and you know I have a son who's one of them, but any baseball player will tell you, you have an approach before you walk up to the plate. We have an approach before we enter the leadership team meeting or before we have our one-on-one. Our approach has to be about can we see the curveball? Do we identify it and say, okay, this is not what we expected? It might not have been what we wanted, but it is what we're seeing. Two, can we manage our own emotional reaction? This is a big one. Emotional regulation is hard. You care a lot about the company. Most people that are on an executive team have been wildly successful, they don't like screwing up or failing or making the wrong call. All of those are dysregulating thoughts because You're still seeing the curveball.


All the things you make the curveball mean, all the what ifs, it comes down to that's emotional and it's flooding your body with all these hormones that puts you into your limbic system. Well, that's great if a bear is chasing you and you need to run faster. If you actually have to make a thoughtful decision, all that stuff coursing through your body is bad for you. You want to get it leveled and get into our very powerful frontal lobe. We have to be able to recognize it. We have to be able to be patient and cool our own jets, and we have to have an approach. The approach is going to depend on what are your strengths, your strengths as a leadership team, as a company, as individuals. We can understand what our weaknesses are, but how we want to approach the curveball should be about our strengths. Being able to again, calmly say, okay, we're overextended here. We have some strengths in dealing with this situation or some patterns.


What do we think about this? Then create a conversation. Oh, Randy, I like that. What if we added this to it? Oh, Randy, I like that, I'm concerned about this part. What if we shifted it this way? Now your leadership team is literally coming together to figure out how to swing the bat. Now, unlike baseball, you may not have to swing it immediately. You might, I mean, SVB was pretty much an immediate thing, but most curveballs are actually not moving as fast as they look like. That's actually how they strike out batters. You have a little bit of time to say, okay, let's come up with some ideas and let's step away. Let's look at it again. Let's look at our ideas and let's make a measured choice with some metrics of is our choice working. Because good news, if the choice isn't working, you don't get out on the first strike, so you get to swing again.

Randy Wootton (40:51):

That's a great metaphor to hear.

Joelle Kaufman (40:55):

Thank you.

Randy Wootton (40:56):

Have you written about this in this metaphor?

Joelle Kaufman (40:58):

I have a little bit. I'm still teasing the whole thing out. Yet for me, I think what I do when I coach as a revenue catalyst is I teach people the curveball method and how to develop their own approach and their team's approach for the curveballs of work. Inevitably, they also approach the curveballs of life.

Randy Wootton (41:21):

I think what's interesting is it also ties in with what we were talking about earlier in terms of higher empower and improving people and allowing people to take risks, and sometimes those risks don't play out. I know, gosh, we just had something happen last week at the company, and I was like, "Oh, for God's sakes. Really?" The natural emotional reaction is, well, why did this happen? How do you call out the person that was responsible for it? Scold them and tell them to get back to work, and instead having a mental shift around saying, "Look, it already happened, so what can we learn from this? What can we do to put guard rails in place as we go forward?" Then there's a lesson learned in there and people are taking risks because we're trying to do something different and then they will learn going forward.


I think the executive team's collective ability to manage change and react to change is one of those indicators of a great executive team. We, at our executive offsite next week for example, we're going to have a set of big rocks. Big rocks are those things that are either big problems we need to take on or opportunities we need to exploit. To your point, we don't have to make the decision next week, but we certainly want to move the thinking forward. Because of the other end, what you don't want to have, I think, is just having the same conversation again and again and again. There's some way, I think in the way you described it is how do you approach this as a team with articulating the goal, being clear about the roles and responsibility?


I think about that as decision making, how are you going to make the decision? Who's on point for the decision? Ensuring there's a line around action. In the next month, how are we going to move this forward? What information or data do we need to go? What experiments are we going to go execute? Then come back as a team and say, "Okay, what are we going to do now?" Then just being humble enough to recognize like you were describing like, hey, you may take a strike on this one, but you're not going to go out. How do you create context where you're able to invest an appropriate amount of investment and time that you can move it forward without just sucking up everybody's energy and efforts? Those are great guides.

Joelle Kaufman (43:25):

Well, I think that's very wise how you've summarized it. I'll add to you, put a timeline on the decision making. We don't need to do it right now, but we need to do it by, and what are some metrics that our decision was the right one because we want to be able to come back. The good thing about baseball is when you strike, the umpire says that's a strike. In business and in life, when you strike, often we try to hide it like, "No, it wasn't a strike. It was just a funky swing." No, let's know, that was a strike. We don't think that's working. That's not bad. That's just information.

Randy Wootton (44:03):

That's right.

Joelle Kaufman (44:06):

Do we want to make an adjustment? If you listen to ball players, they will tell you, "You have your approach, you see the pitch and you make an adjustment." You get down two strikes, you make an adjustment. When we lead our leadership teams, what tells us if our swing is working and what kind of adjustments can we make without judgment? It's all about learning and getting better. If we're always getting better, I think there's another author that writes 1% better every day or whatever. If we actually are doing that, if we're actually doing that, we're doing it because we're making mistakes and we're learning, and that becomes invigorating.

Randy Wootton (44:47):

I think you're right. I mean, I talk about this idea of my entire life in trying to operate at the edge of my own ignorance. What is it that I can learn or do differently? It's part of the reason I left go to market tech, go to CFO tech. It was like, well, here's a new world. Go figure it out. I'm going to make a bunch of mistakes. I do think at some point, a CEO, you got to be right more than you're wrong.

Joelle Kaufman (45:05):

You do.

Randy Wootton (45:06):

You got to get the right things done. There's judgment that you have to apply in these situations, I think as an executive team as well. I guess playing out the metaphor a bit is how many at bats you've had. You start to recognize a curveball and you recognize how to swing the bat in this specific situation and what the expected outcome. Well, Joelle, look, it's been great. We could go on for another hour, but I think we got to wrap up at this point.

Joelle Kaufman (45:30):

All right.

Randy Wootton (45:31):

I just want to say thank you very much. I really have learned a lot. I've taken a whole bunch of notes on my outline of this conversation with you. What a great conversation. I've learned a bunch. Congratulations on all your success to date. If people wanted to find you, we were talking about one thing in particular about fantasy forecasts, which we're not going to get a chance to chat about, but it's on YouTube. You've got these one-minute overviews of how to avoid fantasy forecasts, and we are going to include that in our show notes. Where else would people find you if they want to get in touch with you or follow you? Is LinkedIn the best medium?

Joelle Kaufman (46:06):

Sure. You can go to LinkedIn, which is, I'm Joelle Kaufman. No double F or double M or double N, it's just Joelle Kaufman. You can also go to The name is because when you're a team, when particularly your go-to-market team is operating at the height of its ability, it feels like a flow state.

Randy Wootton (46:30):

Right, that's great.

Joelle Kaufman (46:31):

It's a wonderful thing.

Randy Wootton (46:35):

It would be nice to be there. I do appreciate your time. Thank you so much, Joelle Kaufman.

Joelle Kaufman (46:41):

Thank you, Randy.