159. The #1 Thing Great CCOs Do in Year One ft. Alexis Hennessy (Heidrick & Struggles)

We used to be able to assume that our scaled customers, our long tail customers, would kind of auto renew, but that's not necessarily the case anymore.

Alexis Hennessy:
So.

Josh Schachter [Host]:
So I think you're right. It just makes, it's just raising the stakes that much higher. You're listening to Unchurned, brought to you by the Gaulsight Podcast Network. Twelve years ago, Alexis Hennessey helped stand up something that didn't exist. A practice dedicated to placing post sales leaders. She did it at Heidrick and Struggles, one of the world's premier executive search firms. She watched the role of chief customer officer surge then fall off a cliff. And today the market is hot again.

Josh Schachter [Host]:
Candidates who were available yesterday are gone today, but the rules have changed. Retention has become existential and the CCOs who succeed aren't the ones bringing old playbooks today. On Unchurned. Alexis Hennessey on why the best ccos start by listening, what it really takes to land the role, and why the path from CCO to CEO might finally be opening up. I'm Josh Schachter. This is unchurned. Welcome back everybody. I'm Josh Schachter, your host of Unchurned and I'm excited to be here this week with Alexis Hennessey.

Josh Schachter [Host]:
Alexis is a partner at Heidrick and Struggles, one of the world's leading executive search firms. She helps lead the tech practice and helps co found the post sales practice over there. Alexis, did I get that right?

Alexis Hennessy:
Mostly I, yeah, partner within our global tech practice, help stand up our post sales officers practice about 12 years ago.

Josh Schachter [Host]:
Okay, thank you. Well, we were, we were classmates, we were peers 14 years ago. And you always helped correct me that. So I appreciate giving me the verse this time around too.

Alexis Hennessy:
It's an ever changing title too, Josh, so.

Josh Schachter [Host]:
Yeah, yeah, okay. So you are one of the most knowledgeable people of leadership positions in post sales in what it takes to get those roles, you know, recruiting those roles, hiring those roles. And so you're going to have a lot of very captive listeners, very intently interested on the lessons and tales that you can bestow on them in this episode. I want to start with this first question. You've placed a lot of these folks, a lot of CCOs and MVPs of customer success and what are some of the patterns that you see most prominently that are being successful for people that are making it into the CCO positions?

Alexis Hennessy:
Yeah, I think it's. You know, it's interesting because a lot of the folks who are hiring for CCOs, whether it's a CEO or a chief revenue officer, president of field operations, a lot of them come to us and still don't understand what they're looking for. And so part of it is showing up in those conversations and being able to sort of educate your audience on what good looks like for that role and what are the best practices and what would a great CCO be able to do for your business, you know, if they. If they came aboard? So I think that's part of it. Right. Just knowing that there's still some skepticism, there's still some like. There's still just, like, lack of clarity, honestly, from a lot of. You have to.

Josh Schachter [Host]:
Do you have to convince some of these boards and some of these CEOs and senior leaders that they need a CCO, or do they come to you saying that they need it?

Alexis Hennessy:
So what happens is they'll come to us saying, we need someone. I know I need someone. I don't know exactly what I'm looking for. Let me talk you through our problems or what we're trying to solve for or where we're trying to go. Sometimes they'll come and say, I think I need one, but I'm not quite sure. Help me understand what it would look like, what would I get out of it? And then the third, you know, kind of bucket is my board's really pushing me. I feel like the industry wants me to hire this person, so here I am. Those are the people or the instances, the scenarios we want to stay away from if possible, because they're not always in it for the right reasons.

Alexis Hennessy:
Right. And sometimes you can get a client who says, the silver bullet, we've got a churn problem. If I hire a cco, the problem will then take care of itself. Right. And we all know that that's not necessarily the case most of the time.

Josh Schachter [Host]:
And there's a little cya and they're trying to check the box on that one for the ones that come in there with the right intention, right mindset of what they're looking for. What are they generally looking for in a CCO candidate?

Alexis Hennessy:
I think they're looking for somebody who can be a strategic business partner. Right. And truly help educate them, help them set the strategy for the customer journey, who can be a Great partner and reach across the aisle and is going to work very well cross functionally with, literally, I mean finance, marketing, certainly the sales leader, right. To kind of facilitate and build and nurture that customer journey. And then I think, you know, the last part is like how do I know that you're good? Right. And it's somebody who can walk you through their metrics in a way that keeps you elevated at that C level. That, that really does help that person, the audience, understand how you drive results. Because sometimes I think customer success can get a little nebulous, it can be a little squishy.

Alexis Hennessy:
So the more you can educate and weave those numbers that demonstrate the value add into your narrative, the better on the candidate side.

Josh Schachter [Host]:
I mean, I certainly hear from a lot of folks that are out there looking for their next role, a lot of folks that are trying to level up as well in VP positions or in director positions, trying to make it to vp, VP, trying to make it to CCO who are like what, what does it really take from a resume perspective these days to get a role as a Chief Customer Officer? Do you have to be have already had been in the position?

Alexis Hennessy:
No. And I think that holds true for virtually every C level role right now. Supply does not meet demand at the moment for anything. Right. You just have a large number of people in the workforce who are retiring either because they can and they want to or because they're at a natural age where it just, it makes sense and they're ready to do it. And so I think regardless of the role, you're getting more first time insert C level position here. Right. Than ever before.

Alexis Hennessy:
So I think most hiring managers and boards are comfortable with a step up candidate.

Josh Schachter [Host]:
So you're telling me there's a large demand for this role right now?

Alexis Hennessy:
We have definitely seen an uptick. It was pretty quiet. It was dark days, I would say.

Josh Schachter [Host]:
Or is it an uptick from zero, from zero to one?

Alexis Hennessy:
No. Honestly, right now the market feels hot for this role right now. It's not always called cco. Sometimes the scope is what I would consider a full stack cco, sometimes it's not. But in general it feels like the function as a whole has rebounded and the market's moving very quickly. So I'm seeing, you know, people who are available yesterday and today they're not. Right. Because they're taking their next role.

Alexis Hennessy:
I've just seen a lot of activity. So I would say, you know, that it's like CCO maybe isn't what it was four or five years ago. Not everyone is going to hand out that title. Not everyone's going to be a direct report to the, to the CEO. But in general we're seeing a rebound, which is good.

Josh Schachter [Host]:
So it was more. There was more. There were more ccos four or five years ago, you're saying this is. Well, I guess this is during the nice zert days. There were some dark days. The winter came and now we're back on the uptick is what you said.

Alexis Hennessy:
That's what it feels like. Yes. Yeah.

Josh Schachter [Host]:
Okay, so how about the VPs out there? Many more VPs of customer success than existing CCOs. If you're looking at candidates that are crossing through your desk, you're getting ready to filter them out and present them to a board. What are some of the things that would stand out for you from a VP's candidates?

Alexis Hennessy:
Scale is always going to be something of interest. Right? The scale's got to be relevant in terms of headcount managed, in terms of the revenue responsibility. Right. When it comes to renewals, even if you don't own the number, but just some familiarity and relevancy of scale as always going to be, you know, a key criteria. I think the breadth of functional responsibility has to align now with most opportunities. If it is cco, the hiring manager is going to be comfortable giving on something. Right. So for example, maybe you don't have to have own support, but you have to be really deep on services and success.

Alexis Hennessy:
Right. I'm making that up. It's different for every company and every role. But having some sort of breadth that aligns with where they really need this person to spike is important. I think the experience with telemetry and AI and are you thinking about how to modernize and build the one to many model, the one to one model in the most efficient way, the most scalable way, and you know, in a way that really helps you measure the results that you're driving and then be able to bring those results back to the business again using that data, using those numbers. Right, to demonstrate how you created Lyft. That's, that's what I think most hiring managers want to understand from me. To bring you in, what can I expect? What results do you drive?

Josh Schachter [Host]:
Are you getting explicit mandates around AI that hiring managers are saying, we want somebody that's run an AI transformation before. You know, they're AI native or any themes that you're seeing in the resumes around AI?

Alexis Hennessy:
Yeah, not so much AI native because I think everybody is pretty realistic that there just aren't many AI native. Companies out there at scale, but somebody who's been thinking about it, who's been experimenting with it, someone who's going to bring what I call this engineering mindset of iterate test and repeat and they just have this level of agility to say we're going to try new things, we're going to run a beta and let's see what happens. And then just it's sort of hiring for the, the ability around AI and technical advancements within the post sales organization versus somebody who has all the answers and has it figured out for the most part, you know, we know those people don't exist yet.

Josh Schachter [Host]:
Yeah, yeah, that makes sense. I've heard a lot about this concept of convergence, convergence of roles through AI and it's a little bit more at the individual contributor level that you've got convergence of different types of post sales roles, of onboarding specialists versus support versus you know, they're kind of converging into one. And then on the. I was reading an article today around marketing roles converging as well. Are you seeing any types of convergence probably as a result of AI is what I'm applying at the C suite.

Alexis Hennessy:
Level as well, you know, not yet, but the C suite's certainly thinking about it and talking about it. Right. And so you have leaders who are saying, you know, we might be seeing this in support and so how am I going to get the next VP of global support? You know, in reality, if those entry level jobs are sort of converging and going away or you know, being delegated to AI agents. So it's something that they're thinking about, but I haven't seen it at court, the C level yet.

Josh Schachter [Host]:
Okay. When you hire a cco, one of the things that you do is continue to check back in on them. And you know, I want to know when you do check in on your CCOs, let's call it a year later, what are some of the themes that you're seeing emerge of what the best hires have been. Do have done in that first year?

Alexis Hennessy:
So there's a couple things I would point to. I think. One, the best ones come in and they don't immediately do anything other than listen for a year. Not a year first, like solid, like couple months, truly.

Josh Schachter [Host]:
Yeah.

Alexis Hennessy:
I think they come in, they listen to the customers, they listen to their team, they listen to their peers. Right. It's before they decide what to do. Because every business is, I mean there is so much transformation happening right now. Either transformation because of AI, transformation because businesses are going from traditional SaaS to a consumption model. We're even working with clients who are still transitioning from on Prem to SaaS or Cloud themselves. Right. And so come in and say, I'm going to bring my playbook and day one, I'm going to go execute on my playbook for this function in these times that just, it doesn't work.

Alexis Hennessy:
So there has to be this level of humility. I think there has to be this level of I go back to this agility and like flexibility point that I was making before and again the humility comes in to say, I'm going to go listen, I'm going to go on a listening tour and then I'm going to try to figure out what to do for this particular business at this very particular point in time. And I have to be flexible and humble enough to know that, you know, in a year or two I may need to change the plan and tweak it because the business is ever evolving, the market is ever evolving. So those are very broad brushstrokes. But I think if I could boil it down and say this is what the best of the best do you know, that, that those are at the top of the list. And then I think the last part is just like building those KPIs, like did you build the right KPIs in order to really track how efficiently you're managing your business, your PNLs and how big of an impact you're making on the business.

Josh Schachter [Host]:
Are there any like characteristics of a successful CCO from what you've seen in candidates or people that you've checked back in on is like personality types? I think, you know, they're more quantitative, they're more humanistic, they're servant leaders, they're bold and aggressive. Like, what are you, any thoughts on that?

Alexis Hennessy:
Yeah, I think CCO is like one of the most complex and difficult roles because I do think you have to be very good with people. You have to be a huge empath, right. To put yourself in the shoes of your customers on a daily basis and act from a place of serving them as best you can. But you also have to be able to think about the bottom line. Right and under again, that P and L mindset. Right. And you have to be somewhat technical, right. To be in this role, especially if you want to be that credible voice of the customer and bring that feedback back to product and engineering.

Alexis Hennessy:
So it's, you have to be an extremely well rounded individual I think, to do this job and to do it really well.

Josh Schachter [Host]:
Yeah, yeah. The role of CCO as it relates to all the changes in SaaS that we've been seeing. Changes in SaaS companies are under attack in some way. AI is such an enabler and such an opportunity. But agentic is also something that is coming at a lot of legacy organizations.

Alexis Hennessy:
Totally.

Josh Schachter [Host]:
So in this world of agentic and consumption based pricing, outcome based pricing has that impact the role of the CCO.

Alexis Hennessy:
So I think it's impacted the role of CCO1 because again CCOs are now expected to be leveraging this technology internally to do better. I think it's also obviously impacted software companies like you said, at a macro level. And so the install base has become more important than ever. Right. Like you, you have to protect that install base and you have to figure out how to get the upsell cross sell motion. Right. Because in many cases there aren't that many new logos to go and acquire. And so I just think it makes the role of the CCO that much more important right now for those traditional SaaS companies.

Josh Schachter [Host]:
Yeah, I mean the way we think about it at Gainsight is that retention has become existential right now with you know, with the option of people being able to build it more themselves or buy from just a flurry of other solutions. The agentic of X that's out there for every single category these days. And we used to be able to assume that our scaled customers, our long tail customers would kind of auto renew but that's not necessarily the case anymore. So I think you're right, it just makes, it's just raising the stakes that much higher. Can CCOs become CEOs?

Alexis Hennessy:
I think there is a small percentage who can and who will. I think with the rise of consumption models that is going to breed a new, a new generation or a new type of animal in terms of what CCOs look and feel like and the experience that they bring and where they spike. So and like I said before, there is a vacuum of proven CEOs right now. You're going to have to look somewhere else. Right now the industry is mostly looking to chief revenue officers and on occasion, you know, looking to chief product officers.

Josh Schachter [Host]:
As well to fill CEO spots.

Alexis Hennessy:
Correct. And so, and that's just because, I.

Josh Schachter [Host]:
Mean is that just the same old story that we've been hearing for years is just the legacy of, you know, who's got a seat at the table and perceived value to the organization?

Alexis Hennessy:
Yeah, exactly. But I think then if you know ccos can continue to show their worth especially in this age of retention being hair amount and they are again, you Know, they think about top and bottom line. They're commercial, they're technical. Why not? I really, I mean, I, you know, I, I like that, I like that skill set. I would like that skill set in a cc, in a CEO.

Josh Schachter [Host]:
Have you placed a CCO into a CEO role?

Alexis Hennessy:
Not yet, but you know, we, we, we have placed CCOs into businesses as broader presidents and they have assumed the CEO role and have been successful in it. And I, So I think we're going to see more of that.

Josh Schachter [Host]:
You mean like running that the go to market function effectively as the president of the org.

Alexis Hennessy:
Correct.

Josh Schachter [Host]:
Yeah. So a little bit more of that CRO type of role as well.

Alexis Hennessy:
Correct. And there's, you know, one I can think of where she, she did become the CEO and has been highly successful, I guess. You know, again, that's just one. You got to start somewhere.

Josh Schachter [Host]:
Yeah, I mean, well, you hear about like, I mean, I don't know that you place Yamini or not, but you know, Yamini at HubSpot, right. CEO of HubSpot, where she started in that CCO role. But that CCO role at HubSpot was almost a little bit more like a president type of role. It was, it was already running the go to market and then made the leap into there. Into running all of C, you know, all the organizations.

Alexis Hennessy:
Yeah, she is one great example. So I mean, I can think of another. I mean, Christina Kozmowski, you know, she came in as president, been running that.

Josh Schachter [Host]:
Business very part of like the, like the origin of like creating the function of customer success, if I'm getting my, my names correct.

Alexis Hennessy:
Yeah, she worked at Salesforce with Maria Martinez, you know, the undisputed maybe godmother of customer success. So Maria became COO of Cisco, you know, and so I, I think there is a track record. Eric Kelleher right now as in president role for Okta. He was former CCO. So I think there's some really amazing CCOs out there that are laying the foundation for this to be a viable path to CEO in the future.

Josh Schachter [Host]:
And what's your prediction for the role of CCO in years to come?

Alexis Hennessy:
You know, I was, I was so excited by the traction, the momentum that the CCO role had a couple of years ago. And then it was so it was such a bummer just to kind of see CCO hiring fall off the cliff, see the role get dismantled over the last couple of years. But again, it's, it's making a rebound. And I think that tells us that it's, you know, it is here to stay. And it really does fall on the shoulders of today's CCOs to really be able to win the hearts and minds of their, their peers and to build the right dashboards and KPIs versus building huge teams and, you know, building big moats around their organization. I think I'd like to make the prediction, but I, you know, I think if we do this right, I think the role is here to stay. And I think it's a clear path for CCOs to take on broader roles within organizations, take on board roles that are meaningful. So I'm very optimistic.

Josh Schachter [Host]:
Well, listen, we'll both root for it together. Alexis Hennessey, my friend, thank you so much for being back on the program. I think it was about a year ago since we had you last. Incredible to see the career growth that you've had as a friend, you know, forming this post sales group at one of the leading executive recruitment firms in the world, Heidrick and Struggle. So we'll keep an eye on you as well. And yeah, thank you so much for informing us all about the role of the cco. And let's get some folks into that C suite at the CEO level as well.

Alexis Hennessy:
Love it. Thanks for having me.

Josh Schachter [Host]:
Thanks.