CRO Spotlight

Stumble-Proof Your First CRO Role, With Stephanie Valenti

September 13, 2022

CRO Spotlight

A B2B podcast for current and aspiring CROs, CEOs and other leaders. In each episode revenue experts Warren Zenna and Lupe Feld are joined by a guest as they set out to explore every last area of a business that you can leverage to generate revenue and drive meaningful change. Warren and Lupe speak your language - join their revenue crew.

Regardless of your department, stepping up and out of it into the C-Suite puts you in a lot of new territory. You wouldn't have taken it if you didn't want a challenge, but you still want to avoid any missteps you can–you're about to find out how.

In this episode, Warren and Lupe are joined by Stephanie Valenti, CRO at SmartBug Media. Follow her adventurous footsteps to the CRO role (featuring networking, touring via alternate perspectives, and growing as a leader), how to stay in your lane so you succeed at your job, where to start when you land behind the desk, and protecting yourself from becoming a CRO In Title Only.


Connect with Stephanie on LinkedIn.

You'll find Warren and Lupe on LinkedIn too.

Be CRO ready from day 1 with Warren's CRO Accelerator course here.

Warren Zenna
Co-Host @ CRO Spotlight Podcast + CEO @ CRO Collective
Lupe Feld
Co-Host, CRO Spotlight Podcast
Stephanie Valenti

[00:00:00] Warren Zenna: Hi and welcome to the CRO Spotlight podcast. I'm Warren Zenna from the CRO collective and I'm here with my co-host Lupe Feld. Hey Lupe.

[00:00:15] Lupe Feld: Hey Warren. This is Lupe Feld, and I'm glad to be here with you.

[00:00:19] Warren Zenna: So this podcast is really for aspiring CROs and CEOs and current CROs whom are interested in learning from not only us, but the great guests that we're going to have.

[00:00:28] Lupe Feld: We're here to tell you that there is other areas of the business that can drive revenue and we're going to look and inspect and come up with some great ideas for us to bring in as much revenue as we can, and drive some meaningful change for the business.

[00:00:41] Warren Zenna: So tune in, we have some exciting opportunities coming up for a really amazing conversations and any B2B leaders I think you're really going to enjoy it. So thanks for tuning in and we look forward to seeing you.

Okay. Hello and welcome to the next episode of the CRO Spotlight Podcast. I'm Warren Zenna. And how you doing Lupe?

[00:01:04] Lupe Feld: I'm doing great, Warren.

[00:01:05] Warren Zenna: All right. Good, good. So how is it out there? Is it is it winding down the summer heat in, in Arizona?

[00:01:10] Lupe Feld: It's been the summer of rain in Arizona. We've had monsoon after monsoon, which essentially keeps it cooler. So no complaints here.

[00:01:18] Warren Zenna: Oh God, God. B. So yeah, it's a nice, nice day here. Beautiful day here. I wanna introduce our guest. I'm real excited about this. You know, we've been looking for accomplished chief revenue officers and we're happy to today to have Stephanie Valenti. So I'm just, what I'm gonna do is instead of doing the whole, like read the intro thing, I'm gonna let Stephanie introduce herself. Where she works, her background, and then let's take it from there. Stephanie, welcome. And thank you so much for being here today.

[00:01:42] Stephanie Valenti: Thank you for having me Warren and Lupe. So gosh, what do I do today? So I am the Chief Revenue Officer for SmartBug Media, which is. Yep. SmartBug Media. So it's marketing agency that is really large in the HubSpot ecospace.

So number one, partner there and also in the eCom space on the Clavio side. So full circle, full cycle marketing agency. And so CRO means something different. I feel like everywhere these days, but at SmartBug Media bug, I run and responsible for sales marketing and all of our client delivery teams. So anyone that to a client is responsible for clients. That is my responsibility. So some ups in there.

[00:02:19] Warren Zenna: Got it.

[00:02:19] Stephanie Valenti: Yeah. So been there for a short period of time. I think I'm coming into my eighth month, so haven't been there all that long. But really enjoying it. It was a brand new industry for me. And so it's been a, it's been a good time, a lot of learning, a lot of growth opportunity for myself, for sure.

[00:02:35] Warren Zenna: How did you get. But what, how did you get to become a chief revenue officer? What was your pathway?

[00:02:39] Stephanie Valenti: I've got a weird journey. I've got a weird journey. So I, I started out at least my sales and corporate side of my career. I started at Staples Business Advantage and I was doing B2B selling of contracts.

For mid-market organizations and really found that I loved helping companies do whatever they were doing just a little bit better and found this passion for sales too. Right. Knowing that if I worked hard and more that I could have. More success. Right? And so I was like, oh, this is in my DNA. I love this.

And so stayed with staples for about eight years and did everything I could there. Right? So from business development, business development, leadership, account management, leadership, and even more of like a GM specialized project type role running, not just mid-market, but huge enterprise deals like $12 million and all the ancillary stuff included.

And so So that was a lot of fun. And I learned a ton there. It was very, very beneficial, beneficial to be with a large company and learn all of those processes but was ready, right. For something different. And so got my opportunity for my first executive role and came over to Verdes. They're now called very, and was their head of sales.

So came. 40 people. And it was all inbound, very e-com centric. And they wanted me to launch a B2B division and help them scale into full project, opposed to transactional e-com product. And so that was a wild, wild ride. You know, my first time being an executive, but also my first time scaling a business, cuz I was with fortune 100.

So. When you're with big companies, right? You think everyone has these processes, like these things are all so normal. Like they're everywhere and you get out of that fortune 100 and you're like, oh, just kidding. Right. There's so much to learn. And so did that for about two and a half years when I left, we were about 200 sales people.

So really had the opportunity to scale that organization and wanted to learn the other side of the house. So I took a COO role. And this was everything but revenue. So all the things I know. So dear to my heart, I said, okay, I'm taking a step back and I'm gonna lead finance and operations and manufacturing, like walking on a lab, a floor with labor and machines.

And HR. I may have said that, but so it was, it was just the other side of the house. And so got to learn how to be a better revenue leader, right. Because I learned how to use my brake pedal. A bit and slow down and question things opposed to constantly pushing on the gas loved that team, loved that dynamic and decided I missed revenue though.

And I wanted to get into a new industry. And so I was in a lot of like goods for a while, like selling product. And I wanted to get back to that feeling I had at staples that I said in the beginning where I wanna help businesses do things better. And so I'm a part of a, another group here. And so I got connected.

Through Jen Spencer, who is our CEO and she was looking for a CRO and, and it was magic from there. And so so that's, that's how it happened and, and it clicked all the boxes for me. Right. I got to bring in that operations arm that I had all that experience with, from my COO role, but also got to continue being in sales and marketing, learning something new with the new industry.

And it's been a lot of fun.

[00:05:48] Lupe Feld: Well, that is amazing. I, I think. Perspective that you can gain, you know, stepping into somebody else's shoes and then coming back into the revenue side where you're comfortable. Is I, I think it, it can help being a little bit more aligned in a business. So that's awesome.

[00:06:07] Stephanie Valenti: Yeah. Yeah. It definitely has been helpful even in like CFO relationships, right? Like that was something I really struggled with in my first role. I didn't know how to speak to a CFO differently and I, they would. They would demand something and I would shut down. Right? Like I didn't understand what that relationship needed to be and going into the COO role when I was the one leading that and challenging sales, I got to learn a whole nother perspective.

So that's helped me a lot in my new role today, for sure.

[00:06:35] Lupe Feld: I love it.

[00:06:36] Warren Zenna: Stephanie's it's interesting question, cuz the great. Background of all the things you did, right. Running sales, and then doing operations, which of those skill sets do you think was the one that made you most suited for a CRO role? Given the nature of a cRO role?

[00:06:51] Stephanie Valenti: You know, I think every step in my career gave me something that made me suitable for the role I'm in today. I, the one, the one constant throughout that is the ability to truly lead. And understand how to lead and delegate and hold people accountable and keep them engaged because no matter, no matter what, like when you're a strong leader, you can kind of lead anything, takes a while to learn.

Right. But you build these strong people underneath you that can help. Teach you, and that you get to then just lead them to be the best versions of themself. Then you can, you can do anything. And so I think that's what I learned over the years. I made a lot of little mistakes. I learned from those mistakes, I didn't make the same mistake again.

And then I, and then I went and made a different mistake. Right. And, and learning from those over and over again has helped me be the, the leader that I am today. And I'm still learning every day.

[00:07:41] Warren Zenna: Yeah. I sort of asked the question mainly because so many CROs Lupe and I talked to came outta sales. And, you know, what we've seeing a lot recently is people who are coming more out of operations and marketing being CROs and the other different types of brains.

And, you know, do you think a CRO needs to have been in a sales organization to be a good CRO? Like how important do you think the sales experience is?

[00:08:08] Stephanie Valenti: You know, gosh, that's, you know, that's interesting. I haven't, I haven't thought about that, but putting, putting that question out and. In the world there, I, I, I think that you have to have a gas pedal, right?

Because you're in charge of revenue and revenue. You've gotta have like some tenacity and some like, let's get some stuff done, but, but I think you can have that in marketing. And I think you could probably have that in operations, right. It could be fueled from project. And if you have a right sales leader underneath you, then I do think it's probably possible to be a cRO you know.

I look at the CRO as you're responsible for all of the customer journey and in my case, I'm responsible for every piece of revenue that goes in and out of the door based on, on my role. And so the thing that's most important is I understand from a, from a far, far away point that organizational efficiency, I understand the customer journey, both internal and external, and that I'm able to communi.

Where we are internally and externally to my counterparts. And so it's really, I'm like master of communication. right. Mm-hmm and then a lot of process and a lot of like data too. And if sales people I've heard sales leaders in the past, like, oh, I'm not good at Excel. I'll figure it out. You know, when, if I have to, or I'll have someone do that for me.

Yeah. That doesn't work. Right? Like you need to be able to manipulate some of your own. And so that's where operations, I think, starts to come into play is they're like operational minded. People are thinking about structure, process efficiency. And you need that as a CRO. You have to have that

[00:09:42] Lupe Feld: That's yeah, that's such a great point. You know, I think you, you have such an advantage when you understand the CFO language, when you understand, you know, the, the ability to Speak everybody's language and also. How, how to bring that back and elevate your team because typically in sales, unless you've been kind of led in a very highly developed way, you're right.

You avoid a lot of those, a lot of those administratively labeled things that aren't sexy, but they're very necessary as you kind of aspire to go higher and, and be in the C-suite. What was it like? When you were in a C O O role, were you surrounded by women? Were you surrounded? I mean, I know your current CEO is a woman, but in, in the past, was that difficult? Different? What did you learn from it?

[00:10:42] Stephanie Valenti: Yeah, crazy enough. My entire career, I have never had a female. Leader ever. I have never had a direct female leader. This is my first time. And in my COO role the entire executive team was was men, right? I was the only female. And if you think about it, I was leading manufacturing.

And so all of labor. All of my team, other than I had an HR female that reported to me and I had our our demand planning was a female. But outside of that, it was majority male. And you know, I, I think the biggest difference is it took me a long time to realize that I can speak up and stand up and that I don't have to be intimidated.

Or hold back. Like that was my, the biggest thing. I had to figure out how to overcome and not so much in my COO role, but just over time, like, there was so much fear of if I don't know, or if I'll sound incompetent, if I ask this question, all of those stories we like to tell in our head Lupe right.

Like that was the biggest thing I had to overcome is. You know what? No, like, self-talk almost like you've got this, you're strong. Like what's the worst thing that could happen in this. And so that's the biggest impact piece I saw as a female coming up, but in the COO role, the interesting thing is the most friction I got was external.

So like vendors coming in and you wanna meet with the COO and they're like a steel manufacturer. Right. And they're like, wait, I'm you're the boss. Like they wouldn't even make eye contact with me. They would give like the quotes to my operations director. Like it was, it was strange. That was a really weird experience.

cause I just hadn't seen it before. Right? Like growing up in sales, like, yes. There's some, there's some things when you have to speak up, but like, females are accepted in the individual contributor in sales and as sales leaders, at least throughout like my generation. It's been pretty well accepted.

[00:12:33] Lupe Feld: Yeah. That's interesting. That's interesting to hear. I, I I, I think finding your voice is so important and it's so often I think the biggest challenge for women. You know, and I, I'm not sure why that is. I think maybe we're programmed from a young age to, you know, sit quietly and, and be a little bit more reserved and, and, and not necessarily show our, our weakness and, and sometimes speaking up when you're comfortable about something appears to be weak, but that's, you know, it's through the mistakes and through the challenges and through the difficult times that you learn more.

[00:13:13] Stephanie Valenti: Absolutely. Absolutely.

[00:13:15] Warren Zenna: Yeah. It's interesting. We talk about this a lot, you know, Lupe and I met for this purpose originally. I think it's something like 11% of CROs are women.

I mean, the number might have gone up. I'm seeing a lot more now. So, you know, I don't know what to, if there's like something to be done about it. I think that you're right there is sort of a, as I said before, I think there is. Maybe like a perception of some sort, like when you think of a CRO, maybe from a caricature standpoint, you see some sort of, you know, Silicon valley guy with like a gulling car, you know, and making all this cash.

And he's got a big Rolodex. I think there is this sort of perception, particularly in the tech tech space for sure. But it's, I'm seeing a big shift in this right now, a lot. I mean, I've been having conversations now a lot over the last year and it's been changing. What do you think that's about? I mean, do you think that's what it is?

Is it because of a perception or is it, is it just the industry just kind of is evolving? I mean, I ask the question mainly because there's a lot of women listening to this. Yeah. I, I have a lot of women who are in my courses and are taking my courses and they're, they wanna become chief revenue officers.

[00:14:20] Stephanie Valenti: yeah.

[00:14:20] Warren Zenna: What are some things that they might benefit from your experience?

[00:14:23] Stephanie Valenti: Yeah, I think it's a relatively new role. Right. And so it's, it's also, what does that role mean? And if there are current. Within their experience in order to get to that role, like exposing that. Right. So me coming on and saying, this is what a CRO role looks like in my organization.

And this female that wants to be a CRO is grown up in sales. The immediate red flag comes. Do you know how to run marketing? Do you understand operations, operational efficiency, revenue, operations, like, like organizational structure and design. And if you don't get to learn that as much in your sales role, what are the things that you're doing to expose yourself to those other things so that when you have the opportunity to even talk about this role, this CRO role, you're able to think bigger and larger picture.

The problem is is if you look at the VP level, you're in individual. Right. Like you're usually VP of sales or VP of customer success or VP of marketing. And so how do you get yourself elevated out of your department? Thinking big picture enough to be able to talk to some of those points that you don't necessarily get exposure in, in your internal organization.

And so I would, I, I, I do mentor quite a few aspiring CROs that are females and I Al they'll I'll ask 'em very generalized questions, right? In this situation, what would you do? And I always sense that they immediately go into fixing something in their exact department. And that's where I challenge them.

No, no, no. Like get up. Right. And, and sit on the clouds up here and look down at everything and then talk about how you would fix that and how it would impact cross depart. So I would say like that piece alone would be helpful if there was a way for them to. And, and probably through even some of your courses were, and they're getting that, but like, how do you think about exercising that operations arm or exercising that strategy arm or whatever, the, whatever the gap is, right, for them proactively addressing it.

[00:16:18] Lupe Feld: Yeah. You know, and I think one of the challenges for, as you mentioned, there's a lot of women in sales. And that seems to be a, a place of, you know, acceptance and comfort. And I think sometimes when you are in sales, you know, crossing over into operations, You know, sometimes means a pay cut and that's part of, you know, the price of admission to the C-suite.

You have to make those lateral moves. You have to make those, you have to take those opportunities that are different, that help you bolster. And if you're not willing to do that, then you really have to invest and supplement and augment with courses education. Mentoring with somebody in a different area of the business.

People tend to mentor within their vertical and typically don't cross out and, and learn from, from others. So I think that that's a really great point. You make Stephanie?

[00:17:13] Stephanie Valenti: Yeah, no, thanks.

[00:17:15] Warren Zenna: Yeah. I wanna switch gears. Cause earlier we were just chatting a bit. You mentioned something that's a really fascinating topic and that is the one.

How does someone in the C-suite a leader stay out of the weeds and. And not get sucked into execution, which is the big, you know, it it's like, it's like this sort of draw. Not only that, is it tempting for people to want to get their hands on things, but people wanna pull you into them too. So there's yourself. And then there's the environment. So what are some ways in which you're navigating that?

[00:17:43] Stephanie Valenti: Conflict. Yeah. You know, what's interesting is I just went through this, so I'll tell a story. Cuz I think it, it will hopefully be relatable on the topic, but I came in at new industry, leading marketing in a marketing agency for the first time.

Right. So yay. Marketing, right? I'm learning like I know marketing from a sales and operations perspective, but like running that. And so I'm very much in learning mode coming into the organization. We had a lot of different things going on, so it wasn't, as I could sit back and just learn and. Seek to understand, right?

Like those are the things you wanna do when you're a new executive, but we had an acquisition we needed to manage. We were you know, getting them integrated and I took that over. And so there were just a lot of immediate things that needed to be handled. And one of the things that had happened recently is I needed to part ways with my sales leader.

Right. We were scaling and growing and, and there just wasn't an opportunity for that person to stay with us. And so what happened is I had to in the interim take over, right? I have to lead the sales team. And when that happens, guess what happens? Right. I put on a sales manager hat because I'm being a sales manager.

And so I need to execute and support and take on things that they need. I can't delegate to the salesperson. I want the salesperson focused on. Selling and process, and I don't wanna make them more efficient, not less efficient. And so I had to take that on. And what happened is I didn't realize I was doing it, but I didn't take that hat off.

Right. And it was about six weeks long, but I left the sales manager hat on and I went and I was leading my VP of client services and talking about all this, and he'd say, this is what's happening. I'm like, I'll take care of that for you. I'll take care of that for you. And then I'd go over to marking. And I was like, I got this.

I'll I'll reach out to the CFO and ask him. And my desk looked like someone threw up a post-it note, like truck explosion. like there were legit, it was legit post-it notes everywhere. And I was working. too much. Let's just put it that way, way too much. And I wasn't being strategic and there was no, I was getting in my own.

Right. And I'm gonna guess I don't think my people probably loved it. Like, yes, I thought I was supporting them, but these are executives. Like, do they need me to do this for them? Probably not. And so it took me like sending my CEO a message and saying I am swamped and I'm overwhelmed. And if I take one afternoon for myself and don't like, St like if I don't keep working and stop at five, I am so behind that, it's a mess.

And she's like, what are you doing? Right. Just that question, like, read me a couple of your post-its and I'm like, all right. And I'm feeling good. Right? Cause I'm like, I'm gonna read you these post-its you're gonna see what's on these post-its right. And I start reading 'em and she's like, what in the world?

Like, you shouldn't be doing that. You shouldn't be doing that. You shouldn't be doing that. And I just sat here and she said, Stephanie, reset. right. And I was like, well, crap, you're a hundred. I know exactly what I'm doing. I'm an executor mode. I'm wearing the sales hat. I'm not taking it off. And and what's funny is I look back in my career.

So I feel better now. Because I am reset, I realize the hats. But I realize I look back at my career and I think about my time during very, as the senior vice president and it was constantly chaos, right? Like you're in a, there they, you know, multiple hundred million revenue, right. It's a lot of volume, a lot of people.

And it, it was wild and I can look back. that I have this like nice baseline and I go up, I was executing. I, I kept saying I was never been so reactive in my life. Well, it's because I wasn't delegating enough so I can look back now and see where I did that. But I even do like a challenge of if I need to wear my sales hat.

Like hold something in my hand and let it go. Would I leave that meeting right? While I'm doing this interim leadership, because sometimes you need that physical thing to remind you what role you're playing at the time. And that's helped me, but. Man. Oh man, it's really easy to fall into, especially when you have like economic downturn, right.

Or you're all of a sudden your team's not performing. You immediately should as a strong and, and experienced leader, gather your team brainstorm and then delegate and execute and continue like pushing that strategy. But when you're in like stress mode, you roll up your sleeves. You're like, what are we gonna do?

Let's do it. I'll call this person. I'll do this person. And that's not always the best thing to. But it's very easy to fall into it.

[00:22:03] Warren Zenna: It's great. I, I, you, so many things are Popp while I'm listening to this story. I mean, same thing happened to me once I got castigate, like, why are you doing that? But more importantly, I'm curious about something, this I'm gonna dig into this a bit because it's, it comes up a lot with my, the people I talk to.

This is a big thing. One person said to me, once I was talking to him about this particular topic, it was a really great moment. One of my, the people I was coaching and training was really high level sales leader said. I'm kind of confused if I don't do all that stuff, what do I. like there was this sort of moment where this particular executive recognized that their life had become all about all this executional stuff.

And in the absence of delegating everything, they were sort of having an identity complex. Like what's the role now because they're measured by activities. Right. So I, I was curious to know, like, because here's the, it's the balance, right? There's a balance of some sort, because the thing that got we got into about this topic was the question centered around.

I gotta lead by example. If I'm gonna come in as a leader and be a C-suite executive, I gotta get into weeds. Like my people are, cause they gotta see that I'm willing to do what they are. That's how they'll respect me. Right. There's there, there's some logic to that, but. I firmly disagreed. I'm curious to know what your thoughts are.

Like, how does someone balance this idea of not seeming like you're a PR Madonna and I don't mop the floor, you mop the floor, but at the same time, you know, making people understand that there are boundaries and setting them so that you gain the right level of respect to keep yourself above things that you can do the job you're supposed to do.

[00:23:33] Stephanie Valenti: Yeah. Yeah. So I guess my question back in that is that this leader was falling into that. Did he lead if he had all the layers right. Then his job was to lead his leader. To be their best sort of leader. Right? Which the metrics then are, are you doing your one on ones? Are you challenging this leader?

Are you supporting them in the right way? Your, your job isn't to focus on the metrics? That's that leader's job. And so if they're coming and saying like, I've got this. Struggle. And I'm seeing that we're not hitting our SQLs or we're not hitting our our numbers. And they're asking you for support.

Yeah. Right. Pull up the reports and help them understand the analytics, but let them deploy it. And the, the sales reps will start to see their leader elevate, and they will know that their leader is the one helping elevate that leader. Right. That will domino down. I think that like a CRO, like, let's just keep it on sales, for example.

So this, this head of sales that, that realized once he delegated didn't have much to do, like, you've gotta remember the C level is, or the, or the, or the VP in this case, right. Depending on the layers, their position is to cast vision and assure that we're we're cultivating and, and continuing the creation of whatever culture is in place and that, and that we're leading our people to the best of their.

That is their job. If everyone else is doing theirs, that is their job. It's executing on the vision from a very high level and pushing that down.

[00:24:59] Lupe Feld: Yeah. And I think, you know, another perspective is if, if you come from sales, you know, as your background and you get into the CRO role, I think there's a little bit of that kind of imposter syndrome in your head that forces you to feel like you need to be busy.

You need to be. Hands on and you need to be successful at driving revenue. And delegating is something that you are not. Accustomed to, it's not in your, you know, kind of his history of performance, you know, I mean, sales is if it's gonna be it's up to me and as you get into leadership, again, it's an elevated level of that.

So I think it's kind of programmatic in. The way that people have ascended into the CRO as well.

[00:25:48] Stephanie Valenti: You're totally right. You're totally right. A hundred percent. And I think that's why so many CROs have trouble, right? Because to Warren's point so many CROs come from sales backgrounds and you're right. We execute like no one's business.

And we know what did I say in the very beginning? Right. We work harder than you can be more successful. And so you, that mentality is like innate in us. Right. And so being able to figure out. Sure. Could I go in and help close every single one of my team's deals? And would our deal close rate, maybe be a little better and would that mean that our revenue would be higher?

And so should I be spending my time doing that? Absolutely not. Right. What I should be doing is training my leadership to make sure that they're working with their team to improve their closing skills. And so people wanna take like the shortcut, like the candy land, right. They wanna go they wanna take the, the shoot and ladders.

Right. But. But you have to invest in training and development and leaders wanna take shortcuts sometimes. And sometimes they do it, not, not, not purposefully, right? Like they truly just love closing the deal. But it takes it, it takes the opportunity away from the next person, right. That needs to help close those deals.

So, yeah.

[00:26:57] Lupe Feld: And Warren, I think also you have. Smaller companies, smaller B2B companies that are bringing in a CRO and haven't established maybe all the layers to support that CRO. And so the job of the CRO is to manage all of those things. And then, so that becomes a different job. It's not like a true CRO.

[00:27:22] Warren Zenna: Yeah.

[00:27:22] Lupe Feld: It's almost like a CRO. Escalator.

[00:27:25] Warren Zenna: Yeah. It's like a, you know, you eventually will get there. Yeah. Yeah. This is, this is a big topic that we talk about, which is sort of like, we call it the different stages and different types of CROs, you know, there's the startup CRO and then there's the growth CRO.

And then there's the turnaround CRO and there's the scale CRO and there's the enterprise CRO and you know, the job while it has the same definition, it it's executed differently. In different environments because there's maybe less people. So, you know, the people that I'm working with most of the time that are, that are growing into the role, they usually will get their first CRO role at a smaller company where they won't have as much freedom to have that ex executive kind of level thing.

But they have to find out ways to do it, cuz their job is to sort of train the organization, to develop leaders that don't do things. So the culture needs to sort of be ready for, this is a big part of what we're talking about. This kind of leads to a question, Stephanie, which is how much should a CRO be in deals or not in deals, because, you know, you have experience, you could probably step in as an executive and, you know, sort of move things through or make a decision, or maybe bring some, you know, fire power to it.

But you know, if you do it too much, now you're selling again. So what's the way that you balance that. If, if, if any, you know.

[00:28:33] Stephanie Valenti: Yeah, yeah, I do. And so even like take aside that I'm not running sales directly or, you know, right now with the interim, you know, miss, but we do executive sponsorship is how we do this.

So there is a task in our CRM in which new business can say I'm requesting an executive sponsorship reach out. And so that allows me to not be in the minutia of the. But if something's feeling stalled or not working, or it feels a little like they need support, then it gives me the opportunity to come in and give them that.

But I don't push myself into the deals. right. Mm-hmm so I need to be requested request. I say, I see that's right, because otherwise then, then what am I doing? I'm just looking at every single one of their deals in detail and being like you missed

[00:29:18] Warren Zenna: and it's tempting, right? I mean, you want to, oh my God. I can handle that one better. I like that deal. Oh my God. I wanna talk to that person. I, I know I'd be like that for sure.

[00:29:25] Stephanie Valenti: For sure. Yeah. Yeah. And I, I did a little bit of that. Like in my first SVP role, I did, like, I saw the deals, we were building a new product line and our CEO is heavily wanting to be involved in deals all the time.

And, and I, I looked and said, if we're at a scale, because I'm a scaling C CRO, right. So if we're gonna scale. And build out like processes and efficiencies and right structures and responsibilities, they can be supported, but I've gotta let them figure out how to do their stuff. And so even in small business, I think just defining who's responsible for what and, and together deciding when do you need my support?

And when can I help this team and allowing the team to speak. Right to see what they want and they need is a really great place to start even with small companies.

[00:30:11] Lupe Feld: Yeah. And I think there's also the opportunity, you know, not to even have to be in front of the client, but be kind of that strategic mind to help guide the deal.

Because if, if you've had any time in sales, you either hate it or you love it. And if you love it, you're gonna love forever. The thrill of the kill. I mean, you're gonna love to close that deal. That just never goes away. It never goes away. So you have to be disciplined. So I, I get that. That's a, I really appreciate you sharing your story because one it's very vulnerable for you to do.

But also it's a great illustration of the missteps that a CRO can make. Yeah. And I think it's incredibly valuable.

[00:30:56] Stephanie Valenti: Oh, good. Well, thanks. Yeah. And I think too, like to your point another just tactical thing is, you know, then do focus five or focus 20 and do those like corporate round table. You pick five or 10 accounts and the team gets to come in and say, here's all I know.

And how can we dive in and come up with strategies together? Like those are fun and they give you your. But they let the, they let the salesperson lead it like the salesperson needs to lead. And if you get on a call with the salesperson, I, and you're not on calls often. Oh gosh, anytime I come on, like, I can't, I can't hold myself back.

So just don't put yourself in this situation, right. Because you're gonna wanna talk. And then the, the contact's gonna wanna talk to you because they wanna talk to the senior person on the phone and then your salesperson's just sitting and watching. Right. So just another, just another piece I think, but.

[00:31:43] Warren Zenna: You know this is great.

I, I want to ask you from a different perspective now. So I, I talk to about five to eight, let's say average CEOs a week, whom are at the point where they're looking for a chief revenue officer and, you know, I, we can get into this topic a lot, but I don't wanna get into it too much. Won't stop talking.

It's, it's really a difficult decision for them to make because they recognize a need for something. Right. And, but those things are we'll, we'll kind of couch for a second, but what would you say? Okay, let's say a CEO of a uh, 15 or 10 or 15 million revenue company called you and said, Stephanie, I'm about to, I'm looking for a chief revenue officer.

What are some of the things that you'd say that a CEO needs to think. Before they hire somebody to take on that role. How do they prepare for that role? What's the way that they can make sure that that CRO succeeds.

[00:32:32] Stephanie Valenti: Oh, I could talk about this the whole rest of the time too. Let's do it. Yeah, I, so I'd wanna understand the current dynamic of the existing executive team who's responsible for.

What has that looked like? What is the current health of the team? And are they ready for someone that is gonna come in and own? Obviously very, very important piece of the organization, which is revenue I'd wanna understand what departments were in mind to report to this role and then who would be losing responsibility.

And how would that be managed? I'd wanna understand expectations, especially around revenue and bookings modeling and growth, expectations and performance. And, and what is the purpose like? Right. Why do they need a CRO right now? Is what are they looking for? Is something not working, right? I'd ask a lot of questions around that.

You know, I have C CEOs call me once in a while and say, here, this is what I'm doing. And usually it goes even all the way back to like, I'm thinking I'm gonna move this department here and this here, but there's no like, what's forcing that what's guiding that. What's the reason. So I, I talk a lot there.

One thing I wouldn't wanna hear is I need a CRO because my VP of sales isn't hitting the numbers. Like that's, that's not a, that's not a reason to bring in a CRO. So I'd wanna understand that I'd also wanna understand how they think growth is created. That's a big, hot topic that I talk about often on social and, and in, and in podcasts and whatnot, like it's, it's growth is not sales head count equals money.

Right. So, so let's talk about what your vision is for growth for the organization. And as a CRO, like. Especially if your total customer journey, and it depends on the organization, but you're kind of a, you need partners in the organization. Like your executive team should be your partners. And so that CFO relationship that CEO should feel like your partner, like everyone's rallying together.

And so I think that's another thing, like, are they looking for a partner? Are they looking for an elevated VP of sales?

[00:34:33] Warren Zenna: Hmm. Yep. Matt tends to be the issue mostly that we are trying to resolve is that is usually the impetus. And again, I don't wanna get into this too much cuz it's a bit self-promoting but the CR CEO is usually under pressure to make some changes and it usually is reaction to failing or threatened pipeline or projection hit numbers, right?

Yep. Being hit. So what they do is they wanna bring in somebody that's gonna shake things up or you know, whatever. So to that point, If in fact, and we have this a lot, right? If in fact you see from both sides, there's a kind of collision going on here. I'd be curious your way of to navigate this conversation between the CRO who's interviewing for the job and the CEO.

Who's looking for a let's call it like a C title only, or I call a Curto. Okay. This is like someone who like is gonna get the title, but they're really gonna run sales. How. How does what's the best way for those two people to navigate that conversation so that the placement is proper and, and everyone sort of wins on it.

Like what's the way that you'd kind of coach that conversation. So it's more effective as opposed to people making a deal that, you know, in 18 months is gonna not work out. Yeah.

[00:35:45] Stephanie Valenti: Oh, I would, I would prepare like a, I have a list of a hundred question. That I put together of all things you need to do before signing off on a number, which is kind of the same thing as signing off on a new job.

Yeah. If you're just gonna be the VP of sales, right. And a lot of that is other departments responsibility. And so everything from If you're responsible for sales and driving net new revenue to the organization, you depend on every department in the company. So you need to know everything that's going on in the organization.

For example, HR people ever think about HR on how are they gonna support us, hitting the number? Well, if they're required for recruiting. Yep. right. If they're required to recruit and they have an average days to fill time of 45 and you forecasted that your new reps will be failed by 30, you've gotta disconnect, right?

Yeah. Yeah. And, and if you're not allowed to let someone go on a performance plan for 90 days, but you know, in. 30. They were a real bad hire we have a disconnect, right? Yeah. But the, if the list goes on and on and on and on and on, because those are the things they should be asking. And as they start to ask those questions, the goal of that conversation would be to show this CEO that thinks they're only looking for this pseudo what did you call it?

[00:36:59] Warren Zenna: CRO in title only.

[00:37:00] Stephanie Valenti: I love it. Cryo. Yeah. What, what, what they show though in asking all of those questions is no, they understand so much more in the company. And so pushing even then and selling yourself into more as I am I'm I think the entire customer journey is important. I think the entire.

Like our entire revenue number is important. And so in order to be truly responsible, then I need to be responsible for more. And so I, I would encourage those people to ask the right questions and push themselves into the opportunity to be able to take on more. And yes, it's more responsibility. So so higher risk, but at least then it's under your control and it all funnels up in the right way so that things can work together.

[00:37:47] Lupe Feld: Yeah. And. So often when people are interviewing, it tends to be so one sided, it's usually the company kind of putting. The applicant under the microscope, even if they've gone out and like searched for this individual and they come highly recommended, you still kind of go through and especially at the C level role, you go through six, seven interviews and maybe you get, you know, 10 minutes at, for out of every hour interview to ask a few questions.

And the last thing people typically wanna do is be contentious. They don't wanna ask questions. They don't wanna push the envelope and our nodding instead of asking those tough and difficult questions. And I think that in itself is why this title has, you know, a life cycle of 18 months because. People are not asking those tough questions.

[00:38:50] Stephanie Valenti: Absolutely. Yeah. I, I think, you know, I talk a lot about the other piece of why it's 18 months is no one teaches a CRO to be a CRO and, and no one teaches a CRO how to do bookings forecasting. And no one teaches them that, you know, marketing and product are also responsible. And so every time, I mean, everyone I talk to and shoot, I did it myself.

In my first role, the CFO says here, Here's your number? How many heads do you need or, or what's your budget that you need to hit this number? And no one, no one taught that person to say, oh no, no, like you've got to push back. You've got to slow down. You have to look at reality and, and you're allowed in your role.

To push back like that is allowed, right? And, and that's not taught, that's not taught you figure the CFO's the boss. They give you. You're the, board's the boss. They give you your number and Hey, go tell me what you need. But man, is that a recipe for disaster? That's why everyone gets let go, because they don't know how to forecast their revenue.

[00:39:48] Warren Zenna: Yeah. You know? Well, the, the advice I give my the aspiring and even CROs is before you sign the papers or do the job, this number of things. An important one is you need to be given in his agreement. You need to have the proper authority, the proper autonomy, the proper resources and the proper runway to do your job.

And I'd say honestly, the one that's the hardest of those four. Is runway, cuz nobody wants to give you the time in market to get things done. That's why most things get pulled is because they don't let them sit in the market long enough to show the results. So if I'm a CRO and I have to forecast future events and I'm being asked to produce short term outcomes, you can't do both the same time, which to your point, Stephanie is why I have to push back on the projections and say, hold on a second.

How did you guys generate these projections? What consciousness was the behind these, you know, and that's where that conversation comes in. If, if you have that runway and you have that authority and that autonomy, you're gonna have a more likely chance of being able to be given the permission to ask that stuff.

If you don't, you're sort of hampered from the day to start and that's sort of what we're trying to get people to

[00:40:57] Stephanie Valenti: understand. Yeah. Yeah. That's exactly right. But

[00:40:59] Lupe Feld: you also, but you also have to have enough knowledge. In other areas of the business, to be able to intelligently question the numbers, you have to figure the, you know, you have to be able to intelligent.

You have to be able to talk to a CFO in a way that the CFO's gonna respect and give you the right answers back. And so that kind of goes to like your original point, Stephanie, which. You, you have to kinda lean into those, you know, not so sexy parts of the business. If you come from sales, you have to learn that.

[00:41:34] Stephanie Valenti: Yeah. Yeah. No excuses that, like I said before that, oh, I don't ne I'm not a numbers person. Well, go figure out how to be a numbers person, because you're not gonna be in the C-suite if you don't, if you don't consider yourself to be savvy with numbers, like there's just no excuses.

[00:41:48] Warren Zenna: Right. So I'd like to kinda ask one final question, which is more focused on CRO.

so their chief revenue officers listening to this right now, and they're in their own, you know, sometimes world of hell, you know, trying to figure out how to navigate the things we're talking about. So if you, if you have one of these CROs, that's found themselves in a situation where. They're one of these, you know, they ended up in a situation where they're folks too much on sales or two in the weeds, and they're not really having a high level of business.

What might be some things you'd say to that person that could recalibrate their position and get them more into a higher level. What's some actions or ways they can operate that might. Turn things around for them as opposed to accepting their fate

[00:42:25] Stephanie Valenti: so to speak. Yeah. So one of the things that I do this with my team, because it's, it's, it's relevant for every role, depending on the, the responsibility at that level.

Right. So the first thing I do is you've gotta put everything that, that you're responsible for out in the open, put it all out there. What are all the things on your plate? And then start to prioritize. Right. So, and, and even go back to like, what are the core KPIs I'm responsible for and, and what matches?

And what's just living out here, like that's a communication or a project or something that your team would be able to support you in and start making piles. Like I used to make piles, right. So I'd say, okay, like, this is stuff that I really should. It'll be an opportunity for my team to grow and learn, and I can support them in that, but I'm going to give them that responsibility.

These are things that should not be needing to be done at all. Right? Like these are a hundred percent, REDX not a priority. Scratch 'em off the list. Tell people it can go into Q4 or next year, not a priority alongside the, the priorities for the organiz. And then lastly, it's okay. This is the stuff that you are responsible for.

And so let's figure out how to get it done. Right. So, so it's really separating that stuff out. It's all about prioritization and understanding where you're at. And then sometimes you do just need that kick in the butt. Like I said, Jen telling me the word reset, that that one word I immediately was able to be like, Aw, dang.

It I'm an executor mode. Right? Like it was a trigger mode for me to pull me. So much so where I have a sticky on my monitor right here, that just says the word reset, because I don't wanna get back in that. And it's very easy. Lupu you made a great point that it's very easy for people that started in sales to go into executor because we like being busy.

Right. And so, but if you're able to be strategic, you can do such, such big things in this role. Right. I could create a new product in this role because I'm responsible for services. I could decide we're gonna build a new. Brand campaign and, and pitch ideas, right? So there's, there's a thousand things that I could be spending my time on.

That's way more valuable for the future of the organization than daily tasks. And so that's, that's something that has helped me with my direct reports who are new VPs, right. For the first time, figuring out how to make sure they're delegating. So it really is good for every level. Hmm.

[00:44:50] Warren Zenna: That's really great,

[00:44:51] Lupe Feld: great advice.

This has been, you know, really, really interesting and helpful, and I, I believe it will really land well with a lot of our listeners because you, you've given a lot of very useful things that you can apply. And, you know, I couldn't agree more on prioritization. and, you know, making sure that you prioritize, so you give yourself enough time to focus on strategic type of activities, thinking, planning, et cetera.

Because if you focus on just doing, you're not planning for the future, you're reacting to it. Yeah. So great conversation. Thank,

[00:45:29] Warren Zenna: thank you. We're so great having you and I look forward to having this episode be deployed to our listeners. Where is there anything, are you doing anything may want people wanna know about?

Do you have anything that you're writing or do you have any, how can people get in touch with you? Do you want that? Like how can we help you?

[00:45:44] Stephanie Valenti: Yeah. Yeah. So I am pretty active on LinkedIn and so definitely connecting with me there. You just type my name, Stephanie Valenti and I'll come right up.

[00:45:51] Warren Zenna: Got it. Well, thank you. Yeah, it was so great talking with you.

[00:45:54] Stephanie Valenti: Thank you. Yes, it was, this was wonderful. Thanks for having me.

This episode was digitally transcribed.

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