Stumble-Proof Your First CRO Role, With Stephanie Valenti

The CRO Spotlight Podcast, powered by the Sales IQ Network. 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.

Hey, Warren. This is Lupe Feld and I'm glad to be here with you.

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.

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.

So tune in. We have some exciting opportunities coming up for really amazing conversations and any B2B leaders 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 Sierra Spotlight Podcast. I'm Warren Zenna. And how you doing, Lupe?

I'm doing great, Warren.

All right, good, good. So how is it out there? Is it winding down? The summer heat in Arizona?

It's been the summer of rain in Arizona. We've had monsoon after monsoon, which essentially keeps it cooler. So no complaints here.

God bless. So, yeah, it's a nice, nice day here. Beautiful day here. I want to introduce our guest. I'm really excited about this. You know, we've been looking for accomplished chief revenue officers and we're happy today to have Stephanie Valente. 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.

Thank you for having me, Warren and Lu. So, gosh, what do I do today? So I am the Chief revenue officer for SmartBug Media. Smart Bug, which is. Yep, Smart SmartBug Media. So it's a marketing agency that is really large in the HubSpot eco space. So number one partner there and also in the E Comm space on the klaviyo side. So full circle, full cycle marketing agency. And so CRO means something different. I feel like everywhere these days. But at SmartBug, I run and responsible for sales, marketing and all of our client delivery teams. So anyone that talks to a client is responsible for clients. That is my responsibility. So Some ups in there.

Got it.

Yeah. So been there for a short period of time. I think I'm coming into my, 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.

How did you get there? How did you get to become a Chief Revenue officer? What was your pathway?

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 organization 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, but huge enterprise deals like $12 million and all the ancillary stuff included. And so that was a lot of fun and I learned a ton there. It was very, very 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 Veridesk. They're now called Vari and was their head of sales. So came into about 40 people and it was all inbound, very E comm centric and they wanted me to launch a B2B Div. Help them scale into full project opposed to transactional e comm 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. Cause I was with Fortune 100. So when you're with big companies, right, you think everyone has these processes, like these things are also 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 salespeople. 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 going to lead finance and operations and manufacturing. Like walking on a floor with labor and machines and hr. I may have said that, but. So 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 want to help businesses do things better. And so I'm a part of 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.

Well, that is amazing. I think that 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 think it can help being a little bit more aligned in a business. So. That's awesome.

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. 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.

I love it.

Stephanie, interesting question, because 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?

You know, I think every step in my career gave me something that made me suitable for the role I'm in today. 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 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 themselves. 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 went and made a different mistake.

Right.

And learning from those over and over again has helped me be the leader that I am today. And I'm still learning every day.

Yeah, I sort of asked the question mainly because so many CROs Lupi and I talked to came out of sales. And you know, what we've been 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?

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 the, 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 got to 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 great, 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 my role. And so the thing that's most important is I understand from a far, far away point that organizational efficiency, I understand the customer journey, both internal and external, and that I'm able to communicate where we are internally and externally to my counterparts. And so it's really, I'm like master of communication.

Right.

And then a lot of process and a lot of, like, data too. And if salespeople, I've heard sales leaders in the past, like, oh, I'm not good at Excel. I'll figure it out, you know, 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 data. 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.

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 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 be in the C suite. What was it like when you were in a CEO role? Were you surrounded by women? Were you surrounded? I mean, I know your current CEO is a woman, but in the past, was that difficult? Different. What did you learn from it?

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 men.

Right.

I was the only female. And if you think about it, I was leading manufacturing. And so all of, all of my team, other than I had an HR female that reported to me and I had our demand planning, was a female, but outside of that, it was majority male. And, you know, 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 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 like, 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 want to meet with the coo, and they're like, a steel manufacturer.

Right.

And they're like, wait, 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. That was a really weird experience because I just hadn't seen it before.

Right.

Like, growing up in sales, like, yes, there's some things you need 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. Yeah.

That's interesting. That's interesting to hear. I think finding your voice is so important, and it's so often, I think, the biggest challenge for women, you know, and I'm not sure why that is. I think maybe we're programmed from a young age to, you know, sit quietly and be a little bit more reserved and not necessarily show our weakness. And sometimes speaking up when you're not 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.

Absolutely. Absolutely. 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. The number might have gone up. I'm seeing a lot more now. So, you know, I don't know if there's, like, something to be done about it. I think that you're right. There is sort of a. But as I said before, I think there is a maybe like a perception of some sort. Like, when you think of a CRO, maybe from a caricature standpoint, you see some sort of Silicon Valley guy with, like, a gull wing car and making all this cash, and he's got a big Rolodex. I think there is this sort of perception, particularly in the tech space, for sure. But 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 asked the question mainly because there's a lot of women listening to this. Yeah, I have a lot of women who are in my courses and are taking my courses, and they're. They want to become chief Revenue officers, Right?

Yeah.

What are some things that they might benefit from your experience?

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 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 if you look at the VP level, you're in individual departments, 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 do mentor quite a few aspiring CROs that are females and I'll ask them very generalized questions, right? Like in this situation, what would you do? And I always sense that they immediately go into fixing something in their exec department. And that's where I challenge them. No, no, no. Like get up, right, 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 departmentally. So I would say like that piece alone would be help if there was a way for them to get and probably through even some of your courses wherein they're getting that. But how do you think about exercising that operations arm or exercising that strategy arm or whatever the gap is for them proactively addressing it?

Yeah. 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 place of acceptance and comfort. And I think sometimes when you are in sales, crossing over into operations sometimes means a pay cut. And that's part of the price of admission to the C suite. You have to make those lateral moves. You have to take those opportunities that are different, that help you bolster. 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 learn from others. So I think that's a really great point you make, Stephanie.

Yeah, no, thanks.

I want to switch gears because earlier we were just chatting a bit. You mentioned something. I thought it'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 lead and not get sucked into execution, which is the big, you know, 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 want to 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?

Yeah, you know what's interesting is I just went through this, so I'll tell a story because I think it will hopefully be relatable on the topic. But I came in a 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 want to 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 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 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 way, 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. Like, if I don't keep working and stop at 5, 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? Because I'm like, I'm gonna read you these post its. You're gonna see what's on these post its. And I start reading them, 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 100. I know exactly what I'm doing. I'm in executor mode. I'm wearing the sales hat. I'm not taking it off. 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 are, you know, multiple hundred million revenue, right? It's a lot of volume, a lot of people, and it was wild. And I can look back now that I have this, like, nice baseline and I go up. I was executing. 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 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 and 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 do. But it's very easy to fall into it.

It's great. So many things are popping while I'm listening to this story. I mean, the same thing happened to me once I got castigated. Like, why are you doing that? But more importantly, I'm curious about something because I'm dig into this a bit because it comes up a lot with the people I talk to. This is a big thing. One person said to me once I was talking 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, well, I'm kind of confused. If I don't do all that stuff, what do I do? 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 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 we got into about this topic was the question centered around. I got to lead by example. If I'm going to come in as a leader and be a C suite executive, I got to get in the weeds like my people are, because they got to see that I'm willing to do what they are. That's how they'll respect me, right? 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 prima donna and I don't know, 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 and keep yourself above things that you can do the job you're supposed to do.

Yeah, yeah. So I guess my question back in that is if 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 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 struggle and I'm seeing that we're not hitting our SQLs or we're not hitting 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 this, 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 got to 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 cultivating and continuing the creation of whatever culture is in place and that we're leading our people to the best of their ability. 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.

Yeah. And I think another perspective is if you come from sales 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're not accustomed to. It's not in your kind of history of performance. You know, I mean, sales is. If it's going to 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 world as well.

You're totally right. You're totally right, 100%. 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, then you can be more successful. And so that mentality is like innate in us.

Right.

And so being able to figure out, like, 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 want to take like the shortcut, like the candy land, right? They want to go, they want to take the shooting ladders.

Right.

But you have to invest in training and development, and leaders want to 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. 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, it's almost like a CRO escalator.

Yeah, it's like a.

You eventually will get there.

Yeah. 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'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 executive kind of level thing, but they have to find out ways to do it, because 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 it. This is a big part of what we're talking about. So 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, firepower 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 any, you know?

Yeah, yeah, I do. And so even, like, take aside that I'm not running sales directly, 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 minutiae of the deal. 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.

So I need to be requested.

So it's request only. I see.

That's right.

Because otherwise, then what am I doing? I'm just looking at every single one of their deals in detail and being like, you missed it.

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 want to talk to that person. I know I'd be like that. For sure. 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 was 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 seat CRO.

Right.

So if we're going to scale and build out, like, processes and efficiencies and Right. Structures and responsibilities, they can be supported, but I've got to 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 together deciding when do you need my support? And when can I help this team? And allowing the team to speak up.

Right.

To see what they want and they need is a really great place to start, even with small companies. Yeah.

And I think there's also the opportunity 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 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, and 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 get that. I really appreciate you sharing your story because, one, it's very vulnerable for you to do so. But also, it's a great illustration of the missteps that a CRO can make, and I think it's incredibly valuable.

Oh, good. Well, thanks. Yeah. And I think, too, like, to your point, another just tactical thing is then do Focus 5 or Focus 20, and do those, like Corporate Roundtable. 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 thrill, but they let the salesperson lead it. Like, the salesperson needs to lead. And if you get on a call with the salesperson 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 the situation. Right. Because you're gonna want to talk, and then the contact's gonna want to talk to you because they want to talk to the senior person on the phone. And then your salesperson is just sitting and watching.

Right.

So just another. Just another piece, I think.

But, you know, this is great. I want to ask you from a different perspective now. So I talk to about five to eight, let's say, on average, CEOs a week whom are at the point where they're looking for a chief revenue officer. And we can get into this topic a lot, but I don't want to get into it too much because I won't stop talking. It's really a difficult decision for them to make because they recognize a need for something. But those things are. We'll kind of couch for a second. But what would you say? Okay, let's say a CEO of a 15 or 10 or 15 million revenue company called you and said, stephanie, I'm looking for a chief revenue officer what are some of the things that you say that a CEO needs to think about 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?

Oh, I could talk about this the whole rest of the time, too.

Let's do it.

Yeah. So I'd want to understand the current dynamic of the existing executive team. Who's responsible for what? What has that looked like? What is the current health of the team? And are they ready for someone that is going to come in and own this obviously very, very important piece of the organization, which is revenue? I'd want to 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 want to understand expectations, especially around revenue and bookings, modeling and growth, expectations and performance. And what is the purpose? Like, why.

Right.

Why do they need a CRO right now? What are they looking for? Is something not working?

Right.

I'd ask a lot of questions around that. I have 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, I'm thinking I'm going to move this department here and this here. But there's no. What's forcing that? What's guiding that? What's the reason? So I talk a lot there. One thing I wouldn't want to hear is I need a CRO because my VP of sales isn't hitting the numbers. Like, that's not a reason to bring in a cr. So I'd want to understand that. I'd also want to understand how they think growth is created. That's a big hot topic that I talk about often on social and in podcasts and whatnot. Growth is not sales. Headcount 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 the other thing. Like, are they looking for a partner? Are they looking for an elevated VP of sales?

Yep.

Yep.

That tends to be the issue mostly that we are trying to resolve is that is usually the impetus. And again, I don't want to get into this too much because It's a bit self promoting but the CEO is usually under pressure to make some changes and it usually is reaction to failing or threatened pipeline or projection hit numbers. Right. Being hit. So what they do is they want to bring in somebody that's going to shake things up or you know, whatever. So to that point, if in fact, and we have this a lot, 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 CRO and title only or I call a croito. Okay. This is like someone who like is going to get the title but they're really going to run sales. 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 going to not work out.

Yeah. Oh, I would, I would prepare like I have a list of a hundred questions that I put together of all things you need to do before signing off. Off on a number which is kind of the same thing as signing off on a new job. If you're just going to 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 going to support us hitting the number? Well, if they're required for recruiting.

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 filled by 30, you've got a disconnect. Right. And if you're not allowed to let someone go on a performance plan for 90 days, but you know in the first 30 they were a real bad hire. We have a disconnect.

Right.

But the list goes on and on and on and on and on because those are the things they should be asking. And as they, 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? The CROITO Croito.

CRO and title only.

I love it. Croito. 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 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 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 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.

Yeah. And you know, 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, especially at the C level role, you go through six, seven interviews and maybe you get, you know, 10 minutes out of every hour interview to ask a few questions, you know, and the last thing people typically want to do is be contentious. They don't want to ask questions, they don't want to push the envelope and are 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.

Absolutely. Yeah. 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 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's your, here's your number. How many heads do you need or what's your budget that you need to hit this number? And 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 you're allowed in your role to push back. Like that is allowed.

Right.

And that's not taught. That's not taught. You figure the CFO is 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.

Yeah. You know what? The advice I give my aspiring and even CROs is before you sign the papers or do the job, there's a number of things.

But.

But an important one is you need to be given agreements. 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, because 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 at 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 going to 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 you start. And that's sort of what we're trying to get people to understand.

Yeah, yeah, that's exactly.

But 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, 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 is going to respect and give you the right answers back. And so that kind of goes to like your original point, Stephanie, which is you have to kind of lean into those, you know, not so sexy parts of the business. If you come from sales, you have to learn that.

Yeah, yeah, no excuses. Like I said before, that, oh, I don't. I'm not a numbers person. Well, go figure out how to be a numbers person, because you're not going to 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.

Right.

So I'd like to kind of ask one final question which is more focused on CROs. So their chief revenue officer is 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 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 focused too much on sales or too 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, so to speak.

Yeah. So one of the things, and I do this with my team because it's relevant for every role, depending on the responsibility at that level, right. So the first thing I do is you've got to put everything 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 the them, right. So and even go back to like what are the core KPIs I'm responsible for 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 delegate. 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 100% red X, not a priority. Scratch them off the list. Tell people it can go into Q4 or next year. Not a priority. Alongside the priorities for the organization. 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 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 one word, I immediately was able to be like, oh dang it, I'm in executor mode, right. Like it was a trigger mode for me to pull me out so much. So where I have a sticky on my monitor right here that just says the word reset because I don't want to get back in that. And it's very easy. Lupi, 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 pitch ideas, right? So 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 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.

That's really great, great advice.

This has been really, really interesting and helpful, and I believe it will really land well with a lot of our listeners because you've given a lot of very useful things that you can apply. And I couldn't agree more on prioritization and 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. So, great conversation.

Thank. Thank you. It was 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 you may want people want to know about? Do you have anything that you're writing? Do you have any. How can people get in touch with you? Do you want that? Like, how can we help you?

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.

Got it. Well, thank you. It was so great talking with you.

Thank you.

Yes, it was.

This was wonderful. Thanks for having me.