John Smallmtn (00:00:00)

Welcome everybody to another episode of The Founder’s Growth Show, where we look at high performers in performance roles and figure out how they’ve had to adapt to find success in those roles. Today, we’re joined by Stephanie Valenti, who’s been a four-time executive in these kinds of roles. She has been giving back, facilitating with CRO courses, and also pouring back and giving back to her network, helping other people figure out some of this path.

Super excited to have her on the show. We’ve been connected on LinkedIn for a long time. Her content is epic. You should be going and reading it if you’re not already. Welcome to the show, Stephanie. I’m so glad that you’re here.

Stephanie Valenti (00:00:36)

I’m so glad to be here, John. This is going to be a lot of fun today. I just know it.

John Smallmtn (00:00:40)

Awesome. There are so many areas and pockets that I’m excited to dive into with you on this conversation. But the first one that I want to talk about—and this is going to be maybe not the direction that we want to start in—we’re coming out of Women’s Month. Being a salesperson as a woman is unique. I didn’t realize exactly where all these differences were for women in sales until I started actually coaching. As a practitioner, I was just doing my own thing, and then I started to see some of the stuff that I can do because I’m a guy that might be harder for some women to do in the same sales role. Can we start the conversation talking about that as both a salesperson and also as an executive? Where do the struggles of being a female in these kinds of roles show up, and how are we working on that?

Stephanie Valenti (00:01:37)

Yeah. You know, it’s interesting. I had some experiences throughout my career that I’ve used in many conversations to share the differences in communication, treatment, et cetera. The thing that sticks out to me the most is when I was applying for my first director role in a sales organization. It’s at the end of my interview—so I’ve done all these interviews, right? I’m well known in the organization; I had been there for about six years at that point.

John Smallmtn (00:02:05)

Mm-hmm.

Stephanie Valenti (00:02:06)

Well known for success, President’s Club, everything as a leader. I get in there, and before they hand me the offer, he goes, “So I’ve got to talk to you about something.” He leans back, and I’m like, “What’s up?” He’s like, “Well, I heard you can be a bit of a bulldog.” I’m like, “Oh my God, what the heck is that?” I was proud of myself because in the moment I said, “What do you mean by that?” A lot of it allowed him to elaborate. At this point, I might be 31 maybe, and he’s an older gentleman—he’s probably 60. He says, “You know, like you’re direct, and you push, and you don’t stop until your team hits what they need.” I said, “Let me ask you something. Would you say that same category to a man?

John Smallmtn (00:03:00)

Okay.

Stephanie Valenti (00:03:03)

If I was sitting across from you and I was a guy, would you say, ‘I’ve heard you’re a bit of a bulldog’?” He just kind of stared at me. That experience stuck with me forever. Things have happened like that again. In my first executive role, I was the SVP of Sales. The CMO sat with me and pulled me aside. He’s like, “Hey, you can kind of be a bit aggressive sometimes.” I’m totally taken aback. The CEO is over here telling me, “Speak up. You own the largest headcount in this organization. You own our revenue, so speak up.” So I do it, and then someone else is telling me I’m too much. That’s been something I’ve had to learn for a long time, and I think is a huge differentiator in the way that people see women and see men—not just in sales, but in general. If women behave in some of the same ways through speech, communication, and ownership, it’s put into a category where it would never happen the same way for men. So it’s still a balance. I don’t want to be called out for that. I don’t want to have to get argumentative or combat my natural self of being direct. But at the same time, I don’t want people to have that negative view of being too forward.

John Smallmtn (00:04:30)

Yeah.

Stephanie Valenti (00:04:30)

I still am challenged with it. How far do you go? How far do you fight?

John Smallmtn (00:04:34)

Absolutely. I was coaching a woman recently, and we were doing her personality stuff. That’s where everything starts for us. She’s very direct, very logical, and wants to win, so she’s all in that space. I’m showing it to her, and she was visibly frustrated. I was like, “Okay, what’s up?” She goes, “All my managers are telling me that I need to be funny and smile, and I’m trying not to get offended by it.” It’s like, if you don’t want to be that person at work, you shouldn’t have to be that person at work. But I’m speaking from a place of privilege because everyone’s expecting me to be direct and clear, push for the goal, and do all these things. It would be nice to where you didn’t even have to go fight for the right to be that person—it would just be that’s who you are, you fit with the culture and the team, and let’s go get it. Because as a rep, none of this was even in front of me. I would meet certain women who were very bubbly, and if anything, I would feel this pull like, “Well, I’m not bubbly; maybe I need to be bubbly.” I was feeling this pull in the opposite direction sometimes because I can be very critical, kind of cold, and probably too direct at times. You’ve got to figure out which battles are worth fighting and which ones aren’t.

Stephanie Valenti (00:05:59)

Yeah. At this point, I’ve learned what that balance is. Sadly, John, there’s always going to be politics at work. There is. People say, “No politics; get rid of the politics.” Good luck. It exists. No matter what, we’re humans and there’s psychology. Learning yourself—you can’t do it early on. You’ve got to make the mistakes. You’ve got to have someone confront you, and you’ve got to decide how much of myself am I going to bring to work? How much am I going to adjust? Unfortunately, that’s the way the world works. People say, “I’m unapologetically me.” It doesn’t work—not at work.

John Smallmtn (00:06:40)

Yes, absolutely, because you’re part of a bigger machine. I was in sales for about 10 years before I started to work with a coach. We did the personality stuff, and he shows me, “Hey John, you’re way over here. This is where most salespeople hang out, which is why you’re feeling some of this friction that you feel in the role.” It goes to the other part: you’re desperately looking to be taught, and most people in sales don’t have anything to teach because they’re all just instinctually guided. I was already doing Kung Fu and had gotten to a decent level there. I was like, “Well, I can do hard things whenever I know what the path needs to look like to go do that.” But my frustration was because I was working with someone who was very instinctual at the time. My first day of being a field rep was, “Don’t tell anyone you’re new,” which is my superpower. I love being the new guy, hanging out, and making it happen. That was the summation of all my training to go out and be a medical device rep in the field for the first time. Terrifying. I was not prepared in any way, shape, or form.

Stephanie Valenti (00:07:45)

Oh, that’s so all-inclusive training. I mean, come on, you can’t be successful at that! What’s wrong with you, John?

John Smallmtn (00:07:48)

And I’d come from a very corporate environment. I didn’t realize how much greatness I was getting from the corporate training stuff. A lot of it was frustrating because I wasn’t really ready to hear it yet, but I did come out with stuff like WIIFM (What’s In It For Me?) and some of this little stuff that just sticks with you for a long time when you’re in these kinds of roles. But in small business, there wasn’t this path of development. It was so much more just tossing you in the deep end. That’s honestly why this show exists—because it’s hard to figure out how to keep your head above water in the deep end until you’re ready to figure it out.

Stephanie Valenti (00:08:27)

Yeah, for sure. Then take being that new person in a medium-to-small business and then be a brand new executive there. Oh, no training manual for that!

John Smallmtn (00:08:38)

Yeah, absolutely, for sure. When we first got connected, I think you were still at Vari. As we speak, I am using my Vari desk. This is maybe one of the best investments I’ve ever made in my entire home office situation. What was it like leaving Vari? Was that when you went into more of the smaller business, on the exit from Vari?

Stephanie Valenti (00:09:06)

No. Coming to Vari, I grew up in the Staples organization and was there for eight years. At the time, they were Fortune 100 with 10,000-plus sales reps. It was an incredible machine. The training I got there—not just sales training, but leadership training—everything was amazing. Then coming into Vari, although they were about that $300 million range when I joined, it was all marketing, DTC, and e-commerce led. It was like coming into a mid-market company, but starting from zero because I was supposed to build out that B2B engine. That was kind of when things changed, when I needed to learn how to be an executive for the first time.

John Smallmtn (00:09:54)

A potentially interesting question from my side: they’ve got the e-commerce and DTC stuff down, and you’re tasked to come in and build the B2B stuff. Were you constantly having to validate and work harder to show the work because they weren’t moving in this direction? Or were you given a lot of leeway to figure it out and room to fail? How pressurized was that environment when you were walking into Vari?

Stephanie Valenti (00:10:24)

In the moment, I thought it was highly pressurized. Looking back, I wasn’t pressured at all—not compared to what I’ve experienced with PE. But there was a lot of freedom. The interesting thing is I was working at the executive table reporting to the CEO. My peers had insane experience; these were executives in DTC retail-based companies for a very long time, but none of them really had B2B experience. They allowed me to do my thing. They gave me freedom and let me decide how things should be structured, what processes, what tools, and what systems to use. But I was just pulling from my experience at a Fortune 100, which was helpful because through all the training and structure, I’ve seen what worked and what didn’t work over my eight years of time. It was helpful, but there were a lot of things where I was just pulling it out of thin air. There wasn’t community yet; I couldn’t go to Pavilion and pull a template or grab a colleague. I had no one to lean on, and no one on the executive team had done this either, so it was very lonely. I was a bit siloed as well.

John Smallmtn (00:11:48)

Was the siloing helpful to you? Did it give you room and space to figure it out, or do you think it slowed down your process and your growth there?

Stephanie Valenti (00:12:00)

In the moment, I think it was helpful. I had relocated for this role, so it was just me. I would go home on the weekends to my family. I was down in Texas for a week, and I did that for three months. I worked 12-to-14-hour days constantly, just trying to figure things out. But I was in my own head—you only know what you know. I was researching, but there wasn’t AI. We’re talking eight years ago. I was thoughtful about all of my approaches, but would I do it the same way today? No, I wouldn’t, because I know so much more. I would reach out to peers. I would work with my departments to gain leverage and buy-in. I would do things differently. The biggest part that I remember that was exceptionally challenging—that I definitely wouldn’t do anymore because those that know me know that I teach forecasting—I talk about this example in annual planning and forecasting a lot. The CFO was real tough at this organization. He was your very stereotypical, negative person, and he was real tough on me. I remember him coming to me and saying, “How many headcount do you need to hit [X] amount of revenue for next year?” I started in September with that company, and we were coming into January, and they’re asking, “How many headcount?” I didn’t know that sales capacity planning was bad. So I was like, “Oh, I got this.” I had a giant spreadsheet. I took entire books of business and created account management roles, figuring out what growth we needed in each, and if we had a business development team, what could they do and what should the quotas be? I was so thoughtful and did so much work. I know now that that is a fool’s way of creating a forecast—you don’t ask me headcount and go the opposite way. But that’s what I did, and it was problematic, to say the least.

John Smallmtn (00:14:20)

I want to touch on this because one of the coolest things that has happened are these pockets of community. It’s weird because everyone kind of has their walls up around coaching, consulting, and mastermind groups. But as someone who does recruiting and placements, if you’re not taking time to upskill yourself, I have a hard time thinking that you’re going to put in the work to rise to the occasion. Things like Pavilion, which I’ve been eyeing for a hot minute now—because I’m doing more fractional stuff and probably need a bigger community focused around that—I have a network of people doing similar things that I can turn to. Much like yourself, I have this moment of: why would I ever try to figure this thing out completely on my own when I know people? That community aspect is one of the most helpful things on this path. From your side, as someone who is at the executive level, how important is it when you’re looking to place people or bring people onto your team that they’re doing something to upskill themselves or keep the edge on their craft?

Stephanie Valenti (00:15:47)

Mandatory. In the past, when I got started in sales, there was only one motion: outside sales. You went out, met with businesses, did your discovery, did your price proposal, and you left. It wasn’t marketing supported, it wasn’t partnership supported, and there was no channel. That’s how you did it. The world has changed. What works today may not work tomorrow, and the volatility of the market and the change of go-to-market motions is dynamic. Without a community, continuing education, and continual intentional research and learning, you’re screwed. You can’t just rest on your old-school morals and expect them to allow you to continue to produce. Community changed my life. When I was at Staples and at Vari, I never learned how to look externally to community, LinkedIn, or personal brand; I was all internal employer brand. After Vari, when I left there, it felt like a divorce. I had nothing. I hired all of my people, and they all still worked there. It was a little traumatizing. When I went to figure out what I wanted to do next, I didn’t have any community, network, or people to talk to. What are you going to do? That’s when I found Pavilion, and some of my best friends now are from that. Now I have an entire network every day that I can reach out to. I’m interviewing right now, and I didn’t apply to any of the places I’m interviewing with—it’s all because of the relationships and community that I’ve built. For people in big companies who only have their internal employer brand, I would rethink that real quick. Create your own.

John Smallmtn (00:18:07)

Yeah. There’s all this pressure about developing a personal brand and posting content. I make content and I’ve written a book. It takes time, but the lift is worth doing. My voyage into small business and entrepreneurship allowed me to work with a mentor back-to-back, so I had a lot of insight. I was working with a coach on the sales stuff, and then I just started networking locally in Dallas-Fort Worth. All of a sudden, I realized I don’t have to figure most things out by myself—I can talk to someone with more expertise and experience so I don’t have to recreate the wheel. That’s a hard place to get to when you’re young and ego is high, trying to prove yourself and figure out who you’re going to be when you grow up. You’re not even aware that you’re carrying more weight than you need to.

Stephanie Valenti (00:19:13)

Yeah, you try to carry it all because you have something to prove.

John Smallmtn (00:19:17)

Yes, absolutely. Something to prove. You talked about interviewing now and finding your next role. What are potential red flags for you that might indicate that a role or place wouldn’t be a good fit for you?

Stephanie Valenti (00:19:51)

What I’ve learned is you can’t come up with the red flags until you truly know what you want. I’ve coached people on this forever, but I never took my own coaching. Isn’t that funny? We’re great coaches to others, but we don’t take our own guidance. This time I did. I’ve had a lot of opportunistic things happen to me where I was at one organization and got pulled to the next, pulled to the next, pulled to the next. But it didn’t have a lot of intentionality to it where I said, “I want to do this, so I am going to interview for this.” That hasn’t happened. This time, I got my notebook out, and I wrote down: What are my superpowers? What is important to me? Where do I thrive? What are the things that haven’t been great, and what do I associate with that lack of goodness? I wrote it down, and then I spoke with Amy Volas, and she said, “Get the scorecard out, Steph.” So I created a scorecard. What I identified for me is the size of business that needs my expertise. Doesn’t mean I can’t do startup—I can—but my strength is in scale-up. What size business do they need to be? Where are they at in funding? Are they profitable or not profitable? What type of roles are currently in the organization? What am I leading—individuals, leaders, or seasoned leaders? What am I selling? That’s important. I wrote all of those things down. Now, every time I have a conversation—because I don’t say no to conversations—I’m checking my boxes. Is it fitting my boxes? Because if it’s not, I’m going to get in there, do great work, and make a really big impact, but I am going to be a bit miserable and probably not very happy in the background. I’m going to let it overtake my personal health, which I’ve done many times, and then it’s not going to work out, and we’re going to go our separate ways anyway. I’m looking for a home this time; I want to stay around for a while. So I’m just being very, very particular.

John Smallmtn (00:22:29)

I love that. I talk a lot about being intentional with my stuff because in martial arts, it’s one of the biggest things. Also, I played poker professionally for a while and I had a coach there who talked about, “What is your intention? Are you trying to win the hand? Are you trying to win the day? Are you trying to win the tournament? Are you trying to make sure that you make smart enough decisions so you can come back and play tomorrow?” That was a whole different way of thinking for me. I find that professionally, I would get poached, or I would go find something, but I wasn’t really intentional with it until I started my company, honestly.

Getting to that place of clarity of, “Oh, they’re in the ‘no’ pile; they’re in the ‘no’ pile.” And also being honest enough to really identify where you can have the impact that you want to have. Because as a coach and a trainer, the best thing I can do is say no to a bad fit, because I can’t coach into that brick wall of dissonance.

I tell people—this is going to be a weird metaphor—pretend that you’re the surgeon. If someone dies on the table, you’re going to have a big malpractice claim, like a lot of money, and you should feel bad about it as well if someone dies on the table. So just don’t take that gamble. Be intentional. If it smells weird, you should probably put it down and go focus on finding something that doesn’t smell weird, as opposed to just thinking you’re going to be enough.

Stephanie Valenti (00:23:52)

One thing on that, John: especially—and I don’t want to stereotype women in this—it’s more about people that are helpers. For me, I’m a helper. I always want to fix something or help someone, and you can get yourself in big, fat trouble when you’re interviewing when you’re like, “Oh, I see these problems,” or, “This doesn’t look good, but I can fix it. I can fix it; I can make it better.”

That’s now something I watch for. Do I think that I want to join this organization because I can help or make it better? Not that you shouldn’t want to do that, but it shouldn’t be the number one thing that you’re feeling, because otherwise you’re going to be put in a situation in which we just discussed.

John Smallmtn (00:24:42)

100%. One of my very early fractional roles, I got to come in and sit on top of it. I wasn’t wearing the label of CRO because I didn’t want it, but I was sitting on top of marketing support, or marketing success, and sales. I had the cape on too much because the CEO was a little bit too emotional and too easy to fly off the handle. I had this thing of like, I think I can make him consistent, which he didn’t want at all. My intention wasn’t really super solid there, and it led to some friction.

Now I try to do the same thing. One of my red flags is if we’re talking about it and someone’s like, “Hey, I need you to come fix my team.” Nope, nope, we’re done, because that person isn’t even aware that they’re part of the problem. Then I’m going to have to go in there and show them that they’re part of the problem, and they’re probably not going to want to hear that from me. This is a lesson from poker: I’m just going to fold and wait for the next hand.

Stephanie Valenti (00:25:48)

I love that. That’s really great advice.

John Smallmtn (00:25:51)

When you were sitting down and doing the deep reflective work of where you want to—like, what does this home need to look like for you? Honest reflection is super important, sitting down and being honest with yourself. Did you learn anything on the deficiency side that you’re now purposefully trying to shoring up or work on? Or are you at the place of, “I’m just focused on my lanes of greatness. I know I have deficiencies, and that’s like a ‘who, not how’ kind of situation”? How are you thinking about your development from this space?

Stephanie Valenti (00:26:29)

I wrote down the areas that I haven’t done well over the past and what I would need to overcome that deficiency. I can talk hypothetically, but a great example is during my time at SmartBug. I was brought on at SmartBug—they’re an agency, so it’s services. I’d never run services. I was running their total go-to-market, so I had marketing, sales, all client delivery, RevOps, and even some product in there. So it was a big role.

I didn’t have a problem with the transition to services; I found that to be applicable. What I did have problems with is I’d never run marketing before. I had said very transparently in the interview, “Look, this is a marketing agency. I’ve never run marketing before, and now marketing is reporting to me and I’m leading a bunch of marketers.” I bold-face asked in the interview multiple times, “Do you have concerns with this? I’m being transparent with you that I don’t have this experience.” It was like, “No, we have enough marketers in the organization. It doesn’t matter; you can learn it.”

What I found, though, is that I had a VP of Marketing that was a first-time VP of Marketing. It was during a volatile change in marketing where inbound was hot, hot, hot, and then it was not, not, not. I fumbled a little. I knew basically what to look for, but I didn’t know exactly tactically how to fix it. Speaking of deficiencies, that’s on my list.

If I’m going to come on and be a CRO that’s also running marketing, awesome, but I have to have a wicked marketing leader underneath me. I can lead a leader of any department—technology, HR, finance, I’ve done it all. But that leader needs to be an expert at their craft, because I’m curious enough to ask them questions and lead them to where they need to go, but I tactically cannot do their job. So that’s on my list.

John Smallmtn (00:28:47)

I love that.

Stephanie Valenti (00:28:49)

I’m not a practitioner there; I didn’t grow up with it. It’s things like that where I can’t do that, so it has to be this. Or, I move really fast, so I need someone to slow me down. What are the things that I’m going to do to slow myself down in my personal life, like puzzles or coloring, to slow my mind down? I’ve got a lot of things like that off to the side where if this, then that.

John Smallmtn (00:29:17)

I love how you talked about realizing that that was not your lane of strength, and then also figuring out how to talk about it in the interview process. Fake it till you make it isn’t really that great in my opinion. It’s going to get you to mid-tier, but it’s not really going to get you to high levels of performance. Being able to show up and communicate honestly—if they don’t like what you’re bringing to the show, it’s probably for the best.

It takes a long time to get to that place of maturity where you can live and let die, if you will, and let the cards fall where they may in those kinds of situations. But being able to clearly talk about those things—your strengths, where you have not performed as well as you would like in the past, and then how you’re not going to allow that to happen again because you can see the gap and speak positively to fixing it—that’s amazing. That’s so cool.

Stephanie Valenti (00:30:19)

My tagline is, “Oh, I’ve made that mistake before, so I won’t do it again.” When you’ve been in this many different businesses with this many different go-to-market motions, and you’ve been thrown into all these things, I have made so many mistakes. But I always say I’ll make it once; I won’t do it again. I hope I’m starting to get to the precipice of not having to keep learning from them—maybe I’ve learned enough. Mistakes are just the way that I’ve learned, and I’m not ashamed of them. It’s risk-taking. You’ve got to jump in and try, and you’re going to make mistakes and hopefully come out on the other side just a little bit smarter.

John Smallmtn (00:31:06)

Well, that’s really the point of this show. Certain people are expecting salespeople to show up day one ready to essentially pull rabbits out of hats. And with leadership, I’m sure you’ve seen this as many times as I have: you take the top-producing person and you put them in the leadership role. There’s no grooming, there’s no development, and then no one is even talking about or understanding why that’s a struggle. It’s a different role with a different skill set and craft that goes along with it.

It’s very interesting, but I keep seeing the same repeatable issues that people make. That brings me to my next question: You’ve done a lot of different things, and you’ve been really connected to this for a while. What are you seeing that you’re psyched about in this realm? And what are you seeing that you’re nervous about?

Stephanie Valenti (00:32:02)

As it pertains to people coming into new roles or promotions? I still think that we do not train our people the way that we need to. If I think back to my time in the Staples organization, the amount of training that I got as a new business developer in outside sales was in-depth. They flew me out for training for two weeks. I had six weeks of in-depth training. I did ride-alongs with my leader. It was not coaching, not supporting, but true training—someone saying, “Do this, do this, do this, do this, do this.”

I’ve had the opportunity to see my son’s training. For those that don’t know me well, I have a 23-year-old who is an SDR. So I’ve got to see his training, I got to be a part of multiple organizations that had salespeople coming on and going through training, and I’ve got to be someone new coming into an organization to see what my training would be like. We do not invest enough there; we just don’t. Even to the point where we don’t train new people coming into the business world on basics, like 101s.

I think I posted about this the other day: we don’t train people, “When you come to a meeting, come with a notebook to take notes so that you have takeaways.” We don’t train them on basics. We expect people—and this is where the root of this comes from, it’s not because we don’t care—we as leaders will naturally think that people just know things because we do.

John Smallmtn (00:33:49)

Yep, the curse of knowledge.

Stephanie Valenti (00:33:51)

It is the curse of knowledge, and they do not. So I’m not excited about us not making a big enough transition on that.

What I am excited about, though, if you take the individual contributor piece out of it or someone that recently gets promoted, look at the leadership side: community, coaching, fractional, coursework, LinkedIn. There are so many more resources than there were in the past. If a new leader comes into a role and they are on the internet and have Google search down, guess what? They’re going to find some things to really enable and make them strong, because they should know at least what to look for.

Whereas for someone coming new into the workforce, we need to be better there as leaders. We just do. We need to invest more resources and more time, and expect less in the beginning and more at the end result.

John Smallmtn (00:34:45)

Changing topics a little bit: If a salesperson is coming in day one, what’s the most important thing that they should be doing, reading, or asking for? How can they take those first steps on that path toward success? What would you recommend?

Stephanie Valenti (00:35:14)

First, make sure you really get time one-on-one with your direct manager. They will make or break your career. The first thing I have told even my son is to understand what the expectations are, really clearly and in black and white: “Okay, I want to make sure, in order to be successful here, what are the five things that I need to do every day?” Then you can work on the how, but you need to know the what first. Like, “Okay, if I make this many dials, if I convert those dials at this amount, if X amount of my appointments convert to closes, is that how I’m successful? Cool, I’m going to write all that stuff down.” That’s the number one thing that I feel like especially new managers forget to be very clear about—how success is delineated. So I think that’s first.

Second, join a community. There are so many communities that are free, especially in this remote work environment that still exists for SDRs. My son does work in an office, but for those that are not, the people that work in the office have a benefit: they get to hear their peers and talk about what’s working and not working. If you don’t get that, go be a part of a community and say, “Hey, here’s my call recording. Will you listen to it and give me feedback?”

My son will text me his calls and be like, “Mom, will you give me feedback on this call? What do you think I did well? What do you think I didn’t do well?” Not everyone has a CRO mom, so you can’t always do that. But do that. If there was a salesperson that sent me their call on LinkedIn and asked me to give them feedback, you better believe I’d do it. So ask.

John Smallmtn (00:37:06)

As a founder, I get all this outreach because everyone wants to sell me everything. Most of it is just the worst AI-driven spray-and-pray stuff. I feel compelled to be like, “Hey, I’m not angry at you for doing the job, but are you going to be able to find the volume to hit your numbers using this?”

Here’s the other part: I can’t take feedback off of everyone who is like, “Well, John, here’s a way to improve your messaging,” because you can’t take advice from everyone, which is the other hard part of this. Do you have any advice that you’ve heard or hear a lot that you think is overrated or not helpful?

Stephanie Valenti (00:37:51)

Personally, I don’t love unsolicited advice from people that you don’t trust or respect. Let me use the example of LinkedIn messages. I get a whole lot of those. I’m not going to give that person any feedback. They don’t know me, I don’t know them, and they didn’t ask for it. Maybe they don’t care to improve their craft.

I like using the investment methodology of, “I’ll invest my time in you.” I’m going to give you my dollar, and I know I’m only going to get 50 cents back for a while, and that’s okay. But I’m only going to keep investing in you when I know that there’s going to be a return. That’s how I look at mentorship, training, and whatnot.

That’s my biggest thing. Another reason why: I have a friend that’s interviewing right now, and she’s calling all these people for advice on her final interview and her pitch. She’s coming to me and she’s like, “I’m so confused. I feel like this, and now I’m getting in my head about this.”

I’m like, “Wipe it. You’re overthinking it. Just stop getting advice from people. Go with your gut, be authentic to your talent, be authentic to yourself, and just run.”

Those are a couple of different tactics that I think through. But my guidance for salespeople or even sales leaders out there that are looking like, “How should I get feedback, get information, or learn?” Ask for it. That’s it. Be the squeaky wheel. If your leader stinks—I’m sorry, but it happens—if you’ve got a stink leader, there’s not just community. Go on LinkedIn. Go connect with a bunch of VPs of Sales or CROs and say, “Hey, maybe I don’t get free mentorship from it, but at least…” Say, “Hey, I feel like my calls are kind of yuck. Will you just give me some guidance here?” No one is going to say no.

John Smallmtn (00:40:01)

The hard part of that is accepting the coaching when you’ve asked for it. As a martial arts instructor, one of the things that would always drive me crazy is when they’d say, “Well, John, you don’t get it.” I’m like, “What don’t I get?” “Well, this is easy for you.” They’re building that wall.

That is one of the things that I look for as a coach. Nothing drives me crazier than talking to someone who has their arms crossed and isn’t open to the improvement that we’re there to try to find together. I get so dismissive of someone who’s like, “Help me, help me, help me.” “Okay, cool. Have you done this?” “Well, no, I shouldn’t have to do that. I’ve got to go over here.”

Stephanie Valenti (00:40:43)

Do you want my help or no? You asked for this. You asked for this.

John Smallmtn (00:40:48)

Diving in, I’m curious—and I’m going to break this question apart a little bit—moving from the individual contributor to a sales leader role, what do you think the hardest part of that jump is?

Stephanie Valenti (00:41:04)

There’s a lot there. I remember being an individual contributor taking over a team for the first time. The biggest challenge for me was learning that not everyone thinks and does things the way that I do.

I remember I was running my first big call day for a business development team and we were supposed to make appointments. I couldn’t understand why people wouldn’t just pick up the phone. Someone told me you needed to hit an “eight and late,” right? You get to make eight appointments and then you get to say later—like you get to leave for the day. Why wouldn’t you just go make eight? Pick up the phone! I didn’t understand that everyone wasn’t wired the way that I am. It took a minute for me to understand that not everyone is motivated by leaving early or exceeding an expectation. You’ve got to really figure out what makes the individuals on your team click. That was a big one for me.

The second one is I didn’t know how to be a leader yet, so what I did was copycat lead. Copycat leadership is trying to lead like the person that just led you when you were coming out of your role. My leader was exceptionally successful—President’s Club every year, always the number one team in the region. So I’m like, “Oh, well if I copy the way that that person led, then I’m going to be wildly successful.” It was weird, right? It was so weird. I’m sitting here trying to be quiet and analytical and like, “Well, what do you think?” That’s not who I am. I am authentic, high energy, and supportive naturally in my leadership style. It took me a while to figure out the authenticity needed and the leader that I needed to be. That was really difficult.

By the time I figured those two things out, I was able to lead a successful team. But the other number one thing I learned during that transition is stop saying, “Oh, when I was in the role.” People do not care. They don’t want to hear “back in my day.” No one wants to hear that. Make it about them, come up with your own authentic leadership style, and understand what motivates each person, realizing that not everyone thinks and does things the way that you do.

John Smallmtn (00:43:41)

Talk about hitting the nail on the head. I’m this kind of fish out of water for most sales roles because I like to communicate and I like to help, but I’m not zero-sum. I’m not driven to crush other people or any of that stuff. I just want to help and do a good job.

When I first did DiSC with my sales coach and he was showing me, “Hey John, here’s why you struggle,” first of all, it was beautiful to know that I wasn’t the only person having these struggles. Before you go through an evolution like that, everyone thinks they’re on their own individual struggle bus path. He was trying to talk me out of sales. He was trying to say, “Hey John, maybe you should go be a developer. Maybe you should go be a CPA.” Because as a C-style personality, there was some greatness there for me. It was bouncing off of me because I was having this moment of, “I just need to go find some Cs that have been successful in this role. They’re going to be able to help me out.” Now, it’s hard to find a lot of Cs in sales and marketing, so it’s been quite the journey, but that was a huge moment for me—realizing that I was not alone and giving me a path.

Same question, but going from sales leadership to the executive level, where you’re now coaching leaders: Was it more of the same at a bigger level, or were there different lessons that you had to work through and figure out?

Stephanie Valenti (00:45:31)

Definitely different lessons. When I think about a sales leader, you are working in the day, the week, and the month to achieve activity, people results, motivation, pipeline expectations, and ultimately hitting that quota. Every single day, that’s what you’re doing. As a leader of leaders, you should be thinking in the month and the quarter. As a manager, you’re thinking in the week, the day, and occasionally a month, but as a leader of leaders, you’re thinking broader—today and the future.

How do you do that mindset switch when you’re focusing on priorities? Initially, I got a little carried away and wanted to do too much. I’m thinking of the future, so I’m like, “If we did this and that, this training, this initiative, and this motion, then we’ll be able to create efficiencies and drive growth.” But I wasn’t remembering that my leaders have all of these day, week, and month tasks. It was a bit overwhelming in the beginning. I needed to put myself back into that seat to remember: What are my leaders doing every day? What can I actually take off their plate to make them more successful? Not what can I put on, but what can I take off. That was a bit of a learning in the beginning for me.

I also remember a huge leadership mistake during my time at Vari. There was a lot going on. It was in year two, and we maybe had 120 salespeople at this point. Everything was working and growing. A sales leader that I’ve worked with since my time at Staples was in the room with me. I had my SDR leader, and we were brainstorming about something. I was really empowering them to make the decision. I’m like, “Guys, figure it out.” They’re like, “Well, we just don’t know.” I walked away and said, “I’m leaving the room. You guys figure it out.” I was at a very high stress point, and I left.

This person had worked for me for a long time. She came to me after and said, “Steph, no. We actually need your support. We can’t figure it out.” We were both really upset that I was not realizing the support that they needed. That was a balance I had to learn early. Your leaders don’t always have the answer. Sometimes it’s good to push them, make them come up with it on their own, and let them fail; sometimes it’s not. I didn’t do that again.

As you’re taking over bigger teams, you expect certain things out of your leaders, and sometimes they don’t have it. You’ve got to come back down, go back up, and know when people need certain leadership styles. That’s what really got me into Situational Leadership. I love it now. It’s a staple I go to for learning when people need training, coaching, supporting, and mentorship. I use that to guide myself as well.

John Smallmtn (00:48:53)

Very interesting. We’re coming up on time, and once again, I’m so glad that we were able to make this happen. I love your content, and what a great interview. I hope this helps a ton of people.

Some rapid-fire questions: What do you do to work on your craft at this stage?

Stephanie Valenti (00:49:20)

Mentorship, mentorship, mentorship. Not just being mentored, but mentoring others. I’m going to tell you, I learn from my mentees almost more than I learn from a mentor. I do have a mentor, but if someone asks me for something, I’m generally giving. Right now, probably five or six times a week, I’m talking to somebody about something.

John Smallmtn (00:49:47)

For someone who wants to move into leadership, but the path isn’t right in front of them—let’s say they’re applying. I actually applied for a sales leadership role at Vari. I drove out, had the interview, and I thought I was ready. The guy came in and said, “I think you’d be great in an individual contributor role.” I said, “I really want to take the next step.” It didn’t work. I had had some stints where I was performing well on a team, and when an assistant manager role would come up, the pushback I got was, “Well, John, you’re not bubbly.” Because I’m this colder, critical person. All of this stuff that everyone sees now is intentional. What would your advice be to someone who wants to be in leadership, isn’t getting the lane, and wants to start walking down that path to be prepared?

Stephanie Valenti (00:51:00)

Understand your why. Why do you want it? I think people forget: Is it just because it’s the next step, or is it truly something that you want? Leadership can be thankless. It is about others, not yourself, and it takes a special type of person to have the patience that you need to be a great leader. Write down why you want this.

Once you’ve figured that out, if it’s for the right reasons, you need to speak up—not just when it’s time for interviewing or for the role, but say, “Hey, I want to be a leader. Here is my why. What are the key things that I need to work on that you see as deficiencies today that I can proactively enhance to get into that role?” Those are the things that I would do.

Leadership has come a long way since the idea that it needs to be bubbly or high energy. People now respect diversity in personality and what people bring to the table. Proactively talking about a weakness is a strength, in my opinion.

John Smallmtn (00:52:13)

I agree. It’s a sign of maturity.

Who are your favorite people to follow in the world of leadership? Who do you like? Who do you read? Who do you invest yourself in because they’ve got good content or lessons that have helped you?

Stephanie Valenti (00:52:37)

I am a superfan of Patrick Lencioni—by far my favorite author. I’ve been to conferences. I believe in organizational health and what it does to promote growth within an organization and its people. When I say superfan, I mean superfan. I absolutely love it.

John Smallmtn (00:52:59)

Getting Naked is one of my favorite sales books, but it’s not even really a sales book. It’s a clarity book about really getting deep and figuring out the why, the how, and all that stuff. Listening to that book worked in me while I was going through the rringer of realizing that I was being a little too opportunistic. In Kung Fu, we call it being rooted—you’re sunk into your stance. I was not rooted; I was just like a buoy getting pushed around everywhere. That book led me down the path of needing to figure out who I am and how I want to get things done. Amazing book. It’s on my top shelf of recommendations.

Sales-wise, who do you like in the world of sales that is providing really good content? The hard thing about sales is there are a lot of mantras and social media stuff that doesn’t provide depth. Who do you like who goes deeper and is helping sellers figure it out?

Stephanie Valenti (00:54:11)

These people are friends at this point. I like Jen Allen. She does a stellar job. She worked for Challenger, so that’s her background, but I really enjoy the tactical guidance that she gives on understanding the deal.

KD [Kevin Dorsey] is a friend. He does great work on understanding motivation and the why behind the activities and actions that you’re doing within sales. I really like him as well.

Kyle Coleman is great. He gets tactical, so I enjoy that too.

As far as books, I really love the fables and real-life concepts, which is why I like Patrick Lencioni so much. These books that are step-one, step-two and repeat themselves a thousand times, I’m not a superfan. My favorite selling style is Sandler because it’s discovery, it’s strong, it’s curiosity, and it uses emotional psychology to bring the deal to fruition.

John Smallmtn (00:55:22)

Agreed. I spent a lot of time in Sandler before. I was actually going to buy my coach’s business; we were in deep conversation about it. Then I started to see some of the gaps in the cracks in the veneer. I was getting a very interesting version of Sandler because my coach had been doing it for so long, and I realized that was not common. There are some really top-tier coaches and trainers in Sandler, but there are also a lot of people who were just trying to build a business. I was getting this philosophy and life approach—a way of being, not just something you put on to go close deals.

You mentioned earlier that marketing was something that you had to figure out. On that marketing lane, who do you really like? Who has been helpful to you on your path of looking at data the right way and making the right decisions?

Stephanie Valenti (00:56:24)

Dustin Joost is a sales leader, but he is a marketing-based sales leader. I love being able to speak in sales and operational language and have him translate it into marketing language for me. I really enjoy him and my time with him.

During my time at SmartBug, I became very close with a whole lot of marketers. Any time I have a marketing challenge or question, I go to them. They were generally directors within that organization, so I spend a lot of time working with them.

Of course, Kyle Lacey and I are friends. We’ve spent time at Pavilion events together, and he’s got a great understanding of intentional marketing that goes beyond the silo of marketing cross-departmentally and how it affects other organizations.

Latane Conant is great, right? I got to spend some time with her in the Pavilion community as well.

There are so many. Building a strong brand means that you have unlimited resources of people to reach out to. Especially when you give as much as I do, people are always willing to reciprocate. Keep giving, because you’re going to need that same amount of help at some point, too.

John Smallmtn (00:57:53)

I love that. Last question: Who should I have on the show that you would like to see me talk with?

Stephanie Valenti (00:58:00)

Her name is Danielle Press. She was SVP or VP at Hotel Engine, which was a rocket ship over the last five years. She had twins, took some time off, and she’s about to get back into it as a CRO. She is definitely someone worth talking to. She is brilliant, very smart, and always in sales, building large sales organizations.

From a community standpoint, I think Leslie Greenwood would be fantastic. She’s a dear friend and she’s here in DFW, too. She’s a community evangelist. Talking to her about how important community is would be a great one for you.

John Smallmtn (00:59:01)

I’m looking to explore all these different ways of getting it done. People will talk about sales motions, but community-led versus social-led versus channel-led are all very different, and how you build them is very different. When you’re the hammer, everything looks like a nail, but there is nuance and depth to each one of these motions.

Thank you so much for coming on here and doing this. You mentioned you didn’t have any more calls today, so you didn’t even really need to do this one, but I appreciate you hopping in here, keeping it real, honest, open, and authentic. No talking heads, no people with ghostwriters—you really brought it, and I appreciate it.

Stephanie Valenti (00:59:47)

You’re so welcome, John. This was so fun, such an easy conversation. Thanks for having me.

John Smallmtn (00:59:50)

Where would you like people to come hang out with you if they have questions, are looking for roles, or are interested in working for you after you get into your new home?

Stephanie Valenti (01:00:03)

LinkedIn is my social of choice. I’m fast on response in my DMs. If you request to follow me, I’m going to accept it, and if you write to me, I’ll write you back. That’s my preferred.

John Smallmtn (01:00:18)

Awesome. I hope you enjoy the rest of your day. This was really awesome. I appreciate it.

Stephanie Valenti (01:00:24)

Of course. Thanks, John.

John Smallmtn (01:00:26)

Cheers.