Skip to content

New episodes sent directly to your inbox. Subscribe now.

Season 2, Episode 1

Against All Odds: How Two Powerful Female Leaders Made Their Way to the C-Suite

Jen Spencer, CEO, SmartBug Media® and Stephanie Valenti, CRO, SmartBug Media®

On this very special episode of The Intelligent Inbound® Podcast, recorded at INBOUND 2022, Jen talks with Stephanie, Chief Revenue Officer of SmartBug, about what it’s like to be a woman in a C-suite executive leadership role today.

The path to success hasn’t been easy for either of these women, from first launching their careers, to working their way up the corporate ladder. But with equal parts grit, gumption, and determination, they’ve learned how to take big risks and make big moves without letting adversity get in the way of their next great audacious goals. 

Listen in as Jen and Stephanie chat:

  • Gender and racial disparities at the C-Suite level (02:48)
  • Stephanie’s early days as a working mom (04:08)
  • Jen’s first career ambitions in the non-profit sector (11:26)
  • “Can I pull up a chair?” Learning as you go (12:56)
  • Client > CRO > President > SmartBug’s CEO (16:30)
  • Navigating male-dominated workspaces (19:29)
  • Overcoming imposter syndrome (23:58)
  • “You’ve got to take a risk.” (27:57)


Jen Spencer (00:54):

Hello, and welcome to the Intelligent Inbound podcast, brought to you by SmartBug Media. I'm your host, Jen Spencer, and today's episode is how against all odds, two female leaders made their way to the C-suite. And it's an extra special episode today because we are recording live from Inbound in Boston. As I mentioned, I'm Jen, I'm not only the host of the Intelligent Inbound podcast. I'm also the CEO of SmartBug Media. We are an intelligent inbound marketing agency, an elite HubSpot partner, and the highest rated partner in the HubSpot ecosystem, according to our customers at least. You can learn more about us over at booth number one. Now, today I'm also joined by our chief revenue officer at SmartBug Media, Stephanie Valenti, and Stephanie is very well known in the Pavilion space. If you're Pavilion members, she teaches classes on revenue modeling and forecasting.


Although we're not going to be talking about that today, we're going to be talking a little bit more about our journeys and ourselves. Honestly, we're going to get a little bit vulnerable and real and authentic. And if you know me, that's how I roll. And so this is going to be fun. So Steph, I mentioned we're here to talk about us and as women, sometimes that can be a little bit challenging in a business world to do. Your journey has really inspired me. I know you've found inspiration in my journey, and we're going to share those stories. Before we get into sharing some of those stories. I think it's important that we recognize that diversity in the business world continues to be a challenge for us. And before we get into to our story, I want to share a couple of statistics that I think are important for framing this conversation.


So according to the Society of Human Resource Management or SHRM, women make up 56% of frontline employees, but only 29% of the C-suite. So quite a disparity there. When you then look at black and indigenous people and other people of color, they make up 31% of frontline workers, but only 17% of the C-suite. And if you look at black women, women of color, the numbers are even lower. Also an organization out leadership. They're a business network that places LGBTQ plus community members into executive positions. They've reported that fewer than 1% of Fortune 500 CEOs identify as part of the LGBTQ plus community. So in short, we have a lot of work to do as a community, but today what we can do is we can share our stories, hope to inspire others and acknowledge what work we need to do as a collective. So with that, Stephanie, why don't you start tell us a little bit about your journey to becoming a C-level executive.

Stephanie Valenti (04:08):

My story starts off with a little bit of adversity. I had dreamed of being a doctor, always wanted to be a doctor, was going off to college, and my senior year of high school that summer got pregnant. So that was going to be off the table. Going away to college was off the table. I was having a baby. Instead of following that doctor dream, I was working three jobs, going to school, and had a little baby. So it was a lot.

Jen Spencer (04:43):

That's a lot. Can you give us an idea of what a day in the life was like for you? I can't believe that, being a mother of twins, myself, understanding what that could have been like, working three jobs, going to school. What kind of community, what kind of support did you have?

Stephanie Valenti (05:02):

Yeah, yeah, it was a lot. I had great grandparents, so I attribute a lot of the help to them, but they were hard on me. I would get up at 7:00 in the morning, I would go to a doctor's office job. I worked at his doctor's office. I'd drop off my son at the daycare and then I would come back. I would wait tables at night and they would let me put him down, do all of the nighttime things, put him down and then go to work. Then three to four times a week, I was a karaoke DJ at night too. A lot of fun there, but that would be till 2:00, 3:00 in the morning. Then I would have to get up at 7:00 again and so running on very little sleep, I remember very little of that first year, but it gave me some grit. And I do thank my grandparents every day for being able to be there for me and also making it hard on me, they didn't get them up in the morning for me. I had to do that myself.

Jen Spencer (06:00):
So you intended to go to school originally to become a medical professional? You're not in the medical
space now. So when did you make that transition in your career?

Stephanie Valenti (06:14):

I did my first year and a half or so of classes in medical and while at the doctor's office, I started at the front desk, and then I went to medical billing, and then I got to the back office, and then I got to surgical assisting, and then I got to x-ray, and what I realized was unless I go get a license, this is it. I went and I did my journey and there's no more for me. And I was always someone that wanted the next thing. And so I realized I better switch this up a little bit. And so what happened from there is I did the same thing at restaurant I was serving and I made my way up to corporate office and realized, oh, well, I don't know if I want to do this either. And so got my first shot when I was 25 with Staples Business Advantage in B2B outside sales, selling programmatic office supply contracts with print and promo and man, did I have a good time with Staples.


It was about seven and a half years and they taught me everything, all of that foundation. So from business development to business development leader, to account management, to account management leadership, to more of a director of a general management type role where I was running multiple different centers of excellence, as well as enterprise type business. So got a ton of experience throughout that journey and had a lot of challenges throughout that journey too. You guys can probably tell today, even from my voice, that I'm high energy. I've got a lot of energy and that was deemed cheerleader, or not strategic enough. And then I would then shape myself and change myself a little bit and be direct and lose some of that cheerleader and then I was a bulldog. So lots of different challenges throughout my way, but I wouldn't change it for the world.


And then after Staples, went ahead and moved into my first executive role, someone took a shot on me and I became a senior vice president of global sales, starting with a real small 40% inbound type of people were calling and saying, I want your product. And they had asked me to build and scale that away from transactional and eCom into a B to B centric organization doing project inside sales, outside sales, outbound motion. And I learned so much in my first two and a half years, first executive role, and so lots to share in that journey. But after that, what I realized in that first executive role was I need to figure out how to work better with a CFO because coming from a Fortune 100 and then being at the executive table, it was like, oh man, I'm not speaking his language, there's disconnect.


So I had the opportunity to go be a COO. And now I was running finance and I was running manufacturing operations, and I was running HR in a pandemic. So that was a lot of fun. Anyone that wants a side conversation about that totally open to it. But it was crazy, and I learned to be a better revenue leader because I went to the other side. Now I also got to learn my brake pedal because I'm all gas and I got to learn, oh, this is why people stop and ask questions. So that was good. But I had been in supply and commercial office furniture and a little bit more of an antiquated business. And what I loved so much about Staples when I was there is I got to help customers.


I got to help them purchase and improve their procurement. And I was really hungry for that again. I wanted the opportunity to help. If you go all the way back to wanting to be a doctor, I wanted to help people. And this opportunity at SmartBug allowed me the opportunity to get back into helping customers grow, helping my team grow. And so met Jen through Pavilion and we were connected by a mutual contact and the rest is history. So now I'm in a CRO role, a new industry for me, this is my first inbound conference. So excited to be here, but learning new things again, running sales, marketing, and operations, client delivery.

Jen Spencer (10:31):

I think I want to go back to something that you had said about someone took a chance on you. And I think it's interesting that you're saying that. I think it's something that we tell ourselves, especially as women. Is it because on paper you wouldn't have been that candidate?

Stephanie Valenti (10:49): Yeah.

Jen Spencer (10:50):
But is it that someone saw something in you? It was you had the skills. Why did you say that, they took a

chance on me?

Stephanie Valenti (10:56):

Yeah. Why do we do that? I don't know why I said that, right? Yes, I was qualified. I was going into a small organization at the time and I came from great systems and process and leadership experience. And so no, I earned that role.

Jen Spencer (11:12): Okay. Lovely.

Stephanie Valenti (11:15):
All right. Why don't we flip it. Love to get you a little vulnerable here, Jen, and hear your story. How did

you become the CEO of a very well known agency?

Jen Spencer (11:26):

Well, unlike you, who always knew what you wanted to do, when I was young, I wanted to be in charge and that's pretty much it. I wanted to be in charge. It just depended, it didn't matter what it was going to be. No, but I ended up getting my degree in secondary education in English and theater arts and 

drama journalism. And for four years I was a high school English and drama teacher. And I loved it. I really did, but I liked the content. I liked the idea of connecting with an audience. I liked the rhetoric. That was the part that I really craved more so than all of the good that teachers do and continue to do for our children, which they should do. And they're wonderful, but it wasn't like the thing that just filled me, it was more of the content.


I was volunteering my time with a nonprofit professional theater company. And it was my first, what I've referred to over my life as golden ticket opportunities. And I think when I look up my career, anytime I've had an opportunity where I think I would regret it, if I didn't take this chance, if I didn't take this leap, I'm going to do that. Because someone had once told me that you will always fall back on yourself. So I knew I'm a good teacher. Listen, I was student teacher of the year. I was rookie of the year. I knew I could go back and do that, but let me try, what else is out there? What else can I do? So I was volunteering with this theater company and then they said, well, would you want to come on in a full- time role, all in the education space.


And I was in that role for about six months when the marketing director at the time said, "We've been trying to fill this PR role and we think you'd be really good at it. And what do you think?" And I said, "Well, I think I don't know anything about PR or marketing, so I don't know why you want me." And she said, "Well, I think you do. And the other stuff we could figure it out. We'll train you." And man, if you want to just be thrown into the fire and just sink or swim, a nonprofit is a really great place. And I was there for eight years. My strategy was if someone was doing something that I didn't know how to do, whether it was a direct mail campaign or it was something more technical in nature, I just said, "Hey, can I pull up a chair? And can I just watch, can I shadow?"


And then watching and shadowing turned into helping and my role expanded. And so I went from being PR manager to over the course of eight years, by the time I left the theater company, I was director of sales and marketing. I was responsible for generating 75% of the organization's revenue, about a $7 and a half million size company. And it was great, but I did face some challenges, a lot of criticism as a young female, even in the arts community, which might surprise you. And I was tired. It was the kind of stress where I would go to bed at night and I would think, okay, if we don't sell $10,000 in tickets tomorrow, then we can't make payroll on Friday. And that got to be exhausting. So from there, I actually decided I'm going to sidestep and transition, and maybe I'm going to take a little bit of a backseat and take a marketing role in a B2B organization.


And the backseat didn't last for very long, because I am who I am, the kid who wants to be in charge. So got into B2B SAS and had some really extraordinary mentors, had an opportunity to implement HubSpot back in 2013. That had an extraordinary opportunity where a CEO said, "I have a million dollars. I want to spend it on marketing, and I want you to tell me how to do it." And I said, "I will take that job." And the first purchase I made was buying HubSpot and building an inbound strategy and took that company through acquisition and had a chance to work for a multi-billion dollar publicly traded company and learned very quickly, I do not belong in a multi-billion dollar publicly traded company. I belong in a company where I can have an idea in the morning and then execute that afternoon.


I then left and joined an early stage startup called Allbound and when I joined, we were pre-product and pre-revenue, which means we had an idea. We had won free office space, and when I first started as director of marketing, the CEO and founder, literally day two of me walking into this teeny tiny room said, "So do you want to do sales also?" And I had never done sales, but I thought, well, let me try. What's the worst that can happen? And I'll always fall back on myself. I know I'm a good marketer. And I marketed by night and I sold by day and I would adjust my marketing strategy based on the demos I was getting and began just growing that presence and that company's now, I was there for two years, they're doing extraordinarily well now. I got their first $2 million in ARR in the first two years. And I know I was also tired.


I do want to mention both companies I was at, I also hired SmartBug. I was a client of SmartBug before I joined the company. But there was one day I was watching what SmartBug was doing. I was watching the brand. I had connected with the founder and CEO. I understood what he was building and growing. And I literally texted him one day for him out of the blue and said, "I can't help but think that I maybe should be part of what you are doing. There's something special that's going on at SmartBug. And I see you have a director of sales role and I see you have a director of marketing role open. I would like to do both. And oh, by the way, I would like a VP title." And he said, "All right, well, let's talk."

Stephanie Valenti (17:15): Way to ask for what you want.

Jen Spencer (17:16):

Yeah. And that was not the first time I asked for what I wanted, because that was 2017. We did extraordinarily well. When I got in, I had that hunger. I had that drive of being a non-profit or being a startup where you don't know where your next meal's going to come from. And implementing a lot of those SAS business tactics inside of our professional services company, we grew 70% year over year, my first year of running sales and marketing. And so I earned the opportunity. I earned in my opinion, the right to say, "Hey, let me talk to you about what I want next." And what I had next said in my sites was chief revenue officer, the role you have now, and I had joined Pavilion and they had an alpha program just getting off the ground for a CRO school.


So I told our founder, my boss, I said, "I think I want to do this, but I need to know that it's going to be okay with you because it's going to take some of my time and attention away from my job. And there's just nothing I can do about that. I will put in all of the work possible. I will go work extra, but I just know myself." And he said, "No, this is great. I support you." And he did. And so that carved the path for me to move into the CRO role and gave me more exposure to the organization, taking over client services in addition to sales and marketing, so that when it was time for him to decide to move on in his role and he was thinking about succession planning, I was who he went to and when he asked me, "Hey, do you want to take over as CEO of SmartBug?" I said yes. And it was everything in my being new. This is exactly what I was meant to do.

Stephanie Valenti (18:58): That is awesome.

Jen Spencer (19:01):

So some inspiration, powerful stories, but I think we got to talk about all of the times in our career stuff where we've heard feedback like, you should smile more, or be less emotional, or maybe soften your approach. What advice do you have to other women here that might be facing some of those gender biases?

Stephanie Valenti (19:29):

I talked about it a little bit in my story, where I was deemed this cheerleader and a great rah rah person, which meant I didn't know how to deploy strategy. So then I adjusted myself and I went bold and I went direct and then I was a bulldog. And so what I started to realize is not everyone's going to like my approach and the best approach is authenticity. That's step one. That's the big piece of advice, is be your authentic self when you're a leader, because anytime you try to be someone else, you're not going to be a good leader. The second piece is you have to address it. You have to talk about it. And so if we go back to that bulldog story, I was at the end of an interview, I had gone through a long series of interview and they were dropping me back off at my hotel because I had to fly in for this interview and I'm sitting there and he looks across at me and it was a more casual environment.


And he goes, "I just have to address this with you. I've heard that people can say you can be a little bit of a bulldog." And I don't know if it was the environment, I don't know what it was, but I straight looked at him and said, "Would you say that to me if I was a man?" Flat out said it, and once you address it once, you can address it forever. It's that first time, getting over that hump. And so he kind of chuckled a little bit and laughed, and then I knew, okay, I called you on this. You've got this and we're in line.


So that's the second piece. Figure out how you can address it in the right place and the right time. It doesn't have to be an uncomfortable conversation. That's the second big piece. The other piece is you're going to get people having biases forever. They don't go away. Even when we're trained, unconscious bias is something that we talk about all the time. And so being able to look for those and address them in a proper way is always good. But you need to be mindful of where they are and what those are.

Jen Spencer (21:30):

I think about my, because I have these moments across my career where I wish I would've had that strength that you had to say something. I remember being told once I went to my boss because I was having a really challenging time working with one of my peers, a male peer, and I didn't feel there was respect in the relationship. And my boss, who was also a man said to me, he's like, "Well, Jen, a lot of men have a really hard time with strong, intelligent women, which you are. And so when you work with this person, you might want to make some adjustments so that he feels better about the conversation." And we were in a car, we were coming back from a meeting and I was just like, I knew it was wrong, but I didn't know it was wrong enough to say something.


The other thing I want to add really quickly. And this is really, really important to me, and why I value just building a company where people can really be their true selves and bring their full selves to work is for years, it took a long time to unlearn the fact that I tried to hide that I was a parent because I also had an executive tell me that I would never be as dedicated to my job as a male counterpart because I was a mother. And so for years I would not openly share that I was a mom. My boys just moved into college. They're great and I love them, but it took a long time in my career for me to just embrace that and lean into it. And it makes me sad, you know?

Stephanie Valenti (23:09):

Yeah, yeah. It's funny, as you say that, I think about what did I do? I didn't pretend, I was pretty out with it, but you know what? I always had a caveat statement that would be like, "Yeah, I have children, but my husband stays home." I more took the career path and he owns a small business, but I would, "Oh, but my husband's with them. So it's fine." Why did I have to say that? But I did. I did always say that.

Jen Spencer (23:34):

When I worked in the theater and I would do PR and I'd be at the theater at night, people, anyone would come to me and say, "Oh, well, who's watching your kids? And sometimes I would get really sassy. And I would say, well, "I have a really nice house cat. She's great. She's super responsible." So you wouldn't ask my husband that if he were here right now. Anyway.

Stephanie Valenti (23:58):

Yeah. Well, Jen, something that is big right now that we're all talking about is imposter syndrome. It's become something that's way more well known today and maybe didn't have a name in the past, but it does now. And I know that this is something that you're passionate about talking about at SmartBug. We have to do a mentorship program. And so I'd love to hear what you tell those mentees.

Jen Spencer (24:20):

Yes. Well, first I want to say is everyone assumes that I don't have imposter syndrome anymore because I'm the CEO. You don't have that. It's a every day, every day kind of battle for sure. And so there's two ways that I work through my imposter syndrome because I don't envision that it's going to go away anytime soon. I've had people tell me, you don't just ignore it. Don't let that get in your way. Well, that is not actionable to me. So what's actionable first is preparation. So typically if I'm feeling that sense of imposter syndrome, like I don't belong, it probably means I skipped some kind of a step. I didn't take the time to prepare myself in some way, shape or form. So that for me is a trigger or a signal for me. And it's something that I focus on being as prepared as I possibly can.


The other thing is when I took this role as CEO, the board was very, very generous in wanting me to attend a program, Wharton's Executive Development Program. It was basically a two-week MBA, so it was exhausting. I haven't pulled all-nighters like that since I was back in college, but it was great. And I had an executive coach who really helped me during those two weeks, because I'd be in a room with 42 people, CFOs, COOs, global VPs of sales at big companies, like 10X-sized companies, 50X, big, massive organizations. And we were going through deep financial records and talking about M and A strategies. And I'd be sitting there like, what am I doing here? I don't belong here. And what my executive coach taught me was a visualization technique.


So she said, imagine, recognize that. So I envisioned that voice as this red sort of blob, red, because it was like a stop sign for me, it was like, stop. It's preventing me from interacting, exchanging with the group, and to picture it and acknowledge it. Like okay, I see you, but I don't have time for you right now. So I'm going to take you and I'm going to put you over here on this shelf. I'm going to get you out of my way. And then what would happen is it would free me to just engage in whatever was happening and if that imposter syndrome was invalid, then it would just disappear.


And if it wasn't, if it still lurked around and I saw it on the shelf, then guess what? It means I needed to go back and I needed to do a little bit of preparation and to get myself into a more comfortable space. And so that simple visualization technique I share with my mentees through our mentorship program, you mentioned, Steph, that we have at SmartBug. And it's good for not just imposter syndrome, but also things like when you're navigating a difficult customer conversation or management related conversation. And you've got these little voices in your way, telling you a story that's not actually happening. So those are things, I'm a physical tactical visual type of person, that have really helped me.

Stephanie Valenti (27:19):
That's awesome. I'm going to have to try that one.

Jen Spencer (27:22):

Wonderful. Well, I want to ask Steph, if there's any other examples, any other advice that you have, if there's a woman that's listening to this, or maybe even if there's a male executive who's thinking about, I think about Ryan, our founder and how much he's invested in me and mentored me and saw, we say take a chance. I don't have that resume necessarily of CEO. Although it makes sense for SmartBug, any guidance you would give those folks?

Stephanie Valenti (27:57):

I talk about this in a lot of the courses that I teach and people that I mentor. And I think the biggest thing is you've got to take a risk. And so when people ask you or offer you opportunities, even if they're uncomfortable, you have to raise your hand and say yes, and eventually they become comfortable, right? What's uncomfortable today is comfortable tomorrow. And so that risk taking piece is huge. I lost myself a little bit in that first executive role, I didn't feel like myself anymore.


When you get really stressed out, you become somebody different. And I was talking with the CFO, who I had not had a great relationship with. And I had said, "I don't know what's happened. I don't know where I am." And he said, "Steph, you're somebody that takes a risk." And so the quote that he said that has stuck with me forever is "Think about the risk and think about the worst thing that could happen. What is the worst outcome? And if you can live with that outcome, then what's the risk?" So that is in my head always. And so I would encourage everybody, just raise your hand a little bit more.

Jen Spencer (29:07):

Excellent. I think I would share as some examples, I think that's great. And it goes into my idea of falling back on yourself and taking those leaps. But I would also say there were times over my career where there were male leaders who were unaware of biases that were happening in the organization. And so it's be aware, do you have a group of male team members going to a basketball game and are you not inviting that woman because you're assuming that she doesn't want to go. Just think about all of those kinds of out of the office, our new world of office, of those sort of offline activities and just to be conscious of it, because you never know who you might be. You might be expecting something from someone and missing out on such an extraordinary opportunity to grow someone in your organization.


Excellent. Well that is all the time that we have today for today's episode. Steph, thank you so much for joining me, being your vulnerable, authentic, real self. This is who you are every day. I'm so glad we had a chance to share our stories with everyone. Folks who are here at Inbound, the Intelligent Inbound podcast is on Apple podcasts, on Spotify. You can rate and review us. If you learn something today, I always ask, please pay it forward. Share with a friend and thank you all. Have a wonderful day.

Stephanie Valenti (30:39): Thank you.

Keep Listening

Building a Brand Your Customers Trust with Rob Giglio, CCO at HubSpot

Rob Giglio, Chief Customer Officer, HubSpot

On this episode of the Intelligent Inbound Podcast, Jen and Rob Giglio, Chief Customer Officer at HubSpot, sit down to chat all things inbound.

Read More & Listen

Creating a Seamless Digital Path for Customer Engagement

With Graeme Watkins, CEO of Valutrades

On this episode of the Intelligent Inbound Podcast, Jen and Valutrades’ CEO, Graeme Watkins, discuss the power of inbound in the FinTech space.

Read More & Listen

Learning How to Pivot in the Midst of a Global Pandemic

With Christina Rice, COO at Pyx Health

On this episode of the Intelligent Inbound Podcast, Jen and Christina talk about meeting customer needs, even—or perhaps—especially, in the midst of a pandemic.

Read More & Listen
Back to All Episodes

About the Intelligent Inbound Podcast

Join your host, Jen Spencer, CEO of SmartBug Media®, HubSpot’s most-decorated global partner, as she and her guests explore the breakthrough ideas, innovations, and strategies that drive big results in marketing, sales, and revenue operations.

This is not a same-old, same-old leadership podcast. If you are an executive looking to break out from the pack, the Intelligent Inbound Podcast is one you will want on your shortlist.

Learn more about SmartBug Media®
Jen in front of a microphone