Breaking Barriers in B2B Sales with Jill Rowley, Stage 2 Capital

Hi, this is Clint,

And this is Lizzy.

Today we interviewed Jill Rowley, sales evangelist, speaker, podcast host and all around super cool person.

Yeah, Jill is our first social influencer guests with over 300,000 followers on LinkedIn.

And that certainly came across loud and clear in today's interview. Jill is pure energy. I loved her stories about driving change at Martech companies over the past 20 years.

And Jill has such a refreshing approach to selling: she's all about putting the customer at the center of everything she does as a seller and creating value for customers through partnerships.

And she's taking that idea one step further with her new company Nearbound and the idea of partner tech for customer success.

I also really appreciated her comments on the power of women in sales. And that segment certainly hit home for you Clint, didn't iy? You opened up more personally today than I think I've ever heard from you before.

Yeah, so very true. All right, folks, enjoy today's pod! Joining us today is Jill Rowley, a trailblazer in social selling and digital sales transformation, renowned for her dynamic approach to reshaping the role of sales and companies around the world, with an impressive sales track record spanning over 20 years, including pivotal roles at Oracle and now as a sales consultant. She's a powerhouse of innovative sales strategies. Her philosophy, centered on the give to give principle emphasizes the power of meaningful connections and community building in the digital age. As a much sought-after speaker and advisor for top B2B companies. Jill's influence extends far beyond the boardroom, inspiring a new generation of sales professionals to thrive in an ever-evolving marketplace. Welcome, Jill!

Thanks, Clint and Lizzy! I'm excited to be here.

We're happy to have you Jill. I love the powerhouse comment, by the way, Clint. So Jill, I know you're higher on energy in all the best ways. I got a question for you is what we'll call our icebreaker. Before we start hopping into the meat of our conversation today. Can you share with us what your not-so-guilty or maybe guilty pleasures are during what we'll call downtime, if that even exists for you in your world?

Yes, actually more downtime these days than when I was in my extreme workaholism mode, living in the Bay Area. And just accessed to unlimited opportunities for meetings and coffees, and lunches, and dinners, and networking events, and conferences. I live in Charleston, South Carolina now, and I love orange theory. If you haven't done orange theory, and you want to know about it, I am happy to connect offline. It is a HIIT workout with cardio and the weight room. And as we get older, it's important to not just run on the treadmill, but to lift weights and strengthen our core and everything else in our bodies.

Well, now I know what I'm Googling right after this interview. Orange theory, huh?

Okay, it clicked. I actually know what Orange theory is. And I'm laughing because I would not have ever considered that downtime. But I just find that very amusing. And it's not something admittedly I've ever looked into or had an interest in.

I think that that tells us a lot about Jill right there.

It's my me time. It's one hour that I don't have a cell phone. I leave it in the locker or in my bike mascot because I ride my bike to orange theory. It is me time.

Well, me time is is probably the most important part of that. Well, Jill, let's learn even more about you. Tell us the Jill Rowley origin story. How did you get started in your sales career and what took you to your latest company Nearbound?

So, I graduated college in '94 UVA undergraduate Business School Program. I actually spent six years in consulting after college. I didn't know what software was, I didn't know what the tech industry looked like. It wasn't until I made my way out to the Bay Area that I stumbled upon a company called Salesforce and back then it was salesforce.com. And that was in 2000, the year 2000. And I ended up being one of the first 100 employees at Salesforce. That's how I got my start in software sales. HR, actually. The question to the interviewer was "You don't have any quota carrying experience. That's a concern of ours." And I said: "You knew that when you brought me in. And based on the conversation that we've had today, what else do you need to know, to know that I can do the job?"

Look at you, knocking down objections right out of the gates.

I have Googled "objection handling", I had actually Googled like sales terminology. So that like "buying sign", I had Googled all these things so that I could go in to the interview with some language around pipeline and forecasting, and all the things that I then learned in the in the profession of sales.

What came next after that? Because I know you've done a variety of different roles. And there's a couple, there's a couple of cool stories that I want to start navigating towards in there.

Sure! So I joined Eloqua in 2002, as employee number 13. And in 2002, there were maybe a handful of Martech companies. Ketto didn't exist. HubSpot didn't exist.

Well, I was actually at epiphany at that time working with Phil Fernandez and John Miller, who then went on to start Marketo. So you're right. Marketo hadn't started because we were all over at epiphany. Then you joined Eloqua, which really defined the marketing automation industry.

Exactly. Demand Generation wasn't a function when I joined Eloqua, because it was still very much brand marketing, and very much analog. The web www.whatever.com was actually quite new. And websites were corporate brochures, They didn't have "Signup for our newsletter", they didn't have "Download our eBook", there were no landing pages, there were no forms. So I helped create the category of of marketing automation. I spent 10 years at Eloqua. And very few people really understand that I was an individual quota carrying sales rep, for all of those 10 years. Inadvertently, I built a personal brand, as an evangelist for martech, marketing automation, digital marketing transformation, the modern marketer, revenue marketing, and also coined part of the the early group that coined the term "Social Salary", and ultimately ended up doing professional speaking on what is social selling. And what is digital sales transformation was on the NASDAQ when Eloqua went public in 2011, or sorry, in 2012. And then four months later, we were acquired by Oracle for just under a billion dollars.

And then that takes us forward to several years of you being an evangelist, a public speaker. And now you're, involved with a new software company called Nearbound. Tell us a little bit about Nearbound.

Yes, quickly in between I went to Marketo, which I think is important, because in the year leading up to the acquisition by Adobe, the CEO Steve Lucas at the time recruited me, he recruited me because of my market knowledge and influence.

That must have been a little tough because you went from from Eloqua, now Oracle, to Marketo. And those two companies were fierce enemies, right? They were number one competitors against each other. And so you, you went over to the competitor. How did that feel?

It felt right, because, it was 2012, when Eloqua was acquired by Oracle. And it was December 2017, when I joined Marketo. And what we had built at Eloqua was no longer and the more time that it was owned by Oracle, the less it looked like the Eloqua that we had built. And so for me, it's always been about what is right for the customer. What is right for the market and what is right today. And I knew that Marketo was more of what was right.

We definitely want to hit on that to the fact that Well, what I'm hearing to the theme of change and your you sound like a change enabler is what we refer to them as Jill, internally at Sugar, is you went on from Oracle and Marketo, and now you're with Nearbound. Do you want to start on that and then we can shift to the changes that you've seen and how things have evolved?

Yeah, so great. I'll distinguish between Nearbound is a new category. And I've been part of category creation, right? Marketing automation, actually salesforce automation when I was at Salesforce, the delivery of a subscription model that was category creating. Marketing automation, martech more realistically, social selling category creation; Nearbound is category creation. It is more of the philosophy. It is the vision of outbound interruptive, prospecting, stealing someone's time, inbound, attracting and pulling people in through content and other things of value. Nearbound is a surround strategy. It's a surround. So outbound inbound, near bound, surround. And the idea is, you're going to be surprised who's at the center: the customer is at the center of a nearbound strategy. And what you say is who surrounds the customer. I want to get closest to the customer, she who is closest to the customer wins, she who stays closest to the customer continues to win. So you ask yourself who surrounds the customer today? Who does the customer already work with? Who do they trust? Who do they buy from? And these could be partners, right? But complementary software providers that integrate with Sugar. It could be service providers, right?Agencies, SIs, who actually configure software help companies set strategy around digital transformation, supply chain optimization. And so you say in communities, where does this customer learn? Who do they trust? Where are they influenced in various communities that they might be a member of? And my strategy will then be, I want to get nearer to those who are nearest to the customer. And I want to learn, I want to leverage Intel, I want to earn influence and get introduced to the customer that I want to have from the people who already work and influence the customer. Nearbound is the vision. It's a strategy, having worry. And there are software companies that actually help companies operationalize Nearbound. And the software, the B2B software, is all about partnerships, partner ecosystems, and the core of the software is account mapping, it is the ability to second party partner data. It is the ability to compare simply customer lists. So, how many mutual joint customers does Sugar have with Mediafly? So, Sugar and Mediafly could be great partners, and probably our great partners. What is the overlap? What is the overlapping customers? When you look at the overlap and customers, you say, "What is the joint value proposition? Why are customers more successful when they use Sugar with Mediafly, integrated?" Okay, now you say Sugar has customers that are in Mediafly's ICP. Actually, Mediafly has open opportunities. These companies that are already Sugar customers, how do you share Intel and influence and make intros so that you can win more joint customers. The same is true that Mediagly customers that could be Sugar customers.It's this ability to actually have a shared safe CRM, where historically that's been done via spreadsheets and spreadsheet is outdated. The minute you give it to a rep at the other company with a partner manager at the other company. So there's this whole new category of what I'm calling partner attack, where because partner ecosystem is becoming a more dominant business model, a more dominant way to go to market. You have to have a tech stack to support this new go-to-market motion. Is that helpful?

You know, it's super helpful. It's very inspiring, and I love that you are a category creator, Jill! Thanks for describing all of that. You're you're answering some of the questions that I wanted to talk with you about today, which is around the evolution of selling techniques. You're hitting on the social selling, the digital transformation, and now this new nearbound-surround approach. Can you talk through as you're engaging with sellers, the people that are are prospecting, they're on the front lines, responsible for bringing in these new deals, new customers. They should know that customer. Can you talk to us about how you go in and educate, or I think you have the term, was it "edgy teen" or?...When we were chatting. Can you talk about that?

Yes! I'm an entertainer, not a trainer. So I am more of the why. Right like I give people the AHA ot the "oh, s**t" moment, right? Now, the AHA, I was like, "Oh gosh, now that makes a lot of sense. There's language around it." I needed language. I needed definitions, for example, like social selling. My definition was using social networks, not social media. Salespeople it's about a network. Salespeople, it's about relationships; Marketing, it's about social media. And it's about reach, right, more and more of this broad reach. So my definition of social selling was teaching sales professionals how to leverage social networks that their buyers were using (LinkedIn) to do research on the buyer, the buying committee, the smarty-pants people who influence the buyer. So it's first to do research, to be relevant, to build relationships that drive revenue, but beyond revenue, customer lifetime value, and advocacy. And so it's really a just another channel just like podcast. Now, if I want to learn about someone, I'll go and search Google: put someone's name in and put "podcast", and then it'll give me what podcast this person has been in. And there's nothing better than going in listening to a podcast, hearing the words that the person you're trying to earn their attention, and build trust with. There's nothing better than going to a podcast and listening. It is just a way to drive deeper connections, to understand what motivates someone, right? And so, this this modern selling, it isn't modern. It's the modern way to uncover information about the buyer, the customer, the people who educate and inform the buyer that you want to hen house. Do you think that sellers need to have an inherent curiosity to do what you're describing, go out and research? Or do you find it that's a trainable knowing that you don't train? But somebody else may, do you find that that's a trainable quality, something that you can train someone on? I think it is more innate, in the way someone's wired. That doesn't mean that someone can't learn to be more curious, much like creativity, right? So much like creativity, you can learn how to be more creative, much like writing. I'm not a writer, but I can learn to do better writing than I do today, I'll never be a journalist, I'll never do content marketing, I'm less of a creator of content than I am a curator of content. I used to call myself the information concierge for buyers. I was the information concierge, I was the content kind of sewer, because the information wasn't as widely available for the buyer, as it is today. Today, it's not about information. It's about insights. So you can have all of this information, the buyer has all this information. But what can I bring to the buyer, that actually is an insight that connects this information that's available to put it in the context. Curiosity, context. Context is one of the most important things as a professional seller, you have to be able to put things into the context of the customer.

Just for the sake of time, Jill. I want to actually switch topics. So, in in sales, and also leadership, and all of the companies that you've been with over the last several years, especially being an employee, one of 10 or 100, give or take depending on the company. Can we talk about the role of women in sales? And how you seen that change, if at all? Where does it stand today, compared to the past?

I've been asked the question many times. Being a woman in sales, especially in software, that must have been har, being one of the only women in the room. For me, personally, I've actually looked at it as an advantage in the sense of that for me, I would rather stand out then blend in. And so, I was prepping last week for a session I'm doing for Zoom Info's "Women in Sales" organization. And I realized that for me the the curiosity and the confidence and the conviction that I have is more uncommon than common. And in doing research, and being part of many now different women's organizations, the data is what motivates me to actually be part of the conversation about how do we change the opportunity for women. The data shows that in the frontline salesperson that it is actually 50/50 men and women, the data shows that women in sales perform, they have higher win rates, they have higher quota attainment, and they're more relevant and empathetic with their buyers. When you look at the women in sales, quote, leadership, VP and above, the numbers are very different. There are 24% of VP and above in sales is women, and 76% men. And every layer, you go up in the hierarchy, there are fewer, and fewer, and fewer women in those positions. Same with venture capital, it is really lopsided, the number of women in investing roles, in venture capital, and also in the funding of female-founded companies, it's very lopsided. And so what we need is we need more women lifting women more community and resources for women to be more successful in being able to earn going up in the ranks of an organization. We also need more men who are willing to follow, answer, support, mentor, coach women, and I look at men who have daughters, and I say, "Don't you want your daughter to have the same opportunity that your son has?"

It's such an amazing mental block that that we operate in as a society. It's is all about...my experience of success in the sales ranks of women versus men are exactly what you've described, right? Over and over again, the top performers that I've worked with in my career are female. But when you get to that, that sales leadership ranks, it's stunning. It's hard to understand why it changes the way you just described, and certainly agree with your comments that we need to take a proactive stance on changing. Have you seen, what have you seen most successful in your career in terms of changing that dynamic? You have, like anything you could point to specifically that "Here I saw it work really well differently". There's just a culture that starts at the top and leaders need to change the way they think. And we need to have more female leaders and just It starts there?

It's really a whole host of things, much like anything, it's never one thing, right? There's not the one thing that I could do to build more pipeline today; it is more of the mix of things that are necessary. It actually starts at the earliest development of boys and girls and the things that we teach little girls versus the things that we teach little boys.

Language at the early stage. I agree!

Manners versus how to win right little girls learn about "Pleasing and thank you!", and being courteous and kind. And boys learn about how to be brave and get in the game.

You're right. I'm a father of both young men, young women and I hate the blue versus pink thing. That drives me crazy. My daughter Juliette never liked pink ever, ever, ever had any interest in pink and when it became evident to her that that she was being stigmatized or put into a certain definition if she wore pink, she just hated pink from that point forward and never work. To me, that's it. If there's one thing that we can all change as parents out there is to get rid of that blue-pink thing. Why can't I like pink as a guy? Why can't you like blue is a girl? Frankly, why are we caring about colors?

No, Clint, it's getting worse. If you go on TikTok or Instagram, and you search "gender reveal parties", it's obnoxious. The extent that people are going to on these gender reveal parties, they're spending 1000s and 1000s of dollars to you know, have a plane fly over. Understand

I don't even understand why that's important. I have a true mental block and I do not get paid. Yeah. 10 fingers 10 toes, that's all I care about. I gotta tell you, one of the proudest moments of my entire life was when my daughter came to me and said, "Dad, I'm gay." And I did the worst answer, which was "I know", right? And that is truly a horrible answer. Because, right answer is, "I'm so proud of you for telling me because it's such a hard thing for her to say to me." And I kind of looked there, said "Yes, I know." And, she looked at me almost a little deflated, because there's this moment that she had built towards, and, I brushed past it, because I did know, as parents, we know our kids. Yeah, it's a crazy world that we live in at times, it's time to change it. But I'm gonna pull us back towards towards our conversation here a little bit. I love where we went. In fact, I want to do a whole podcast on on that very topic.

Wouldn't it be well thought out or it should be? Are they healthy look, and I watched a documentary National Geographic did it with Katie Couric and it was on essentially transgender and we do these gender reveals and "Who hasn't kid and thinks they're going to be gay?" And I had dinner the other night with a couple from California and very conservative, wealthy background, Country Club and the woman shared with us her son is gay. And I like wanted to clap. Like that's amazing. One of my best friends in Charleston that I worked out with Orange theory's gay.

If we summarize that, I think, Jill, what I'm hearing from you is it starts with competence. And that competence starts with probably parents or your environment. And then at some point, as you enter the workforce, you need support. You need people there to give you opportunity and trust and believe in you.

Absolutely. See it, be it, as well. If you can see it, then you can be it. And I wrote an article on LinkedIn, in 2014-2015. It's still there. And it was titled, to be provocative, "Why Women Can't Be Leaders?" And it was "We can, but we don't see enough of it." And I talked about women who were my mentors who didn't know I existed, and it was women that I, you know, Beth Comstock was an example. I ended up meeting Beth Comstock and working with her when she was at GE, she wrote a book and it's on my shelves. But one of the beauties of the web and YouTube and podcasts and social media is that we can see more of what we want to be. You might not have someone to officially mentor you, but you can absolutely learn from that person.

Question for you, but this it's a reallyfun discussion here. Let's let's bring it back to an interview for a second here and ask you, how have you changed over the years? We've talked about so much about how the industry is changing, and how sellers need to change the way they approach. But if you look back on your career as a salesperson, as a information concierge, if you will look back to that beginning 20 years ago, and look to where you are today. Tell me about that. That growth, that evolution of Jill Rowley.

I would say that I got real clear on my purpose as I matured and had more experience and more wins, individual wins, right? And sales, oftentimes, you're the rep of the quarter, you're the rep of the year, your Presidents' Club, I loved those trophies, I have a bunch of them. What I really felt the shift was my purpose is more broadly to enrich other people's careers and elevate the marketing profession, elevate the sales profession, elevate the partner profession. And not just the profession, like sales profession, like let's change the image of when you when you hear about someone who's a sales professional, you think of them as a professional, because they are doing things that are professional, they're not tricks. But there's the shift of impact at scale. For me, I really dream and scale and I want to have impact at scale. That can be made through many individuals. And I'm attracted to people who are learn-it-alls. I'm attracted to people who have a growth mindset. I say I'm a talent spotter. And I I want to instill the confidence and the courage, the commitment and conviction that I have into others.

Well maybe that the next step in your career is Professor Rowley. Yeah, how about that one? I like that one: teaching people how to be the best sellers right and selling is as you said, it's about unlocking the world of possibilities for somebody who's looking to buy. That's fantastic. I love it.

Thank you, Professor Rowley.

I was just gonna say let's stick with that. So, Professor Rowley I have one last question for you. Where can our listeners find you and learn more about you, whether that be we always see LinkedIn, blogs, website, anything that you put out.

ChatGPT, I've ChatGPT'd myself, right? Of course, I Googled myself. Go to that ChatGPT "Joe Rowley" and prompt it in B2B SaaS. "What is Joe Rowley known for?" "What has she accomplished in her career?" Go to ChatGPT it's the first time I've said that on a podcast. Love it.

Love it! I haven't heard that one before. That's we typically hear the LinkedIn response but you just gave us the new one ChatGPT response, right ? You do have over 315,000 followers on LinkedIn. So, we might be able to follow find you there too, right?

Yes. But don't send me a generic invite to connect.

I saw that on your profile.

If I opened up my invites in my LinkedIn, there are like 330. And none of them are personalized, because I don't want to accept generic invites anymore.

I appreciate that. You're you're setting the standard.

I love it. Don't be generic. That's good advice. All right, Jill. It was a pleasure having a nice chat with you today.

Jill, thank you for meeting us today.

Yeah, this was great. Thank you so much for allowing me to share my wisdom and my passion.