EPISODE 481: How Women are Dominating in B2B Sales with Salesforce Sales Enablement Leader Jen Ferguson

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[EDITOR’S NOTE: This is a replay of the Women in Sales virtual learning session sponsored by the Institute for Excellence in Sales on March 1. 2022. It featured an interview with Salesforce Sales Leader Jen Ferguson. She is a co-author of Heels to Deals: How Women are Dominating in Business-to-Business Sales.]

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JEN’S TIP: “Define success for yourself. Find out what you’re good at, find out what you’re not good at, or what you don’t like to do. Determine it for yourself. Don’t let other people put their expectations on what your career journey should look like, but really just own it. For anyone out there considering bringing more women on, or for people with open roles, considering transferable skills and the value that a different perspective brings to the table is so important that that diversity of thought will help your sales organization be more successful.”


Gina Stracuzzi: My guest is with Salesforce, which is one of our favorite companies because they really got behind the Women in Sales Leadership Forum, but also, they’re a great place to work. It is the beginning of National Women’s History Month. I’m very excited to have Jen Ferguson as my guest. Her and her collaborators, their Heels to Deals book comes out on International Women’s Day, although it is available now. Welcome, Jen.

Jen Ferguson: Thank you for having me, Gina. I so appreciate it.

Gina Stracuzzi: Well, you’re more than welcome. You’re a perfect way to start off the month of March as we talk about women history and all that we’ve done to make the country great and help people along. I really love your topic, which is how do you define success? Because success, as you and I were talking about a little bit offline, means so many different things to different people.

Jen Ferguson: Especially at different stages of your life. I remember when I was a new seller, success for me was all about my quota and making sure I knocked it out of the ballpark. Then I became a parent and success is just managing my quota and my life, my children. Being a parent, making sure my little people were going to turn into good humans. Then later in life, defining success for me was like, “How do I make a contribution and make a valuable impact while balancing that work-life balance?” We go through seasons of our life, and how you define success through each season is going to be entirely up to you. I think that the important part for women is that you’re defining it, not someone else. Not your leader, not someone else on your team, but that you take ownership of your career journey.

Gina Stracuzzi: Absolutely, which is I’m sure a huge part of the so-called mass exodus, it isn’t so much that people hated what they were doing necessarily, but it’s like, “Is this important to me?” Now that I have all these other things that need my time and attention, homeschooling kids and bringing sometimes ill parents into the house, all of those things have really changed how women are looking at their careers, and what they’re getting out of it, and what success means to them. I want to take a few minutes before we get into our actual topic. I’d like you to tell us more about yourself and how you got to this point, this season in your career, and the career stages that led up to it.

Jen Ferguson: I’ve had a pretty interesting journey. It’s more like a jungle gym rather than a ladder. I started out actually in retail as a leader. I was in college, I had an opportunity to travel the country and I moved to Florida. Then I got into the cigar business where I was managing cigar clubs. It was through managing cigar clubs where I stumbled upon software. As people used to come in and reserve our conference room, when they did that, I noticed they were software salespeople. They’d hang out in the club. I was like, “You’re just hanging out, building relationships. I could do that. I’m working so many hours a week in order to just pay rent, where I could be doing what they’re doing. They have private membership clubs that they’re just chilling. That doesn’t look hard at all.”

I got into software and it’s funny because I remember logging into my first instance of Salesforce while I was selling green screen DOS software, logging into my Salesforce instance to try and track those opportunities. From there I got into leadership and eventually I made it into this. As a working parent, I was impacted by the pandemic, so I was laid off. I’ll be honest, I was relieved. I had my kindergartner next to me, who couldn’t read, reading the screen to him while I was working. To have my daughter sitting on the other side, and it was just so much. What I did was I got laid off. I was like, “I have to do this virtual schooling thing. That doesn’t mean I can’t show up online and be present.”

I started posting every day and I started meeting everyone, networking, every sales community, and really just putting myself out there doing LinkedIn Live. Then I got a scholarship for a program for a VP of sales program with an alumni of Salesforce. It’s funny, that’s how I determined I absolutely did not want to be the VP of sales. Not at all. I started to look at, “What am I good at? What do I like to do? Where is the most value that I bring when I join an organization? What are my superpowers?” By digging into that, I really found enablement as, “This is my superpower. I’m able to help ramp sellers really quickly.” I’ve done so much sales training in my life that I figured out what’s the best way to reduce ramp time. What are the stories that define me and what’s the impact that I’ve made that I’m able to take and bring to organizations to define that next chapter for myself?

It’s been quite a journey, but I remember at first I had a hard time even getting sales enablement positions or interviews. It’s funny, it’s because there was this predetermined thing because there was no enablement in any of my job roles, even though I’ve always been a sales leader. That’s always what I’ve done, what I was always good at. Because I didn’t have it in my job title, not as many organizations would even talk to me. When Salesforce came along and they were open to my transferable skills, that was amazing. I’m very happy to be here.

Gina Stracuzzi: There’s so many things in that story, Jen, that really highlight so much of what is important if you’re going to be successful. That is the networking piece and putting yourself out there and helping people to see the transferable skills. But if you don’t have the network that can open the doors for you so you can go in and blow them away with what you know, even though it’s not in the title, you don’t get those opportunities. That’s a perfect example of how well you leveraged the situation and you really put yourself out there with doing LinkedIn lives and posts, because it would’ve been just as easy with kids around you that needed your attention, to just do that and sink into the background a little bit and not take advantage of all the opportunities in front of you.

Jen Ferguson: I think in every failure, there’s an opportunity. I think back to my Dale Carnegie days, I’ve already told you, too much training in my life. My Dale Carnegie days from the Sales Advantage program of how to eliminate worry and stress. How can I improve upon the worst possible outcome? Well, if the worst possible outcome is, “Now I’m laid off and I’m not going to find a new job,” the only way for me to improve on it is to do more networking, be more present, show people who I am. Through that journey, I found that I was actually eliminating even a portion of the market, because all of the stories and all of the experiences I had that make me me, some of them were not pretty.

Some of them are like my journey to parenthood and having miscarriages and traveling so much, not realizing that’s why I was having the miscarriages. That was the vulnerable post that actually got me that scholarship. My journey, and even though that’s not a sales story, it is a sales story because it’s about being a woman salesperson who traveled the country, and kept on traveling, and kept on traveling, until I realized that that was the thing that was impacting my ability to have a family. The things that you don’t think necessarily are business, are sometimes entirely business because everything about who we are is our experiences, everything we bring to the table. As a parent, as someone in my community, all the things that I bring are part of that relationship building that happens in sales.

That’s why I think sales is a life skill. It’s not just a career. It’s like in order to get my kids to eat vegetables, I need to sell them on the idea that, “If you don’t eat the vegetables, there’s just going to be consequences.” [Laughs] What are those consequences? Setting those expectations early and communicating them often. That’s all sales.

Gina Stracuzzi: Absolutely. Again, there’s just so much in your story that is a perfect example of everything that one needs to do to advance their career. That is the networking. It’s putting yourself out there, it’s being vulnerable. It’s sharing your story, sharing your journey. Certainly, the world has never been more receptive to vulnerability and personal stories and the behind the scenes than it is now. Utilizing that, that’s a nice lead into the rest of our conversation, and defining success. One of the things that we talked about talking about is how we measure our own worth and how that plays into what we consider success. Can you talk to us a little bit about that, and even how that plays into your role in sales enablement? Because I would imagine, ramping people up to be successful in sales, you’ve got to help them appreciate having these markers and knowing what success means to them.

Jen Ferguson: To each individual person it might be different. On global enablement, we’re very scalable. But when you look at and you talk to individuals, being able to define that and knowing their expectations of their leader and their leadership team is super important to know when they’re on track versus off track, and knowing how to define those steps of how to get on the board in that first period of time, so that they know that they have that sense of achievement, that they’re on track for their onboarding, for their journey. Then knowing for yourself, you start a new role, and knowing what that journey should look like, but also understanding the expectations and everything that goes into it from a one-on-one standpoint. Communicating where you are with your leader in your career journey and where you’re wanting to go. What does your career journey look like and where does it evolve? All of that is super important when you’re looking at defining success for you.

But also your values. What do you believe in? Why do you believe in it? How do you want that to cross over into your professional life? In Salesforce, one of the things I’m very grateful for is my ability to volunteer. It’s part of something I do to make an impact. I volunteer with mentoring others, mentoring specifically women to get into the roles that they’re looking to get into. But also volunteering for my community, for my PTA, and being able to make a contribution there. How one defines success is basically entirely up to them, but also to know where they stand with their leadership team and know what success actually looks like for those individuals. Because how you define success is yours, but how your leadership defines success you need to know, because you’ll never measure up to those expectations if you don’t know what they look like.

Gina Stracuzzi: That raises a question. How do you coach the people you work with as you ramp them up, or you continue to work with them throughout their careers? Let’s say they find that there’s a mismatch between what it is they want or thought they wanted, and their version of success and what their sales leaders want and expect. What advice would you give?

Jen Ferguson: That’s why communication is so important, to communicate early and often. I think I even gave you that example with vegetables with my kids. Communicating and having that regular one-on-one communication of what the expectations are, where you stand with those expectations, and being able to have good open communication, and building trust, especially in onboarding. When you’re new and you’re coming on board and you have a new leader, spending that time to get to know that leader as well as letting them know you is super important, because that’s what’s going to define how successful you are. Knowing their expectations, but also knowing how to get to where you’re going. Knowing when those expectations change and having that open communication.

Gina Stracuzzi: Let’s talk a little bit about what one might do to find the right path for them. But let’s say they find that they’re on the wrong path. Just for instance, when you mentioned you went into that training for the VP of sales, and you were like, “Whoa, this is what I don’t want.” What if you have someone that maybe you’re coaching or mentoring, or is on a sales team and they now feel that the path isn’t right for them?

Jen Ferguson: To explore new paths. First, talk about it with whoever it is that they’re working with. Communication is so important, and you never know what opportunities can arise if you’re already in a place. But also, exploring that skillset. Let’s say you’re in a role and you’ve defined, “Maybe I want to go in a different direction.” Finding opportunities to start moving in that direction and having a pathway there could be something that you do with your leadership team. It just depends on where you are and where you’re going, and where those transferable skills come into play.

I joke all the time that there is no difference between liquor inventory and SaaS sales. If you look at that ability to have recurring revenue, what’s the difference? You need to be able to produce so much revenue. Well, in liquor inventory, you’re able to sell so much liquid and have enough liquid so that you have it on hand. Looking for those opportunities for areas that you’re interested in to further develop those skills. I love graphic design. I’m not a graphic designer, but on my LinkedIn live, you’ll notice my graphics are pretty and my PowerPoints are amazing. My Google slides, I like to make things pretty. Is that my main job objective? No, but I know that that’s a skill I bring to the table and I enjoy doing.

Making a list for anyone. What are the things that you enjoy doing that you can just lose hours doing it, just because you just enjoy it? Those are the things that you leverage, because those are your superpowers. There may be things that you’re good at that you don’t like. I have things I’m good at that I don’t like. I’m really good at Excel. I hate it. Finding the things that light you up and that are the things you do enjoy and you’re good at, versus you’re good at and you don’t like, but you happen to be good at it is also important. Because everybody wants to find a place where they can make a valuable contribution, but also can thrive, where they can do their best work and be their best self, and really be able to just knock it out of the park and be celebrated for success.

Sometimes that’s not a straight path and you have to be open to the possibilities, even for yourself, that, “Okay, a ladder looks like I go to the next step and I’m going to be a VP of sales.” Determining, “What would I actually do in that job role? Is that what I enjoy?” Some people, that’s amazing for them because all they want to do is win. Just win, win, win. But some people enjoy investing time in others, like myself, where I’m more geared towards sales enablement. I enjoy mentoring. I could mentor all day long. Just, “How can I help you?” I enjoy that, but not everyone is like that.

Figuring out what you’re really good at, what you enjoy, what you may be good at and don’t like, and what just you don’t like at all, and just reducing that in your life. You could probably find a position that fits you best while still maximizing your potential, doing your discovery into what compensation looks like for those roles. Being able to determine what it looks like for those roles in different geographic areas. What are the companies that have the best workplaces to consider? Because money isn’t everything. You want to know your worth and you want to know the worth of your job role, but you also have to realize that the cost of a place that isn’t good, no matter how much you’re paid, costs a great deal more. Especially as a woman in sales, being able to find a place where you can thrive, be seen, heard, valued, equipped to succeed, where your voice is celebrated, where your success is celebrated, sometimes isn’t the easiest thing. Sometimes it takes a little while to find those places. As long as you’re always learning and growing and trying to add value, you’ll be okay.

Gina Stracuzzi: The trainers and coaches, facilitators that we have in the forum, that is some of the biggest advice that they give. Especially if you want to try something else within the company, volunteer to be on a team that will give you that visibility and that experience so you can see firsthand if you really do want to be part of it, and what it’s all about and what it looks like in the middle of it. That’s all great advice, Jen. It’s a nice transition, I want to talk a little bit about the Heels to Deals and the message that you all hope will resonate with readers and the real genesis behind the book, what you all wanted to accomplish, and what’s at the heart of it.

Jen Ferguson: Heidi Solomon-Orlick reached out and she was like, “I’m doing this project to amplify the voices of women.” Of course, I’m always all in for that, for amplifying the voices of women. But then as it evolved, it really turned into, “How do we inspire the next generation of women to consider an intentional career choice in sales?” Because I think it’s so important to recognize sales has a great capability for leveling the playing field, for allowing women to really own their destiny, their career choice. If you want to be intentional and find that path to financial freedom, you can own your journey in sales.

I don’t have a college degree, I left college to go work in sales. I’m happy with how that turned out. That’s not everyone’s journey, not at all, and that’s okay. Everyone’s going to have their own unique journey. But with this book, we gathered, there’s I believe 33 women who all collaborated and contributed chapters to inspire that next generation to think of sales as an intentional career choice of, “Let me think about whether I want to be in sales.” Because at the end of the day, sales is all about helping people. There isn’t any other career that you could really go down where you can help people. If you’re wholehearted into helping people, you can achieve great success. We all know women have higher win rates as a whole in B2B sales, but also that they have the ability to accelerate stage sales cycle faster. It leads to higher profitability when you have more women.

For organizations as a whole, getting and finding more diverse sales talents is huge. Just reaching more women to do that. We’ve been talking to colleges and more young women early stage into their career to really think about, “Maybe sales is for me.” Instead of that perception of the old boy’s club, the used car salesmen. That is really not the reality of what’s out there. The reality of sales, people who are the best sales people are the best storytellers, are the most invested in helping their customers succeed. They’re not the used car salesmen.

Changing the face of sales is so important to establishing more trust in salespeople, as a whole sales community, how do we establish more trust? We get more women into sales and make sure people know that that’s what we’re doing, is that we’re helping our prospects and customers succeed. I’m so excited about the book. Heels to Deals: How Women are Dominating in Business-to-Business Sales.

Gina Stracuzzi: I applaud all of you. As Fred and I were speaking with you earlier, we know a lot of the contributors so we’re so happy for all of you and for what you’re doing for the industry as a whole. We like to leave our conversation with our guests giving our audience one piece of advice that they can put into play today that will help advance their careers, take it to the next level, sell more stuff, whatever it is you’d like to leave us with.

Jen Ferguson: I would suggest you define success for yourself. Find out what you’re good at, find out what you’re not good at, or what you don’t like to do, find a mentor. Just determine it for yourself. Don’t let other people put their expectations on what your career journey should look like, but really just own it. For anyone out there considering bringing more women on, or for people with open roles, considering transferable skills and the value that a different perspective brings to the table is so important that that diversity of thought will help your sales organization be more successful.

Gina Stracuzzi: That is great advice, which is why the networking is so important. Because 90% of the resumes go through AI and don’t ever see a human because it’s looking for certain words. If you don’t have them, you need the network to be able to have those conversations offline. That is phenomenal advice, Jen. Well, thank you so very much for joining us. Congratulations again on your book. Thank you so much and come back and see us sometime.

Transcribed by Mariana Badillo

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