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Special Episode: Driving Diversity: Highlights From Top Women in Sales

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Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. Driving diversity at the sales executive level [1:00]
  3. How to run great meetings [5:13]
  4. Creating pivotal moments [10:56]
  5. Putting customer experience at the center of the business [14:34]
  6. Overcoming imposter syndrome [19:35]
  7. The three traits of an organic career path [25:50]

Show Introduction [00:10]

Sam Jacobs: Today on the show, we have a very special episode. October is Women in Sales Month. To celebrate, we are highlighting some of the best moments and insights shared on this podcast by female sales leaders who are elevating the entire sales profession. It’s got clips and highlights from some of my favorite conversations with the best women sales leaders that have appeared on the Sales Hacker Podcast. I hope you enjoy it.

Let’s dive into our Women in Sales bonus episode.

Driving diversity at the sales executive level [1:00]

Sam Jacobs: The first person we’ve got is Lori Richardson, really a pioneer for women in sales. She’s the founder of WOMEN Sales Pros, which is helping smart, savvy women get into B2B sales positions and sales leadership, and helping companies find and develop great women sellers. She is also the founder. She runs the organization, Score More Sales, which is helping leaders of B2B companies solve problems with their sales team, so it’s a sales consultant organization. And she is a main figure driving diversity and women representation, not just in the sales force, but at the sales executive level. Let’s listen to my conversation with Lori.

I do want to ask you about women in sales. It’s a big initiative and the organization that you started, WOMEN Sales pros, why do you think it’s so important to have diversity in sales?

Lori Richardson: The most important reason now, Sam, is because you need a selling team that matches who your buyers are. We’ve seen this in many instances lately where people just aren’t going to settle for what used to work. They want a diverse group of folks helping them who are listening to what it is that they need. And the other advantage to having diversity inclusion on a sales team of all types is that you have different answers to problems.

I saw an instance for myself once where I took over a sales territory from someone else, and a company had not let us bid on a huge project because they didn’t like the rep. The rep was a guy. He happened to be very egotistical, and I was very egoless at the time. I hope I still am, at least to some point, but I just had a whole different style. And because of that different style, I got an opportunity. We won a huge deal because of it, and that happens all the time. It takes different sets of eyes, different questions, different sets of empathy to work together. And we know that that happens in business. That boards that are diverse are more successful, leadership that’s more diverse is more successful. It’s the same with sales teams.

Sam Jacobs: Yeah, I believe that. Regardless of the demographic diversity, do you think we should be rotating accounts more often within a sales team because different approaches can uncover opportunities people thought were dead, closed, or lost?

Lori Richardson: It’s an interesting idea, isn’t it? I mean, I would have hated that when I was a rep. “Don’t take my account away,” right. But there’s a lot to be said. And team selling, there’s a lot to be said for that.

Sam Jacobs: You were telling me before that some of the folks that have said that diversity isn’t a priority for us. And now they’re saying, “I don’t know about that. It’s a pandemic. We’re just trying to stay alive.” What’s your response to that? And how do we make sure that diversity and inclusiveness stays a priority even as we’re trying to make sure that the economy stays afloat?

Lori Richardson: It really got me thinking because I don’t want to be promoting something that’s just a “nice to have.” I don’t think that diversity is just a “nice to have.” Some people think that it’s what we “should” do, but I think it’s much more than that.

And I think today, when we’re working to get this economy going again, we’ll be working to get the economy going, and it will take all hands on deck and it will take diverse points of view like we were talking about. I just think that it’s a requirement now more than ever. I think that we know that women have a very good dose of empathy, communication skills, listening skills. These are all things that we need in the new economy going forward.

RELATED: Building Diversity Into Your Revenue Organization with Simmone Taitt

How to run great meetings [5:13]

Sam Jacobs: Great little sound bite from my conversation with Lori. I love these bonus episodes because you get to hear just the hits, just the best parts of every conversation.

Next up we’ve got Mykal White. One of the things she talked about was how to run great meetings. Another thing that she talked about was just bringing the human back into the sales conversation. Making sure that we’re not just referencing marketing copy, but we’re also referencing how people really speak. And she runs an organization called NUNDA. Mykal, she’s a force. She’s really honest and authentic, and I really enjoyed this little snippet. Take a listen to my conversation, to this part of the conversation, with Mykal White.

I did have one question for you. We have our guests fill out a little one-pager. And one of the things that you said is, “The way most weekly sales meetings are held is bullshit.” I want to hear more about that. Why do you think that’s true and how should they be run?

Mykal White: Bullshit. Bullshit. It’s actually two things. The weekly sales meetings are completely ridiculous, but then the one-on-one meetings are even more or equally as ridiculous. The sales meetings are supposed to be a time and place where the sales team comes together. We learn from each other. We learn from successes. We learn from failures. We learn from mistakes. There is some sort of training. There is some sort of way that these reps are being developed during these meetings, where it’s like, “All right, so I’ve been hearing a lot of this this week. I want to focus on this. I want to focus on the first seven seconds. What are you doing to get their attention?” Whatever it is, there needs to be some sort of developmental aspect of these training sessions.

What happens in these training sessions instead is the team comes together. They’re sitting in front of a huge screen. One by one, the pipeline of each rep is put on the screen, where the rep now has to explain their pipeline to the manager in front of the team. It’s the same meeting every single week where it’s like, “Well, where are we with this one?”

“Yeah, so talked to his guy. He blah, blah, blah. This is what’s happening. Yeah, so… ”

And then the manager’s like, “Yeah, make sure that you connect with them again next week. Make sure that blah.”

“Yep. Will do.”

“And what’s going on with this deal?”

“Yeah, so this deal, it’s been a couple of weeks, but I think he’s on vacation.”

But it’s never… and that’s all it is. It’s just, where are we? There’s never any actual training. There’s never any, “Hey, Luke, there’s this thing that you did this week that I thought was actually really smart. Can you share that with the team? I pulled you to the side and I told you that I thought it was great. Just let the team know about our conversation or whatever, and tell them where you got that from or why you decided to do that, that day. And what did the clients say?”

But it should be an opportunity for everyone to come together and learn and get on the same page instead of being a dog and pony show. It’s just a waste of time because you’re not actually even getting real answers.

Again, I was talking about the ego. If I’ve said in a sales meeting three weeks ago that I have Pepsi. “Oh, I spoke with Pepsi.” And it’s like, “Oh wow, that’s really cool.” I don’t want to tell you in front of everyone, that Pepsi hasn’t answered any of my calls for the last three weeks since that one conversation we had. I’m just going to keep speaking in the affirmative. “Oh yeah, yeah, no, for sure. I think they’re on vacation… ” And there’s no honesty, so there’s no authenticity.

Then with the one-on-ones, terrible waste of opportunity and resources, and really opportunity. The whole point of the one-on-ones is it is this protected time between a leader and the seller, where this leader is there to help develop the seller, is there to give them a voice in the privacy of this room where they have questions, they have concerns. But they’re able to call them out. They’re able to say things like, “I know you keep saying that you’re doing all these dials, but the dials don’t make sense for the numbers. The productivity that I’m seeing based on what you’re saying you’re doing doesn’t actually make sense, so let’s talk about that. What are you actually saying on these calls?”

Because the numbers tell a story. If they’re not converting, if they’re making a zillion dials, but rarely are they converting to a first meeting, well, then we know that the problem is probably on that very first call, so why are they not coaching them? Why are they not role-playing? Why are they not having a conversation? Instead, they just kind of bypass the whole thing, and they’ll just say things like, “What can we do to increase your pipeline? How can we make more calls? What’s going on with this opportunity?” And it’s the same conversation week after week without the training, without the development, without even calling them out on their bullshit. So, yes. Can you feel the passion though, Sam?

Creating pivotal moments [10:56]

Sam Jacobs: The passion is coming through the microphone. Thank you for that, Mykal.

A great little interaction with Mykal White there. I’m struggling to figure out what to call these things. Blurbs? Snippets? I feel like “snippet” is a little condescending. Micro moment? Moment, maybe we just call it a moment. Okay, it’s a moment. All right, here’s the next moment.

RELATED: Tips for Building a Diverse Team of High-Quality Salespeople with Wesley Ulysse

The next moment is with somebody that’s a friend and that really is a pretty incredible sales leader, and also just a leader that demonstrates true empathy and authenticity, and somebody who manages to navigate her career in such an exceptional way. She is… I think the latest title, I don’t have LinkedIn up in front of me, but she works at LinkedIn. It’s Alyssa Merwin. Last time I checked, she was running North America sales for LinkedIn for Sales Solutions, which of course includes Sales Navigator. She started her career at Corporate Executive Board. She is well-known across the sales scene. She’s going to be CEO at some point, whenever she chooses, and here’s her advice for creating pivotal moments. Let’s give it a listen.

You’ve had such an incredible career. We look at average tenure in kind of high growth companies, and you’re trumping that in spades and your tenure runs both at CEB and now at LinkedIn. When you think about giving advice to some of the people that are earlier in their career, what advice do you have? I guess, specifically, there are probably some pivotal career moments that you think helped land you in your current role. What were they, and how did you handle them that you think was beneficial, and share those lessons with the audience?

Alyssa Merwin: Sure, and thanks for the very, very kind words. But I think that there are probably just a couple of things that I would say that made me stick out slightly, sometimes in good and sometimes in not so good ways from the crowd. And one of the pieces of advice that I had gotten, probably early and then you hear it repeated throughout your career, is really making your boss look good. But it’s not really making your boss look good, it’s basically doing your absolute best to perform at the best of your abilities so that you are the person that your boss never has to worry about. And that doesn’t mean just results. It means being a great team player and having a great attitude; it means helping other people.

It also means, and this is where sometimes I get myself into hot water, It also means at times giving feedback to your boss and highlighting things that aren’t really resonating or working. Or that feedback on behalf of the team that you can channel in a constructive way that helps them to be more effective or helps them to identify a problem they didn’t even know they had. That one can be a little tricky and it has to be done delicately depending on who your boss is and what their personality is. But I actually think it’s a combination of those things throughout my career that has enabled me to just take on more responsibility because I showed up in a slightly more mature way than maybe the role called for or what they would have expected at the stage of my career.

And then I mentioned earlier about that one move where I said to my boss, “I want to take this job even though I’m the least obvious candidate, but I think I’m exactly what you need.” I think it’s also being willing and comfortable to state what you want and ask for it. And even when he said, no, the first couple of times, we had some really constructive conversations about why I didn’t agree with his perspective. And ultimately, I really think it was the role that unlocked this next role for me. And so I think it’s finding the confidence to be willing to have those conversations when you’ve earned the right.

Putting customer experience at the center of the business [14:34]

Sam Jacobs: A great moment. See, I’ve learned, they’re moments now. A great moment with Alyssa Merwin and really she is exceptional, and I can’t wait to see what companies she gets to run over the course of the next one, two, five, 10 years. But she’s an incredible sales leader. I know that she’s in the DC area now. She relocated from San Francisco running all Sales Solutions for North America.

Next up, the next moment that we will present to you is Leah Cheney. Now Leah is based in Portland, Oregon. In fact, after our interview, I recruited her and her team to run the Portland chapter of Revenue Collective. This is conflict of interest time, where I’m using the Sales Hacker Podcast to meet amazing women and then getting them to be leaders for the global community that we’re building with Revenue Collective. But Leah’s expertise is customer success and customer experience.

And what we talk about in this next topic is the process for putting customer experience at the center of the business. How do you put the customer right at the center of the business? Leah Cheney tells us. Let’s give it a listen.

Let me ask you, when BetterGrowth is going into a company and first thing, as you mentioned, there are first principles and one of them is that they’re not the customer, they’re something other than that. They are the guests, they are human beings and we need to give them a great experience and make sure they have a seat at the table. I’m sure you have some process by which when they say, “Okay, Leah, I want to put customer experience at the center of the business. Tell us what to do from a step-by-step perspective.” Do you have a methodology? What is the process by which you deliver that and you potentially help them reorganize so that they can put customer experience at the center?

Leah Cheney: That’s a great question, Sam. And it’s different for every organization, just like the customer success metric is different for every customer, right? I think if you try to blanket things, it gets really hard. Where it gets scary is you want to scale. The tricks to do that at scale, in my opinion, are to start internally. There needs to be internal conversation. The company needs to understand that they’re bought in.

One of the things that BetterGrowth does immediately before they touch on churn and everything else is they help the company to create the customer experience journey. What is every step that the customer goes through? BetterGrowth to help that along has created different tools and tricks to do that. One of those is just simply identifying different areas, like if it’s a relay race that everybody would be responsible.

We’ve broken it up in our case to what we call the 4 A’s, so acquisition, activation, adoption, and advocacy. And so basically, that is the journey that most companies have. Acquisition is the marketing outreach, right? The brand image we’re putting out there, outbound sales, anything that’s going to acquire a customer is the first step in that experience. As your collateral out there, like if it’s a theme park, right, is it representing what their experience is going to be? Are you just putting things out there that’s going to be clickbait or get people in, and then they sign up for it and feel like they’ve been bamboozled, right? That’s the first step in a good customer experience is making sure that the outreach is true to what the experience is going to be.

From there into act activation of it, that’s where the customer is signing up, they’re paying for it. That’s where sales is involved. That’s where the baton passes, back to that relay race, is going to go from sales to customer success and to the customer support team. That’s where they start getting onboarded.

The adoption phase, which is the red hot, most important phase in the customer journey is when the customer has actually started using it. And unfortunately, this is where a lot of people get super lazy and go into what I call “maintenance mode”, right?

And then from there, the last phase is advocacy. This is where most companies fail because they panic and ask the real questions in this last 90-day window when customers have already made their decision at that time. That’s why instead of calling it renewal phase, I call it advocacy. Because they should have already made up their mind and you should now be using them to bring on more customers with their customer stories or their reviews, et cetera.

Yeah, so I think that that’s one of the main things. I will tell you that there’s some things that are really handicapping companies right now, and that is relying solely on metrics like NPS. I’m not saying they don’t have their place. But in my opinion, it’s a vanity metric in its own way, right? You’re only looking at how the customer feels about you and you’re not looking at what the customer needs. And that’s why, oftentimes, I find out that companies that are just relying on a simple metric or even a five-star rating, it doesn’t have to just be NPS, whatever you use for customer sentiment, now the renewal comes up and you’re like, “But you love us.” Yeah, but that’s not what makes a customer renew, right? I know that’s long winded, but hopefully I’ve touched on your points enough.

Sam Jacobs: You have no reason to be self-conscious about being long-winded again.

Leah Cheney: Can you tell that to my wife? Can you write that down?

Sam Jacobs: You’re the guest. I just want to listen and learn.

Leah Cheney: Awesome.

Overcoming imposter syndrome [19:35]

Sam Jacobs: Another great moment. Great moments abound in this bonus episode featuring women in sales. That was Leah Cheney talking about how to put the customer at the center of the business, of the company, of really the whole thing.

Next up, we’ve got a friend, a member of the New York Revenue Collective, a sales leader herself but also a woman that stepped back from being a sales leader and became a founder and entrepreneur, and that is Stephanie Blair. Stephanie started an organization called Know & Flourish.

And she has really been really important to the Revenue Collective during COVID. We created a community called On the Bench for people that were out of work and we wanted to bring in great coaches and great people, service providers that could help people that were in need, right? They had been fired, they had been laid off, they were suffering; and On the Bench helped them reposition themselves, helped them overcome imposter syndrome, and helped them achieve their career objectives and get back to the workforce.

That is Stephanie Blair, an incredible human being. She’s had over the course of 2020, specifically, an incredibly positive impact on a number of people. And we just get amazing feedback about the work that Stephanie does. If you’re not familiar with Know & Flourish, go check it out. And we’re going to listen to this moment. This moment is about overcoming imposter syndrome, which is just so important and so critical. Let’s listen to what Stephanie has to say.

You’ve spoken a lot in the past about imposter syndrome and it’s something that so many people relate to. Why don’t you help define it for us and explain how you think it holds people back, and then what do we do with it if we have it or if we think we’ve self-diagnosed as having it?

Stephanie Blair: Well, the generally accepted definition of imposter syndrome is the inability to believe that your success is deserved and legitimately achieved and the result of your effort and skill. I see it showing up in a couple of ways. People who have perfectionist tendencies or sort of super human tendencies, the do-it-all person. Or they call it a soloist, somebody who’s just this lone wolf who just says, “I’m just going to take it all on myself because nobody else can do it as good as I can do it.” But all the while, they’re sort of doubting themselves in their mind, “Should I be on this table amongst these great leaders or not?”

And so I think it’s important to acknowledge and I do think it shows up in different parts of life. There was a study that said, I think it was a 2011 study so this is not a new concept, but it said that 70% of people will experience it at one time in their life. And this was by the Behavioral Science Research Institute who published a paper on imposter syndrome. I mean, if 70% of us are going to face it, we really shouldn’t be pretending it doesn’t exist. It tends to show up more with women than men, according to these studies. And I think that’s just due to self-doubt is more prevalent, but really it can impact anybody at different times.

And so it’s important to acknowledge it, not hide from it, but then try to use it as fuel to say, “Okay, here I am. What are my gaps? Maybe I have gaps and that’s okay.” Let’s work on taking action against that, filling them, or working with a peer or a leader in my organization to identify if my thinking about my gaps are the actual gaps, and just sort of level setting what’s real and what’s in our own mind. And so much of our own self chatter is what holds us back. And so it’s about sort of arming people to acknowledge it and move past it, and then figure out their way forward.

Sam Jacobs: In terms of actionable, is there a thought process? Is there an exercise? Is it just mentally reassuring yourself? Is it some kind of mantra? I feel it frequently, just as an individual. But if you’re out there and you sort of wake up in the middle of the night feeling like, “Oh shit, I don’t really know what I’m doing even though I’m telling everybody I do.” What do you do besides say, “Well, maybe I really don’t know what I’m doing.” How do you know the difference between what’s valid and what’s not?

Stephanie Blair: That’s probably the toughest question you’ll ask me. I’ll do my best here. But I do think, first of all, it’s acknowledging that like, “Okay, everybody’s felt like this,” even if they don’t admit it to you, right? Again, if studies show that 70% of us are going to feel it at some point, chances are other people in your org have experienced it, even the best leaders. That’s number one is just to normalize it a bit.

And then it’s about like, I think a mindful leader is also a leader who recognizes that your job is never done. We’re always on a pursuit of learning, of excellence. And so in that spirit, you can apply that to your imposter syndrome and say, “All right, well, maybe there is a gap here and what can I do that’s actionable to achieve it. Is it around my communication skills? Is it around how I’m showing up each day? Or is it around forecasting? Maybe there is something that I’m missing here. Maybe I need to take an Excel course to re-up my abilities there.”

It’s about sort of parsing it out and saying, “Okay, what is just like fabricated in my mind and what is something that I can actually move forward with.” And I suggest to people to have an accountability partner in this. When I come into corporate settings and do workshops around this, we often will have the groups identify what type of imposter syndrome they face. That way they see their peers, first of all, admitting that they’re feeling this way and then also they have somebody to turn to in your organization when it shows up.

I also think it’s important to have an open dialogue with your direct manager about this. Or if you’re a leader, to have it with your teams so that perfection is not the only acceptable result.

Sam Jacobs: Well said.

Stephanie Blair: The founder of Spanx, Sara Blakely, talks about her father growing up and he would say, “How did you fail today?” This is what he would ask at the dinner table, right? It’s embracing that concept of failing, failing fast, but learning and growing from it.

The three traits of an organic career path [25:50]

Sam Jacobs: What a great moment with Stephanie Blair talking about how to overcome imposter syndrome. The next up on this bonus episode is perhaps one of the more senior women. Alison Wagonfeld, she’s the Chief Marketing Officer of Google Cloud. She is, as we say, a very important person.

She’s also been on the buy side. She worked at Emergence Capital Partners. She wrote the original business plan for Quicken Loans in 1996. She’s brilliant. Of course, she’s a graduate of HBS, Harvard Business School. She went to Yale undergrad. The point is how she’s constructed her career.

And what we’re going to talk about is we’re going to talk about the three traits of an organic career path, how to put your career together. And who better to do that than Alison Wagonfeld, who is the chief marketing officer of Google Cloud, and just an exceptional human being, an executive? Let’s listen to this final, final moment from this bonus episode featuring incredible women that have been on the Sales Hacker Podcast.

When you’re thinking about advice maybe for people that are starting off in their careers, that are trying to replicate some kind of approach similar to the journey that you’ve been on over the last however many years because it seems to have gone so well, are there specific insights that you have or frameworks that you’ve used as you’ve made different career decisions? Because to your point, these roles and functions, they all have commonalities, but they’re all quite different.

You went from being a banker to an operator within a very large company, to an operator at a very small company, to an investor, and now back to an operator, but this time at a much larger global company. What are the frameworks that you use as you think about making these decisions and advancing over the course of your career?

Alison Wagonfeld: Yeah, it’s interesting because, as I said, it’s not a particularly linear career path and it’s actually to some degree been somewhat organic, but there are common themes in that I’ve always liked to build. I’m a huge believer in how technology can really make a fundamental difference in people’s lives, in organizations, in everything. Essentially everything that I’ve done has had technology at its core. I’ve always been really curious and able to ask a lot of questions, and comfortable with ambiguity, and able to then learn and frame messy problems or complex areas, and try to distill as to what needs to be done next, and kind of with a bias to action everywhere along the way.

I’ve always surrounded myself with really strong people. I feel like every role that I’ve been in, I’ve been working with a top-tier team, and so that’s been another commonality. And then I’ve always found it interesting how much overlap there always is. I mean, the same person that hired me at Microsoft, as a summer intern while I was in business school, was the person who then became a partner at Kleiner Perkins, that recruited me into that startup as the VP of marketing.

And so one of the frameworks that I tell people, and even tell my kids, is remember that life is often a series of back channels and that the people you interface with you will likely interface with again. And always do things in a way that whenever somebody asks about you, that you feel proud about what they would say and the contributions that you’ve made. And so there’s been a lot of commonality in terms of the people in the companies and everything as a common thread through everything I’ve done.

Sam Jacobs: That’s it, folks. A great moment there from Alison Wagonfeld. And that is our episode. That is it. That is a compilation. I hope you enjoyed this bonus episode and the insights shared by these incredible sales leaders, these incredible women, as much as I did.

If you have questions or are facing a challenge at work or just need a community with listening ears, join 7,300 other sales pros in the Sales Hacker community at saleshacker.com. Any sales professional can join the community as a member to ask questions, get immediate answers and share their experience with like-minded B2B sales professionals.

Thank you so much for listening to this bonus episode. October is Women in Sales Month. We hope that you celebrate the women that you’re working with, the women that are your bosses, the women that are leading you because they are a critical part of driving overall revenue growth across the entire ecosystem, the sales universe that we all work in. That’s what I have to say about that. I hope you enjoyed the episode.

If you want to reach me, you can, LinkedIn.com/in/SamFJacobs. If you haven’t applied to Revenue Collective yet, we’ve got an incredible community. Women of Revenue Collective, it’s a private community, and it’s focused on helping women, led by women, achieve their career goals as is everything that we do at Revenue Collective. That’s revenuecollective.com, click apply now. And without further ado, I will talk to you next time. Thanks for listening.

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