Episode 250: Lindsey Boggs – Mastering Sales Leadership: Navigating Relationships, Empathy, and Technology in the Digital Era

Lindsey Boggs  00:00

Having an opportunity to get to know people through social channels and develop relationships that can foster into something great. You never know when you are connected with somebody that might be able to give you an introduction to a place that you’ve been yearning to work or maybe yearning to prospect into. It’s about making it fun, It’s about making it real, It’s about humanizing this whole digital world that we’re in.

Intro 00:29

Welcome to the Making Sales Social Podcast featuring the top voices in Sales, Marketing, and Business. Join Brynne Tillman and me, Bob Woods, as we each bring you the best tips and strategies our guests are teaching their clients so you can leverage them for your own virtual and social selling. Enjoy the show! 

Brynne Tillman  00:54

Welcome back to Making Sales Social, I’m really excited about our guest today. Lindsey Boggs is someone that I followed on social for years and then got to meet her back in 2015. And fortunately got to see her when we were at LinkedIn during Dreamforce, about a month and a half ago. Lindsey is VP Sales Development and Enablement at Glassbox. And Glassbox is such an interesting company, as they really help the customers’ digital journey on websites so that it reduces friction. And Lindsay, now as a VP, is running the sales and enablement team, Welcome to Making Sales Social.

Lindsey Boggs  01:37

Thank you so much for having me, Brynne, it’s such a delight.

Brynne Tillman  01:40

Oh, my gosh, when I saw you at LinkedIn, I was like, “Oh, my gosh, it’s been too long.” And I was so excited about the things that you’re up to and how you’re impacting sales. You have done so much over the years, including shedding light on the mental health challenges of balancing work life, family, and getting, and you really by being vulnerable and sharing your story. I’ve impacted so many people because most of us have some level of that. But there, you took the shame out of it. And I can never tell you how much I have appreciated that over the years.

Lindsey Boggs  02:21

Well, thank you so much for sharing that. I mean, it’s been a journey, for sure. And my goal is sharing stories. If I can impact one person’s life, I feel like I’ve done a good job. So appreciate that. 

Brynne Tillman  02:34

Well, you’ve impacted thousands, at least. And it’s, you’ve really, you know, put your stamp on that. But beyond that, you are a brilliant sales and sales enablement professional. And I’m really excited to dive into that. But before I do, the one question we ask all of our guests is, “What does making sales social mean to you?”

Lindsey Boggs  02:58

What does making sales social means to me is having an opportunity to get to know people through social channels and develop relationships that can foster into something great. You never know when you are connected with somebody that might be able to give you an introduction to a place that you’ve been yearning to work or maybe yearning to prospect into. So I think it’s about making it fun. It’s about making it real. It’s about humanizing this whole digital world that we’re in.

Brynne Tillman  03:30

Oh, I love that answer. And I agree it really is why it’s the most fun selling, building those reports and raptors in the relationships. So tell me a little bit about your philosophy on managing team sales teams. Because you have this deep empathy. And so I’d love to hear a little bit about your over arching philosophy around leadership. 

Lindsey Boggs  03:58

Yeah, absolutely. It really changed a lot for me during COVID, I read a book called the trillion dollar coach. And what it allowed me to internalize was really take a look back at my one on ones and my staff meetings and how they were run. And before I read the book, my one on ones and staff meetings, I would say, Were mediocre at best. I didn’t necessarily have an agenda. I didn’t have them bring an agenda to me. And if I had somebody let’s say that’s less outgoing, or somebody that is less forthcoming with information, or one on ones would be very, very brief. 

And so I changed my whole structure and philosophy around sales leadership after reading this book, and so now my one on ones are incredibly structured. I have let the team know that it is their opportunity to, you know, share with me what’s going on in their world. It is their agenda, not mine. I’ve implemented some software around that to have really effective one on one At my staff meetings, I changed completely. I have visuals, I have icebreakers, I start every meeting off with gratitude. So I go around the room and ask every person what they’re grateful for. 

And, you know, it changed during COVID. And leading a team remotely has its challenges. But I think the biggest thing is having empathy. When I start a new company, I always share with them my TEDx talk on my mental health journey, because I want them to know that I’ve been through struggles, I understand when somebody needs a mental health day, probably more than most people. So that’s kind of my philosophy is just leaning into being vulnerable for the team, but also holding them accountable as well.

Brynne Tillman  05:42

I love that. It’s okay, I kind of want to keep going down the sales leadership journey, because this is the area where I think so many people can learn from you. So let’s talk about hiring. What do you look for when you’re interviewing a sales rep?

Lindsey Boggs  05:59

Curiosity, I make sure also that they’ve done their research on me and the other people they’re interviewing with if I get on an interview, and I start off by, you know, small talk, and then I say, “Okay, what did you learn about me before today’s interview,” and they say, “Are they scramble?” And they obviously haven’t researched me, a simple Google search can bring up a tonne of stuff on me. If they haven’t researched me, how do I know they’re going to research a prospect that is part of their job.

Brynne Tillman  06:29

I love that curiosity. I think you can teach a lot. But curiosity, I think, isn’t neat. You could even teach them how to research but if it’s not in their heart, they’re just going to get some bullet points, right? They’re not going to really, so I love that. You know, everyone has a different definition of sales enablement, right? You could talk to 10 people in sales enablement, and have 11 definitions. What does sales enablement mean to you?

Lindsey Boggs  06:59

Sales Enablement means to me having the right resources in your toolkit, but also, this is the big thing, the leadership leading the sales team has to have accountability with the team to use it. And that’s the biggest gap I’ve seen is like, I’ve been at companies or I’ve consulted for companies in the past where they have every tool stack you can imagine. But if they’re not using it and not using it the right way, what’s the point of having it so it’s about accountability and teaching the leaders of sales to have accountability with their teams.

Brynne Tillman  07:35

So when sales stack is an interesting dilemma, right, like, there are some times I will talk with the sales team, and they don’t even know what’s in their sales stack, like their companies buying and pushing. And some things are more for leadership. Other things are for customer success. Others might be, you know, process driven, but rarely do they play together. So what do you do in a sales enablement role that helps adoption of new tools.

Lindsey Boggs  08:10

show them how they work, by me showing them how to prospect and how to close business by using the tools in my tech stack that we have. So it’s getting in there and saying, “Hey, you want a meeting with this company?” Let me show you how to do it. And I do it. And that’s all the buying they need is like, “Oh, Lindsey, Lindsey just showed us how to do it from start to finish.” I couldn’t do that. So it’s about showing them and leading the path for them. 

Brynne Tillman  08:35

Yeah. And that gives you so much credibility, right? When they go, “Oh, she’s been there, She’s done this, She gets it, She and it’s not just sales leadership, She understands having a quota, She understands.” So I think that that’s, I think that’s so great. You practice what you teach. Exactly. So I love that. So this company, glass box, right? This is about the digital experience about UX about making websites easier to navigate and probably creating more leads for the company’s rights. 

Tell me a little bit about how you help the sales team position this company in a way that creates new opportunities, because in some ways, it’s its own, kind of a new market, right? Like it’s not, it’s not website building necessarily, or if it is, you know, but so how do you position this new idea in the minds of your buyers?

Lindsey Boggs  09:44

Yeah, absolutely. And I think you’ll like this answer. To me, First and foremost, it comes down to us all having our own personal brand. Because when we’re outreaching to a prospect, and if our profile isn’t filled out completely, or we don’t have a value prop on what glass boxes, they’re not Gonna be as inclined to reply. So it starts internally with our personal brands being developed. 

And then also it, it starts with making sure you’re engaging with your prospects on LinkedIn and making sure you’re tagging them on content around a glass box. And the first time you outreach to them will not be the first time they’ve heard your name, or they’ve seen your name. So it’s not about, you know, batching and blasting, it’s about being really strategic and how you’re going after that prospect.

Brynne Tillman  10:28

So yeah, I absolutely love that. In sales enablement, are you kind of bridging between the content and in the marketing department and what your sales folks need in order to start those conversations?

Lindsey Boggs  10:42

Absolutely. I work very closely with marketing and product marketing to make sure that our messaging is on points. You know, the messaging we’re sending out through email through LinkedIn is definitely top of mind for the prospects we’re going after and personifying it. We don’t want to send a message to somebody that doesn’t resonate with them. We want to make sure it’s all based on their persona.

Brynne Tillman  11:04

Yeah, I love the way that you think in the way that you’re, it’s all kind of aligned and working together. I think. It really, I do believe it’s the difference between sales management and sales leadership, and you are definitely coming at this from this leadership role, where you’re going to create so much trust and credibility that your sales team is really going to thrive. And I think it’s exciting. So as we start to wrap this up, I’m going to ask you, is there a question I didn’t ask you that I should have? 

Lindsey Boggs  11:40

Ohh, questioned that, I would say, the one and only AI, what’s going on with AI?  

Brynne Tillman  11:49

And, of course, so God, share, share your thoughts on AI and sales.

Lindsey Boggs  11:54

Yeah, AI and sales are interesting. I mean, I think it’s probably at the top of our feed every single day how to leverage it, I’d say, Don’t be overwhelmed with how much talk is going on with AI. But I would encourage folks to explore it in terms of using it for your advantage, meaning, you know, I use Bard personally to ask the prompt to tell me what are the top five initiatives for so and so company in their latest earnings statements, so I don’t have to read 150 pages of an earnings statement.

I can just consolidate and ask for five bullets and be really specific on what I’m going after. So that’s a way to save time, but I don’t want people to over rotate on AI and think, Is it going to take my job? Or how am I? How am I going to use all of these AI tools? Because there’s so many I mean, I get prospected on a daily basis. I’m sure you do as well with AI and I can pick out AI versus non AI. And that’s still important to humanize this process, right? Yeah.

Brynne Tillman  12:58

Oh, perfect. Thank you so much. So, um, how can people get a hold of you? And why? You know what, like, maybe around a glass box and what you do? How can they get a hold of you?

Lindsey Boggs  13:10

Yeah, LinkedIn is the easiest way to get a hold of me. I am an open book, I like to engage with all sorts of different types of people. And I’m always exploring, you know what’s out there. So please connect with me on LinkedIn or follow me on either one, happy to be a resource. And I just wanted to say congratulations to you, Brynne for making LinkedIn top voice because that is a goal of mine one day to make that so I’m so proud of you. And I know that it’s such an honor to receive that award.

Brynne Tillman  13:40

Oh, it’s been a lot of fun. And I’ve really enjoyed it’s really stemmed through the LinkedIn in sales insider through sales solution. So that’s how we met.

Lindsey Boggs  13:53

I know. 

Brynne Tillman  13:54

So that’s how we re-engage. But thank you. It’s been a fun journey.

Lindsey Boggs  13:58

That’s awesome. Well, terrific. 

Brynne Tillman  14:01

And I really love the insights that you brought to the audience today. And I’m sure there are some nuggets in there, some of our leaders can take and really leverage to increase team success. So thanks so much for being part of this. And for all our listeners when you’re out and about don’t forget to make your sales social.

Outro 14:23

Don’t miss an episode, visit socialsaleslink.com/podcast. Leave a review down below. Tell us what you think, what you learned, and what you want to hear from us next, register for free resources at LinkedInlibrary.com You can also listen to us on Apple podcasts, Spotify, Stitcher, and Google Play. Visit our website socialsaleslink.com for more information.