Southwest Airlines Secret to Strong Sales Enablement Group

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A big hello from Portland, Oregon. Welcome to another episode of B2B Marketing & More. Today, I have a fantastic guest. Emily Bendorf, Manager at Southwest Airlines, leads the Sales Enablement team for Southwest Business. Emily was a founding member of the Sales Operations group and helped build processes and tools to support the B2B sales organization.

Sales enablement at Southwest and on the Southwest business team is mostly focused on being the liaison between the marketing department, enterprise marketing for consumers, and then their B2B sales team. There’s a sister team that focuses on training and development of their salespeople, and our team manages our sales enablement tool, our CRM tool, and all of that is within the Sales Ops organization.

Today we’re going to talk about sales enablement, and how to work with the sales team. Let’s get started.

In this episode:

• What does it take for a company to become customer-centric?
• How can companies make the transition and decide to form a sales enablement group?
• What is the secret of effective communication with salespeople?
• What are some common sales team requests, and how to resolve them efficiently?
• How to hire and develop a great sales enablement team?
• How to connect and work with management and sales enablement team on prioritization, resilience and flexibility
• What approaches could be used to filter requests from the sales team?
• What are some of the challenges of working with sales teams, and how to resolve them?
• Looking ahead, what are the two things that sales enablement teams should do in 2021 and 2022?

Quotes from the episode:

“One thing that’s so fortunate about our group is that we have such a great working and personal relationship with both of [our] teams. That really sets us up for success and allows us to do our job well.”

“We’ve really tried to balance chase and perfection. So that can be hard to do. It depends on the leaders you work for, in terms of the grace given there, but we have many initiatives and things we want to deliver to our customers.”

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To expand your knowledge about sales enablement, check out some of my previous episodes.

Does My B2B Company Need a Sales Enablement Team?

What is Sales Enablement Planning?

Who Owns Sales Enablement and B2B Marketing

How Sales Enablement Benefits Marketing

TRANSCRIPT

A big hello from Portland, Oregon. Welcome to another episode of B2B Marketing & More. I have a fantastic, I mean, fantastic guest for this episode, Emily Bendorf. She’s a Senior Sales Enablement Manager for Southwest Airlines. Yes. Southwest Airlines! Can you believe it?  

She has been working actually with their sales team very, very closely? So we will talk about our favorite topics, sales enablement, and how to work with the sales team. Let’s get started. All right. Emily, how are you?

Emily Bendorf: Hi Pam! It’s so great to be here. Thanks for having me. 

Pam Didner: Oh, that’s the least I can do. I enjoyed working with you. So, um, how is the weather in Dallas right now? Talk to us, please (laughs).

Emily Bendorf: The weather today and this week has been a bit crazy. Um, we’ve got the first few inches of snow, I think, since 2011 and then the coldest temperature on record in 80+ years. So it’s been quite the week here in Dallas. 

Pam Didner: Oh my God. Did I hear about the 150-car accident in Fort Worth? And that that is ridiculous. But you are safe, right? I mean, nobody got hurt, and you’re good, and your team is good? Is everybody good? 

Emily Bendorf: Yes. Some of my team is still without power, so definitely keep them in your prayers. But, um, everyone is safe and healthy and huddling by the fire, trying to keep warm. 

Pam Didner: Very good. So talk to us a little bit about your job, your scope. Um, you are doing sales enablement and working very closely with sales, and there’s always a perception out there in terms of sales enablement is sales onboarding and sales training.

Is it just that? Or is it a whole lot more than that? 

Emily Bendorf: So, um, sales enablement at Southwest and on the Southwest business team is mostly focused on, um, being the liaison between our marketing department, enterprise marketing for consumers, and then our B2B sales team. Um, so we have a sister team that focuses on training and development of our salespeople that we work super closely with and our team that manages our sales enablement tool, our CRM tool, and all of that is within, uh, the Sales Ops organization.

And we’re a small but mighty team of about ten people, um, that works very closely with our sales team, like you said and alluded to that, you know, sometimes at organizations, there can be a bit of a rift between sales and sales, enablement and marketing. And one thing that’s so fortunate about our group is that we just have such a great working and personal relationship with both of those teams.

So, um, that sets us up for success and allows us to do our job well. 

Pam Didner: Southwest Airlines is such a people company. And for the longest time, based on my perception of it, even flying Southwest Airlines and reading a lot of literature. It tends to be very consumer-focused. Why did you guys change to focus on the enterprise on the B2B or even decide to have a sales enablement group? 

Emily Bendorf: Sure. I can speak to that a bit. So, um, Southwest has strong roots in business travel. You know, even from our very beginning, that’s the customer we served here in Texas. And I think as the years went on, we’ve been, uh, perceived as a bit more of a leisure airline who you want to fly for your vacation. 

The airline has a very strong value proposition for business travel. We’re super flexible at the last minute if your meeting runs late and you need to change your flight. We have no change fees. You know, very, uh, very flexible, great, um, point-to-point network.

And so, for all those reasons and more, I think Southwest has always been a great option for business travel. But we’ve never really, or we hadn’t until about five years ago, invested in growing the team that builds relationships with travel buyers and nurturing that B2B customer experience.

Five years ago, we did a study and identified that we were just leaving a ton of opportunity on the table. There were so much more that we could do to build relationships with, uh, travel buyers at all companies–Fortune 500 companies, small-to-medium enterprise companies, universities, state and local government, um, travel agencies and corporate travel booking tools.

And so, uh, since then, we’ve grown the team to now, um, just under 200 strong. And that is still very small compared to– 

Pam Didner: Yeah, compared with the other carriers and airlines. Yes. Yes. 

Emily Bendorf: Definitely. Um, and then to answer your initial question, why sales enablement? My team’s job is to ensure that the sales team and our account managers have the tools to build those relationships. To reduce friction with travel buyers and, over time, create a better, stronger, digital and in-person customer experience for the B2B audience since Southwest has always had such a strong B2C experience. We want to build on that and help our sales team create that for business travelers and travel buyers. 

Pam Didner: Yeah, that’s fantastic. And I know that you talk to your salespeople regularly and what are the one or two things that they usually request your team to do in general? 

Emily Bendorf: We get a lot of requests for collateral.

Pam Didner: (laughs) I know you do!

Emily Bendorf:  As I’m sure most sales enablement and marketing team do, um, and really to evolve that collateral from, you know, one-page handout to something that’s a little more interactive and digital and personalized. So that’s something that we’re focused on improving. Then really this year, just given the environment that we’ve been in, our travel managers and our sales team have tried to create engagement opportunities in the virtual space. So we’ve hosted quite a few, um, webinars or, uh, digital events. And that has been helpful, you know, to get information out to our customers en mass, especially things that are really hot topics for them. Yeah. So, um, so that’s a way that we’ve been partnering very closely with our sales team this year, as well. 

Pam Didner: So you were one of the founding members. I remember that vividly. And in terms of to start the sales enablement organization, and then, uh, kind of led, uh, the organization from the inception in terms of setting up the sales enablement group.

Now you look back on your journey. What were the two things that, from your perspective, you did right, and you did very well? And what were the two things that you wish you have known earlier–that if you have a chance to go back, you will do it differently? 

Emily Bendorf: Great question. (Pam laughs) A loaded question. I think two things that I’m proud of and that looking back, we’ve done right is that we have hired a great team, um, and developed a great team. So some of that group, um, is new to Southwest and external. Um, but other folks joined our team from within the organization. And really, we just have such a strong group of folks who want to build something new and who are innovative and uh, tenacious and ready to go after, um, those new customers. 

And so it’s, it’s a really fun group as you got to experience firsthand, but also a smart, hardworking, and, you know, I think one of the best in the business. So that would be one of the things we did right.

Pam Didner: You have solid talent, and I liked that, so that’s good. 

Emily Bendorf: Yes. I think the second thing that we have done is, right and it’s a challenge at any big organization. Um, I know you probably remember this from Intel and other groups you’ve worked with, but we’ve tried to balance chase and perfection. So that can be hard to do. Um, and you know, it depends on the leaders you work for, um, in terms of the grace given there, but we have a lot of initiatives and things that we want to deliver to our customers. You have to balance getting all of those done with getting everything done perfectly.

So that’s something I think we’ve done well. And I’m proud of the team for continuing to do it daily.

Pam Didner: So basically, is that coming from prioritization? Do you work closely with your management to determine what to prioritize and what needs to be done? Or is it coming from a team’s perspective to be incredibly resilient and flexible or a combination of both?

Emily Bendorf: Yeah, I think the combination of both, um, probably more the latter. Um, we struggle with prioritization, um, as do probably many teams out there just because we’re also passionate about this work and, um, you know, there’s a lot to do. We’re excited about doing many things, but you definitely can’t do a lot of things well, um, and so just balancing that with making progress, I think. And so a bit more of the latter when you said, you know, resiliency and, um, being focused and doing what it takes to get the job done. 

Pam Didner: Yeah. You know, by, I was, I had a great pleasure, um, and also opportunity to work with you and your team very closely last year. And there is one thing I think you guys did very well and, uh, probably you are too close to it that you don’t see it. You guys stayed very, very close to the senior management. And I think that was, that’s very important. So you’re in a constant conversation with the VP of sales, Senior Director and the VP of Marketing to make sure that they are engaged and updated.

I think that was supercritical in terms of the team’s success, as well. I mean, I see it as an outsider and want to call that one out. 

Emily Bendorf: Thank you. I completely agree. And, one of the things that I realized right away when I joined Southwest, um, and I continue to appreciate daily, is just how approachable, humble, um, and invested our leadership team is up to the executive. Um, and I think that’s unique about our company. 

Pam Didner: True. True. True. So on the flip side, what are the two things that you wish you had more? 

Emily Bendorf: I thought you were going to forget about that!

Pam Didner: (laughs) No! Are you kidding me?

Emily Bendorf: Just kidding! So, one thing that I wished we had known from the start or thought about a bit more is that once you build something or launch something, you also need to staff the resources to maintain it. And so I think that sustainability exactly, um, and especially when you’re moving quickly and growing fast, that’s an important thing to remember.

So we’ve added new platforms to our tools, and we’ve built an amazing collateral library, and you know, many examples I could list here. Still, we also have a small and mighty team that needs to continue building and maintain those great new resources. So, um, that’s something I think that I wish we had recognized a bit more, um, early on, but, but we’re getting there.

Um, and then secondly, I think sales enablement as a term, as a team profile, is still relatively new. And I think, you know, just pausing to define what we want that to be at Southwest and within the Southwest business group. Um, just so that it didn’t and doesn’t become a catch-all. Um, I don’t think, I don’t think we risk that, um, today, but for a while there, you know, there was just so many things that didn’t seem to have a home.

And, and so, um, you know, sales enablement and sales ops kind of can become that, um, the group that, that is responsible for those, you know, random ad hoc things. And I think we just really had to build out that roadmap, um, you know, in partnership with you, which was wonderful and then stay true to what those, um, key tenants of the plan are, uh, and, and get comfortable saying “no.”

Pam Didner: Yeah, I hear you. I think you bought a very good point, and you are not the only one talking to many, uh, customers and clients. Uh, every company define sales enablement a little bit differently. Right? I remember I say it earlier, uh, in the industry, um, the convention definition tends to be sales onboarding and sales training, but the way I see sales enablement is so much more than that. And I think you take sales enablement to another level. It’s not just working directly with sales. You guys are also a conduit and work very closely with the marketing team within an organization. I think that is also another true essence of the sales enablement team that can offer.

So I think that. For you on your team, trying to define what sales enablement is moving forward, so you don’t take all the requests from the sales team. I think that’s very, very smart. 

You know, Given that you experience, uh, working with the sales team, right. And, uh, you stay very close to them, and they tend to make many requests. And what are some of the challenges that you encounter in terms of working with them? 

Emily Bendorf: Absolutely. Well, um, it’s gotten a bit easier since we defined and established an intake process so that at least if we’re not able to deliver on all their requests from our team, they know that we have tracked it and logged it. It is on record as something that we eventually want to prioritize and get to. So I will say that that has helped a lot. But we have such a great sales team with so many great ideas that there are a lot of things that we just don’t have the resources to build or to respond to.

So I think that’s probably one of the challenges we’ve encountered, ensuring that we deliver value to our internal customers and our sales organization. And that even if we’re not able to get them exactly what they’re looking for, we can provide them with something similar that’s already created or a timeline with when, um, we hope to be able to meet their needs.

And I think probably the biggest requests, there is just for things that are a bit more personalized, um, for our external customers. So before the pandemic, we were, and will at some point again, look at, um, uh, content management tool and plug into our CRM that will allow us to do that a bit more feasibly.

Pam Didner: I think the challenge, the challenge that I do encounter, is very consistent across many, many companies. It’s how to scale. It’s how to scale, um, the content support, for example, two different accounts. I have heard that actually from many clients in terms of: “What are some of the easiest ways to scale and personalize content salespeople can actually take out and use it quickly.”

Uh, to be honest with you, I don’t think anybody has found a solid solution on this one yet. Even though they will create semi-standardized templates or presentations or sales collateral, it still requires some work on the sales side, and it’s not something that they can automatically take out and use. So the challenge that you encounter, what I’m trying to say, is you are not alone. I think everybody’s trying to figure out that Holy Grail. (Pam laughs)

Emily Bendorf: Yeah. Well, I hope we can. We can be one of the first to figure it out. 

Pam Didner: Oh, that would be great. If you do, can you just ring me very quickly? I will love, love, love to bring you back and then share your biggest secret with all of us. Well, speaking of, post-pandemic, given with the vaccination rollout of with this year and hopefully that the majority of the population in the U.S will get vaccinated. Looking ahead, what are the two things that your team will do in 2021 and 2022? Do you mind sharing them with us? 

Emily Bendorf: Sure. Our big focus as a company–and that trickles down to our team–is a focus on getting new customers. So you may have seen in the news Southwest. While other airlines are shrinking, Southwest is flying to 12 new cities. We’ll be continuing to announce new cities over the coming weeks and months. Just trying to capture travelers and demand where we can.

And so our team is working on the right tools, resources, campaigns, alternative currency packages and promotions and loyalty to allow our sales team to go out and get that new business. So that’s a focus for us in 2021. Then, a bit more tactically, we recently added Pardot to our tech stack at the end of 2020. Which is super exciting. So we will be working on a strategy for that tool. We are just building a plan to create a more automated campaign and email cadence for our customers who don’t necessarily interact with the Southwest business account manager. 

Pam Didner: You know, I love, love, love the ideas that, um, you guys are rolling out new cities and a new destination. And from my perspective, that’s the product offering. So you continue to update and refresh your products, which gives the sales and marketing team something to work with and something to communicate with your customers. So your job of landing new accounts or working with the B2B marketing team and the sales team to do that is great.

Because as long as you guys are rolling out to a new city, there’s always an opportunity to bring new accounts because that’s a new product offering. So I think that’s fantastic. In addition to that, you have tools in place. And you try to do the marketing outreach and marketing campaigns. Working with a B2B marketing team to make a tie and the connection between the sales and marketing.

Hey, you’re all right. You know, sales enablement is incredibly valuable for Southwest airlines. You guys are small and mighty indeed! 

Emily Bendorf: Thank you, Pam. I appreciate that.

Pam Didner: So, um, any parting thoughts that you want to share with us? If anybody wants to do any kind of sales enablement or is in the process of supporting sales, do you have one or two insights that you want to share with them us?

Emily Bendorf: I think business tends to think of empathy a lot of the time as more of a soft skill and, um, something that’s maybe not as critical, but I think you win a lot more friends and, um, you win more business. You consistently put yourself in the other person’s shoes and deliver your pitch or your product or whatever it is that you are sharing, um, with that top of mind.

One thing that my team has started doing this year, because our internal customer is the sales team, is joining more of their meetings, their sales kickoffs. They have weekly alignment calls. They have “wins of the week” calls where they celebrate successes. And we’re very much a part of all of those. Not sharing necessarily, but just to be a fly on the wall so that we can be more empathetic of their challenges, their day-to-day priorities. Then we can layer that into how we structure our time and how we prioritize our work.

And so, um, I think that it has been successful for us to be so in tune with what they’re doing.

Pam Didner: I think you brought up a very good point, and I emphasize that, uh, in every single webinar I do, especially on sales enablement is a stay close to the sales team. And, um, be part of what they do and try to understand the challenges they encounter. And I agree, um, be empathetic because they have to meet the monthly quota regularly. A lot of time, their minds and their eyes are focusing on getting a customer and getting a new logo. So they are not necessarily a lot of time to pay attention to how marketers feel in all. Even though they appreciate everything we do, they don’t make an effort to say thank you. That doesn’t mean that they don’t appreciate you or that everything you do, it just because they are busy. 

Emily Bendorf: Uh-huh.

Pam Didner:  And, uh, I agree with you that be very empathetic about that and understand their needs and where they come from and do what you can to support them. I appreciate you share that insight.

Thank you so much, Emily. 

Emily Bendorf: Thank you, Pam. Um, and I’d be remiss if I wouldn’t be on a sales team if I didn’t put an in for Southwest business and just remind our listeners that, you know, we, we offer travel solutions for companies of every size. So when people are ready to fly, we are the most reliable carrier out there. Um, and they should be choosing Southwest. 

Pam Didner: I 100% agree with you. I fly. Yeah. I fly Southwest Airlines all the time. And, uh, yes, it’s incredibly efficient. Everybody bought it right away and you guys not waste a single minute when everybody’s situated, you kind will” Is everybody ready? Is it good? Is it good?” And then you guys like, “okay, now it’s ready to go!” You don’t wait. You know, it was incredibly efficient. So I appreciate that.

So thank you so much for putting a plugin for Southwest Airlines, but before I let you go, I want to ask you one silly question. Okay. Did you have a ridiculous going in your life? What do you want to accomplish? Like you were like, Oh my God, this is outrageous. 

Emily Bendorf: I, I did have a goal, um, that I’m sad to say, I barely met. A few years ago, before my 30th birthday, I had a goal of visiting 30 countries before I was 30 years old. 

Pam Didner: That’s, that’s a big audacious goal. (laughs)

Emily Bendorf: Yeah. I mean, when you work for an airline, right? You, you, you usually love to travel and take advantage of those flight benefits. So, um, now I need a new goal, Pam. Now I’m well past 30, and, um, I need to set a new, ridiculous goal for my life that I need to get back to you on that next time I join your show. 

Pam Didner: I would love that. I will love to hear that from you.

All right. Thank you so much, Emily, for joining me on my podcast. It’s wonderful, wonderful to have you on my show. You will come back, and we’ll talk a little bit more about the Phase Two of your sales enablement journey at Southwest Airlines. 

So now that’s a wrap. Uh, again, thank you so much for listening to my podcast. It means a lot to me. Suppose you can subscribe to my show on your favorite channel. If you have a guest you like me to invite, reach out to me anytime to see what I can do. If you have any specific questions, reach out to me on any social media channel or email me hello@pamdidner.com. You can also join my Facebook community, Build Your Marketing Skills to Get Ahead. I answer everybody’s questions within my community. Okay. Again, love, love, love to hear from you. Take care. Bye.