EPISODE 433: Sales Leaders Jeffrey Wolinsky and Billy Biggs Offer Tips for Success as Your Sales Career Journey Continues

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[EDITOR’S NOTE: This is a replay of the Sales Game Changers LIVE virtual learning session sponsored by the Institute for Excellence in Sales on November 10, 2021. It featured an interview with sales leaders Jeffrey Wolinsky of WTOP and Billy Biggs of WalkMe.]

Find Jeffrey on LinkedIn. Find Billy on LinkedIn.

JEFFREY’S TIP: “The journey continues. I think for new sellers, we were talking about people who’ve joined the Institute for Excellence in Sales, people think that they can do something and then be there, they can have arrived and be successful, be a senior salesperson or a sales leader. The journey always continues as things change, what has been made very available to everybody is that embracing change, adapting to change and actually changing to get better is a big part of being a successful salesperson. Stay on a journey for making yourself more valuable to both your organization and your customers’ organization, and you’ll be well served.”

BILLY’S TIP: “Figure out the top 10 challenges that each one of your prospects have and how you can provide value. I don’t think sales reps do this enough, they sell the product and/or service. Figure out the top 10. For me, the top 10 IT transformational projects at each agency level, that’s what I want my AEs focused on and how we can provide value.”


Fred Diamond: Billy Biggs, it’s great to see you. Jeffrey Wolinsky, it’s great to see you. Jeffrey, you’ve been on the show before, WTOP. Why don’t you tell us a little bit about how things are going right now? We interviewed you down at the Glass-Enclosed Nerve Center, the beautiful old studio. You guys have moved since then. We did the interview live and in person and then of course, we had you on during the pandemic last May. How are things going today? Again, we’re doing today’s show November 2021.

Jeffrey Wolinsky: Things are going fantastic because what is clear with any sales organization is that if you have a guiding mission and stand by that mission, you can continue to have success. Our guiding mission, to be a trusted extension of our clients’ marketing team. By taking that guided mission and applying that filter to everything that we do, we can make distinct decisions about what we should and conversely, should not be doing. When you think about all of the things that have been thrown at people during the last 18 to 20 months that they’ve been in unique circumstances, decision making is one of the biggest skill sets that businesses need. The decision making is made easy when you have a guiding principle and a vision for what your organization both is and what it isn’t. Then decision making becomes easy. Because of those reasons, things have been going really well for us.

Fred Diamond: Billy, what is your take on that? Jeffrey talks about the guiding mission, the principles, if you will. You work with WalkMe, I’m not sure if everybody’s familiar with WalkMe. Why don’t you tell us a little bit of what you do? You manage and you lead public sector sales as a lot of the previous guests are on the Sales Game Changers podcast. Is there a principle guiding mission that Jeffrey talked to? Tell us a little bit about how you guys are doing as well.

Billy Biggs: I appreciate you having me on. WalkMe, we’re a digital adoption platform. Our value prop is significant in that we can deploy on any enterprise technology and really understand where users are getting caught in workflows and optimize that experience. What we recognized the last 10 years is that public sector and even the private sector has bought a lot of enterprise technology, but the return on investment is basically flat, or productivity is basically flat. I think we have a unique value prop specifically in public sector, I can tell you that I’ve never been more bullish about the public sector space. There’s a lot of major initiatives going on right now with cyber security, technology modernization, AI, digital services. Really bullish from that perspective. All of our conversations have been going really well. To Jeffrey’s point, around having a mission, I totally agree. Mine is more about a personal thesis and what I believe at my core to support my team and our customers. I totally agree with Jeffrey.

Fred Diamond: What are the top priorities right now? You guys are leading teams, you’re working with a lot of customers. Jeffrey, your industry has had some degree of disruption. As a matter of fact, when we had you on the show the first time around in 2017, we were talking about shifting from just radio sales into digital marketing. That was actually a great show and I encourage people to go back and check that. It was, I think, one of the first 10 episodes that we ever did. Talk a little bit about what you’re focusing on and what some of the priorities are. Jeffrey, why don’t you go first? Then Billy, how about you?

Jeffrey Wolinsky: Two different things, the focus of our business versus the focus of our sales department. The focus of our sales department is to make sure that we are being somebody who adds value to what our client is doing and not just selling them something. That is a critical piece. You were mentioning before we started today that there were some members of the IES that are joining events and seeing each other in person, seeing people that they work with in person for the first time and had just graduated college. To anybody who’s new to sales or anybody that needs to be reminded in sales, your job is not to sell something. Your job is to help somebody get value out of the products or services that you represent. When you make it about yourself, “I want to sell something,” or “I want to close these people,” or “I want them to do this,” then you’ve completely missed the mark. Because it’s about helping somebody get what that is your product or service offers.

What’s taken place with virtual meetings and with people working from home is they want to speed up the process, I want to make money, I want to make my sales goal, I want to be more efficient, my time is an issue right now. People are trying to speed up the sales process. When that process gets sped up, they miss the step of understanding that until the client, until the customer can identify exactly what they need based off of a needs analysis and a conversation that you’re having together, you’re not able to add value. You’re just trying to sell them something. What we’ve done in this time is to spend more time focused on the sales process and where within that process you can benefit your customer, rather than thinking about yourself.

Fred Diamond: Billy, you mentioned you focus on public sector. We’ve had a lot of public sector leaders on the Sales Game Changers webcasts and podcasts that we’ve done. Talk about an industry that didn’t miss a beat. We took the government to the cloud, you’re in that space and they had to continue to provide service, obviously. The public sector does a lot of things for citizens, protect, defend, build infrastructure, health was a huge topic. Talk about your industry and how you guys responded to continuing to service. Like Jeffrey mentioned, you’ve got to bring value to the customer. Talk a little bit about how the government, public sector has continued through the last 18 some odd months.

Billy Biggs: I’ve been really impressed with the government productivity over the last 18 months. Most of my peers will recall a time in which it was almost unheard of for the government to support a remote work policy, there was a lot of debate about productivity and if that could be allowed. I’ve been super impressed with how the government has responded around folks that really support the mission. Productivity I think is at an all-time high around government, and obviously, the debate has been settled on whether they can be supported from a work-from-home policy. I think telework is there to stay, I don’t think it’ll go back 100%, certainly from what I’ve seen and talked to my customers.

I just want to respond real quick to Jeffrey on his top priorities. For us, it’s a little different. WalkMe is a new category of technology, so right now my top priority’s around demand gen and market awareness. How do I get out to prospects so they understand the unique value proposition that we bring to the market? We’re in the beginning stages of that rolling out into 2022 around field marketing. Obviously, there are some concerns and challenges with events and conferences, Fred, we talked about that at the forefront, but it’s all around demand gen, market awareness and getting a reaction from prospects on the value prop on what we can deliver.

Fred Diamond: We have a question here that comes from Jean, “Could you ask Jeffrey and Billy if they think that virtual selling will continue through the next year, or if we’re going to get back to seeing people live?” I know you guys don’t have crystal balls per se, and Jeffrey, you’re obviously in an office right there. What do you all think? Do you think it’s going to continue for the most part in the virtual setting? We’re only going to see our customers on this rectangle? Or do you think our customers are also interested in us getting back? We talked about events, for example, that are beginning to come back. Billy, why don’t you go first? What do you think sales is going to look like in 2021? Jeffrey, I’m interested in your thoughts as well.

Billy Biggs: Moving in the next 12 months, I do think we’ll get back to in-person events and in-person selling. I do think the industry as a whole is going to have to adjust to that. It’s been a while since folks have had to do that. For me in public sector it’s critical that we have an opportunity to do that, because it just connected to the ecosystem. I was with my team in DC this week kicking off plans for 2022, I make it a point, hey, if you’re comfortable meeting in person, would love to grab coffee or lunch. I think a lot of people were reciprocating to that. I think that you’re going to be seeing more and more, but somebody has to go first, even with events. I think everybody’s playing a waiting game to see who goes first and who’s more comfortable meeting persons versus staying on Zoom or whatever technology you want to use.

Fred Diamond: Jeffrey, how about you? How do you think that’s going to shift over the next 12 months?

Jeffrey Wolinsky: There will be a shift for sure, human beings want to be in person. The real thing that dictates it is what’s the incentive? A salesperson has an incentive to be in person because we all know, Billy knows, you know, Fred, I know that we are more effective in person. We can work from home, but we can be great sales leaders in front of our people and our customers. What’s the incentive of the customer to see us in person? If they request us in person, they understand that they can better communicate with us and get greater value from us. The big question’s going to be, what’s the incentive? If I’m calling somebody for the first time, I want to come see them. Maybe they’re working remote, maybe they’re in and out of their own office. What’s their incentive to see me?

Our valid business reason for why they should see us in person has to be stronger than before. In the past, before any of this happened, we could get by on the given that we’re going to come to your office and the meeting is going to be in person, but we have to dictate and direct that. Rather than saying, “Would you like to have a meeting?” or, “Can I talk to you about this thing?” we have to structure the ask in a way that the ask is to be in person, and that the ask is beneficial enough for the person to make the decision to say yes to in person.

Fred Diamond: Let’s talk about a little follow up to what Jeffrey just said. As sales professionals, we want to be with the customer. Not just in with them, but at least some type of interchange and that’s where salespeople thrive for the most part. Not when you’re sitting at your desk watching a webinar, creating a plan or filling out your CRM, it’s when you’re with customers and you have to bring them the value for them to want to spend time with you. One term that we’ve used a lot over the last year and a half or so is the concept of being an elite sales professional. Billy, why don’t you go first and then Jeffrey? What are elite sales professionals doing right now and how would you encourage sales professionals to be elite?

Billy Biggs: That’s a great question. I think that there’s a lot of talk about growth mindset and having a growth mindset. If I’m a sales professional, obviously, you need to be curious. That lifelong learning aptitude. I always think about my team and I ask the question, what are you doing every day to be better? And it has to be outside of your 9 to 5, whether you’re reading or rereading or a podcast or some kind of group to get outside counsel. I think from a leadership perspective, I’ve always had a strong opinion. Don’t just be a sales manager, be a business leader, have a 360-degree view of your business. When you think about attracting salespeople and AEs now, in The Great Resignation I think organization culture will be a differentiator. It will be up to those leaders to differentiate themselves among what I would call, other sales managers.

Fred Diamond: Jeffrey, how about you? What does it mean to be elite right now?

Jeffrey Wolinsky: I agree with some of the key points that Billy had there, the culture aspect is a unique one to get into further. But my specific salespeople are back to focusing on how are we servicing our client? When I look at the folks on our team who are elite, it’s researching and understanding how we fit in to the client that’s buying from us, and understanding why they buy from us. At our launch that we did at the end of September, our sales year starts essentially October first, really understanding why people buy from you. Why each individual sale you made, what made them purchase? By dissecting that, just like the medical industry dissects the frog to understand how the body works, dissecting the sales that you’ve made and why somebody said yes to your ask. Understanding that makes you elite in the next sale and the next sale and the next sale, because you understand how to treat each objection or each diagnosis that you have from a different client. That’s where our research is done. Why do they buy from you? What benefits are they seeking and how can you better explain that to other clients and new prospective clients?

Fred Diamond: I want to talk about conversations. You talked about when we get the opportunity to be in front of the customer, there’s a lot of words that have come up. Daniel here mentions authenticity is something that the elite salespeople have. We’ve talked a lot about vulnerability, transparency, authenticity. One of the challenges because people aren’t yet back to the office is that every interaction for the most part is over Zoom or something like that and we have to schedule it. People are Zoom fatigued and you can only get so much interaction going with a Zoom call.

Talk about how you would encourage people to engage in conversations right now. You’re right, Jeffrey, we want to understand what their challenges are and what they’re concerned with, so we have these types of conversations. But at the same time, we also need to drive business. One thing that we learned a year ago was that sales is the organization that’s going to lead us through this. Talk a little bit about the types of conversations you’re encouraging your people to have. One of our members at the Institute for Excellence in Sales said that they realized that all the conversations over the last year were the “How are you doing?” type of conversations heavy on empathy, which is critical in sales. Then they woke up and said, “We realized that we weren’t really moving the sales process along, so now we’re steering through that.”

Jeffrey Wolinsky: I really subscribe to the elimination of uncertainty. When somebody makes a decision, they’re able to make a decision when they feel safe and comfortable. Right now, there’s a lot of uncertainty in their job, their company, the world, The Great Resignation, people on the team, culture. You have to eliminate uncertainty with what’s taking place. When you eliminate uncertainty, somebody can make a decision that’s in your favor. When uncertainty exists, whether it be with your proposal or something else that’s taking place, they can’t make the positive decision you’re looking for them to make, and you can’t get the result that you want.

So, identify what they’re uncertain about, eliminate it and anxiety goes away. When anxiety exists, sales do not. When uncertainty exists, sales do not. When you eliminate that from the conversation, whether that be something that your company offers in terms of worry-free, invoicing, whatever it is that you can eliminate that they’re uncertain about, then you’ve taken down those barriers to getting the answer that you want, which is, “Yes, let’s do business together.”

Fred Diamond: Billy, I have a question for you as a hiring manager. Jeffrey just alluded to The Great Resignation and one of our guests last week talked about the fact that we’re thinking from ourselves, how do we stop The Great Resignation? But the biggest challenge with The Great Resignation is the fact that it’s impacting our customers. They’re also struggling with The Great Resignation, and their customers are struggling with The Great Resignation. People, rightly so, are evaluating their lives, what they want to do, where they want to live, things like that. I know you’re expanding your team over the next couple of years. Knowing that we’re in a different place than we were two years ago, what are some qualifications, characteristics that you’re looking for, for potential sales reps selling into your space?

Billy Biggs: It’s a great question. I think obviously it’s nice to have existing public sector experience selling to federal, state and local, etc., because of the nuances and then differences between the private sector. That’s experience, what connections they have selling through the ecosystem, the partner network, those are all core. But then I think about upside. I talked about what are they doing, what are the AEs doing and the reps doing outside of work to be better, to be elite? I interview based on culture, so they have to be a cultural fit on paper.

I see a lot of resumes. In fact, I probably reached out to 300 people directly as a VP because of The Great Resignation. From a recruiting perspective, I do a lot of my selling to candidates on considering WalkMe as an opportunity for employment. I think from that perspective, culture is a big thing for me. Are they going to fit within then team and are they going to make the team better in one specific way? I always end the interview with folks with, “What’s your superpower? How are you going to make the team better?” Because you have to make the team better coming over and it can’t be just, “I’m going to go out and crush my numbers.”

Fred Diamond: Jeffrey, we have a question from Darlene and she basically says, “Can Jeffrey answer that question as well?” Media. Again, we talked before in the beginning about how your industry’s been disrupted. When we first met you in 2017 and had you on the Sales Game Changers podcast, we talked about how your industry was automatically getting disrupted. Radio companies, media companies and audio companies have shifted to digital and offering more services to the customers. What are some of your thoughts on the type of characteristics someone should entail to be successful in selling media?

Jeffrey Wolinsky: In selling anything, you have to ask a lot of questions because ultimately, there’s a difference between selling somebody and helping somebody solve a problem. Selling somebody is that old movie central casting belief of the salesperson is a person who was popular and got along with everybody, a big-time extrovert, but that you couldn’t trust that person. That has created a long-lasting negative culture in how people outside of sales in the organization viewed sales. What I subscribe to is that if you ask questions and truly show interest, understanding and care about what problems that the customer needs solved, that’s when you can partner with them. You’re not selling them something, you’re helping them to solve their problem.

For example, in Billy’s case it’s even clearer what the problem is that people have. They have so much enterprise software that they aren’t getting effective use out of things that they’ve already purchased. They can come in, acquire Billy’s team and software and that will make their investment more effective and successful. Clear, simple, easy, I’d invest in Billy’s team and his company because they solve a specific problem. In our case, we have to ask significantly more questions because marketing is not magic, we can’t wave a wand and solve the issue. Understanding what the problem is can be slightly harder, so I want people who are naturally curious asking lots of questions, follow-up questions and understanding how the answers to those questions apply to the overall conversation.

Fred Diamond: Billy, I have a question for you. We talk about listening and questioning. This morning on our podcast, one of our guests talked about people listening to talk, listening, paying attention but then they’re really just listening for their opportunity to talk. What are sales reps doing wrong? What have you seen sales reps do wrong today or recently that really irks you and that you would like to correct them on?

Billy Biggs: That’s right, listening to respond versus listening to learn. I agree with Jeffrey, 80% to 90% of discovery should be listening and then asking why, and getting deeper into the why. From my perspective, an effective seller would know the client’s business better than they know themselves, and I agree on selling on value, but without identification of that pain and why it exists, there is no sale. More importantly, you have to get agreement with the buyer to go on this journey with you to solve a problem. That’s a second arc of effective selling. It’s not just identification of the problem or the pain point, it’s that they’re going to go on the journey with you to help solve that. Are you listening in discovery or are you listening to respond?

Fred Diamond: I have a question for you both. Again, we’re in November 2020, the pandemic kicked off on March of 2020. What are some of the positive things? We’re almost two years since this started. We just referred to The Great Resignation, we talked about the challenges that our customer’s customers are facing, but let’s talk about some of the positive things that have happened as we move forward. Billy, why don’t you go first? What are some of the positive things that you’re continuing to grow with based on the last 19 months?

Billy Biggs: I think I heard it a couple months ago. It’s not work from home, you live at work in this remote environment. Productivity has gone up, people are obviously not commuting, they’re spending more time working, but I do think there’s some positive around the topic of mental health. I encourage every single one of my team, if you need an hour during lunch, during the day, go out for a run or a workout, it doesn’t have to be scheduled. I’m not expecting people to be there 9 to 5, that’s unreasonable. I do think that one of the benefits of the last 18 months is this idea or thought process around mental health where everybody’s committed to that. For me, I’m a big mental health person. I exercise when I can and I encourage my team to pick a time and do whatever they want to do around mental health.

Fred Diamond: We’ve had various words over the last 18 months, fatigue, languish. I’ll tell you, man, mental health is huge and true mental illness is something that’s going on out there. How do you guys pay attention to that? I’m curious, Billy had mentioned that. I’ll tell you why. We had a guy named Tim Solms who’s the VP of sales at D&B and I asked him what’s the biggest topic. This was June of this past year, and he said fatigue, he said, managing then fatigue of our people and being very conscious of that. Billy, you mentioned mental challenges right now. Talk about how you as sales leaders are conscious of that at the executive level.

Jeffrey Wolinsky: That’s something that’s extraordinarily challenging, and I look at my own career progression and path and know that I personally haven’t been hit by some of those things. Relating that to people that you’re managing, I’ve never said I’m overworked or I’m fatigued because I’ve always loved work so much and made that a massive part of my life from growing up in the culture that my dad provided to me. But I saw it with people on the team and ultimately, we actually did a program with McKinsey where they did a survey of women in the workplace. It’s the largest survey of its kind, and they found that women managers were spending significantly more time with their teams outside of the work hours to make sure that people felt good about what was taking place where they were.

The biggest disruption that’s taken place from the work-from-home scenario is in the past, people were able to put themselves in roles where either they were given direction of what work to do, or they were in a role that they were able to create their own direction. All of these people now need direction, but they also need support. Ultimately, the only real answer that I’ve been able to come back with is that additional time, you cannot replace time spent with your people with anything. There’s no technology, there’s no magic wand that can replace spending time with people.

Whether it’s on the phone, in person, getting coffee, on Zoom or in an office, you cannot replace actually spending time with somebody, listening and communicating with them and making them feel heard. People want to feel heard, actually be heard, contribute their thoughts and have people understand them, hear them, appreciate them. Those things are more important than they previously were, because we naturally got them through our interactions. Those interactions were taken away from us, that caused the fatigue, that caused this increase in mental health challenges, because the brain didn’t know how to fill that void that was taken from their lives and ultimately, filled it with negative instead of positive.

Fred Diamond: Before we ask you both for your final action step as we typically end our webcasts, Billy, I have one more question for you. We talked about being of service to customers and those kinds of things. What are customers expecting from sales professionals right now? One of the interesting things is we talk a lot about empathy and stuff like that, but everyone’s dealing with stuff. Here we are, in November we’re going to be going back, it’s going to be darker and daylight saving’s time just started. We’re going to be in the middle of winter and it’s going to be tougher because people are going to feel more alone if they’re still living in their apartments by themselves, that was a huge challenge last year. But from a customer perspective, tell the thousands of sales professionals listening to today’s Sales Game Changers podcast. What do you think customers are expecting from sales professionals right now?

Billy Biggs: From my perspective, Jeffrey talked about selling on value. I think value is somewhat subjective at times, so you’ve got to be careful there, but for me, it’s all about business outcomes or organizational outcomes. If you can tie your product and/or service to successful business outcomes and get the buyer to understand that’s how you’re helping solve the problem, I think you’re way ahead versus selling on feature, function or just a widget, for example.

Fred Diamond: Jeffrey and Billy, I want to thank you both for the great insights today. I want to acknowledge you both for the leadership that you provided not just to your customers but to your team and to your organizations as well. As we like to do, give us one final action step. You’ve given us 20, 30 ideas a piece. Give us one final action step for the sales reps to take their sales career to the next level.

Jeffrey Wolinsky: The journey continues. I think for new sellers, we were talking about people who’ve joined the Institute for Excellence in Sales, people think that they can do something and then be there, they can have arrived and be successful, be a senior salesperson or a sales leader. The journey always continues as things change, what has been made very available to everybody is that embracing change, adapting to change and actually changing to get better is a big part of being a successful salesperson. Stay on a journey for making yourself more valuable to both your organization and your customers’ organization, and you’ll be well served.

Fred Diamond: That is a great point. I was on the road today and I was listening to WTOP and there were a lot of companies trying to get their message out, so there are still plenty of services to provide to customers. Billy Biggs, why don’t you give us the final word?

Billy Biggs: I would say figure out the top 10 challenges that each one of your prospects have and how you can provide value. I don’t think sales reps do this enough, they sell the product and/or service. Figure out the top 10. For me, the top 10 IT transformational projects at each agency level, that’s what I want my AEs focused on and how we can provide value.

Fred Diamond: That’s a brilliant point, it comes up all the time. It’s so obvious, but it’s not. Get to understand your customer, get to understand all the challenges that they’re doing and what value they’re looking to provide so they can continue with their business and solve the challenges that we’re solving. I want to thank Billy Biggs and Jeffrey Wolinsky for being on today’s Sales Game Changers Live. My name is Fred Diamond, thank you all for listening.

Transcribed by Mariana Badillo

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