EPISODE 446: Premier Sales Leaders Russ Walker and Pete Mattimore from Datasite and SAP NS2 Offer Very Specific Actions for Sales Success

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[EDITOR’S NOTE: This is a replay of the Sales Game Changers virtual learning session sponsored by the Institute for Excellence in Sales on December 14, 2021. It featured an interview with Datasite Sales Enablement Leader Russ Walker and SAP NS2 Sales Leader Pete Mattimore]

Russ and Pete are IES Premier Sales Leaders. Learn more here.

Find Russ on LinkedIn. Find Pete on LinkedIn.

RUSS’ TIP: “I think we always forget to do this. Ask for a referral in every sales call. If you get a no on the phone, ask if they know somebody you should talk to. If you’re in a sales meeting, ask who else they know in that industry or that market. Ask for referrals, it goes a long way to building your pipeline.”

PETE’S TIP: “Get out of your own way. 2018 is over, there’s a new normal, get on with it. Embrace the change, pick up your game or be left behind. You’ve got to get going.”


Fred Diamond: We have Russ Walker with Datasite and Pete Mattimore with SAP NS2. Gentlemen, thanks for being here. Congratulations on being recognized as an Institute for Excellence in Sales Premier Sales Leader. We launched this designation November of 2021, so congratulations, you’re one of 13 inaugural IES Premier Sales Leaders. Let’s get right into it. Tell us a little bit of what you do. Pete, why don’t you go first? Tell us how things are going for the SAP NS2 salesforce right now?

Pete Mattimore: Fred, first of all, thanks for having me on the webinar. I appreciate being here and thanks for the award. It’s two weeks before the end of the quarter, so like anyone in sales, we are all full of anxiety [laughs] and trying to bring the final deals across the line as our profession dictates. A lot of work to do for all of us in sales over the next two weeks, especially confronting the issues with the great holiday season that we’ll all go through. It’s a lot of work for all of us in this business.

Fred Diamond: Tell us a little bit about SAP NS2, what do you guys do?

Pete Mattimore: I manage the SAP Secure Cloud business for the company. We wrap security around the SAP application set as well as third-party products, and harden the application and keep the bad guys out for our customers.

Fred Diamond: We’ve also got Russ Walker with Datasite. We’ve had some people from Datasite on the Sales Game Changers podcast before, we’ve had your great sales leader, Todd Albright on a couple of times. We’ve had some of your fantastic Women in Sales leaders, we’ve had Nertila, we’ve had Rosie and we’re very excited to have you here. Datasite is an IES Premier Sales Employer as well, that is our great-places-to-work-for-sales-organizations designation and you’re one of our first Premier Sales Leaders, so it’s great to see you, it’s great to have you here. Same thing, tell us a little bit about what you do, a little bit about what Datasite does. How are things going for the sales organization right now?

Russ Walker: Fred, it’s an honor to be here, thanks for having me. Also, great to join Pete. Like SAP, Datasite is very much into security. We provide a secure M&A lifecycle platform to dealmakers around the world. Think about things like mergers, acquisitions, divestiture specs, fundraises and IPOs. We are at the epicenter of those deals with investment bankers, private equity, corporations, legal entities. My job is heading up the global sales ops and sales enablement function as well as inside sales in support of roughly 300 people within our global sales organization. Right now markets are hot, our sales organization is running fast and furious to take advantage of every deal out there in the market.

Fred Diamond: Russ, you mentioned sales enablement. Tell us what sales enablement means.

Russ Walker: If you ask 10 people, you’ll probably get 12 definitions, Fred. The short answer is we help enable and equip the sales team with process tools, training, techniques, anything we can do to help make their job more efficient and effective, help them close more deals, generate more pipeline, increase their knowledgebase of what they sell and who they’re selling to, and also to be able to have those focused customer conversations.

Fred Diamond: Pete, you guys also have a really good sales enablement leader, Joe Celentano, who’s one of our contacts at the IES. Let’s get down to some of these things right here. You mentioned end of the year, so priority-wise, what are some of the things that you are specifically focused on right now? Again, you have to end the year but you’ve also got to start the year as well.

Pete Mattimore: In my role, obviously you have to think about both. We need our sales team focused on the task at hand over the next few weeks, but I certainly need to move into next year and think about how we’re going to set the team up for success. It’s like anything else, you’ve got to juggle a lot of balls in a position like this. Keep the team focused, the most important thing is closing the business down and I’m focused on next year growing the team, the security business, as Russ knows.

The tailwinds that we’re experiencing with the security value proposition, there’s a lot going on in this topic. Customers around the world are very concerned about this issue. Cybersecurity is top of mind, so making sure somebody that Joe in our organization enables our team, understands how security changes literally every month, and that value proposition changes as the goal posts move on what the bad actors are doing. You’ve got to keep up with the bad actors. You’ve got to make sure your team’s enabled and ready to address those questions from the customer.

Fred Diamond: Russ, you mentioned if you asked 10 people what sales enablement means, you’ll get 12 different answers. You also have people on your sales leadership team who are helping you determine your priorities and your focus as well, what are some of the main things that they’re expecting out of sales enablement? We’ve had some guests, Roderick Jefferson, who wrote Sales Enablement 3.0 was on the show a while back. I actually was one of the founders, believe it or not, of the Sales Enablement Society a number of years ago with Scott Santucci and Bill Ball and all those people. Tell us a little bit about what sales leadership is asking of you and expecting your team to be doing right now.

Russ Walker: First and foremost, it’s all about the culture. The big thing right now is attracting, retaining and developing talent, so it’s what can we do to help create that culture of excellence, that culture of motivation, inspiration and reward. An example was we just came off our first event in two years at our Accelerator Clubs. We had about 160 people in the Bahamas this past October and it was just galvanizing how thirsty people were to get together, collaborate, network and celebrate success. It’s continuing that trend, continuing that spirit.

The other big thing is we’ve hired over 100 people into our sales organization this year in different types of roles, so enabling, training and getting them ramped up and ready to be productive in market to generate revenue to have conversations with customers, that’s the biggest value I think we’re providing right now. To Pete’s point, we’re also getting ready to plan for next fiscal year which for us starts in February, so all the target setting, quota, compensation, all that fun stuff and operational planning is in flight right now.

Fred Diamond: We’ve been coming through the pandemic, hopefully we’re going to be past most of this in the very near future. You guys have been recognized as Premier Sales Leaders, it’s from the Institute for Excellence in Sales. Pete, we use the word elite a lot. What are elite sales professionals doing right now and sales leaders? What are elite sales leaders doing right now as well to maintain that level of excellence?

Pete Mattimore: It’s been a challenge over the last two years, we went from a world of being able to make direct sales calls to living with Zoom, and there’s no question this has been challenging. Not only for us as sales leaders to make sure we’re hitting our revenue targets, that’s what we do, but also the salesperson in the foxhole who’s got to figure out, how do I contact the customers? How do I establish rapport with the customer to advance the sales cycle? This is not easy at all.

I think what’s happening is it hastened a lot of things that were already in play. As we started in our sales careers, inside sales was very small. Marketing enablement and marketing touches to customers was a very small part of the business, and it was the enterprise salesperson that did the heavy lifting. But as the last 10 years unfolded, you found the emergence of inside sales, you found the emergence of target marketing organizations touching a customer. These things were already in play.

As the pandemic hit, you quickly found, you need a strong digital marketing team. You need a strong inside sales team. The enterprise salesperson also had to change their game from going to be a strong relationship advocate to all of a sudden really harnessing The Challenger Sales approach which is you’ve got to ask interesting in-depth questions to the customer to get them interested in what you’re doing over Zoom. That’s not easy to do for a lot of sales professionals, to make that change that fast in the environment that we’re in. It’s been challenging, but on balance I think pretty successful, honestly. The people that were able to engage the change and cross the chasm to that customer conversation that was more Challenger-based had really succeeded. Those that struggled with that really struggled, I’ll say.

Fred Diamond: It’s interesting you bring up The Challenger Sale. The Challenger Sale just came up with its 10th anniversary and one thing that we talk a lot about was the fact that everybody was challenged the last two years. We talk a lot about us and our sales organizations and the guests we have on the Sales Game Changers podcast, but even more importantly is the fact that your customer’s been challenged and not only is your customer challenged, your customer’s customer has been challenged. It’s not just about hey, customer, here’s some things I think we could do for you to help you. The customer’s trying to figure out how they can help their customer if they’re savvy, and it’s been a huge challenge.

Russ, how about you guys? Again, you service certain marketplace, you were very successful, you still are a hugely successful company. You did the rebrand a couple years ago when we first met Todd, I remember you came up with the new name and everything from – was Meridian the original name of the company?

Russ Walker: Merrill Corporation.

Fred Diamond: How about you guys? What are elite sales leaders doing right now in your space? We’ve met some of your people in Europe and as a matter of fact, one of your guys was nominated for our Rising Sales Star Award, Desmond in Singapore. Talk about some of those challenges and how elite sales professionals are being successful.

Russ Walker: We’re fortunate we’re surrounded by a lot of great talent in leadership at Datasite, whether it’s sales, service, product and all across the spectrum. If you look at our leadership team, Fred, 90% or greater actually came within the sales rank. They were all promoted up versus hiring from outside because it’s really a nuance to understand our business, our value prop.

You mentioned the customer’s customer and even the customer’s customer’s customer. I think in this world of selling virtually you can’t really rely on that in-person relationship as much, you can’t do as many of the dinners, as much of the networking. It’s really about what kind of value you can bring to the client and how can you build trust. Our sellers, our sales leaders really pride themselves on knowing our platform, being a master at their craft and really understanding what they can do to bring value to the client that they can actually utilize in their day-to-day business. And help get their M&A transactions done more securely, more efficiently, and help them drive better valuations and processes as they go into market for all these different transactions. I think it’s all about what we can do to build trust and credibility with our clients is really at the epicenter of it.

Fred Diamond: A lot of this happens with the conversations that you’re having. Most of these conversations are still in Zoom, I know you mentioned, Russ, that a lot of your people just got together recently internally but a lot of customers are still not back. Of course, there’s a new variant, the Omicron that is getting some press and people are still a little bit hesitant to have people come back to the office and meet. But they still need to grow, they still need to have the value that the sales professionals can bring. Russ, why don’t you go first? Pete, I’m really interested in your answer as well because of the type of customer that you deal with. Obviously, we’re not going to ask you for any confidential conversations with what you sell but talk a little bit about how the conversations are now going with your customers. And Pete, same questions.

Russ Walker: Our customers know who we are and know all companies before you walk in the door. All the information out there is public, they do their research ahead of time so they don’t want to hear the company pitch. They want to hear what you’re going to do to help bring value to their day, whether it’s through using artificial intelligence or machine learning to drive better analytics and predictive insights into how they can facilitate their M&A transactions. It’s what can you do to help make them feel comfortable around security and information protection.

Being a global company that’s obviously paramount with things like CAA in California, GDPR, all the different global requirements around security and compliance. It’s all about trust, comfort level and brand awareness, the more that you can talk about the stories with your other clients, if you could come in and say, “I helped company X in this industry similar to yours to solve this kind of problem, here’s what we could potentially do for you,” it’s the old adage of two ears, one mouth. Do a lot of listening and let the customer do most of the talking and then see how you can translate that back into how you can help solve some problems.

Fred Diamond: Pete, you guys are dealing with something very serious as well, security, and it’s such a huge challenge for the customers that you’re dealing with. Talk a little bit about how your conversations are going with your customers right now. What are they expecting from your salespeople when they do have that engagement?

Pete Mattimore: I’ll answer this a little differently in that I think that for the sales professional out there, especially those focused on net new, that’s been the biggest challenge. I think selling back into your current customer base has been a little easier over Zoom because of a lot of the cycle slow-down in terms of new acquisitions. But on the net new side, you’re starting to see the customer base now transition a little bit to saying, this is the new normal and we have to move forward with what we had planned in 2018. For those net new sales professionals that have to go out there and generate a new opportunity and a new cycle and new revenue to the company, that’s where this has been the biggest challenge, frankly.

Russ mentioned you’ve got to master your craft, absolutely, 1,000%. It’s back to Challenger Sale. You really have to know in depth what you’re talking about and you’ve got to carry the load to the company in that first conversation so you can bring in the rest of the ecosystem to help you sell. The salesperson flanked by the right ecosystem, as we all know in this business, that helps you get across the chasm and to a successful transaction. But that first conversation is so critical, so again, mastering your craft, really knowing your topic to make sure the customer is comfortable leading you to the next meeting. That’s the name of the game. It’s been a big transition for a lot of folks in the sales profession, but as time’s gone by, this is the new normal. You’ve got to get with it, get at it or you’re going to be left behind.

Fred Diamond: We have a follow-up question here that comes from Jared, “What do sales professionals need to be really good at moving forward?” That’s an interesting question, and Pete, you just talked about new normal. For someone to be successful in the next two, three years as a sales professional, what are some of the things that the pandemic has changed or the pandemic has made apparent that these sales professionals need to really be good at to be successful? Not just for themselves, but for their companies moving forward for the next two, three years.

Pete Mattimore: Strong online presence is critical. Harnessing social platforms. If people weren’t doing it already, they’d better have learned it over the last two years. A strong way to get into the customer, marketing can help but the sales professional has to also brand him or herself in their topic, figure out a way to get to that customer over LinkedIn, as an example. That kind of stuff is critical. If you’re not doing that, if you don’t have that presence, you’re going to be left behind.

With all that said, at the end of the day Einstein said it beautifully. 90% of life is showing up, you’ve got to show up. In sales you’ve got to show up every single day and figure out a way to penetrate new customers and existing customers, and nothing replaces showing up.

Fred Diamond: Russ, how about you? You’re the leader of sales enablement for Datasite, what are some of the things that you guys are really focusing on right now to ensure that your sales professionals are going to be successful in the foreseeable future?

Russ Walker: I mentioned those 100+ people we’ve hired this year, we’ve had to obviously increase our enablement staff to go along with that sales growth. One of the big things we look at is we have a pretty robust and intensive accreditation program. Every new seller that comes on board has to go through this multistep program around demo skills, discovery questioning, how to deliver a great customer meeting, how do you do a virtual demo so that the client on the other end of the Zoom or Teams call isn’t multitasking? You don’t have the ebbs and flows, you want to keep them engaged as much as you can. Teaching them those types of skills and frankly, Pete mentioned this, it’s around activity.

Sales is an activity game. You’ve got to make sure you’re touching as many customers that fit your ideal customer profile as possible to really optimize your pipeline to support the necessary win rates and number of deals that you need to have to close, meet and exceed your targets. I think it’s knowledge, it’s mastering your craft, it’s being cognizant of the customer and it’s also making sure that you’re generating enough activity to support your success.

Fred Diamond: Let’s talk about what sales reps might be doing wrong. Again, you guys work with a lot of sales professionals, you’ve been around for a long time. What are some things that you see sales pros, maybe junior, maybe more senior, what are they doing wrong? One answer that came up a couple weeks ago is that a lot of people are still thinking the mentality prior to the pandemic. It’s like, if I can’t get inside, I’m not going to be successful. You’re probably not going to be meeting with many people at least for the next six months, it’s still going to be a slow roll as people send their people back to the office and as people object to certain mask requirements or vaccine requirements. There’s not going to be as much in-person stuff, we don’t think. Curiously, Russ, what do you see sales reps doing wrong? Then Pete, I’m curious on your thoughts as well.

Russ Walker: My answer is going to be a high-class problem. Fred, we’ve had so much activity and growth this year that sometimes that can create a seller running so fast, they may forget some of the fundamentals because they’re trying to get deals closed, they’re handling the administrative aspect of their job. I think prepping for calls, prepping for demos, prepping with your sales engineers. Role playing with your manager before a big meeting, that’s the one thing I think we could do better and more of, just because again, they’re running so fast they may shortcut some of those things. But you can’t really have a successful model if you don’t do those things and you just show up last-minute, not as optimally ready to go as you can be.

Fred Diamond: That’s a great point. One of the things we’ve learned over the last two years as things have changed a lot from week to week, sometimes from day to day, if you’re a sales professional – and by the way, if you’re listening to this show sometime in the future, kudos to you for giving yourself a half an hour to listen to two Premier Sales Leaders, you’re taking some time to take your sales career to the next level to learn from two of the top. Pete, what are some of your thoughts on what you’re seeing sales professionals do wrong?

Pete Mattimore: I agree with Russ. As I think through this, ecosystem building. It takes a village for a salesperson to be successful, we all know this. Without being able to meet live, I see some salespeople not getting to know the ecosystem that can help them win. That’s a big mess, and I’m not saying it’s easy to do remotely, but they’ve got to put the time in because you need people in contracts, you need people in value engineering, you need people in application engineering, you need a village to help you be successful as the sales cycle goes along. We’re a demanding bunch, I don’t know if people know that about us sales professionals but we’re a demanding bunch so you’ve got to build an ecosystem. You’ve got to build people that can help you win and the pandemic’s been very tough on salespeople getting to know people inside of their own company who can help them be successful. That has been my advice. Double down on doing your best to get to know the people inside the company that can help you win.

Fred Diamond: That’s a great point. At the Institute for Excellence in Sales we were known for doing a lot of live programs in the Washington DC area. We took 18 months off because of the pandemic and we started doing live programs again in November of 2021. It was interesting, people were meeting people at their company for the first time in public. They were hired after the pandemic started and they didn’t know each other. They knew each other in the shape of a rectangle, from the torso up, so great point, man. Getting to know the people and getting to understand them.

Let’s go back to customers for a second here. What are customers expecting from you? They’re expecting that you’re going to offer them something that hopefully will help them, but what really are they looking for from you? We always hear value add, Pete, you alluded to The Challenger Sale. One of the data points that came out of Challenger was that the customer is 57% already into their decision-making process before they even ask you for things. If you’re already an established vendor, that number probably isn’t as far to the right as they said but it doesn’t really matter. What are customers specifically expecting from sales professionals right now? Pete, why don’t you go first? Then Russ, I’m really curious on your answer as well.

Pete Mattimore: In the use case that we penetrate, it’s security. Customers are engaging with us because they’re very concerned about the bad actors around the world and what they’re trying to do to the enterprise environments that run the world now. What they’re looking for us is they want to see a level of safety that we bring the customer set, they want certifications and they want to understand that your company can stand behind the ability to fort the bad actors. Our sales professionals need to make sure that we are branding the company appropriately and that very important use case.

Fred Diamond: Russ, how about you? What are the expectations?

Russ Walker: Fred, you mentioned the word value. I know that’s overused but when I was a quota-carrying rep, I once had a client tell me, “Russ, price is only an issue in the absence of value.” I’ve taken that to heart throughout my entire sales career, I think two words I’d use for what customers care about, it’s trust and relevance. They need to be able to trust you, your company, your platform, your security, your service model, that your product’s going to work and they need to make sure that you’re relevant.

Right now, in our world, investment bankers don’t have a lot of time. They’re not going to do drinks, they’re not going to do lunches or happy hours, they’re just embedded in deals all day long so you’ve got to be relevant. You can’t show up with a sales pitch, you can’t just show up and have nothing to say, you’ve got to bring something to the table that’s going to help them that they care about, that’s going to make their life better and easier because they’re running fast and hard. They’re all dealing with this pandemic and you’ve got to give them something that they can grasp and sink their teeth into that gives them value every day.

Fred Diamond: Relevance is a critical word. As a matter of fact, the theme of the first six live in-person IES programs in 2022 is relevance. A lot of people have connected. Russ, you and I have connected a number of times, there’s been a lot of empathy, a lot of staying in touch, a lot of making sure you guys are okay. Now it’s back to we really need to help you get past this and achieve your goals. Before I ask you for your final action step, we do have one more question here that comes in from Jonah, “What is it about sales that motivates Pete and Russ?” I haven’t asked this question in a while, tell us that. You guys are recognized as IES Premier Sales Leaders, we announced that in November. 13 initial sales leaders have gotten that designation. Pete, first question for you is what motivates you about sales? What gets you up every day that you have this passion? What is it about sales that really gets you excited to have reached this level, Premier Sales Leader?

Pete Mattimore: It’s a great question, because oftentimes I’m mentoring and talking to younger folks who are trying to make a decision, whether or not they want to get in sales. Should I get into marketing or should I get into sales? I feel a little more comfortable in marketing than sales because let’s just face it, the pressure associated with this profession. It’s a tough question to answer. I think you can teach someone to be a good salesperson, but I think a lot of it is you have the personality set that loves it. It’s a competition. Those that are very successful in sales, there’s a thread that they enjoy the combat and the competition and winning. I think great salespeople love to win that benchmark. It’s bigger than the commission it’s all that stuff that gets tagged with salespeople. It’s the winning that people love in sales. If you like to compete and you like to win, I tell a young person, get into sales. If you love that, you’ll be successful at it.

Fred Diamond: Russ, how about you? Jonah’s question, what is it about sales that gets you up in the morning, that gets you juiced? You guys have a very exciting sales-driven culture. What is it for you?

Russ Walker: It’s the one profession that’s never boring for me. Fred, if I put my leadership hat on, it would be seeing my entire team hit their intrinsic or extrinsic goals. Whether that’s money motivated, whether that’s achieving the incentive Accelerator Club trip, whether that’s being able to put their kids through college, buy a new house, get promoted to sales leadership. Whatever those things are, if my teams can achieve and exceed their goals, that makes me happy and gives me that fulfillment.

Fred Diamond: Russ and Pete, I want to acknowledge you both again. Inaugural IES Premier Sales Leaders nominated by your companies for that. Congratulations on the recognition. We’ve gotten so many great responses when we announced the initial 13 PSLs so we feel good about everyone who’s been designated. I hope you feel good about it as well. Give us a final action step for people watching today or listening sometime in the future, for the thousands of sales professionals who are either listening or reading the transcript. Give us one more specific action step for them to ensure their continued success. Russ, why don’t you go first?

Russ Walker: I’ll make mine simple. I think we always forget to do this. Ask for a referral in every sales call. If you get a no on the phone, ask if they know somebody you should talk to. If you’re in a sales meeting, ask who else they know in that industry or that market. Ask for referrals, it goes a long way to building your pipeline.

Fred Diamond: Pete Mattimore, bring us home. Give us one specific action step for the sales professionals listening or watching today to take their sales career to the next level.

Pete Mattimore: Get out of your own way. 2018 is over, there’s a new normal, get on with it. Embrace the change, pick up your game or be left behind. You’ve got to get going.

Transcribed by Mariana Badillo

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