Dive Deep Into Win-Loss Analysis on September 14-16

Sales Tips From Two B2B Enterprise Sales Legends

Clozd Team

B2B sales can be a tough but extremely rewarding career. You are under constant pressure to hit your sales quota, and there are a lot of factors outside your control that influence whether or not you win a deal. In enterprise sales, those challenges can become that much more intricate. To help with that, we wanted to provide you with some sales tips, techniques, and advice from two incredibly successful B2B sales leaders—Jim Steele and John D’Agostino. We had one of our founders, Spencer Dent, ask them about lessons they’ve learned from winning in sales. Here is what we learned. 

First, just so you know whether or not you should listen to their advice, let’s start with an intro:

Jim Steele

Over the past 35 years, Jim has served in executive leadership and senior sales roles within the enterprise applications, revenue solutions, and data management sectors. As President of Global Strategic Customers at Salesforce, Jim’s primary focus is bringing the full power of Salesforce to its largest and most strategic customers.

Prior to rejoining Salesforce, Jim served as Chief Revenue Officer and President at Yext and President and Chief Revenue Officer at InsideSales.com. Before those, Jim served at Salesforce for 12 years as Chief Customer Officer and President of Worldwide Sales and Operations where he helped grow the company from $25 million to more than $5 billion in revenue.

John D’Agostino

John brings more than 30 years of experience in B2B sales. In his most recent position as the Executive Vice President of Global Sales at Qualtrics, he led sales growth from $42 million ARR to $550 million ARR. He scaled the sales team from 50 to 1,000 sales people in a five year period and helped take the company from a $350 million valuation to an $8 billion acquisition by SAP.

Before Qualtrics, John led the America’s division of the legendary Parametrics Technology Corporation (PTC) for 17 years, running a 375-person enterprise organization. John was also a sales leader at Pitney Bowes for six years, and is widely recognized as an expert in go-to-market and scaling global operations for B2B companies.

Here are some of the best lessons and highlights from these two sales legends.

Put The Customer First

Literally, the first piece of advice Jim gave is to have a maniacal focus on your customer. When you view things from your customer’s perspective everything comes naturally. He talks about using a framework he calls LVI, that he coaches his sales teams to do. LVI stands for listen, validate, and inspire. First, you need to listen to your customer and really understand their challenges. Second, validate. Play back the things you learned in the listening step to make sure you understood the customer and to build trust with them. Third, it is time to inspire the customer and show them how you’ve solved similar problems for others with your solution.

“The number one thing I preach to all of my sales teams, over my 43 years in sales, is to have a maniacal focus on the customer.” 


Jim shared a story about when he first started at Salesforce and a lesson he learned about putting the customer first. He was sitting in his office and Marc Benioff, the CEO, walked in. Marc asked, “what are you doing here?” “I’m your new President,” Jim replied, a little confused. Then Marc proceeded to explain to Jim that he didn’t hire him to be an armchair quarterback. He wanted him out with customers, not sitting in the office. Jim found that if you were not grounded in the customer perspective and experience, Marc would dismiss you.


Don’t Sell—Get Customers To Sell For You

People buy from people they like and connect with. If it feels like you are selling, the customer is probably thinking about how to get out of the conversation. Jim proposes to find similar customer success stories and have them share it directly with your prospect, versus you telling the story. He believes this was a major part of Salesforce’s success.


Jim describes an experience he had at the first Dreamforce, Salesforce’s primary event. Marc Benioff, the CEO of Salesforce, pulled an audible at the last minute and completely changed the program. The plan, initially, was to present the product roadmap and talk about all the great things Salesforce was planning on doing. Instead, Marc told everyone that he would give a brief overview of the Salesforce vision and then they would have an open mic session with customers. Jim shared that they received many genuine and impactful customer stories from this approach.


Sales Empathy is Critical

Do not approach sales with an arrogant attitude and do not take the customer for granted. It is great to be passionate and confident, but that is different than being cocky and arrogant. If you have fully understood the customer and can truly place yourself in their shoes, you’ll approach the sales process with passion and excitement instead of nervousness, and that is the difference between winning and losing.

“It is great to be passionate, it is great to be confident. It is really bad to be cocky and arrogant. It’s going to come back and bite you.”


“If you’ve studied the customer … instead of being stressed and nervous you are excited and passionate. The difference between the two is the difference between winning and losing.”



Get People to Root For You

John is a big believer in working in such a way that people begin rooting for you. He thinks there are too many people out there that depend too much on people doing things for them, and a lack of people that focus on making others successful. If you are authentic, and people can tell that you actually care, they’ll want you to succeed. They’ll start rooting for you. The people you rely on to do your job well will go above and beyond to help you succeed––and in return, you’ll become entirely focused on other people and your customer. This can extend beyond internal teams––your customers will want you to succeed as well. John believes a big part of his success in sales, and in his career, was getting his entire ecosystem to root for him. Doing business this way will lead to more won deals and career success. 



Don’t Give Your Power Away

Jim said one of his pet peeves is salespeople “giving away their power.” It drives him crazy when a potential customer begins negotiating with the salesperson and the salesperson responds by saying they will have to ask their manager. Jim relates this to the feeling when you are buying a car and the salesperson says, “let me talk to my manager.” When you hear that, you immediately want to go around that salesperson and talk directly with the manager yourself. Don’t do this. Here is how Jim suggests you handle it:


Be Confident and Willing to Learn and Grow

Sales people, and people in general, need to have a lot more security in themselves. Insecurity is what makes people inauthentic, or afraid to hear the truth. Go above and beyond and get secure in your own skin. Prove that there is nothing that scares you. Don’t be afraid of the truth. If you have the security in yourself to confront the truth about why you might be underperforming, you can do something about it to learn and grow.

“It is very difficult to help someone improve if they are afraid of the truth.” - John D.
“So that’s why I love so much what you guys do at Clozd with respect to what I call “the truth serum”. You’re getting out the information from the customer and it’s the actual truth of what happened. We don't have to wait for the sales team, or the product people to speculate and make up reasons as to why a deal got lost or why something slipped. We have the truth and we can deal with it... If you have the security to engage in that way, you’re going to win more deals over the course of time.” - John D.



Think of The Sales Process as a Journey with the Customer—Not a Transaction

Salespeople are excited about closing the deal, rightfully so, but they can get so focused on winning that transaction that they lose sight of the customer journey. If you try to slam a deal home, the customer is probably going to feel that. This short-term focus can compromise your relationship with the customer. You need to prove to them that you are their partner for the long term.


Be Open to Reinventing Yourself

If you’re not constantly reinventing yourself, you run the risk of becoming a dinosaur. One of the best ways to do this is by embracing change––don’t become too rigid and don’t be afraid to continually challenge yourself. Jim shared an experience where Marc Benioffwas trying to get him to try new things and Jim was hesitant. Marc said, “if you don’t change you get stagnant and die.” From this experience Jim changed from being passive-resistant to enthusiastically embracing change because he knew it would help him learn and grow.



Here is Some Advice if You Are Leading a Sales Team

Motivating Your Team

You bring the best out of people when you are having fun and they are confident in what they are selling. Jim’s advice when you don’t feel good about what you are selling? Move on. Sales is a stressful position to be in. You are always under the gun. You need to strike a balance between having fun and the pressure you are under. If you are not enjoying yourself and feeling good about what you are doing, you are not giving it your best––and people know that on the other side. It will be extremely difficult to get other people excited about what you are selling if you aren’t excited about it. 


John has a simple litmus test for this. He says to ask yourself, Monday morning, are you excited? Or do you just want to roll over and sleep for three more hours? During the greatest times of John’s career he said he couldn’t wait to get going on Monday. If you are feeling stagnant, it may be time to start thinking about what is next.

“We spend too much time in these roles to not have fun doing it.” - John D.



Don’t Neglect the Importance of Recruiting Great Talent

According to John, recruiting is number one, by far, and everything else takes second place when it comes to reaching B2B sales goals in a company. If you are a manager, it is critical to learn how to hire quickly (especially in a company that is growing fast) but not lowering your standards just to meet a hiring quota. As soon as you do that, mistakes get made that can do untold damage to your company and team. 

“If you can’t recruit, and you can’t hold a high bar, and you can’t move fast enough, you are probably not going to do too well.” - John D.



Attributes Jim and John Looked For When Hiring Successful Salespeople

John and Jim listed five attributes they looked for when hiring successful sales people. 

  • The first one is a motor. Salespeople need to have self-drive. It becomes nearly  impossible to constantly push people to work hard. They should already have the drive to do what needs to be done to be successful. 
  • The second attribute is emotional intelligence (or EQ). How well do you connect and communicate with those around you? 
  • Third: intellect. Especially in B2B sales today, your customers can do so much research on their own that you have to know your product––and sometimes know your prospect’s business––better than they do. 
  • Fourth, similar to a motor: grit. You have to have enough fight to not quit and keep going when things get tough. 
  • The last attribute is genuine authenticity. Being consistent,true to yourself, with the ability to connect with people.



Our Win-Loss Analysis Data Aligns with Their Sales Advice

We really enjoyed learning from John and Jim during this session. One of our biggest takeaways was that B2B sales success doesn’t come down to shortcut tricks, tips, or strategies. It is best done with character, customer empathy, passion, and fun. In the large win-loss analysis programs we run for companies, one major influencer on winning or losing a deal is sales empathy. Both the advice from Jim and John and our data show a clear story about how important it is for the salesperson to put the customer first and truly place themselves in their shoes. Learn more about how Clozd can help your sales team start winning more.


Watch Jim and John’s entire session here.

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