Several years ago, I interviewed Wayne Gomes, co-founder of Grapevine6, in an interview originally published in Thrive Global. Grapevine6 was by Seismic Software and was the second technology company that Wayno built and exited. Here is an excerpt from our conversation:

Adam: How did you get here?

Wayne: I’m an engineer turned sales guy. When I started my first company with friends from engineering school, we were all highly skilled engineers (we’d graduated from Canada’s best engineering school), but we seriously sucked at selling! And we hated the concept of selling!  So we drew straws and that’s how I became the sales guy. Fast forward 7 years and we figured it out! We sold a ton of product and services and eventually got acquired. A few years later we got the band back together and are out there again putting it all on the line, selling enterprise software.

Adam: What is the single biggest sales mistake you have ever made and what did you learn from it?

Wayne: The single biggest mistake I (and probably most salespeople) have made is not listening closely enough. It was 2002 and I was working on my very first 7 figure deal. The prospect (and our champion) was signaling that there was an executive who was politicizing the deal, but she could not outright tell me that was happening. I missed her cue and all hints, and we lost the deal to internal politics. I think we could have saved it if I’d recognized the issue and directly engaged that new executive. My big takeaway was to listen intently to your buyers – This will enable you to do two things:  to understand where they’re coming from, i.e. what their challenges are, and most importantly to build trust.

Adam: In your experience, what are the key pitfalls to succeeding in sales and how can you overcome them?

Wayne: There are several key pitfalls. The biggest one is not listening closely enough to the buyer. Sales to me is the art of REALLY listening to the person with whom you are engaging and most importantly, building trust.  You must listen not just to what they’re saying, but to what they’re not saying. Understanding what they’re signaling will tell you quickly whether it’s time to double down on this effort, or to pass and move on to a buyer who’s serious. The best sales folks know when to give up vs when to stand in. The pitfall most of us, even experienced sales folks run into, is making the wrong call on that go/no-go decision.

Adam: What are your three best tips on the topic of selling?

Wayne: Pay attention to the small details. Hear what is said and not said by your buyer. Watch their behavior before a meeting, in a meeting, and after a meeting. Pay attention to the brevity or detail of their responses to follow-ups. Understand their personalities, their internal politics or challenges and watch their responsiveness to your communications will do a lot to validate buyers as well as disqualify them. These are all really important signals to pay attention to in determining whether you keep working on an opportunity or not.

Adam: What is sales methodology?

Wayne: I’m exclusively focused on enterprise software sales in a regulated industry where we are selling fairly complex software to a sophisticated buyer. Within each buyer account, there are different roles. Marketing vs sales vs legal and regulatory all have different issues at stake and how we engage each role must be customized to their role.  To succeed we need to adapt not just our style, but the subject matter. That means we really have to know our stuff with respect to the software, limitations, regulatory impact on how the software can/cannot be used, etc. It is a highly consultative sale because of the complexity. I seek out buyers who are looking for that. In all likelihood, buyers who are not pursuing that approach are probably not serious buyers because it would be near impossible to implement our software without a consultative approach.

Adam: What sets your approach apart from others in your industry?

Wayne: We focus very much on the product and we let the product do a lot of the speaking for itself. The skill in the sales part of it is understanding which stakeholders you have in play and what their agenda is. Once we know that, we focus attention on the aspect of the product that they really need to see and then we get out of the way and let the product communicate its value. In short, we trust our product to do the selling. We just make sure the context, audience, and expectations are carefully set before we let the product run. For most buyers seeing enterprise software actually running and doing incredible things, in their own hands, empowers those buyers during the actual sales process. Having this personal experience with our product is extremely powerful in demonstrating value and building trust.

Adam: What do you believe is the hardest step in the sales process and how can it best be navigated?

Wayne: The greatest challenges happen at the beginning of the sales process, i.e. getting the attention of the buyer at the start. It’s tough to get buyers to care about your product so you have to work hard at that and be persistent. Listen carefully to the conversations and rejections. Once you have their attention, then know your time is limited and prove quickly why they should keep talking with you. The two toughest things: 1) Winning buyer attention in the early phase and 2) Keeping it long enough to talk turkey about the pros/cons of your better mouse trap.

Adam: What are your best tips for improving your close rate?

Wayne: Know whether your buyer wants to be closed on, which means REALLY listening. I only try to close on buyers I know are actually want to purchase. I believe most failed attempts at closing a deal are with buyers who were never that serious about buying in the first place. And for a lot of sellers, the signals were there all the way along. I know long before we get to that point whether a buyer is in fact going to buy because I have listened, done my homework, spoken with all the stakeholders. I have a champion in the account and I have had lots of conversations leading up to it.

Adam: What is your best advice around making the ask?

Wayne: If you’ve done it correctly and engaged all the right people along the way if you have that champion on the account side that is advocating for you, the ask won’t be “the ask.” It will be a formality. If you get to a point where the “ask” has a lot uncertainty in it, then for an enterprise sale at least, you did not navigate the sale properly to begin with and you need to take a look at your sales process. Luck is always a good thing to have, but most of the time luck has little to do with it. Enterprise sales is old fashioned hard work and if you fail to prepare then prepare to fail.

Adam: What key words or phrases have helped or hurt your chances of success?

Wayne: I could not agree more. Because I work in tech I feel the constant supply of buzzwords is ever-present and personally I like to avoid them because buyers are hearing them ad-nauseam from vendors. I like to find an analogy in the physical world for everything I can. And I find that becomes a powerful way to simplify things for buyers. It’s hard to imagine electrons moving around circuits in a computer system, but it’s much easier to picture water flowing through pipes, so I’ll often use plumbing metaphors to explain what’s happening and I think those metaphors help tremendously. Physical metaphors are an especially potent way of communicating in high-tech.

Adam: On a scale of 1-10, how important are ethics to succeeding in sales?

Wayne: 12! It’s completely paramount. Without ethics, you cannot build trust. And trust is what the seller/buyer relationship is built on. If you ever show poor ethics you give the buyer the impression you cannot be trusted and at that point the buying process collapses. When you establish trust… buyers come back because they trust you.  When trust is established the buying timeline is also drastically reduced.

Adam: What is your best advice on how to best manage and stay on top of leads?

Wayne: I think the key is to manage leads to the signals. Listen carefully to who is showing the best intent signals. There are great sales tools out there that can help with documenting and prioritizing the leads (CRM, social, etc) and then focus on the 5-10 that are most likely for that fiscal period. In the enterprise space that’s as many as a sales rep can reasonably handle and master.

Adam: What is the single best piece of sales advice you have ever received?

Wayne: Pay attention. Don’t give up too easily. But know when to move on.

Adam: What sale are you proudest of? Walk through how you made it happen and its significance.

Wayne: We lost a deal during the initial phase of an RFP. We got an email thanking us for our response and that we were eliminated. I asked for a feedback session with the stakeholders and walking into that feedback session I prepared deeply to understand every aspect of our proposal, product and what aspect about it missed the mark. As we went through, it became obvious that they did not really understand our product and it became an opportunity for me to impart advice on their thinking and requirements. We ran out of time and they booked another call to continue the conversation. We continued this conversation for months and gradually we got back into the process and won it. It was a 3M deal and we came back from a quick defeat to win it on a 9-month come-back win. That was pure sales 101 of understanding the buyer cycle, listening carefully, and not giving up.

Adam: What is one thing everyone can do tomorrow to become better at selling?

Wayne: I think so much of selling is just being authentic and honest. Listening is how you demonstrate that authenticity and honesty. There are 7 billion people on this planet and we all have one thing in common. We all just want to be happy. So when you are trying to sell to someone just remember that. They’re human, they too want to be happy and if you want to connect and build trust, you just need to listen to and understand them. Be honest, be authentic, be yourself – that’s what drives consistent and measurable sales success both today and predictably in the future.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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