$50M Worth of Sales Advice in 10 Minutes

In the last 10 years, I've gone all the way from an SDR to a global VP of sales, generating over $50 million in revenue across the three industry leading companies that I've worked for. Just this year alone, my sales orders will draft tens of millions of dollars of revenue at one of the biggest feature management platforms in the entire industry. I've been fortunate to be the number one AE Sales Manager, Regional Vice President and now Global Vice President, becoming top performer in every role I've taken on. And in this video, I'm going to teach you the five most critical lessons I know about sales. That has me to go from a nobody missing quotas to bringing in millions of revenue across different companies to help you outperform everyone else in your company. Lesson 1 the customer is not always right Two years into my career I was missing my quotas, about to quit my job and completely give up sales. I was constantly stressed out because I couldn't hit my numbers and one of the biggest mistakes I was making was being too agreeable with customers and prospects. I desperately wanted my prospect to like me. I didn't want to make any anyone uncomfortable. I just wanted to map my solution back to what they thought they wanted. That led to nothing but lost deals. So I started pushing back on customers when what they wanted wasn't actually best for them. I knew I was onto something when I had a deal come inbound and they told me everything they thought they wanted. The old me would have just nodded along and built a demo to show them exactly what they had asked to see. But I had learned that yes men don't win deals. So I pushed back. I told them that I understood their desired approach as I had seen it many times. But it wasn't the winning. Then I told them what I thought their approach should be and why. At the end of the call the CMO said, I feel like you understand our industry and our business far better than anyone else we've spoken to. Can we put an NDA in place so on our next call we can get even more specific on our business so we can get your recommendations? They had requested demos from multiple providers. The other providers were happy to show them exactly what they were looking for. I was the only one that pushed back and taught them what they should actually be looking for and why it shouldn't be any surprise that we were the ones that won the six figure deal a few months later. Lesson number Solving problems Don't win deals. Solving the problem does. When I was missing quota, the questions I was asking Were all about small superficial problems that my buyers didn't really care about. That led to conversations my prospects didn't care about. I remember being on a call with an executive at a law firm. I had all my superficial questions planned out. They led to talking about how he spent his time, what he was working on. I was basically trying to get a complete understanding of his day to day so I could then try and figure out if there were any gaps where I could try to fit my products and to make small improvements. Just a few minutes into the conversation, he cut me off and he said, look Kyle, you asked me for this call. Why don't you just tell me what you do? And I kind of stumbled over my a vague pitch. And then the call ended shortly after and obviously the deal went absolutely nowhere. I had to learn that questions about small problems aren't valuable to the prospect. They only care about the answer to one question that they are asking. Does this seller have a solution that helps solve one of my biggest problems? So I had to learn to uncover the biggest problem as fast as possible. Moving forward, I changed my approach to bring a hypothesis of what my prospect cared about most. Then I'd ask them what I got wrong in my assumptions, and they were always very happy to correct me if I was off. Doing this allowed me to quickly understand what is most important to the prospect, Leading to only asking questions about their priority. My prospects became willing to answer my questions because we were talking about what they cared about most. Not superficial issues, not worth solving. And when I could show my solution as something that solved for their priority, My win rates skyrocketed. Lesson number three, it's perfectly okay to say no. When I was failing as a rep, I was afraid to push back, especially on price for my prospects or customers. I felt like any kind of friction would push them away. And I was happy to give them anything they asked for, including massive discounts to keep them happy. I remember working a very small deal. It was around $8,000 and the pirate was pushing me for a significant discount. They pushed me around and promised that if I could get them in the door at around twelve hundred dollars, they would grow, they'd be a great partner. So I pushed for approval with my VP and got them in the door at that $1200 price point, they ended up being a nightma with. They never upgraded. It was a massive waste of time and we made basically no money on the deal. Learning that I can push back changed how I sold. Fast forward a couple of years and I had a procurement leader join a call for a six figure deal that I was working to close. They tried to push me around. They were making all sorts of demands trying to get the price lower. As I heard their pushback, I just said, I understand you're trying to get the most favorable agreement for your team. However, we've done a lot of work to make sure the scope is correct, the value is correct, and your demands aren't reasonable. And then I just shut up. And it was super awkward because it was silent for about 35 seconds, which is a long time, that silence on a zoom call. And then the procurement buyer finally said, I'll only talk to the team. And then the call ended. Two days later the contract came back signed at full price and it was tens of thousands of dollars higher than what he had asked for. From a pricing standpoint, early in my career, I would have met his demands or at least met him halfway and dropped the price just to get the deal done. Pushing back led to earning thousands of dollars more in my commission check. Now, I'm not saying to never consider prospects requests and sometimes there is going to be some give and take in negotiation. However, when you've built leverage by differentiating your value, you've earned the right to hold strong and push back on your prospect at times. Now, if you are finding these tips valuable, I made a free guide talking about how to implement all of these tips specifically in discovery. It's a detailed breakdown that will teach you how to prepare and run discovery calls that will lead to qualified opportunities rather than chasing buyers and you can find the link below. All right, on to tip number four. Only Real Pain Drives Urgency When I was struggling, the only way that I thought I could add urgency was through artificial end of quarter discounts. I started blowing through quota when I learned to uncover urgency that actually matters to the buyer. I remember working with a nonprofit. They had repeatedly told me that they weren't going to be able to buy anything soon because I had to wait until their budget cycle, which was still months away. I was able to uncover some significant pain and tie it back to one of the areas that they needed to excel in to maintain their funding levels. Because that pain was significant, they agreed to see a demo, all while saying they don't have any budget. Thirty minutes after the demo, I got an email from my main contact and he said we need to get our hands on this now. I'll figure out the budget. Budget. The change from no budget to we'll find it was simple. We uncovered a pain. They knew they had and was costing them money that they didn't originally think we could solve for. As soon as they saw we could solve for this massive pain, they were willing to scramble and get off cycle budget approval. Your buyers will only have urgency if there is an agreement that you can solve a significant pain they have today. When you begin the conversation with them, they may not know that you can solve their large pains and they may keep the conversation surface level. You can know that if your deals don't feel urgent, you aren't solving for the right problems yet, because when you find the right problem, there's confidence that you can solve it. Urgency follows right after Finally Tip number five Small Commitments Lead to Big Commitments When I was struggling, I was always afraid to ask for commitments throughout the deal cycle because in my mind I felt like I had to like save up all my requests for one big one at the end. Please buy my stuff. I learned this was really stupid when my prospects would drop out of the sales cycle even before I had the chance to ask for the sale, I began asking for commitments all the time and I even made it easy for them to say no if they weren't willing to be all in on evaluating my solution at the end of discovery, I would say things like based on a conversation today, we might be able to help you solve your negative consequence. We would do this by improving your current state through how we do it better. We'd expect the impact to be improving your priority metric. Is this worth your time to evaluate further at the end of demos? I would say today we walked through our approach to solving your priority. Is what we showed enough of an improvement on your current process to justify spending more time reviewing a business case and a proposal. Throughout my entire deal cycle, I found opportunities to ask the buyer to commit to next steps while giving them an out. The goal was simple. I was looking to communicate that if they weren't excited, that's fine because I've got plenty of people that are. Having that mindset led to prospects consistently buying into my sales process and a much higher win rate. These are tips that have personally helped me scale inside all the companies I've been at throughout the years. They took me years of trials and error to learn and implement. My goal is to help thousands of sellers learn them much faster so your success can come faster and be greater than mine. The faster you put them into practice, the better you'll become at it. To help sellers like you implement best practices as fast as possible, I share my most actionable advice to my email list. To get those tips directly in your inbox. Feel free to join our free newsletter with over 16,000 sellers from around the world with the link in the description.