Several years ago, I interviewed Don Matejkoin an interview originally published in Thrive Global. Don was the Chief Revenue Officer of Showpad at the time of the interview and is currently an executive at UserTesting. Here is an excerpt from our conversation:

Adam: What sale are you proudest of?

Don: In the late 90’s, I managed a sales rep during her very first deal with a huge organization in Lexington, Kentucky. She cold-called the business and secured an initial meeting. The sales cycle lasted nineteen months, and she worked tirelessly to prepare for every question or concern the prospect could potentially throw her way. She was extremely persistent, constantly asking for my feedback and for role-playing opportunities to prepare. It was extremely rewarding to mentor this sales rep and to watch her hone her skills and develop the best sales proposal I had ever seen. Nineteen months later, she secured a major deal with the company, the largest deal our business had ever done at the time. It was truly rewarding to watch a person grow and to feel like you helped that person succeed. No matter if it’s in your personal life or business, that’s what life is all about – sharing your success so others can as benefit.  

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

Don: Early in my career, I assumed that I knew everything about sales. I would talk twice as much as I listened and learned the hard way that you need to really understand your customers through critical listening and attention. The more I thought I knew, the less effective I was, because I overwhelmed customers with too much information before hearing about their needs. It’s not a specific mistake, but I didn’t follow the philosophy of “two ears, one mouth.”

In a way, sales is similar to a doctor-patient relationship. If you go to the doctor for congestion, he or she won’t prescribe you medicine without understanding exactly what your ailment is and if you have any allergies or pre-existing conditions. Without those details, any treatment a physician prescribes is likely useless or potentially even fatal. Now I am not naive to think that sales is a perfect equivalent to the doctor-patient relationship, but the key takeaway here is that just as a physician needs to understand their patient, sellers need to understand their buyers. If a seller can’t point to specific ways that their solution will increase that company’s revenue or decrease its costs, they shouldn’t be prescribing that solution. Once I realized how critical it is to invest time to understand my customers and their specific needs, my results improved exponentially.

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

Don: It’s easy for sellers to cut corners. If you call yourself a “sales professional,” you need to take the “professional” part seriously. Any professional takes a majority of their time to continue improving their current state – learning, listening, and getting advice to grow constantly. It’s vital that you consistently get feedback so you can evolve. Today, I see a sales reps and executives alike fall into a routine and stop the learning and coaching element – and that’s a costly mistake.  

Think of the great white shark – if they stop moving, they die. The same goes for sales reps and executives, if you stop moving, stop pushing yourself, and stop learning, you’ll become stagnant and ineffective. Sellers should consistently seek feedback, adjust current techniques, and not be afraid to do what they need to do to move forward. If they don’t, they will fall behind and ultimately do themselves and their customers a huge disservice.

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

Don: As I mentioned before, always be improving those listening skills. The more you listen, the more information you will capture and the better you will be in targeting the needs of your prospects.  Bottom line, you will earn the trust of your customers by understanding their pains and either increasing their revenues or decreasing their costs.

Understand your product and how it will deliver value to your customers. If you look at modern buyers, they have unprecedented power. Five years ago, sellers held the power, because they held important information. But today, so much of that information is available online, at a buyer’s fingertips. By the time a buyer engages with a seller, they are about 70% of the way down the path of their analysis of your product which is why it’s so important that sellers truly educate themselves and know their solution inside and out. You’re not selling a product anymore, you are selling an experience. From the initial call to the contract close to the ongoing support, you are selling yourself and your company to that buyer. Bottom line, know your business, know your industry, and know how to increase your buyer’s revenues or decrease your buyer’s cost with your service. Keep yourself educated. Clients want to know the specific industry value that will result from their purchase, so it’s imperative that sellers show direct ROI and long-term benefits.

Finally, sellers need to be empathetic with prospects. Before pitching a product or service, sellers should know why clients agreed to your initial sales conversation – what is the success criteria that my service can offer to you as a buyer? Today’s buyers have tons of options Do not waste your buyer’s time, always come prepared and be empathetic in the journey.  

Adam: What is your sales methodology?

Don: At a high level, my methodology has been consistent: understand the budget process, the authority levels, how the buyer wants to buy, and the reasons they are seeking your service. If you look at the market, there are two sales motions that occur most frequently: hunting and farming. Hunters continue to drive the new logo acquisition while farmers work seek to go deep and wide into large, national, or global accounts. Regardless of the sales motion, you need to ensure there is a customer success plan that accompanies either sale.

The hardest part of any customer relationship is maintaining post-sales success. I have said this to nearly every executive I have had the pleasure of working with: as with any relationship, there will be bumps in the road and what matters most is how fast we react and get you back to success. At the end of the day, you’re selling a service and the longer you can drive your buyer’s success, the longer the service is active and develops into a strategic partnership. The great sellers truly spend a vast majority of the selling speaking on not only the buyer’s initial need but the ongoing support to fuel the buyer’s success.

Another important piece of methodology is how to go to market and sell your product – do you verticalize or sell your solution horizontally? It’s a massive undertaking to verticalize a sales approach for every industry because the investment required is huge. The vast majority of software and technology companies try and verticalize – but often fail. And the reason why they struggle is because you need to do more than just veticalize your sales teams. You need to also invest into verticalizing your teams in product engineering, pricing, marketing, support, and knowledge.

I truly believe the solution to attacking a vertical strategy goes back to my first comment: always educate yourself on the buyer. As sellers, we absolutely need to adapt our styles to the different type of customers we sell into pertaining to industry/vertical. It’s really all about building trust – speaking the customer’s language, understanding how their industry is growing, etc. As a seller, having a lack of knowledge will have an impact on the progress of the deal and almost instantly destroy the buyer’s trust. Sellers must understand exactly who they are selling to in order to be successful and tailor their approach every time, across every company, and across every industry.

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

Don: Showpad is a very unique business, which impacts the way we sell to our customers. In essence, our end-to-end platform empowers sales and marketing teams to engage buyers through industry-leading training and coaching software and innovative content and engagement solutions. Our platform uses the most comprehensive set of data on seller behavior and interactions to fuel artificial intelligence that allows our customers to discover, replicate, and automate what’s working for their top performers.

For example, if a seller is meeting a Pharma customer today and a Wealth Management company tomorrow, Showpad provides a seller with the content they need for both interactions and ensures they’re fluent, knowledgeable, and armed to optimize the buyer experience. In some ways, Showpad acts as an “engagement layer” between you and the buyer, helping you optimize the buyer experience and leveraging the investments you’ve made in content systems, marketing automation,n and CRM.

In order to be successful, we have to be fluent in each industry that we sell into. We work with several different industries every day, so we have to demonstrate how our platform is going to fuel the success and needs of every customer. Like I mentioned before, consistency is key, but listening is the critical component that will make every selling and buying experience unique. We optimize and deliver this to our customers.  

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

Don: The hardest part of a sales process is knowing when to close. Many sellers think they know what the customer wants, and they go into instant close mode. But until a seller understands and can articulate exactly how their solution will increase revenue or decrease costs, they have no business closing. They need to ask more questions. Begin the selling journey by listening, ask relevant questions, and be empathetic to the true goals of the buyer.  Closing should be natural and automatic if you do these things right.

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

Don: Most software and technology companies hit a wall with every client at some point during the sales relationship. This usually happens when sellers lose focus on the post-sale process and have done a poor job of defining post-sales success. As I said before, always have a desire to know more. As an example, after a customer becomes a client, find out exactly why they chose your business. Ask questions like: How was your experience with my team during the initial discovery process? Was there a reason you chose my company over the competition? How do we create an ecosystem of support that you can turn to when problems arise? If you want a customer to invest in your business for years to come, these answers are imperative for process improvement and lasting business relationships. Not to mention it’s a necessary step to reach the holy grail of turning your customers into your advocates – referenceability!

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

Don: It’s about the balance of give and get. Often times I see the seller give without getting anything in return. If my buyer asks me for something, I want to get something in return. It could be access to someone within his/her team, a follow-up meeting, etc. The buyer and the seller are building a relationship and the strongest relationships are never one-sided. If done properly, the closing process will be much easier to approach.

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

Don: If your sellers are talking about “products,” they will lose. But on the flip side, if they’re talking about a service and a relationship, they are much more likely to win the sale and gain trust for the long term. Prospects don’t care about the product as much as they care about the service and support that is tied with the deal. People want to invest in other people, and it’s important to use language that captures that need.

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

Don: Ethics scores a 10 out of 10. The moment a business or seller appears unethical, prospects no longer see value in a company and will end the relationship immediately. With the SaaS world now in full force, it’s easier than ever for a customer to cancel that service at their leisure. If they have any reason to distrust a business, they will leave and it will cost your company 5X plus to replace your customer base.  

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

Don: It’s simple, call the lead, qualify the lead, and begin building the relationship. In the process, it is key to ensure your team is aligned to what you define as success and failure of lead flow. If a lead fails to convert into an SQO, sit with your team to discuss what can be done different or how to alter your messaging. When a lead comes to you as a seller, you must act on it fast – within 48 hours, if not sooner. Remember, modern buyers want fast responses and someone who they can grow with to help solve their needs.

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

Don: In terms of sales management, I was told to completely forget everything I knew about sales because management is a completely different beast. As a manager, you are responsible for nurturing and growing your people. It’s imperative to make sure you don’t model eight versions of you, instead, diversify the team and surround yourself with people smarter than you. Trust me, I didn’t get to where I am today by myself. It came from the many people who I managed to round me out as a professional and help me grow as a person.  

From a sales rep perspective, I’ve been constantly reminded that we have two ears and one mouth. I know I keep saying this, but I can’t stress enough how important this is. We should all spend more time listening than speaking. This applies to the same doctor and patient analogy: a seller should not offer a solution without a comprehensive understanding of buyers’ problems and needs. If you do, you risk losing the buyer/patient.

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

Don: If I had to go back to my first eight years as a salesman, I’d tell myself to restrain my ego. Products don’t sell themselves, and a one-size-fits-all approach doesn’t work. Sellers have to listen to their buyers, and they will only have success if they continue to build a habit of listening, learning, and adapting.


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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