Best Sales Advice from a CEO at a $1B Company

Kris Nagel built a 30-year executive career by viewing sales as a structured, customer-centric science rather than an art. Starting at Apple in product management before moving into field sales, Nagel learned that listening 70% of the time and uncovering client pain points is the single most effective way to win deals. Today, as CEO of Sift, Nagel leads a $1B+ digital trust and safety platform that protects enterprise platforms from online fraud. In this interview, Nagel unpacks why sales is a team sport requiring executive commitment, how product-led growth acts as a sales engine, and why early founders must embrace 'no' as a diagnostic tool.

It's still selling. I am Kris Nagel, CEO of Sift, a digital trust and safety company. We are focused on helping the enterprise build great consumer experiences and prevent fraud and cybersecurity risks for the enterprise. I have been in the workforce for about 30 years, and I have had the opportunity to work for a number of venture backed companies. A couple of them had early IPOs, and a couple I joined at a really early, pre-revenue stage.

So I spent close to 20 years in the field, spending time with customers, selling to customers and supporting customers, and it has just been a fantastic run.

I started my career with Apple Computer back in the day, a very different time for Apple. It was a much smaller company. Steve Jobs had just left and John Sculley was CEO. The company was going through a number of trials and tribulations, but I can't think of a better place to start my career. I had the opportunity to do a great many different things, including manufacturing new products, engineering and product marketing.

I was in product management for a while, and I figured out pretty quickly that the real activity and the real lucrative careers were out in the field with customers, selling to customers. So I moved into a customer facing role, and that was my first sales role. What struck me was the idea that every customer I was going to call was going to say no.

And I thought, boy, this isn't going to be much fun. Getting no all day long is not great for the ego, and it's not great for being in a good mood at the end of the day. But learning to accept no as a learning experience was incredibly valuable. They told me no, and I actually got into a pattern.

Why no? I would say, tell me why no, right before we end this call. And suddenly people would start to engage. They would say, well, here's why no, I don't have the budget, or this doesn't fit what I'm trying to do.

The very first sales manager I had watched me come out as a product manager saying, this is my product, it's awesome, it's great, it's got all these bells and whistles, and we're going to accomplish all of these things with it. His advice to talk less than 30% of the time was some of the best advice that I've ever received in my career. Listen to what they're telling you, because they're going to tell you everything you need to know.

If you're ever in a conversation, and especially if you are a young founder, try not talking except for 30% of the time. The investor, the potential customer or the partner is going to tell you what you need to do. You just have to be willing to listen.

For me, the most fundamental thing to realize about selling is that you're not trying to sell somebody something. You're trying to help them solve a problem. What is this person, this team or this organization trying to accomplish? What is the business outcome they're trying to reach, and how are they going to make their decision through that process? You're in a great position if you try to help them solve a problem and they see that you are really emotionally invested in helping them solve it. That is a home run.

That is a core belief of mine. Selling is a process. It's a science, and it's not an art. Understanding that buying process, understanding how you can enable that buying process and taking people through a structured journey is incredibly important. So having process discipline matters, and so does finding out what works and what doesn't work.

I think a lot of people in your audience are just trying to figure out how to sell that first customer and that second customer. It's very early stage, trying different things, trying different messages and trying different PowerPoints. At the companies I've been with that were very early revenue or pre-revenue, I would have half a dozen different PowerPoint decks and half a dozen different messages early on, to see what worked, what resonated, what aligned to their problem and what didn't align to their problem.

But having a process, having a cadence and asking customers for a lot of little yeses along a buying process is incredibly important.

Selling is absolutely a team sport. When I think of selling, it's about managing a team that is responsible for bringing the right value proposition to the right people on that evaluation team. I learned very early that you couldn't do it on your own. You had to be the de facto leader, even though those various different functions didn't report to me.

On a given opportunity, you lead a team through the process, and you lead a customer through their buying process. As the salesperson, the one carrying the responsibility for winning new business or renewing business, your job is to understand what the customer needs. Then you bring the team players to the discussion to help facilitate that customer's learning process about why you're the best vendor.

If a client needs a deep dive on machine learning, good salespeople recognize that they are not the machine learning expert, but that they have a systems engineer who is very good at that. Or the client needs an even deeper dive, so I'm going to bring in a data scientist. Obviously, during this entire sales engagement process, from very early on to the end, the customer is looking at the website, looking at reference materials available to them, doing self-education and looking at peer reviews.

And so your marketing organization is an extended team member. Sometimes it just takes an executive saying, we are committed to your success, or, Miss Customer, I will partner with you to make this successful. That's a lot of the role that I play today. If I believe in something and the customer is struggling, I will sit down and make a personal commitment and tell them exactly what I'm going to do to help them be successful.

That's another member of the team. You're an orchestrator of a process and of a relationship. If you show up with everybody all at once, it's just annoying and overwhelming to a buyer. But knowing that I need to plug in this piece at this point in time is a skill.

Even as a CEO today, I view my job as building the organization in a way that we're building the right team for the sales team to call upon, so they can be successful in their sales engagements, in their renewal engagements and in the things that they need to do to run their business.

I am a big believer in product led growth. At the same time, the best technology doesn't always win. It's about creating awareness, depending on the solution or the product, and creating some kind of viral notion in the market. But at the end of the day, it is still selling. You're selling not with a direct salesperson, but with a product and with a website and with a trial process.

It's still selling. It just so happens that there isn't a salesperson in the middle of that process. Instead of saying, I've got great technology and everybody should buy this stuff, you ask how you expose this technology and what business problem you are trying to solve. That's a form of selling.

At Ping we went through a huge transition. We called it high velocity selling for a certain component of the market, and the idea was to allow the customer to do as much self-education as possible. They had to find us when they had a problem, and we had to align to the problem that they were having. We had to give them a way to learn without talking to us, and at some point they may or may not talk to a salesperson.

So I think for early entrepreneurs and early stage companies, product led growth can be incredibly valuable. It really depends on the macroeconomic situation. There's been a real slowdown in product led growth companies, and it will come right back as soon as the economy improves. But think of it as selling. Don't think of it as having great technology.

The other real dependency here is the nature of the market that you're targeting. No matter how good a product or a technology or a platform might be, enterprises have financial analysts. They have procurement people and they have decision making processes. They have 14 levels of approvals. It's incredibly difficult to get through that buying process in the enterprise without a seller involved in some form or another.

And that sales team is not just your own sales team, it is all of the partners in the ecosystem. There are very well established channel and distribution mechanisms for people to bring products and services to market. There are the large system integration partners that are trying to solve big problems for the enterprise. That is an extension to your selling motion, and you have to think about how to build and grow off of that.

So I really view it as a continuum, with purely product led growth in the early days. Think of it as a sales mechanism where the product has to do a big part of that selling, but awareness, the website and partnering also factor in there. As you move up in the enterprise, you'll have to have direct selling teams involved. You've got to think about where you are and what you're trying to accomplish at a given point in time, and it changes for the company over time. It's a continuum, and you just have to know where you are and what you're trying to accomplish.

Looking back now, your 20s and 30s are a time of exploration, particularly your 20s, when you are trying to find yourself and who you are as a person, how you want to contribute back to society and what you want to do professionally. I encourage everyone at that stage of life to explore, to follow your passions and to follow things that are interesting. Compensation and money will come with time.

In my case, I knew I wanted to be in technology, but I wasn't sure what I wanted to do in technology. So trying different operational kinds of functions in an organization is a great way to explore, and so is trying different technology types. If I look back over my career, it's been everything from hardware to software, enterprise software, appliance driven activities and cloud.

Different technology evolutions happen over time, but exploring those things as they come up is a fantastic opportunity. I really encourage people, don't put too much pressure on yourself to find the right thing until you explore and know what you're truly passionate about. Continue the search.