My reply is probably too late, but I'll post anyway for people referencing this later.<p>My own journey over the last 20 years has been a slow migration from a technical contributor (About 10-12 years of systems engineering, infosec consultant, pentester) to a full blown quota-carrying, territory-running sales guy. Surprisingly, I enjoy the work. My personal view of sales started negative based on my interactions with the last generation of salespeople, but I've seen a generational shift in Enterprise Sales recently, and there are a lot more people like me than 10-20 years ago when I started in the industry.<p>It turns out, sales and running a territory is like engineering to me. Like any good engineer, I enjoy building things. I built out a customer base that can contribute to local chapter events to be where I can't. The job is also highly measureable. I can't think of another role where performance is so easily measured day-to-day and forecasted into the future. It's also a critically important function of the company. Bringing in revenue is a top priority and receives a lot of benefits. One driving force that got me to where I am is that I always took steps of becoming more important.<p>Back to the question.. how to get good at sales? Easy. Take a sales job. A good place to start would be Sales Engineering or Sales Overlay (SME with sales responsibilities). I'd look for a field that is highly technical and complex. Something hard where real technical chops are required and respected. Customers value your output because they genuinely don't have the expertise that you offer. Nothing commoditized.. look for smaller, fast growing segments.<p>As for specific skills to succeed in sales in these environments, it's mostly about understanding the customer's business problems and objectives. Once you have a firm understanding and agreement with the customer on the desired business outcomes, then dig deeper into making the individuals at the customer successful. Make your customer a hero. Help them overachieve on their goals. Financial reward comes quickly after you reach this point.<p>Also important: good communication, systems-thinking (ability to navigate complex organizational decision making processes), and understanding people/empathizing with your customers. Over time you'll develop good instincts to know when to push or when to say no. So much of sales can be subjective, so try to use repeatable processes where possible. Your pricing strategy should be defensible and systematic. Don't make shit up.<p>To get the above to work for you, you must have strong communication skills. Sales is still about talking to other humans. You get small windows of time with influencers, decision makers, and buyers. You have to have good presentation skills and be able to convey value to a customer with clarity. To distill complex ideas down to simple, meaningful value and tie that to the customer's desired outcomes. The customer needs to be able to answer the question of "why choose these guys instead of those guys?" with confidence and expertise. Most of the real selling happens without you in the room, so you need to build them up to be your champion. When you are in the room, you need them to be your coach.. every meeting should be an open book test. Your coach should tell you in advance who cares about what so you can craft your messaging around things that matter to these decision makers or influencers.<p>The idea that there is some magical persuasion element in sales seems dated to me. Enterprise sales campaigns are complex. 6-18 month sales cycles with dozens of influencers, decision makers, users, buyers, and so on. You don't take someone out to a steak dinner and close a deal. Does charisma and charm help? Sure.. in a few marginal ways. But you don't have to be a cliche salesperson to be successful. You have to understand how the organization makes a decision, and then work backwards to provide the right information to the right people. Explain the technical value to the people who care about technical aspects. Explain how the license model scales to the person running the budget. Explain how your added services will help the guy in charge of operations scale up the program and over achieve on his goals.<p>Also, the best sales people pick great products in growing markets. That's where the money is. Mediocre products in stable markets do not attract talented sales people.