5 Things You Can Do to Level Up Your Career in Sales

I’ve been in sales in some form or another for most of my career, and for the past seven years I’ve worked at startups. My sales experiences include working for companies that are super-transactional as well as some companies that are more focused on enterprise sales.

Over time, I’ve identified several things that top salespeople do to propel their success. Here are my top recommendations for people who want to level up a career in sales:

1. Don’t be afraid of transactional sales

If you really want to learn to sell, starting with a more transactional sales process is incredibly valuable. So many companies are moving towards an enterprise sales model, which is great- but it’s so much harder to learn in that environment. My first sales job required making 60-100 cold calls a day and closing 20-30 deals per month, and it was some of the best training I’ve ever had.

With transactional selling you get a lot of reps in early, so you can learn what works and what doesn’t work. If you can put yourself in a situation where you’re qualifying and closing lots of small deals, you can really easily test new approaches. You can literally iterate on a daily basis. It’s a great way to take the risk out of your learning curve and gain solid fundamental skills. When you’re working with a 6-12 month sales cycle and fewer accounts at a time, you just can’t learn at the same speed.

2. Think broadly about the value you can provide your company

Oftentimes people think of sales careers in terms of linear progression. You start as an SDR, move to an AE role, then a manager, and so on. While career progression is important and you don’t want to get stuck in a role, people can get so focused on a particular sales career path that they forget about the real value they’re providing.

I advise salespeople to broaden their perspectives. Look around your company and start asking questions about what the gaps are. Think of it as a discovery process! This enables you find out what roles are actually needed at your company. You might discover that the company doesn’t really need another SDR manager or enterprise rep, but they do need something else that’s a great fit for you. That’s really how you can start to create a meaningful long-term sales career path for yourself. Think in terms of what’s possible instead of just following the steps.

3. Pick what your prospects are putting down

No matter what you’re selling, one of the most important things you can do is to pick up on the cues people are giving you. I’m sure we’ve all seen lots of demos where a prospect says “That’s awesome”, or “I love that” at a critical point, but the salesperson just plows through their standard presentation instead of really taking the time to pay attention to the cue and explore it. This is sales gold! If someone is giving you a reaction, there’s a reason….and if you can uncover that reason, they’re basically telling you why they will buy from you, or not.

Similarly, when a prospect voices an objection let the conversation go in that direction and ask questions to figure out what the prospect really wants. Let’s say someone’s someone’s telling you that they don’t need your product because they have a great internal process. Instead of countering, ask them a question: “Wow, it sounds like you already have this figured out. Why would you ever change?” Sometimes they’ll say they wouldn’t- but usually there’s a reason they’re talking to you and you just need to push a little to find out more.

4. Learn about the same things your clients are learning about.

In sales, we talk a lot about knowing your vertical, and that’s a good place to start. To really get to the next level, you need to learn about what your clients are learning about. You don’t just need to know where they are today- you need to know where their business is going. This enables you to connect in a much more powerful way and align your value proposition with their future goals.

This also makes you more valuable to your company. Once you know your clients better, you can add value to conversations around product, marketing, and strategy. When I started at Panjiva, we had a few customers in logistics, but they were not our focus. Even though it wasn’t our biggest vertical, I went all in. I read about the origins of container shipper, macroeconomics, commodities, oil prices, trends in retail- anything I could find that might affect that industry. In two years, logistics companies became our most profitable vertical because the conversations we were having with prospects changed so much.

5. Create a system for continued learning

It’s so important to make time for your own progress. I use Trello to keep track articles, blog posts, and books that I want to read. Whenever I come across something interesting I’ll add it to the board. Once a week, I set aside an hour or two to read from the board. It’s fun seeing everything you’ve already gone through and makes it super easy to look things up later.

The best salespeople are always learning. To really retain what you learn, you need a more systematic approach. Pick an approach that works for you and go for it!