Article • 11 min read

How to start a sales career (and why you should)

Considering a sales career? Sales professionals weigh in about the perks of the job and share the biggest lessons they’ve learned along the way.

Donny Kelwig

Contributing Writer

“Salesperson” might not be the answer you expect to get when you ask a kid what they want to be when they grow up. But if that precocious youngster has done their research, they’ll know that sales is one of the fastest-growing and most lucrative career paths today. In this article, we’ll take a look at the sales career journey and why it might be time for you to start yours.

Typical sales career path

There’s no “correct” way to move through a sales career. But in general, the sales career path can branch from one of a few starting points:

Sales development representative
Inside sales representative
Outside sales representative
Base account manager

All four have strong opportunities for growth and high earning potential. Let’s dive a little deeper into where a sales career starts and how to achieve your career goals.

Career growth in sales

The sales industry covers a wide range of careers, from the small mom-and-pop shop owner to the VP of sales at a Fortune 500 company. That said, most people start their sales careers in the same place: by working as a sales (or marketing) representative.

These snappily named sales reps are the face of a company. They’re the ones interacting with customers, handling transactions, moving products, and influencing the all-important brand perception. Some people thrive in sales rep positions, especially if they work on commission. But even if your goal is to work your way up, this role is a crucial place to start.

When you work as a sales rep, you learn about every aspect of the business (including marketing, branding, pipeline, and stock). This experience will make you a better manager and supervisor as you ascend through the sales ranks.

How to grow your sales career

The key to growth is being open to learning. Even top executives must continue their professional development to perform at their best. According to renowned sales trainer Alice Heiman, there are four key practices to keep in mind when looking to advance your sales career.

Work for a company with a great sales culture
You don’t want to start your career with a company that doesn’t want to invest in you. Look for companies with low turnover rates and glowing employee reviews. Ensure the company provides coaching and training, too. After all, it benefits them when you perform well.
Level up your sales knowledge
Do everything you can to stay informed about the latest trends and most effective sales techniques. Subscribe to helpful blogs, read books, attend webinars, and listen to podcasts. As you become a sales expert, you’ll be able to help others on your team and establish yourself as a go-to person for answers—helping you move up the ladder faster.
Make your job about helping customers, not selling to them
You’re going to hear a lot about quotas during your first year in sales. While quotas are important for the company’s bottom line, they’re not necessarily a definition of success. You shouldn’t use aggressive tactics to push sales through just to meet your monthly quota—it’s not in the best interest of the customer or your company. Opting for manipulation over ethical selling will likely backfire and lead to customer churn in the future.
Remember: Your clients want a solution, not a product.
Listen to your customers
The faster you can internalize that the best sales are personal sales, the faster you will rise to the top. Your prospects are people with problems, not consumers with money. Practice active listening and consultative selling so you can focus on solutions in a customer-centric way. If you’re offering a product that isn’t going to solve a prospect’s pain point, don’t push it. You might have a different product that’s better suited to their needs and business goals.

Sales career goal examples

Sometimes, it’s hard to visualize the victories in a sales career beyond, well, making sales. Don’t let that deter you from pursuing a sales career. Here are some examples of goals you can set and achieve on your way to making more money and deepening your professional development:

Gain a new skill
Expand your network and networking abilities
Intern with a large company to gain experience
Improve your sales productivity statistics

Start your own business after building experience
Become a sales expert
Reach a leadership position
Win an award

Setting a few career goals is half the battle in finding sales success and climbing your way to the top.

Benefits of a sales career

Sales might not be the first career you think of when someone asks about your dream job, but there are many reasons why it should be. Sales careers are flexible, in-demand, well-paying, and exciting. Don’t believe us? Read on.

Why is sales a good career?

We asked Kyle Osterman, the former VP of enterprise sales at Zendesk, about his career. Here’s what he had to say about sales and the privilege of working in the industry:

“I have had the good fortune to work in sales and sales leadership with several world-class companies over my 30-year career. I had early exposure to some of the finest sales minds in the business, including sales training pioneer Neil Rackham, and forward-thinking sales training programs about SPIN selling, solution selling, strategic selling, the Challenger Sales model, and more. All of these programs offer critical skills and strategies around the successful management of a sales cycle. I took so much from these investments.”

Learning is built into your sales job. It’s inevitable, and it’s what makes sales a great career.

Is sales a good starting career?

Sales is one of the best starting careers. When you enter the sales world, you don’t need to enter with years of experience or a sales degree—you only need ambition and a growth mindset. Both qualities are essential for anyone looking to begin a sales career, especially if you’re pivoting from a previously unrelated career path.

Is a career in sales hard?

Sales isn’t the easiest career, but that’s why it’s so lucrative. A strong sales career requires dedication, persistence, empathy, quick decision-making, and patience. It’s not for everyone. That said, the sales industry encompasses many types of businesses, so there’s likely a niche where your skills and personality are best utilized.

Why sales is the best career

Regardless of where you want to go with your sales career, any sales experience provides you with priceless skills that apply to all types of jobs and situations. When you’re in sales, you’re learning life skills—interpersonal communication, adaptability, charisma, and trustworthiness. All will propel you forward whether you decide to stay in sales or move in another direction.

Considering the learning experiences, high income potential, flexibility, variety, and networking opportunities that come with this career path, it’s easy to see why sales is worth exploring.

Lessons learned from a career in sales, according to professionals

One of the best parts of sales is that it’s always evolving to meet new societal and financial trends. So if you’re looking to become a true sales professional who’s serious about honing their craft, chances are you’ll encounter several valuable life lessons along your career journey.

We asked some Zendesk sales leaders to share the most poignant lessons they’ve learned throughout their sales careers. Here are their indispensable words of wisdom.

Justin Hunt, account executive

“I lost a deal a couple of years ago that still sticks with me. I spent 4.5 months working on it, and it would have easily been a top-five customer for my company at the time. To make matters worse, I had to call my CEO and interrupt the last day of his vacation to notify him. There were a few learning lessons from this experience, but I’ll talk about the most notable.

I had worked hard on this deal and thought we were in a great place. We had met all the decision-makers. I had a kick-a** champion feeding me data on our competition daily. What I didn’t anticipate were the traps the competition had set for us and how it would impact the opinion of two to three key people.

After pulling ahead to the No.1 spot the week before Thanksgiving, I could feel us slipping behind in early December. The line of questioning was clearly indicative of a particular competitor’s playbook. I scrambled to get answers and worked primarily through the chief influencer while getting some inside intel from my champion on the side. When I got the call on December 31, it hit me like a blow to the chest. I debriefed with my CEO and we did a post mortem.

As I said, there were a couple of errors, but the most glaring was that we didn’t fully understand how they were going to make a decision. Yes, I had a lot of people in my corner. But there was one group that I never really spent much time with. And ultimately, their gripes were larger than the kudos I received from my supporters. I had access to the chief influencer, but he democratized the decision to the team. I had a great champion, but he lacked influence and had less insight into the team against us.

If I had a complete understanding of how they were going to make a decision, I could have met 1:1 with the three people who were against us and likely won the deal. You can have all the right pieces in a deal, but if you don’t know precisely how the decision is going to be made (by whom, on what date, in what format, etc.), you’re setting yourself up for failure.”

Michael Logan, VP of sales

“Two impactful lessons come to mind. The first is that I can create my own destiny with a great outbound plan. Feeling great about your product and wanting to tell the world about it is one of the most fun aspects of the job. I was taught how to develop a ‘Destiny Plan’ for my franchise, and through effective targeting and a focused multichannel outreach, I was able to help 22 companies improve their operations over three years.

The second one was learning to translate the excitement around a great meeting and product fit to a financial return for the customer. Sharing with clients that there is a process to get them from their “as is” process to their “to be” state and what that means to the stakeholders is key. In other words, should they buy my solution, improve the cafeteria, or pave the parking lot? What’s the best investment for them, and how can I prove that it’s mine?”

Jessica Jonsson, account executive

“While in a sales cycle, I always have a couple of contacts that I maintain a strong relationship with. In theory, this sounds great, but it also can become your blind spot.

It’s great in that they will hopefully point you in the right direction, push for your product, share information privately with you, and be a part of closing the deal. However, it’s easy to be blindsided if it turns out that your “champion” doesn’t have the influence or run in the internal circle necessary to get the deal across the finish line, or doesn’t understand the ecosystem as well as they portrayed. What’s even worse is if they aren’t as loyal as you thought.

While I still develop these strong relationships today, I have learned over time to continuously test them and make sure that they’re the real deal. I do this by asking tough questions, involving other members of my team, requesting sponsor meetings, etc.

I’ve also learned to take a step back from a deal to see what’s missing and to identify the exact role a champion plays in the overall picture. Otherwise, the very deal that was going to help get you reach your quota may fall apart and leave you wondering what went wrong.”

Learn more sales lessons for your career

Oftentimes, the best way to learn is from the sound experience and advice of others. Reach out to sales professionals in your network to gain a deeper understanding of their work and what they enjoy (and don’t enjoy) about it. This will help you determine whether or not a sales career is a good fit for you.

If you’re ready to take the leap, start beefing up your sales knowledge, writing your sales resume, and prepping for your first sales interview.

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How to start a sales career (and why you should)