9 Tips For Starting Your Career in Sales

Even if you’re not just starting out, there’s something for everyone in this post.

In the last month, I’ve spoken to many people just starting out their careers in sales looking for advice. There are many ways to achieve success, and most paths can be windy. The points below are my thoughts on how to best set yourself up for long term success.

Learn Faster, In-Person

Early on in your career, you need to be with your leadership and other salespeople, learning from their wins and losses on an hour by hour basis.

We’ve all adapted to the remote world, but workers in their 30’s have had the experience of working in the office. If you’re in your 20’s, just coming out of college, learning how to be productive and professional around older colleagues is invaluable to your growth.

The relationships built in your 20’s will open doors for you for the rest of your life. If a company is hybrid, confirm that leadership and your future colleagues are showing up to the office at the same time and consistently.

You can become successful as a remote worker, but you’ll learn and move faster in-person.

Sales Training: Find a Company that Invests

Sales training is expensive, and most companies don’t provide it. Find a company that is committed to providing you with training. If it’s not formalized training, ask what sales methodology the leadership has implemented, or wants to implement, and how they plan on teaching it to the team. 

Find a place that will invest in training you.

Be a Lifelong Learner

Even if you find a place with a robust training program, don’t rely on that alone. Commit to being a student of the game. Read one sales or business focused book a month. Download audible if you need to but begin to digest material and test out what you learn on the job.

Here’s a recommendation: No Excuses! The power of self-discipline by Brian Tracy. 

The author is old school but potentially more relevant now than ever. Take action to begin learning.

Sales Winners Grind it Out

Sales is hard. There is an immense amount of rejection. Success rates from outreach to close are often less than 1%. The real winners are the ones that grind it out. They put themselves in enough places to win.

Look up the metrics of everyone in your sales organization. Open the dashboard daily and be the number one player every day. Set the bar.

Don’t Be a Job Hopper

Commit to a company. If a salesperson stays at a company less than 1 year, there is a good chance the company lost money on employing them. 

With the nature of Leap’s business, I’ve been able to work with early to late stage companies looking for sales talent. No one wants to hire a job hopper. There will be people who tell you differently, but my strong recommendation is to stick to a company for a minimum of 3 years when you’re getting started. 

Yes there are exceptions, but if you have multiple stints of less than 1 year in tenure, you will have to present your case during the recruiting process.

Every organization will have its ups and downs. You’ll have great managers and bad managers. Put in your time and look at everything as a learning experience as you grow.

It’s Not Just About the Pay

One of the best career decisions I made was taking a $36k a year job at Yelp as a SMB Account Executive. I had another offer for $55k as an SDR at another organization. Yelp offered a 60-day training program while the other company didn’t have training. 

It was a tough call at the time. I was coming right out of college and that was a big difference in pay but I knew that their training program would be super valuable. 

Find the environment that you strongly believe has the chance to be your launching pad.

Show Up, Stay Positive, Win 

You’ve heard the term the squeaky wheel gets the grease. That’s fairly accurate in the short-term, but in the long term the people who show up, stay positive and don’t cause drama are the winners.

Company Growth Rate

Join a fast-growing organization to accelerate your career growth. You'll take on more responsibility quickly, and the company will create new roles for top producers who consistently demonstrate a positive attitude and a strong work ethic.

Headcount growth of employees does not always mean the company has a good business. However, for personal career growth it’s important to note that sales departments tend to have more people compared to other departments. If you want to move into management or rise into Enterprise sales, seeing the velocity of hiring is a strong signal that you could have the opportunity to rise in an organization. 

Hit your numbers, stay positive, ask for more work and you’ll move up.

Cross-Vertical & Deal Size Exposure

One of the benefits I never considered about my time at Yelp was that I was able to sell the product into various industries from restaurants to retail to auto. I was also able to experience selling the product from Small to Medium, Mid-Market, and Enterprise sized businesses. 

If the company you choose presents an opportunity to sell to multiple verticals across different business sizes, don’t take that for granted. All of that exposure is valuable learning.

If you’re looking for a company to join, start by building your target list. Here’s an article to help you get started.

Do the research and be thoughtful about why you want to join an organization.

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