14 Things I Learned From A Career In Sales

In short: how to make more money.

May 06, 2025

1. Sell Bigger Deals

10% take-home on a $10M dollar deal is a whole different world than 10% take-home on a $100k deal.

This is core of making more money in sales. Typically the reps that close deals of this size have 10 years of enterprise selling experience closing large complex organizations. Look for companies that already close deals this large—Microsoft, Oracle, SAP, Salesforce. As well as fast-growing organizations like Snowflake, or MongoDB.

2. Timing, Territory, and Talent

The same sales rep will likely have been to President’s Club and put on a PIP (performance improvement plan). Skill is the least important factor to either. The most important is timing—especially in tech sales. Get into a company that’s exploding and even a bad sales rep will look like a rainmaker.

Skillz To Get Better At Sales

3. People Do Business With People They Like

My grandpa, who sold at IBM in the 70’s used to say the key to sales is:

“People buy from people they like.” — Ken Varner

All the sales books you read are good when you're starting out but once you're working with millions of dollars on the negotiating table, it’s you they're buying from.

4. Be A Good Story Teller

Remember that you’re helping someone find a solution to a problem. Share stories of how you’ve helped other customers and don’t spend too much time being technical.

5. Take Lots of Notes

When sales cycles get long on large contracts, people come and go on both sides of the table. It helps to have important details documented from the start. Microsoft OneNote is a life-hack.

Work Hard…

6. There Are No Shortcuts

There are no shortcuts. To get to a role where "it's not work if you enjoy what you do" requires you to work the jobs you don't like to do to get there.

7. Keep Pushing

Never take your foot off the pedal. If you close a big deal, take a day to celebrate but then keep pressing. Momentum is everything in sales. It also helps prevent your pay from going up and down each month.

8. Corporate America Has No Loyalty

You might have a good relationship with some people in the organization but when dollars and cents get involved you're just another FTE or number. Complacency is your enemy.

…Play Hard

9. Take Time Off

Personally, I need to work on this one. Taking time off, traveling, spending time with friends and family gives you the fuel you need to stay motivated.

You Network Is Your Net Worth

10. Don’t Burn Bridges

I landed my current job from a former employer from when I was in college. At that time, I was farming, but as it turns out, he sits on the board of my current company. You never know when someone can help you one day, so keep those relationships in tact when you exit any job.

11. Office Politics Is Crucial For Your Success

It can help you get more leads, process your orders faster, get you promotions and make you a lot more money or give you more flexibility with your time. Be nice to everyone even if they can't do anything for you.

12. Networking Is Not Needworking

Don't reach out to people asking for a referral. Reach out to learn about how they got to where they are, see if you can help or provide any intros, pick their brain about their organization. Then, if and when you do apply to their company, reach out.

Have Good Character

13. Do What You Say You’re Gonna Do

If you’re running behind on getting something back to a client (internal or external), email or call them and let them know there’s a delay but you haven’t forgotten about them. This goes a long way in building credibility.

14. Be Humble

No matter your experience, you’ll come across brilliant salespeople with so much to learn from. Take the time to thank them and ask if you can pick their brain.

—Grant Varner