50 Things I Learned From My First Sales Job

This Monday marked the end of my first sales job as an Account Executive at Atmosphere TV, as I was let go along with basically the rest of the sales floor during a second round of mass layoffs.

The last 8 months has been a big rollercoaster. Cold calling was a very new experience for me, one that took a lot to get comfortable with, but ultimately, I’m grateful to have had the opportunity to start learning sales.

After getting hired in April, I was fortunate enough to start out very strong, closing the most deals in my hire class over our two-month ramp period! Overall, I closed about 110 deals, selling to bars, restaurants, gyms, hotels, and more. I compiled most all of them into a map – Check it out below, or here if you can’t see it:

In August, layoffs took our sales team down from about 175 to about 45, and I was lucky/skilled enough to make it through, which came as a big surprise to me as I watched much more experienced salespeople walk out the door that day by the dozen. December’s round of layoffs took that number to under 10, and with that came the end of my job.

I realize the two most valuable things to come from the last eight months are the work experience and the new relationships, and so, with the free time I’ve had this week, I compiled a list of 50 things I learned, ranging from navigating corporate relationships to closing decision makers.

1. Starting off strong makes a lasting impression.
2. Document everything! Conversations, promises, etc.
3. Competition breeds excellence.
4. Learning the CRM/software can have great benefits
5. There’s other ways to get deals besides high volume dialing.
6. Everyone will always act in their own self-interest
7. People will act in your favor if your interests are aligned!
8. Verbal promises of money means no money.
9. The company doesn’t care about you.
10. “Trust but verify” means even the small tasks.
11. Quick deals can be found raiding pipelines of fired employees.
12. Don’t pitch gatekeepers!
13. Get to the point with Northeasterners or get hung up on.
14. “Can you help me with something?” opens doors to decision makers.
15. Corporate businesses take forever to make decisions.
16. Don’t call restaurants during lunch!
17. New businesses are much more accepting to change.
18. Cold text is a viable strategy for getting to decision makers.
19. Odds of closing a deal go down immensely after the first “decision” call.
20. Personal relationships are the easiest deals.
21. After running a demo and handling objections, assume the close!
22. Most objections are excuses to get off the phone.
23. 98% of the time, leaving your name and number is pointless.
24. The less info the gatekeeper has, the better.
25. Be transparent, but don’t lay out all the cards early in a call.
26. Silence is a powerful tool in conversation.
27. Shut up when the decision maker is selling themselves!
28. Brand recognition builds trust.
29. Don’t drop the mic early in a call!
30. The fastest way to a deal is usually a new lead.
31. Referrals are a great source of warm leads.
32. You can’t sell a solution until they realize there’s a problem.
33. Bad calls can throw an entire day off – Take walks to reset!
34. There are two North American time zones east of Eastern Time!
35. In mid-market opportunities, setting a demo is often better than shooting for a quick close.
36. “Champions” can help sell the decision maker, but won’t do all the work.
37. Commissions are taxed at 25%+!
38. Selling desperate greatly reduces the odds of closing.
39. Add value before making an ask.
40. You can’t lose a deal you don’t have.
41. Agreeing with a decision maker’s political statements builds trust (I didn’t expect this one to come up as often as it did).
42. Answer buying questions concisely and directly.
43. The higher the position (role), the greater the disconnect.
44. Drinking at lunch kills afternoon productivity.
45. The best pitches are usually the easiest to understand.
46. Peers can be better mentors than bosses.
47. Creativity dies in monotony.
48. The highest chance of connecting with a decision maker is in the morning.
49. More connections = More opportunities.
50. It’s just a job.

---

As I’m searching for the next opportunity, I look back on my time at Atmosphere with contentment. I got everything I wanted out of the job (except perhaps more money, but I suspect that’ll always be the case), and I can’t wait to see what’s next.