What was your first sales job?

What was your first sales job?

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Mine was selling house painting services door to door at 18 years old.

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Holy sh*t, reflecting back...I learned a lot of lessons that summer that I use to this day.

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👇

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I'm 19 years old in this picture (and still had hair!)

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It's 2008. I'm with my first sales manager, Barry. We're in Cancun celebrating with a few hundred other top performers.

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I sold $101k worth of house painting services that summer. Made almost $30k in profit. #1 rep in the state, top 2% nationwide.

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And most importantly, I learned that I love sales.

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Here are the lessons that have stuck:

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✅ Nothing good comes without rejection

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I ran my business in Brookings, OR. My hometown. Population: 6.7k.

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Must've knocked on nearly a thousand doors that summer.

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35 projects closed

125 sales calls completed

~1,000 doors knocked

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I thought I could handle rejection. But damn, this tested me.

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I interrupted dinner time, weekend projects, and more. Hundreds of no's and doors slammed in my face.

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Starting Outbound Squad wasn't any easier.

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Lesson: The path to everything you want in life is paved with rejection

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✅ Own your price

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The avg. paint job at the time was ~$2,500. But the largest deal I closed was around $12k.

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I was nervous closing that one.

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My sales manager gave me the best advice: "Own the price. Don't be shy about it."

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The homeowners didn't even hesitate. Closed it on the spot and walked away with a check (and a big sh*t eating grin on my face).

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This advice has helped me close multiple six-figure deals at Outbound Squad.

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Lesson: If you're the most expensive option, OWN it

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✅ The beauty of cold calling is the ***predictability***

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Cold outbound is hard. But it's incredibly predictable.

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There are only a few things that can happen during a cold call:

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1) You get hung up on

2) You get a brush off (not interested, send email, etc)

3) You get a legitimate objection (using a competitor, pricing, etc)

4) You book the meeting

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Lesson: Practice so much that you can't get it wrong

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✅ Don't be selfish, share what's working

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I was a top performer for most of that year. At first, I was reluctant to share best practices.

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My thinking: "If I share what's working for me, another rep could use that to beat me!"

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It was selfish. I learned what it meant to be a team player, a world-class competitor, and a great leader that year.

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Rising tides raise all ships.

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Lesson: When you help elevate others, you elevate yourself

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~~~

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What lessons did you learn from your first sales job? What's stuck with you to this day?

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