HeyJaredSell It Like You Mean It
Every Sunday, I share one tactic to help you book more meetings, close more deals, and win without the bro-energy.
- Indexed issues, last 90 days
- 13
- Latest publication
- Sep 27, 2026
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- Earliest in this view
- Jul 5, 2026
Latest issues
How to Build Trust in Sales (opens the original)
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Three years into my AE career, I lost a deal I should have won.Better product.Better price.Better timeline.The competitor had none of those things.But the prospect chose them anyway.When I asked why, they said something that stung:“I just... trust them more.”I remember sitting with that for days.Because I realized something uncomfortable.I’d been so focused on being impressive that I’d forgotten to be trustworthy.There’s a massive difference.And the science of trust explained exactly where I wen
What Happens in Your Brain When You Lose a Deal (opens the original)
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Last month I lost a deal I was certain would close.$90K contract. Nine months of work. All the signs pointed to yes.The email came on a Tuesday: “We’re going in a different direction.”I remember the exact moment.My chest got tight.My thoughts got fuzzy.I wanted to call the prospect and defend myself.I wanted to blame the discount I didn’t offer.I wanted to believe if I’d just done one more thing, they would’ve said yes.For about 45 seconds, my brain was completely unhelpful.And then something in
How to Find Your Way Into Sales (opens the original)
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Six years ago I didn’t have a career.I had a problem.I’d graduated into a Covid. No network. No sales experience. No idea what I was doing.So I took the only job I could get.SDR Intern at $6,000 OTE for three months.When people ask me how I ended up here, they usually expect a story about a big break.A lucky hire.A mentor who believed in me.The truth is messier.It wasn’t a break.It was a beginning.And I almost quit after month one.Here’s what my compensation actually looked like:SDR Intern: $6,0
How I Closed a $100,000+ Deal (opens the original)
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When I started in sales I got taught that big deals moved in a neat sequence.Discovery.Demo.Proposal.Negotiation.Close.Simple.Jesus, I was wrong.The bigger the deal became, the less linear it got.More people appeared.New questions came up.Priorities changed.Stakeholders I had never spoken to suddenly had veto power.And sometimes, the most important signals weren’t things the buyer said to me at all.They were things they did.Someone visiting the ROI page late at night.Someone from Finance looking
I once got pitched a role with a $200,000 OTE. (opens the original)
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The recruiter smiled and said:“Our top reps make it easily.”At the time, that number was all I could think about.I started calculating the commission.The lifestyle.The career progression.Everything.Today, after five years in SaaS sales, I look at those conversations very differently.I absolutely believe there are incredible sales jobs.I also believe great Account Executives can earn life-changing money.But I’ve learned something.Nobody earns a great OTE “easily.”And the bigger the number...
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