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Bryan Charlton joins the show to break down how great reps spot deal risks early and keep momentum all the way to close. He shares real examples, practical tactics, and the mindset his team uses to win complex deals.

🎙 ACTIONABLE TAKEAWAYS:

  • The contract isn’t the finish line. It’s the start. Set the tone for what happens in the first 30, 60, and 90 days so the buyer knows exactly what to expect.
  • If a buyer says they’re looking for a tool, don’t stop there. Dig into the real problems that made them start searching in the first place.
  • Your story has to make sense to everyone. The champion, the leaders, and the end users all need to believe this will actually work.
  • If you’re blocked from talking to power, that’s okay. Just ask what would need to be true for them to feel comfortable making the intro next time.

BRYAN’S PATH TO PRESIDENTS CLUB:

  • Spent more than 12 years in sales @ Salesforce and FICO before joining Otter.ai
  • Consistently hit quota by finding high-value deals in unexpected places—selling large software deals to banks in Hawaii, Credit unions, and even AI into tightly regulated financial services firms, while others focused on big brand name accounts

RESOURCES DISCUSSED:

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578 episodes