How the Deal was Done | Deal Stories Podcast

Ep 55. Transformative $5 Million Digital Banking Deal with Chas Puleo

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Chas Puleo, a senior sales executive at Alkami, shares his experience in closing a transformative $5 million deal in the digital banking space. This episode covers the challenges of resetting a deal after a key decision-maker was promoted and the importance of business cases in complex sales cycles.

Background:

  • Chas started his career in banking and transitioned into tech sales, currently at Alkami as a senior sales executive.
  • The deal took over two years, with an internal team evaluation for a digital banking platform at a financial institution.

    • Challenges:

    • Rebuilding momentum and trust after the main decision-maker was promoted.
    • Navigating a long, complex sales cycle while maintaining consistent engagement over two years.

      • Key learnings:

      • Building a collaborative business case with the client ensures alignment and trust.
      • Leveraging relationships and offering best practices can help smooth long internal evaluations.

        • Timestamps:

        • 07:15 — Chas's background and entry into tech sales
        • 12:34 — First contact and prospecting challenges
        • 21:10 — The importance of building a champion in the client organization
        • 24:45 — Resetting the deal after a key decision-maker was promoted
        • 31:12 — Collaborative business cases and their importance in complex sales
        • 40:50 — The value of integrity and avoiding negative selling
        • 45:30 — Using imposter syndrome as a superpower
          • Resources:
          • Find Chas on LinkedIn where Chas releases his newsletter
            • Find Chas's art online at Chasisart.com
            • Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. 
            • Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
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              How the Deal was Done | Deal Stories PodcastBy Andrew Kappel