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

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