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