Shawn Curtis shares an intense negotiation involving a high-stakes deal at Spreedly, a payments orchestration company. He discusses overcoming internal challenges, strategic decision-making, and lessons learned from pivotal career transitions. Background: Shawn Curtis transitioned from a U.S. Navy career to sales, eventually becoming the first enterprise salesperson at Spreedly. The deal involved a major media conglomerate looking to expand internationally, challenging Spreedly's existing payments infrastructure; it took six months to complete with multiple team members involved in the negotiation. Challenges: Navigating a complex procurement process with stringent and unusual demands from the customer. Overcoming internal resistance and aligning multiple internal stakeholders to meet the deal's requirements and innovate on pricing models. Key learnings: The importance of aligning internal teams and stakeholders to support complex deals. The necessity of maintaining flexibility and openness in negotiations, adapting to unexpected demands and changes. Timestamps: (01:02) Meeting Shawn Curtis and the inception of a pivotal deal. (02:05) Entry into enterprise sales and initial challenges. (05:12) Crucial negotiations and internal alignments. (10:48) Strategic pivot and high-level negotiations with the media conglomerate. (16:04) Critical email and breakthrough in the deal process. (18:29) Finalizing the deal and reflecting on the arduous process. (23:18) Shawn Curtis’s insights on enterprise sales strategies and career growth. Resources: Shawn's LinkedIn RepVue | Sales Organization Ratings, Reviews, Jobs (where Shawn is the Director of Sales) Questions, comments, ideas - reach out to Andrew Kappel