Stuck in Founder led sales mode - it's my baby!

Charlie, a seasoned sales leader with over 25 years in selling and significant experience leading teams at companies like DocuSign and Salesforce, shares profound insights into the evolution of sales organizations. He recounts DocuSign's incredible growth from a 7-person Dublin office to a global powerhouse, emphasizing the critical transition from founder-led to sales-led operations. This shift necessitated establishing clear processes, defining career trajectories for various sales roles (SDRs, BDRs, AEs), and maintaining a cohesive sense of mission through significant expansion, IPO, and acquisitions, a concept he links to Salesforce's V2MOM model.He stresses the vital importance for all employees, particularly in early-stage companies, to understand the foundational "why" of their organization – the founders' vision and how individual contributions drive impact. Charlie observes that this critical alignment often gets lost as companies scale, leading to disconnection. The conversation pivots to the undeniable impact of AI on sales. While acknowledging AI's positive role in automating mundane research and administrative tasks for BDRs and SDRs, he raises a philosophical concern: the "slippery slope" of over-reliance on AI, which risks diminishing natural curiosity and critical thinking. He warns against complacency, advocating that hiring for curiosity is "business critical" to prevent sales professionals from becoming mere output generators. Looking to the future, Charlie believes AI will primarily enhance sales roles, making them more strategic, rather than outright replacing humans, though he anticipates a potential reduction in the number of junior positions. He champions the irreplaceable value of human connection, peer-to-peer coaching, and embedded knowledge within sales teams, arguing these elements are crucial for professional development and will never be outsourced. He shares his personal endeavor of digitizing decades of sales training notes (Challenger, MEDDIC, Sandler, SPIN, SPICED, Holden Power Base Selling) to build his own AI sales coach, demonstrating how technology can augment human expertise when approached thoughtfully. He concludes by recommending "Leadership and Self-Deception" by the Arbinger Institute and Andy Whyte's "MEDDIC" book for sales leaders. A memorable anecdote highlights his "favorite deal" at Dell, where the client’s full adoption and co-creation of the sales process, exemplified by a handwritten mutual close plan and unexpected check, underscored the profound impact of truly engaged human-led sales. He underscores the need for executives to define clear AI strategies, stressing the dangers of uncoordinated AI adoption and the necessity of focusing on why and how AI is used to avoid becoming "complacent" as individuals and organizations.