Staffing & Recruiter Training Podcast

In this episode of The Rainmaking Podcast, host Scott Love speaks with Aaron Gutowski, Chief Sales Officer at Chief Outsiders, about achieving sales readiness and building scalable sales organizations. Aaron shares insights from his extensive experience working with operationally focused firms that struggle to grow beyond a certain point. He explains that “sales readiness” involves evaluating and optimizing four key areas—people, process, platform, and performance—to create a cohesive sales strategy. By aligning these areas, companies can transition from relying solely on the CEO as the rainmaker to developing a sustainable, scalable sales team. Key topics include identifying the right attributes in successful salespeople, creating repeatable sales processes, selecting the appropriate tech stack (such as CRMs and data tools), and tracking key performance metrics like outreach and conversion rates. Aaron also shares real-world case studies, including how he helped a legal recruiting firm double its revenue by