TRP 172: Sales Readiness with Aaron Gutowski

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 building a sales team, implementing a CRM, and establishing structured processes. He emphasizes the importance of top-of-the-funnel activities, such as increasing qualified leads and using integrated platforms like HubSpot and LinkedIn Sales Navigator. This episode provides actionable strategies for professionals looking to scale their sales operations and achieve sustained business growth. Visit: https://therainmakingpodcast.com/ ---------------------------------------- Aaron Gutowski is the Chief Sales Officer for Chief Outsiders, a consulting company that offers fractional part time chief sales officers and chief marketing officers. A senior technology, market research, and SaaS sales management leader, Aaron brings vertical market expertise in consumer, energy, financial, legal, medical devices, pharma, and technology. A senior executive with expertise in direct sales, marketing, and operations, he recruits and retains top sales professionals, changes sales culture, and achieves operational excellence via process-driven approaches. Focused on training top-performing teams, Aaron employs activity-based measurement to boost pipeline productivity. A strategic planning veteran, he also excels at account management, campaign management, and marketing strategy. ---------------------------------------- This show is sponsored by Leopard Solutions Legal Intelligence Suite of products, Firmscape, and Leopard BI. Push ahead of the pack with the power of Leopard. For a free demo, visit this link: https://www.leopardsolutions.com/index.php/request-a-demo/ Links: Here is the link to the Sales Readiness Assessment. https://surveys.chiefoutsiders.com/executive-sales-assessment?tm_campaign=Sales%20Assessment%20Campaign&utm_content=Sales%20Assessment&utm_medium=email&utm_source=email&utm_term=%7B%7B%20contact.hubspot_owner_id.email%20%7D%7D Connect with Aaron on LinkedIn here: https://www.linkedin.com/in/aarongutowski/ Learn more about your ad choices. Visit megaphone.fm/adchoices