Episode Description: In this episode, we're joined by Casey Drake, VP of Sales at a retail tech startup. Casey shares his journey from an AE at a young startup to leading a sales team in a dynamic and evolving company. We dive deep into his experiences, discussing the challenges of scaling a startup, the importance of mentorship, and what it takes to build a successful sales culture in a remote environment. Casey also shares his insights on leadership, onboarding, and fostering a strong team culture, making this episode a must-listen for anyone in the startup world.

Key Takeaways:

• Casey's Journey: Casey discusses his career path, starting as an AE and growing into a VP role. He reflects on the challenges and rewards of working in a small startup environment, emphasizing the importance of resilience and adaptability.
• Mentorship in Sales: Casey introduces his "golden question" for interviews—asking about professional mentors. He explains why having a mentor is a significant green flag when hiring and how it contributes to long-term success.
• Startup vs. Small Business: The conversation explores the differences between startup culture and small business operations, with Casey explaining his preference for the dynamic and challenging environment of a startup.
• Leadership and Team Culture: Casey shares his approach to building a strong remote team, including fostering vulnerability, creating a sense of safety, and encouraging radical candor. He also discusses the importance of giving team members side projects to keep them engaged and contributing to the company’s growth.
• Onboarding and Continuous Learning: Although the book Casey is reading focuses on customer onboarding, the discussion pivots to the importance of effective employee onboarding and continuous development within a company.
• Innovative Sales Strategies: Casey touches on the balance between process and innovation in sales, allowing his team the freedom to develop their own methods while providing the necessary tools and guidance.
• Key Questions for Team Improvement: Casey shares three critical questions he plans to ask his team to improve their effectiveness and strengthen their working relationship.

Books Mentioned:

• The Culture Code by Daniel Coyle
• No Rules Rules by Reed Hastings and Erin Meyer
• Onboarding Matters (mentioned in the context of customer onboarding)