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March 21, 2025 37 mins

Walter Crosby is the CEO of Helix Sales Development, helping growth-minded entrepreneurs build high-performance sales teams and drive repeatable revenue growth with margin integrity. He works with leaders frustrated by underperformance, guiding them toward a performance-based sales culture with transformative results. A University of Michigan alum with a degree from the School of Hard-Won Wisdom, Walter’s sales career spans B2B industries like LED luminaires, financial services, and commercial fire alarm systems. His expertise covers K-12 education, higher ed, contractors, and commercial firms. Known for his love of fine cigars, Walter often reflects in his private lounge and shares insights on sales and cigars as host of the Sales and Cigars podcast.


In this episode, Jason and Walter discuss:

  • Align salespeople with company values through a tailored recruitment process
  • Prioritize strong communication skills over industry experience in hiring
  • Implement a unified "Sifter message" to align sales with marketing strategy
  • Ensure effective onboarding and cultivate a self-motivated sales culture
  • Insights from hosting a podcast that blends business strategies with cigar appreciation


Key Takeaways: 

  • Sales success stems from a commitment to helping customers make informed decisions, emphasizing insightful questioning over traditional pitching.
  • A tailored hiring approach prioritizes communication skills and cultural fit, ensuring alignment with target customers rather than focusing solely on industry experience.
  • The foundation of a high-performing sales culture lies in effective onboarding, self-motivation, and goal alignment, fostering both individual and organizational growth.
  • A salesperson’s values must align with the company’s culture, making the interview process a crucial two-way evaluation rather than a one-sided selection.
  • By equipping salespeople with a clear "Sifter message" that integrates sales and marketing strategies, companies can enhance consistency and effectiveness in their sales efforts.


“Salespeople should be helping their customers. We should be helping them make better decisions. We should be helping them think differently about a problem they may have.”

 - Walter Crosby


Connect with Walter Crosby:

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