Oct. 23, 2025

Building a Winning Sales Team: Key Strategies Revealed featuring Walter Crosby with Helix Sales Development

The player is loading ...
Building a Winning Sales Team: Key Strategies Revealed featuring Walter Crosby with Helix Sales Development

Episode Overview

In this episode of Small Business Origins, host John Kelley welcomes sales expert Walter Crosby from the Sales and Cigars Podcast and Helix Sales Development. Walter dives deep into the world of sales strategies, the intricate dynamics of sales teams, and the essential mindset needed to thrive in business. They share insights on the importance of culture, leadership, and personal development in driving sales success.

Main Topics Discussed

  • The connection between personal experiences and professional success.
  • The significance of sales skills and mindset for entrepreneurs.
  • Strategies for establishing a productive work environment and cultivating team culture.
  • Identifying the real issues within a sales process rather than jumping to solutions.
  • The importance of setting realistic expectations and understanding client needs.

Key Insights

  • “Experience is the name I give to my mistakes.” - Walter emphasizes how learning from failure shapes future success.
  • Work-Life Balance: Both John and Walter discuss the necessity for time freedom and how it directly impacts personal life and professional satisfaction.
  • Sales Dynamics: Walter discusses how mediocrity within teams can hinder overall performance and the importance of having the right people in place to drive success.
  • Custom Solutions: Instead of offering generic training, Walter focuses on identifying specific problems to create tailored solutions for clients.

Notable Quotes

  • Walter Crosby: "You need to be the salesperson that that prospect needs you to be."
  • John Kelley: "If you enjoy what you do, truly enjoy it. If it fulfills you and brings you joy inside, then you're not working."
  • Walter Crosby: “Mediocrity kills performance across the board.”

Timestamps

  • 00:00 - Intro Music and Introduction
  • 00:32 - John Kelley introduces Walter Crosby
  • 02:18 - Icebreaker question about unlimited vacation
  • 10:40 - Discussion on work-life balance
  • 19:40 - Walter shares his entrepreneurial origin story
  • 32:06 - Strategies for successful sales leadership
  • 46:43 - Importance of aligning values and expectations in business
  • 55:01 - Insights on personal branding and sales strategy

Relevant Links & Resources


Other Links:

John The Marketer

Sponsor (Wingman)

Beefy Marketing (Start Your Own Podcast)

If you enjoyed this episode, please subscribe to Small Business Origins and leave us a review! Share this episode with fellow entrepreneurs and engage with us on social media. Join us next week for more inspiring stories from business leaders about their unique journeys. Stay beefy, my friends!

Please don't forget to leave us a review, subscribe to the show to get notified of new episodes, and share each episode with a friend! Thank you for your support.

Walter Crosby

Crosby

Walter is a proud alum of the University of Michigan and holds an advanced degree from the school of hard- won wisdom. He spent the majority of his career as a salesperson who was frequently promoted into sales manager positions. He sold a variety of products with complex B2B sales cycles including LED luminaries, commercial signage, financial services, synchronized clock systems, and commercial fire alarm systems. He’s sold to K-12 educators, colleges/universities, contractors, and manufacturing and commercial/retail firms.
Frustrated by the lack of training he received each time he was promoted to sales management roles, Walter sought his own training and mentors to help him grow as a leader. After training himself and surrounding himself with strong mentors, he saw a need to share his hard-earned knowledge with others to develop successful sales teams. This led to the creation of his own firm, Helix Sales Development. Here, Walter coaches, trains, and supports successful sales teams using evidence-based sales evaluation and assessment tools by the Objective Management Group and sales-enablement technology through Membrain.
Walter’s rocket fuel comes from coaching committed individuals to excel beyond what they thought was possible. Conservatively, his clients see a 37-43% increase in revenue after their engagement.