Rich Cogswell, The People-First Sales Leader - How To Build Winning Sales Cultures, His Take On FinTech, and Why Leaders Should Make Themselves Redundant

In this episode, I welcome  Rich Cogswell (see his bio below), a people-first sales leader, FinTech expert, and the first international guest on the podcast. Broadcasting all the way from Singapore, Rich brings a global perspective on what truly makes a high-performing sales culture—and spoiler alert, it’s not just about hitting numbers.

We dive into:

• The evolution of sales from the "Boiler Room" and "Glengarry Glen Ross" days to a more people-first leadership approach.
• Why culture—not just quotas—determines sales success.
• The challenges of moving from top-performing rep to sales leader (and why so many fail).
• Lessons from leading global sales teams across EMEA, the U.S., and APAC.
• Insights from his book, The Cultural Sales Leader, and his upcoming book on networking your way to success (including the poor treatment of job seekers today by many companies).

Rich also shares stories from his career in FinTech, his family's deep-rooted history in Singapore, and the leadership philosophy that has helped him build winning sales organizations worldwide. Whether you’re a sales pro, an aspiring leader, or just someone who loves a good "ABC - Always Be Closing" reference, this episode is packed with insights, humor, and practical takeaways.

 

Tune in for a fun and thought-provoking conversation on sales, leadership, and why the best teams are built on more than just deals and data.

 

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Rich's bio: Richard Cogswell is a people-first sales leader. He is an organizational team builder who believes that people, vision, values, and behaviors build winning sales cultures. Richard has held multiple senior sales leadership positions within a number of industries, working across EMEA, the United States, and APAC, within startups and listed multinational companies.

 

Whether newly hired or promoted, or for those with experience already gained on the journey, Richard aims to show a methodology focused on how you might best lay down the foundations for exponential and sustained growth through the sales leadership function, and critically through the catalyst of culture.

 

Living and working in Singapore, Richard's second book, MASTERING NETWORKING: Forging your own career opportunities to create the future you deserve; will be out in 2025. You can connect with Richard on LinkedIn https://www.linkedin.com/in/richardcogswell/, or find out more from Richard at www.richardcogswell.com.