Ep. 20: Guest Derek Francis - Create a Winning Sales Culture

This Week's Episode:

In this episode of Software Sales Simplified, Matt Long and Kevin Donville engage with Derek Francis, a seasoned sales executive with over 25 years of experience. They discuss Derek's journey from engineering to sales, the importance of culture in building effective sales teams, and the challenges of scaling in the creator economy. Derek shares insights on hiring for potential, navigating over-hiring, and applying enterprise sales principles to new industries. The conversation emphasizes the need for adaptability, continuous growth, and leveraging networks in sales.

About Our Guest:

Derek Francis, Global Head of Revenue Growth for Merchfarm, is a seasoned go-to-market executive with over 24 years of experience in enterprise software, including 16 years leading high-performing teams ranging in size from 4 to over 100. He played a pivotal role in scaling a $4M startup into a $300M global business—now valued at over $5B—through strategic expansion and disciplined execution. Derek has consistently outperformed sales targets at top-tier companies such as IBM, MicroStrategy, Infor, and Contentsquare, and began his career selling ERP solutions under the mentorship of a former CFO. His expertise spans GTM strategy, operational excellence, and authentic leadership, with a proven ability to build strong cultures and diverse teams. He has led successful engagements with retail giants like Walmart, Amazon, Verizon, and Sephora, and is recognized for pioneering virtual engagement models and developing future leaders.

How to Find out More About Derek:

You can find Derek's profile on LinkedIn:

https://www.linkedin.com/in/derek-francis-176937/

How to Find MerchFarm:

https://merchfarm.com/

Chapters:

00:00 Introduction to Software Sales Simplified

01:12 Derek Francis: A Journey Through Sales

04:05 Transitioning from Engineering to Sales

09:02 The Impact of Y2K on Careers

13:52 Building a Sales Team at Clicktale

19:07 The Importance of Culture in Sales Teams

21:34 Navigating the Challenges of Scaling Sales Teams

27:21 Transitioning to the Creator Economy

32:24 Applying Enterprise Sales Principles to New Industries

35:50 Building Brands in the Creator Space

43:46 Embracing Change and Continuous Learning

47:44 Like, Follow, Subscribe, and Comment!

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Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.

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Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.