In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey sit down with Richard Cogswell, a 20-year sales veteran and author who leads the APAC region in the FinTech space. Richard shares his journey from commission-only sales in the insurance industry to becoming a B2B sales leader in the complex world of payments. Together, they discuss the critical importance of developing a mission-led culture, the pitfalls of sales leadership without a plan, and actionable strategies for creating a structured sales environment.
Join the conversation as they explore how sales leaders can move beyond the typical financial-year focus and elevate their teams with clarity, focus, and purpose. Whether you're a sales leader or a single contributor looking to up your game, this episode is packed with insights to help you build a more robust sales foundation.
Key Topics Discussed:
The Importance of a Go-to-Market Sales Plan (00:01:47): Richard highlights why many organizations lack an articulated sales strategy and the repercussions this can have on cross-functional alignment and growth.
From Surviving Year-to-Year to a Mission-Led Culture (00:04:22): The hosts dive into how sales leaders can shift from short-term financial targets to a long-term, mission-driven approach.
Creating a Structured Sales Environment (00:06:18): Richard explains the necessity of documenting your big bets and aligning your team with cross-functional partners.
Identifying and Empowering Sales Leaders (00:11:00): Learn how to recognize key players within your team and use them to foster growth and cohesion.
The Power of Salespeople Creating Their Own Plans (00:12:48): Richard shares the importance of involving sales reps in the planning process and how it strengthens accountability and execution.
Key Quotes:
Richard Cogswell: "If you're a commercial leader and you don't have a structured sales plan, I'm sorry, but that is your responsibility to create one. How else do you align your team and cross-functional leaders toward the same goals?" (00:03:18)
Sean O'Shaughnessey: "You have to have a plan. Kevin and I are often brought in as fractional VPs of sales, and the first thing we see is the absence of a plan, which is exactly why we’re needed." (00:04:43)
Kevin Lawson: "I love what you said about getting beyond the fiscal year focus and building a mission-led culture. That’s a simple, but powerful, shift every sales leader needs to understand." (00:10:31)
Additional Resources:
Richard Cogswell’s book, The Cultural Sales Leader: Sustaining People, Attaining Results, is available on Amazon, Barnes & Noble, and other retailers. https://a.co/d/1sc187j
Connect with Richard on LinkedIn for more insights into sales leadership and cultural transformation in business. https://www.linkedin.com/in/richardcogswell/
A Significant Actionable Item from this Podcast: Sales leaders should implement a one-page sales plan for their team. This document should clearly define the financial goals, top priorities, values and behaviors expected, and specific actions needed to achieve success. Ensure this plan is regularly revisited and adjusted to align with short-term and long-term goals.
Summary: In this episode, Richard Cogswell brings a wealth of experience to the table, sharing his journey from commission-only sales to leading an entire region in the FinTech industry. His insights into the necessity of structured sales plans, mission-led cultures, and empowering sales leaders are invaluable for anyone in sales leadership or aspiring to be. Whether you're managing a team or just starting out, the principles Richard discusses can help take your sales strategy from surviving to thriving. Don't miss this chance to learn how to build a focused, intentional sales culture that drives long-term success!
To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment:
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You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/
You can reach out to Sean at New Sales Expert, LLC & Sales Xceleration - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/
