In this episode of the DevReady Podcast, host Anthony Sapountzis speaks with Jameel Rehman, Founder of Tech Sales Academy, about the challenges in tech sales education. Jameel, a former top 1% account executive at Cisco and Telstra Enterprise, transitioned into coaching after recognising a significant gap in structured sales training. He discusses the importance of organisation, problem-solving, and genuine customer relationships in achieving top sales performance. Rather than simply selling products to hit KPIs, Jameel believes great salespeople act as trusted advisors, solving business problems with integrity and a service-first mindset. His success in high-stakes enterprise sales has been driven by a structured and ethical approach, which he now shares through his academy.
Jameel’s journey into tech sales was unexpected. While working at a gym, he discovered a natural talent for selling memberships and supplements, which led him to a role in Telstra’s retail division. He quickly became a top seller but faced challenges when transitioning from B2C to B2B due to the complexity of enterprise technology sales. However, his entrepreneurial mindset allowed him to adapt, treating sales like running his own business rather than simply being an employee. This perspective made his transition into entrepreneurship seamless, as he was already accustomed to managing high-value clients and solving complex problems. The conversation takes a humorous turn as both speakers reminisce about their early jobs at Coles, sharing stories about working in produce and dairy.
Recognising a lack of formal training in tech sales, Jameel founded Tech Sales Academy to help individuals develop structured sales skills. Despite achieving top performance globally, he realised that many professionals were left to figure things out independently, without proper frameworks or guidance. After being made redundant, he saw an opportunity to build a practical and structured learning system for sales professionals. Rather than targeting enterprises, he focuses on individual development, ensuring that those who are genuinely motivated receive meaningful training to advance their careers in tech sales.
Jameel’s passion for coaching stems from his own experience as a gifted child who struggled with traditional education systems. His approach combines technical skill development with personal transformation, appealing to those who feel lost within outdated societal structures. He likens his coaching to software installation, helping individuals “download” the mindset and knowledge required for success in tech sales, much like Neo learning kung fu in The Matrix. His mission is to empower sales professionals with both the confidence and the structured processes necessary to thrive in the industry.
While tech sales shares many similarities with traditional B2B sales, it requires a strong understanding of technology solutions and their impact on customer problems. Success hinges on core sales principles—identifying ideal customers, crafting strong value propositions, and effectively navigating sales cycles. Engaging both technical and financial stakeholders often lengthens the process, making it crucial to identify high-leverage decision-makers. Jameel also highlights the importance of structured hiring for startup founders looking to transition from founder-led sales to a dedicated sales team. Finding the right “Frontier AE”—someone with a strong sales structure, a hunter mentality, and a willingness to work within startup constraints—can be the difference between stagnation and growth. Ultimately, in today’s market, building a product is easier than selling it, making sales expertise a key differentiator for startup success.
Topics Covered
- Challenges in tech sales education
- Jameel’s journey from B2C to B2B tech sales
- The importance of structure and problem-solving in sales
- Shifting from employee mindset to entrepreneurial thinking
- Founding Tech Sales Academy to fill the industry training gap
- Balancing technical and sales skills for startup success
- The role of emotional intelligence in tech sales
- Strategies for shortening the enterprise sales cycle
- Hiring and structuring a sales team for growth
- The importance of integrity and a service-first sales approach
Important Time Stamps
- Sales vs. Problem-Solving: The Key to Winning Big Deals (0:07 – 5:21)
- The Brutal Truth About Moving from B2C to B2B Sales (5:22 – 8:24)
- From Redundancy to Reinvention: The Birth of Tech Sales Academy (8:25 – 15:04)
- “Tech Sales is Like The Matrix” – Jameel Rehman on Learning & Growth (15:05 – 19:37)
- Why Technical Founders Struggle with Sales – And How to Fix It (19:38 – 21:21)
- Tech Sales vs Traditional Sales: Is There Really a Difference? (21:22 – 28:03)
- Why Selling is Harder Than Building – and What to Do About It (28:04 – 33:56)
