Proactive Cyber Defense & Offensive Security Leadership - Episode 65, Ray Ruemmele, Evolve Security

In this episode of Cyber Security Matters, hosts Harry Baldwin and Matt Rose sit down with Ray Ruemmele, Chief Revenue Officer at Evolve Security.

Ray shares insights from his 20+ year journey through enterprise technology, from selling typewriter ribbons at IBM to leading offensive security initiatives. The conversation explores the evolution of proactive cybersecurity, building high-performing teams, and why understanding your people is the foundation of great management.

About Ray Ruemmele

Ray brings over two decades of leadership experience in enterprise technology and cybersecurity. Before joining Evolve Security as CRO, he led major growth initiatives as VP of Sales at Kudelski Security and held leadership positions at IBM, Lenovo, Juniper Networks, and Okta. Ray is known for building high-performing teams that drive sustainable revenue growth and specialises in offensive, proactive cybersecurity solutions.

Key Topics Discussed:

• Career evolution from IBM typewriter ribbons to offensive security leadership
• The strategic value of big company experience versus startup agility
• Learning strategic thinking through Harvard training and the Five Forces framework
• Management philosophy: Understanding what makes your people tick
• The 45 sales kickoffs spanning a career in enterprise tech
• How the COVID pivot changed sales forever and hiring for the new reality
• The journey from individual contributor to management
• Building effective sales teams: What Ray looks for in candidates
• Offensive security and Evolve's Academy training mission
• What attracted Ray to Evolve Security and the Chicago connection
• First year as CRO: Team assessment, tools, and the 1985 Bears analogy
• The Zafran partnership and building a partner ecosystem
• Advice for entering cybersecurity: Learning, labour, and patience

About Evolve Security

Evolve Security is a leader in offensive, proactive cybersecurity solutions, specialising in continuous penetration testing and security validation. The company helps organisations move from reactive security postures to proactive threat identification and remediation.

Connect with Ray Ruemmele on LinkedIn: https://www.linkedin.com/in/rayruemmele/