How to Successfully Work Your Way Into a CISOs Inbox

Who is George Al-Koura?

George Al-Koura is the Chief Information Security Officer (CISO) at Ruby Life Ltd. With nearly two decades of experience in the field, George has built a diverse and impressive career spanning military, civilian, and commercial sectors.

George's journey in cybersecurity began in an unconventional manner. He studied political science and psychology at the Royal Military College of Canada and served in the Canadian Army regular forces until 2016 as a communications research operator.

This military background provided him with a unique perspective and valuable skills that he later applied to his cybersecurity career.

After transitioning to the private sector, George quickly made his mark in the cybersecurity industry.

He started as a junior analyst and rapidly progressed through various roles, including building and leading threat intelligence services.

His approach to cybersecurity is shaped by his military intelligence training, allowing him to offer innovative solutions that stand out in the market.

As CISO at Ruby Life, an online dating company, George emphasizes the importance of humanizing cybersecurity and building strong team cohesion.

He is known for his people-first approach, focusing on creating genuine relationships with team members and potential talents. This strategy has helped him build effective teams even in competitive markets.

George is also recognized for his collaborative leadership style, particularly in his relationships with CIOs and other executives.

He has played a key role in achieving important certifications for his organizations, such as ISO 27001.

Throughout his career, George has demonstrated a commitment to continuous learning and adaptability.

His journey from a military background to a leading role in cybersecurity showcases his ability to leverage diverse experiences for success in the tech industry.

George's leadership philosophy centers on fostering real human connections and viewing employment as a means to improve the quality of life for his team members.

Pro Tip for Connecting with George

To connect effectively with George Al-Koura, start by being clear and concise in your communication.

He values straightforward messages that deliver value quickly, so lead with your purpose within the first few sentences.

Show that you’ve done your homework by referencing his specific interests or recent professional milestones.

Personalized messages that demonstrate genuine research will set you apart.

Focus on building long-term, trust-based relationships rather than pushing for quick sales.

George appreciates vendors who can solve problems creatively.

Present solutions tailored to his specific challenges, using case studies or examples that show you understand his needs.

It’s also crucial to respect his boundaries—avoid overly aggressive tactics, especially if he’s shown disinterest.

If George doesn’t respond after a couple of outreach attempts, back off respectfully and try a different angle or time.

He’s drawn to vendors who can support him during critical moments, even when there’s no immediate contract.

Offering timely assistance, like advice or resources, can strengthen your relationship.

Insights and Key Takeaways

The Military-Cybersecurity Career Path: Why It Works

Insight: Many veterans transition into cybersecurity roles, not because of specific skills acquired in the military, but due to a disciplined mindset that aligns well with cybersecurity's demands.

Military training instills a unique, rigorous way of thinking that emphasizes operational security (OPSEC), communication security (COMSEC), and disciplined problem-solving—critical attributes in cybersecurity roles.

Veterans are trained to approach tasks methodically, make clear decisions under pressure, and handle sensitive information.

These traits are not only advantageous in operational roles but also in cybersecurity sales, architecture, and management, where clear communication and disciplined processes are highly valued.

For marketing and sales teams targeting cybersecurity buyers with military backgrounds, it’s crucial to respect their disciplined approach.

Communicate clearly, offer direct solutions, and emphasize operational benefits.

Authentic engagement that mirrors the directness and structure they’re accustomed to will foster stronger connections.

Dehumanizing Sales Tactics are Pushing Buyers Away

Insight: Cybersecurity sales, driven by impersonal and aggressive quotas, often lack the human touch necessary for meaningful relationships, creating a barrier between vendors and CISOs.

George’s frustration with the industry centers on how dehumanizing many sales processes have become.

Sales teams are often pushed to hit unrealistic growth targets, resulting in impersonal “spray and pray” tactics.

The issue extends beyond sales pitches to big consulting firms, where billable quotas, steep prices, and minimal benefits lead to resentment and high burnout rates.

This approach not only harms relationships but also damages brand perception and deters future engagement.

Marketers and sales teams must shift from volume-driven strategies to more thoughtful, personalized outreach.

Building genuine relationships, emphasizing quality interactions, and showing empathy can help bridge the gap with CISOs who often see through impersonal tactics.

Humanizing Sales Outreach for CISOs

Insight: Treating CISOs like humans, rather than targets, is critical to earning their trust and securing long-term relationships.

CISOs are overwhelmed with impersonal sales pitches that often come across as either gimmicky or disingenuous.

George advocates for a humanizing approach that involves personalized communication, custom content, and genuine conversation.

Tailored outreach, including thoughtful video messages or voice clips, is more effective than generic pitches.

Marketers and sales teams should prioritize authenticity and make CISOs feel valued as individuals, not just sales targets.

Taking time to research their needs and engaging in real conversations rather than pushing for immediate sales can pave the way for more successful outcomes.

Achieving Organizational Buy-In is the Biggest Challenge for CISOs

Insight: As the CISO at Ruby, George's biggest challenge is ensuring that organizational stakeholders understand the importance of security initiatives and fully support them, both financially and strategically.

Inheriting another CISO’s security environment often comes with legacy issues that need to be addressed, making it harder to introduce new technologies or processes.

George emphasizes the importance of communication and collaboration among stakeholders to drive security forward.

His management philosophy is rooted in empowering his team and providing flexibility, which results in higher job satisfaction and stronger performance.

Understanding this challenge helps marketers frame their messaging to CISOs in a way that highlights how their solution can ease stakeholder buy-in, address legacy issues, and fit seamlessly into existing operations.

It’s also crucial to emphasize the benefits of empowering security teams with tools that are easy to implement and use.

Shifting Trends: Move Towards Authenticity Over AI-Driven Marketing

Insight: There is a growing market preference for more human, localized campaigns over broad, AI-driven initiatives.

While AI tools have become integral in marketing, George believes that authenticity still matters most to buyers.

He emphasizes that engaging a human artist, for instance, to create marketing materials can make campaigns feel more genuine.

Similarly, marketing strategies are shifting toward smaller, localized efforts that foster trust within specific communities rather than broad, impersonal outreach.

Marketing teams should consider shifting from large-scale, AI-centric campaigns to more focused, human-driven efforts. Investing in local events, authentic storytelling, and genuine buyer engagement will resonate more deeply with cybersecurity audiences.

Building Trust Digitally: Professionalism First, Personal Connection Second

Insight: Digital trust-building requires delivering reliable products and services on time, at the agreed price, while also being open to personal connection.

The first step in earning digital trust is meeting professional expectations consistently.

However, George points out that meaningful personal connections can also be formed digitally.

He emphasizes the importance of finding common ground and being open to vulnerability when engaging with buyers online.

Sales teams should focus on delivering what they promise and creating a sense of personal connection whenever possible.

Use video calls to display genuine interest, look for shared interests, and maintain regular follow-ups that balance professionalism with authentic engagement.

Cardinal Rules for Sales: Avoid Stalking and Recognize Disinterest

Insight: Two key sales mistakes are persistent stalking tactics and failing to recognize when a prospect is uninterested.

George warns that aggressive tactics like social engineering, where sales teams seek personal information about prospects, cross ethical boundaries.

He also notes that if a prospect hasn’t responded after several attempts, it’s time to move on.

Constant follow-ups without a response can hurt a brand’s reputation.

Marketers and salespeople should respect boundaries and read cues more effectively.

When a prospect is unresponsive, it’s often better to shift focus elsewhere rather than persist and risk damaging the relationship permanently.

My Final Thoughts

The cybersecurity world is complicated, but relationships don’t have to be.

At the end of the day, authenticity, respect, and a genuine willingness to help will always win.

The best marketing strategies put people first and metrics second.

It’s about being human in a digital world, taking risks to connect deeply, and embracing vulnerability to create lasting trust.

If you want to stand out in this industry, be the marketer or seller who genuinely listens and makes the extra effort to understand—not just sell.

Until next time,
Dani