Black Hat vs. RSA CISO Perceptions: Which Do They Prefer and Why?

Who is Ira Winkler?

Ira Winkler is a renowned cybersecurity expert currently serving as the Field Chief Information Security Officer (CISO) at CYE, a position he assumed in October 2022.

With nearly four decades of experience in information security, Ira has established himself as a leading figure in the industry.

Prior to joining CYE, Ira held several high-profile positions, including Chief Security Architect at Walmart and President of Secure Mentem.

His career began at the National Security Agency, where he served as an Intelligence and Computer Systems Analyst.

Ira is widely recognized for his contributions to the field, having received numerous prestigious awards.

These include the Hall of Fame award from the Information Systems Security Association, Security Magazine's 2021 Top Cybersecurity Leaders award, and the 2022 Cybersecurity Champion of the Year from the Cybersecurity Association of Maryland.

As an author, Ira has penned several bestselling books on cybersecurity and intelligence, including "You Can Stop Stupid," "Security Awareness for Dummies," and "Advanced Persistent Security."

He is also a frequent keynote speaker at global events and is known for his expertise in performing espionage simulations and developing cost-effective security programs.

Ira’s approach to cybersecurity emphasizes the human element, focusing on awareness and practical solutions to address user-related vulnerabilities.

His diverse background, which includes roles in government, industry, and academia, provides him with a unique perspective on the complex challenges of modern cybersecurity.

Pro Tip for Connecting with Ira

When reaching out to Ira, show him you’ve done your homework.

He values authenticity and a genuine interest in his work, so referencing one of his books, articles, or even a specific post on LinkedIn goes a long way.

Ira advises against generic pitches—he prefers thoughtful, relevant engagement that reflects an understanding of his unique perspectives on cybersecurity.

So, skip the cold call and instead open with a personalized insight or question related to his content.

This approach demonstrates respect for his time and an appreciation for the value he brings to the industry.

Insights and Key Takeaways

The Tiered Nature of Cybersecurity Conferences Limits Growth and Access to Information

Insight: The tiered system at cybersecurity conferences provides high-ranking attendees, like CISOs of major corporations, access to exclusive networking events, VIP dinners, and private discussions.

Meanwhile, junior or mid-level attendees are limited to general sessions and vendor-driven interactions. This model creates barriers, as access to the most valuable insights and networking opportunities is based on hierarchy.

This approach impacts more than just the attendee experience; it restricts knowledge flow and discourages cross-functional mentorship and learning within the industry.

Mid-level and junior practitioners are often the ones implementing cybersecurity strategies, and they need access to these insights to stay effective.

With limited networking and educational opportunities, they miss out on critical skills and connections, impacting the industry as a whole.

• Restricts Knowledge Flow: By reserving key networking and discussions for senior leaders, conferences limit exposure to emerging trends and strategic conversations for practitioners who need them most.

• Limits Career Development: Access to seasoned cybersecurity leaders for mentorship and guidance is critical for early-career professionals, yet tiered events prevent this, stunting talent development.

• Creates Division in the Industry: This exclusivity reinforces divisions within the cybersecurity community, with senior leaders gaining benefits while the next generation lacks similar access to resources and connections.

Broadening access and dismantling these tiers would allow professionals across all levels to learn from each other, driving collective growth and addressing knowledge gaps that could otherwise widen as threats evolve.

Commercialization Undermines the Educational Value of Conferences

Insight: Cybersecurity conferences, originally intended as forums for cutting-edge research and technical insight, are now becoming platforms for vendor promotion.

Black Hat, for instance, is often criticized for prioritizing commercial interests over unbiased, educational content, diluting its value to attendees seeking actionable knowledge.

When education is replaced by vendor sponsorships, the conference’s purpose shifts from sharing knowledge to selling products.

Attendees, who come looking for technical insights, may leave with few practical takeaways, impacting their ability to address emerging threats effectively.

Additionally, it drives seasoned practitioners away, weakening the community’s overall knowledge pool.

• Erodes the Conference’s Reputation: Attendees seek actionable, research-driven content. When this is replaced by pitches and promotional content, it reduces the conference’s perceived value and impacts attendee loyalty.

• Alienates Experienced Professionals: Practitioners looking for in-depth, technical insights will avoid events they see as vendor showcases, eroding the event’s influence and credibility.

• Missed Opportunity for Industry Progress: These conferences are meant to foster industry-wide innovation and collaboration. By focusing on sales, they miss out on potentially transformative discussions about vulnerabilities and solutions.

Refocusing conferences on education over commercialization can ensure they remain relevant and valuable for practitioners, allowing for honest dialogue and exploration of real-world challenges.

The Importance of Personalization in Outreach to CISOs and Security Leaders

Insight: Ira shared his experiences with impersonal and aggressive outreach tactics, like cold calls and repetitive LinkedIn messages, that often alienate rather than engage.

For cybersecurity professionals, especially CISOs, personalization in outreach is essential. Understanding the unique challenges of a cybersecurity leader’s role and tailoring outreach accordingly fosters genuine interest and trust.

Personalization isn’t just a best practice; it’s critical to building trust with CISOs and influencing their buying decisions.

Impersonal outreach only reinforces the stereotype of vendors as pushy and out of touch with real challenges.

For marketing and sales teams, creating content that resonates with a CISO’s specific pain points and values demonstrates expertise and a commitment to understanding their needs.

• Builds Long-Term Relationships: Taking the time to address a CISO’s unique challenges creates rapport, leading to potential long-term partnerships.

• Improves Brand Perception: Personalization reflects well on a brand, signaling that the vendor cares enough to understand the CISO’s role and challenges rather than blanket-marketing to them.

• Demonstrates Industry Credibility: Customized thought leadership, such as insightful whitepapers or tailored content, establishes the vendor as a knowledgeable resource.

Incorporating personalization and relevant thought leadership into outreach strategies can change how cybersecurity leaders view vendors, positioning them as valuable partners instead of sales-driven outsiders.

Broadening Engagement Beyond CISOs to Include the Whole Security Team"

Insight: Vendors often target only the CISO, believing this to be the most effective way to secure a contract.

However, cybersecurity purchasing decisions are often influenced by various team members, from architects to engineers.

Engaging this broader team builds stronger relationships, as they are usually more involved in the product’s day-to-day application.

Marketing to the entire security team provides vendors with a more nuanced understanding of an organization’s needs and builds a more genuine connection.

It also positions vendors to address specific pain points at different levels, increasing the likelihood of their product being selected and successfully implemented.

• Increases Relevance and Buy-In: By engaging those who will use the tool directly, vendors can understand technical needs and gain product champions within the organization.

• Creates Stronger Brand Loyalty: Engaging the broader team creates a brand connection across multiple levels of an organization, which can result in better product adoption and customer retention.

• Reduces Reliance on a Single Decision-Maker: Engaging only with the CISO is risky, as they may not be as involved in the final product decision. Engaging multiple stakeholders reduces this risk.

Reaching out to various levels within an organization is a smarter strategy that aligns with how decisions are made and ensures vendors are perceived as truly in tune with the organization’s needs.

The Pitfalls of Targeting Large Enterprises for Small Startups"

Insight: A common mistake among cybersecurity startups is attempting to secure deals with large corporations before they’re ready.

While it may seem lucrative to land a Fortune 100 client, the complexities involved can overwhelm a small team.

Instead, mid-sized organizations may offer more manageable opportunities and allow for sustainable growth.

Targeting massive corporations can lead startups into costly, lengthy engagements they aren’t equipped to handle.

The legal, technical, and administrative demands of large corporations can drain resources, delay implementation, and potentially damage the startup’s reputation. Instead, focusing on mid-sized companies provides a more achievable path to growth, allowing startups to refine their product and build momentum.

• Aligns with Startups’ Resources: Mid-sized companies require less red tape, making contracts easier to navigate and increasing the speed of deployment.

• Provides Room to Scale: By focusing on mid-sized clients, startups can refine their offerings without overwhelming their capacity, setting themselves up for growth rather than potential burnout.

• Builds Credibility for Future Enterprise Clients: Successfully working with mid-sized companies provides a track record of success and stability that future enterprise clients will value.

For startups, targeting mid-sized companies provides a realistic growth path that aligns with their capacity and prepares them for the more complex needs of large corporations over time.

The Decline of Technical Content in Cybersecurity Conferences

Once known for technical research and cutting-edge content, conferences like Black Hat are seeing fewer research-driven sessions.

The traditional appeal of Black Hat, with its focus on zero-day vulnerabilities and high-level technical insights, has been replaced by more commercial topics, with a noticeable decline in truly technical sessions.

This decline in technical content is not just a disservice to the attendees; it also represents a missed opportunity to address pressing cybersecurity challenges.

When conferences prioritize commercial over technical content, the depth of industry knowledge suffers.

Without engaging, research-driven sessions, security practitioners may skip these events or lose respect for them, potentially weakening the professional community.

• Weakens the Conference’s Value Proposition: As more events move away from technical content, practitioners may lose interest and feel they’re not receiving actionable insights.

• Impacts Real-World Solutions: Conferences are a place to present and discuss advanced technical issues. Without these discussions, the industry’s ability to address complex cybersecurity threats diminishes.

• Erodes Trust Among Practitioners: CISOs and security practitioners want practical takeaways, not vendor-driven content. By neglecting this, conferences risk losing the trust and attendance of experienced professionals.

Returning to technical content can restore the reputation of cybersecurity conferences, drawing in attendees who are seeking real insights and practical solutions.

The Misleading Concept of Hacker ‘Summer Camp’

Insight: The phrase "Hacker Summer Camp" has become synonymous with Black Hat and DEF CON, trivializing the serious nature of these events.

By branding them as casual, social events, the term detracts from the critical research and security work the industry needs.

The relaxed connotation can create a misalignment with the industry’s core mission and may discourage new talent from engaging with these conferences seriously.

This casual branding does more harm than good, as it diminishes the importance of cybersecurity as a profession.

In an industry where the stakes are incredibly high, framing conferences as “summer camp” misses the point and can alienate practitioners who take their roles seriously.

The term reinforces a culture of elitism, as those who take part may feel validated, while others may see it as exclusionary or unserious.

• Devalues the Profession: Framing serious cybersecurity work as “summer camp” sends the wrong message, downplaying the industry’s importance and potentially deterring serious professionals.

• Reinforces Exclusivity: This branding can imply that the conferences are only for a select few who fit a particular culture, potentially turning away practitioners who don’t identify with the “hacker” archetype.

• Confuses the Industry’s Image: “Hacker Summer Camp” portrays an unprofessional image to outsiders, potentially affecting recruitment and talent retention.

Rebranding and reframing these events as serious professional gatherings could help the cybersecurity community reinforce its importance and welcome a more diverse range of participants.

My Final Thoughts

I’ll be honest—cybersecurity conferences are losing their way. '

When I first started attending, these events felt like places where anyone, at any level, could connect, learn, and challenge ideas.

Now, too many conferences seem more like exclusive clubs, where the VIPs have their own dinner parties, and the rest get vendor pitches and crowded networking “opportunities.”

It’s as if we’ve forgotten what these gatherings were supposed to be about.

I’ve seen how this affects the industry.

When only a few get access to valuable insights and high-level networking, it leaves out the voices and ideas we need most—the junior professionals, the hands-on experts, the ones doing the work every day.

We’re creating a gap in knowledge and opportunity, and that gap doesn’t just hurt those on the outside; it weakens us all.

The industry needs fresh perspectives, shared insights, and collaborative problem-solving, not just the same voices in the same VIP rooms.

So here’s my hope:

Let’s take a hard look at these events and ask ourselves what they could be.

Imagine if conferences truly centered around learning and community, with open access to real insights, not just a race for who can throw the flashiest after-party.

Imagine if every attendee, from intern to executive, left feeling like they’d gained something valuable.

That’s the industry I want to be part of—and the kind of conference I’d be proud to support.

Until next time,
Dani