Name: Winning the War for Talent 2026: Crushing The Skills Gap, AI Disruption, Leveling Up Your Position and the Cybersecurity Executives Path to the C-Suite
Start: 2026-10-09T13:15:00-0700
End: 2026-10-09T14:00:00-0700

Winning the War for Talent 2026: Crushing The Skills Gap, AI Disruption, Leveling Up Your Position and the Cybersecurity Executives Path to the C-Suite

LIMITED

Friday October 9, 2026 1:15pm - 2:00pm PDT

➡️ 8. Empathy (Expo)

Limited Capacity seats available

Slide 1: Introduction & Speaker Bio

Founder and CEO of RED SKY Consulting: A 19-year-old provider of cybersecurity & IT staffing, executive placement, workforce management, advisory, and professional services—primarily to Fortune 100 & 500 clients.
Industry Veteran: Over 30+ years in the technology workforce management industry.
Strategic Advisor: Specializing in career pathing, compensation analysis, executive placement, cybersecurity/technology staffing, retention & attrition, culture building, and market growth.
Thought Leader: Frequent speaker at conferences; participant in advisory boards, think tanks, and summits for industry pulse.
New AI Note: In 2026, AI is reshaping cybersecurity roles—requiring expertise in AI-driven threat detection, ethical AI governance, and automated security tools—further intensifying the war for talent.

Slide 2: About RED SKY Consulting

Track Record: 19+ year history serving 50% of the Fortune 100, 25% of the Fortune 500, and progressive smaller organizations.
Approach: "High touch/white glove" approach with deep relationships and patented recruitment process for superior results.
Goal: Build long-term relationships with integrity, sincerity, and professionalism.
Philanthropy: RED SKY Foundation (forming/launching) to provide fully funded college educations to underprivileged young adults in partnership with clients (starting 2026).

Slide 3: Discussion Topics

Talent attraction and retention strategies for leaders/companies in the "War for Talent."
Trends and practices for landing the job.
Executive Focus: The evolving path to the C-Suite for cybersecurity leaders.
What to expect from a staffing partner/headhunter (candidate or hiring manager perspective).
New AI Addition: How AI is transforming the cyber workforce—new opportunities in AI security, challenges in upskilling, and AI tools for recruitment/retention.

Slide 4: State of the Cybersecurity Workforce – The Facts

Global Gap: Predicted >4 million unfilled cybersecurity jobs globally by 2026 (actuals exceeded estimates).
Rapid Growth: Unfilled jobs grew 375% (2015–2024) to 3.5M.
U.S. Reality: ~600K openings in 2024 (only 68% filled); shortages impact 85% of organizations' security.
Impact: 69% of F1000 CISOs report understaffed teams; 78% have unfilled roles; 42% take 6+ months to fill.
New AI Impact: By 2026, AI has widened the gap—demand for AI/ML specialists in cyber (e.g., adversarial AI defense, automated incident response) has surged. AI tools help fill routine roles but create new high-skill voids; organizations using AI for threat hunting report even greater talent needs.

Slide 5: Talent Attraction Strategies

Prioritize: Comprehensive understanding of priorities ("Right person – Right seat").
Source: Establish sourcing strategy (internal/vendor recruitment, referrals, etc.).
Sell: Clarify value proposition (culture, benefits, mentors, career track).
Vet: Engage/evaluate candidates (technical, personality, cultural fit).
Close: Finalize search and onboarding.
New AI Injections:
- Sourcing: Leverage AI-powered sourcing tools (e.g., LinkedIn AI, predictive analytics) to identify passive candidates with emerging skills.
- Upskilling: Highlight AI training opportunities in value prop—e.g., "Learn to govern GenAI" is a massive draw for top talent.

Slide 6: Talent Attrition – The Data & Reasons

Churn Rates: 2024 average attrition in enterprise security programs: 31%.
Top Reasons: Feel underappreciated/unable to grow (42%); lack of clear career path (35%); lack of recognition (31%); limited skill development support (25%).
Drivers: Growth dissatisfaction, low pay, poor work-life balance, feeling overlooked.
New AI Impact: AI automation of routine tasks (e.g., basic alerting) is reducing job satisfaction in entry-level roles if not paired with upskilling. Conversely, AI analytics can now predict "flight risk" employees before they resign.

Slide 7: Retaining Top Talent – Best Practices

Alignment: Accurate role positioning and satisfaction focus.
Desired Support: Workers want C-suite listening (68%); defined cyber ownership/culture (62%); training + emerging tech investment (59%).
Actionable Items: Market-aligned comp; recognition; remote work (94% desire remote options); role rotation.
New AI Injections:
- Invest in AI-specific training (e.g., prompt engineering for security, AI risk frameworks) to combat skill gaps.
- Emerging tech investments must now include AI Security Platforms—this is a top retention driver for engineers who want to stay relevant.

Slide 8: Diversity, Equity & Inclusion

Business Case: Diverse perspectives lead to better decisions, outcomes, and culture.
Moral Case: Simply the right thing to do.
RED SKY Data: 31% ethnic diversity placements; 24% gender diversity (2019–2022).
New AI Note: AI tools can reduce bias in sourcing/screening (e.g., anonymized resumes), boosting DEI. However, leaders must audit these tools to ensure the AI itself isn't biased.

Slide 9: Cybersecurity Executives' Path to the C-Suite"The modern CISO is no longer just a technologist; they are a business risk executive who speaks the language of the Board."

The Shift to "Business Executive":
- Financial Acumen: Successful executives must articulate cyber risk in terms of P&L, ROI, and Brand Reputation, not just "vulnerabilities" and "firewalls."
- Reporting Structure: Only 12% of CISOs in large enterprises report directly to the CEO. The trend is moving toward reporting to the Chief Risk Officer (CRO) or General Counsel to separate "Risk Strategy" from "IT Operations."
The "Must-Have" Skills for 2026:
- Communication: 85% of Boards cite "ability to translate technical risk to business impact" as the #1 CISO skill.
- Regulatory Navigation: Mastery of SEC disclosure rules, GDPR, and liability laws.
- Strategic Resilience: Moving from "Prevention Perfection" to "Business Resilience" (how fast can we recover?).
New AI Note:
- AI is the Boardroom Key: The fastest path to the C-Suite today is owning "AI Governance." Executives who can enable the business to use Safe AI (profit generation) ra

Speakers

Séan Donovan

CEO, RED SKY Consulting

With over 30 yrs of experience as a CEO and advisor, I have the knowledge and understanding of dynamics that can significantly enhance organizational and individual objectives within which we focus.
**About RED SKY-
> We have 8 Fortune 10, over 50% of the Fortune 100, and over 25... Read More →

Friday October 9, 2026 1:15pm - 2:00pm PDT
➡️ 8. Empathy (Expo)

Career

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Séan Donovan

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ChiBrrCon 2027

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