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ChiBrrCon 2027
Type: Career clear filter
Friday, October 9
 

10:15am PDT

The challenges of tech education and the lack of practical experience
FULL
Friday October 9, 2026 10:15am - 11:00am PDT
Limited Capacity full
Today's technological studies do not address the needs of the industry, graduates arrive with a methodology but without practical experience - the discussion will discuss the challenges and solutions
Speakers
avatar for Rasin Alexander

Rasin Alexander

Professor, DePaul University
Challenges of matching cyber&tech workforce - the content currently taught in relation to the needs of the industry.

The general cybersecurity landscape and the insufficient focus on fundamental research and operating systems research to solve current cyber problems. ... Read More →
avatar for Dean Cantave

Dean Cantave

Deputy CIO IT Infrastructure and Operations, State of Illinois Department of Innovation and Technology
I am an IT executive and people-centered leader with more than 25 years of experience leading IT infrastructure, IT project management, operations, cloud platforms, and enterprise modernization across complex public-sector and private sector enterprise environments.

I currently serve as Deputy CIO for IT Infrastructure & Operations supporting the Illinois Department of Children and Family Services (DCFS) within the State of Illinois. In this role, I oversee large-scale infrastructure and cloud operations, IT service management (ITSM), operational... Read More →
avatar for Oron Mincha

Oron Mincha

North America GM, cyberpro.ai
Challenges of matching cyber&tech workforce - The content currently taught in relation to the needs of the industry
avatar for Michael Phillips

Michael Phillips

Proud ChiBrrCon Board Member!Michael Phillips is a seasoned Information Security and Technology leader with 40 years of experience in the Financial Services industry. He has held executive IT & Security roles at the Federal Reserve Bank of Chicago, UBS, SBC Warburg Dillon Read, Rosenthal... Read More →
Friday October 9, 2026 10:15am - 11:00am PDT
↙️ 4. Paranoia (Hermann Lounge) Hermann Hall Conference Center, 3241 S Federal St, Chicago, IL 60616, USA

10:15am PDT

Partner Expo and Sponsor Recruiting Desk Area
Friday October 9, 2026 10:15am - 4:00pm PDT
Meet and greet our Partners at their expo tables, and Sponsors who have recruiting tables!
Friday October 9, 2026 10:15am - 4:00pm PDT
⬇️ 7. Hope / Village 1 (Gallery Lounge)

11:15am PDT

From Immigrant Resilience to Cyber Resilience: A Practical Roadmap for Career Pivoting
FULL
Friday October 9, 2026 11:15am - 12:00pm PDT
Limited Capacity full
1. Opening – “From Lima to Cyber” (5 min)
  • Arriving in the U.S. at 17
  • Waiting years to adjust status
  • Navigating out-of-status challenges
  • The resilience that shaped the cybersecurity pivot
2. Education & Reinvention (6 min)
  • Pivoting into cyber in 2024
  • Bootcamp → peer mentor
  • Graduating top of cohort (4.0 GPA)
  • Turning adversity into fuel
3. Certifications With Strategy (5 min)
  • Studying Security+ efficiently
  • Building consistency and momentum
  • Making complex topics simple
4. Networking With Intention (8 min)
  • 52 → 3,400+ LinkedIn connections
  • How volunteering opened doors (BSides, ISACA, Raíces, WiCyS, Mea's Cohort, COTY)
  • Approaching CISOs and leaders confidently
  • Asking boldly, serving genuinely
5. GRC & Entry-Level Cyber Paths (5 min)
  • Why GRC is the choice for me
  • Your value is in who you are, not the title of your role
6. Identity as a Competitive Advantage (6 min)
  • Woman, Latina, Peruvian, immigrant, minority
  • Why these are strengths, not liabilities
  • Why she does NOT believe in imposter syndrome
  • Empowering the young, the overlooked, the seasoned pivoters
7. What has worked and what didn't(3 min)
  • Daily habits and routines
  • How to be visible, credible, and unforgettable
8. Closing (2 min)
  • Purpose, faith, legacy
  • Dreams don’t expire—people just stop pursuing them
Speakers
avatar for Diana Sofia (Sofi) Rodriguez

Diana Sofia (Sofi) Rodriguez

GRC analyst intern, TalentFish
Diana Sofia “Sofi” Rodriguez is a faith‑driven cybersecurity professional and human‑centered cyber advocate, whose journey from Peruvian immigrant to U.S. citizen and emerging GRC leader has inspired thousands. Guided by prayer, purpose, and Kairos time—God’s appointed... Read More →
Friday October 9, 2026 11:15am - 12:00pm PDT
↙️ 4. Paranoia (Hermann Lounge) Hermann Hall Conference Center, 3241 S Federal St, Chicago, IL 60616, USA

12:15pm PDT

CISOs/Senior Mgrs only -- CISO Roundtable: Architecting the Future of the CISO Role
FULL
Friday October 9, 2026 12:15pm - 1:00pm PDT
Limited Capacity full
This session is for CISOs (or the equivalent senior-most security manager), or direct reports to same.
Séan Donovan brings back a favorite session from earlier ChiBrrCons!

In an era of shrinking tenures and expanding liabilities, the modern CISO needs more than technical acumen—they need a survival guide and a strategic roadmap.
Join Séan Donovan (CEO, RED SKY Consulting), strategic advisor to the Fortune 100 "C" Suite, and the industry’s trusted "C-Suite Consigliere," for a high-impact, closed-door roundtable designed exclusively for sitting executives. Séan, a strategic partner to 50% of the Fortune 100, brings his proprietary Triton Methodology and 35+ years of human capital expertise to the table and to YOU & your direct benefit. This is not a lecture; it is a guided collaborative forum. We will dissect the reality of the executive "meat grinder," exploring how to convert pressure into career velocity and command the boardroom. 

Speakers
avatar for Séan Donovan

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 12:15pm - 1:00pm PDT
⬇️⤵️↩️ (Classroom HH-010 Downstairs)
  Career

1:15pm PDT

From the Barrio to the Blue Team: Using AI to Elevate your Career
FULL
Friday October 9, 2026 1:15pm - 2:00pm PDT
Limited Capacity full
Cybersecurity is evolving fast and so are the opportunities to enter and grow within the field. But for many, especially those from underrepresented or nontraditional backgrounds, breaking in can feel overwhelming. At the same time, artificial intelligence is transforming the way defenders detect threats, hunt adversaries and build careers.
 
In this session, Rosaileen Iandolo, VP of Cybersecurity, shares her journey from the barrio to leading security operations, threat intelligence, and detection engineering. She will demonstrate how AI-powered tools can accelerate learning, remove barriers, and empower aspiring professionals to carve out a place on blue teams. Beyond the technical, she’ll also explore how AI can boost soft skills, from drafting professional communications to preparing presentations and interviews. 
 
Attendees will walk away with:
  • Practical examples of how AI can support security operations and personal skill-building
  • Ways AI can strengthen communication, confidence, and career mobility
  • A roadmap for using AI not just as a technical accelerator, but as a career elevator
This session blends technical insight with career strategy, designed for students, early-career practitioners, and anyone ready to leverage AI to create opportunities and drive impact in cybersecurity.
Speakers
avatar for Rosaileen Iandolo

Rosaileen Iandolo

Vice President of Cybersecurity, Golub Capital
Rosaileen Iandolo is a CISSP-certified cybersecurity leader with over 15 years of experience spanning the financial sector and government, including 7 years with the FBI. As Vice President of Cybersecurity at Golub Capital, she leads security operations, threat intelligence and detection... Read More →
Friday October 9, 2026 1:15pm - 2:00pm PDT
↙️ 4. Paranoia (Hermann Lounge) Hermann Hall Conference Center, 3241 S Federal St, Chicago, IL 60616, USA

1:15pm PDT

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
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
avatar for Séan Donovan

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)

3:15pm PDT

WiCyS Panel - Community-Driven Success: How One Nonprofit Transforms Cyber Careers
LIMITED
Friday October 9, 2026 3:15pm - 4:00pm PDT
Limited Capacity seats available
Michael Phillips moderates a wide-ranging discussion panel of distinguished guests from our WiCyS partners. 

Join our panelists as they share how WiCyS (Women in Cybersecurity) as a nonprofit organization has transformed their cybersecurity careers. Discover programming for all career levels, the benefits of membership, and the strategies behind building an award-winning cyber community. Whether you're breaking into the field or advancing to leadership, this panel offers practical insights on how community drives career success.

Speakers
KB

Kevan Bard

Director of Product Security, Morningstar

SC

Stella Camacho

President, Wicys Chicago Affiliate
avatar for Cheton Jackson

Cheton Jackson

Director of Volunteers, Wicys Chicago Affiliate

avatar for Michael Phillips

Michael Phillips

Proud ChiBrrCon Board Member!Michael Phillips is a seasoned Information Security and Technology leader with 40 years of experience in the Financial Services industry. He has held executive IT & Security roles at the Federal Reserve Bank of Chicago, UBS, SBC Warburg Dillon Read, Rosenthal... Read More →
avatar for Uljana Sejko

Uljana Sejko

Director of Marketing, WiCyS Chicago Affiliate
Translation is Uljana's superpower: not just between languages, but between technical complexity, cultural contexts, and business objectives. As a patent-holding Solutions Engineer at Cisco and Director of Marketing for WiCyS Chicago, she turns the technical into business value and... Read More →
Friday October 9, 2026 3:15pm - 4:00pm PDT
⏺️ 6. Harmony (Auditorium) Hermann Hall Conference Center, 3241 S Federal St, Chicago, IL 60616, USA
 
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