Shawn Chakravarty

Certified InstructorSr. Director of Active Defense at Upwork

Specialities

Cybersecurity Leadership

Connect with Shawn

Shawn Chakravarty

Jump to:

Profile
Courses
Webcasts
Resources

About Shawn Chakravarty

Shawn Chakravarty teaches security leadership from the point where incidents, intelligence, cloud risk, and business pressure all need to be handled at once. A SANS Certified Instructor and Sr. Director of Active Defense at Upwork, he teaches LDR512: Security Leadership Essentials for Managers, bringing real-world experience in security operations, cyber threat intelligence, incident response, cloud security, identity, vulnerability management, and application security into the classroom. His work building and leading enterprise security programs helps students connect the course material to the decisions security leaders make when teams, tools, budgets, and business risk all meet at once.

Shawn’s background is grounded in hands-on technology roles across security, networking, cloud computing, and system administration. He previously built SOCs for PayPal, American Express Global Business Travel, and Level3 Communications, and previously served as a Senior Security Consultant for Amazon Web Services, where he helped large enterprises move into cloud environments and build incident response plans. At Upwork, he has established a 24x7 Cyber Fusion Operations Team and a Cyber Threat Intelligence Team, built automation incorporating AI, and developed metrics to show the impact of AI, threat posture and growth. He draws on those experiences while teaching the labs and Cyber42 scenarios, helping students connect topics such as building security programs, briefing boards, SOC capability, ransomware response, cloud security, vulnerability management, and GenAI risk to the decisions they face at work.

Shawn has held 5 GIAC certifications, AWS Certified Solutions Architect - Associate and the GlowUp certification from Harvard Business Publishing Corporate Learning. He serves on the GIAC Advisory Board. Shawn Chakravarty is also a faculty member of the SANS Technology Institute, an NSA Center of Academic Excellence in Cyber Defense and multi-year winner of the National Cyber League competition. Beyond teaching, he contributes to practitioner conversations on SOAR, GenAI in the SOC, identity-based attacks, zero trust, and security automation.

Shawn teaches with the same standard that first sold him on SANS as a student: training should be useful the first day back at work. He focuses on audience-inclusive communication, real incident lessons, and the “why” behind security decisions, especially when there is no clean yes-or-no answer. Students should leave able to evaluate risk, communicate with technical and business teams, build stronger security programs, and know when to flex or hold firm. He also takes pride in mentoring people who have gone on to build successful security careers, seeing their success as part of his own.

Qualifications Summary

GIAC Certifications: GIAC Cyber Threat Intelligence (GCTI), GIAC Security Leadership (GSLC), GIAC Security Operations Manager (GSOM), GIAC Cyber Incident Leader (GCIL), GIAC Information Security Professional (GISP)
AWS Certified Solutions Architect – Associate
GlowUp certification from Harvard Business Publishing Corporate Learning.
Key Achievements: Sr. Director of Active Defense at Upwork; established a 24x7 Cyber Fusion Operations Team and Cyber Threat Intelligence Team; previously built SOCs for PayPal, American Express Global Business Travel, and Level3 Communications; previously served as Senior Security Consultant for Amazon Web Services.
Course: Instructor for LDR512: Security Leadership Essentials for Managers
Community Contributions: GIAC Advisory Board member; CruiseCon speaker; mentor to developing security professionals; active in grassroots programs that encourage young people to get excited about technology