Joanna Wiggum is a U.S. Air Force veteran, former big tech and enterprise security leader, and founder of Countervail. Her talks draw on military air operations, enterprise cyber defense, and real cybercrime investigations to show audiences how adversaries exploit trust, timing, pressure, and human decision-making, and how strong leadership emerges when clarity matters more than rank.
Expect real cases, dry humor at the scammers’ expense, and takeaways people can use the same day. Available for keynotes, conference sessions, executive briefings, workshops, and panels.
“Compelling session on adversarial patterns and human decision risk.”
Mayank M., ISSA Puget Sound
Heard at
- NCW Tech Alliance Cybersecurity Summit
- NAIFA Washington
- DEF CON 34 Red Team Village
- Microsoft Redmond campus forums
- ISSA Puget Sound
- Rotary Club of Chelan
- KOZI community radio
On the calendar
Upcoming engagements
Tue, Oct 27, 2026 · Leavenworth, WA
Stopping Organized Sextortion Before Children Are in Crisis
Washington State Crime Prevention Association, 48th Annual Crime Prevention & Community Engagement Conference. 1:00 to 1:50 PM, Enchantment Ballroom, Icicle Village Resort.
Fall 2026 · Chelan, WA
Rotary Club of Chelan
Returning speaker.
Recent: NCW Tech Alliance Cybersecurity Summit (speaker, “Hacker Tactics 101: Authenticated Access,” Moses Lake, October 2026); NAIFA Washington State Conference (featured speaker, September 2026); DEF CON 34 Red Team Village (workshop leader, The Authentic Operator, Las Vegas, August 2026); large forums at the Microsoft Redmond campus; ISSA Puget Sound; and regular appearances on KOZI community radio.
Signature topics
What Joanna speaks on
Adversary Thinking for Leaders
How attackers exploit trust, timing, and human behavior, and how leaders can build teams that recognize threats early and respond decisively.
Human Decision Risk in Cybersecurity
Lessons from military aviation and enterprise incident response on decision-making under pressure and maintaining clarity in high-stakes environments.
OSINT, Exposure, and Modern Targeting
How publicly available information fuels fraud, impersonation, and harassment, and how individuals and organizations can reduce their attack surface.
Cybercrime, Doxing, and Online Harassment
Insights from real investigations into digital abuse, targeted harassment, and identity-based attacks, with practical steps victims can use to regain control.
Women Leading in High-Consequence Environments
Candid look at leadership, credibility, and resilience from one of few women to serve as a B-52 Weapons Systems Officer qualified for both conventional and nuclear missions.
Audiences
Who books Joanna
- Cybersecurity teams
- Business and executive leaders
- Businesses and nonprofits
- Financial and insurance professionals
- Government and public sector
- Crime prevention audiences
- Women in leadership
- Veteran communities
Background
From Red Flag to red teams
Joanna led incident response at Microsoft across air-gapped, cloud, and AI environments, led Oracle Cloud’s red team and built its anti-abuse program, and built the first red-team program at Starbucks as Director of Cybersecurity. Across those roles she led red teaming, incident response, investigations, trust and safety, anti-abuse operations, vulnerability management, and enterprise cyber risk.
Before that, she served twelve years in the U.S. Air Force and remains a Major in the Individual Ready Reserve. She began as an enlisted airman in a Combined Air Operations Center, managing the tactical data links that share a common air picture across joint and coalition forces, then earned her commission and flew as a B-52 Weapons Systems Officer and dual-qualified Navigator on conventional and nuclear missions. The through-line has always been the same: understand the adversary better than they understand you.
Today Joanna leads Countervail, a Washington State licensed private investigation agency that brings enterprise-grade cybersecurity and investigative expertise to individuals, businesses, and nonprofits facing fraud, impersonation, ransomware, and other cyber threats.
Book Joanna for your event
Tell us the audience, date, and format, and we’ll tailor a session to the room.