Every Tool You Need.
One Powerful Platform.
From AI-powered resume optimization to automated badge tracking, Cyber Wingman gives veterans, military families, and career changers a complete career acceleration toolkit.Built by veterans, for those ready to serve their next mission.
Watch the 45-Second Tour
See how Cyber Wingman helps veterans land their dream cybersecurity role
AI-Powered Career Tools
AI Resume Builder & Optimizer
Upload your resume and let our AI analyze, optimize, and transform it into an ATS-friendly masterpiece. Get real-time suggestions for every section.
Cipher AI Assistant
Your personal cybersecurity career mentor. Cipher provides expert guidance 24/7, powered by Claude AI.
Dynamic Career Roadmaps
Personalized learning paths based on your background, goals, and available time. Track progress across 10 specialized tracks — including 6 AI-augmented security roles.
Automation & Integration
Badge Automation
Sync supported certifications and badges from TryHackMe and Credly, and use the HackTheBox catalog to plan hands-on labs.
Job Description Analyzer
Paste any job posting and get instant AI analysis with tailored resume suggestions, skill gap identification, and application strategy.
LinkedIn Optimization
Transform your LinkedIn profile with AI-generated headlines, summaries, and experience descriptions optimized for recruiter searches.
Learning & Community
Curated Resource Library
Access a curated cybersecurity resource library with courses, labs, tools, and certifications. Filter by role, difficulty, and format.
Community Hub
Connect with fellow veterans transitioning into cybersecurity. Share wins, ask questions, and grow together in a Discord-style environment.
State Veterans Benefits
Comprehensive database of state-specific benefits for veterans: education, tax relief, housing, employment, and more across all 50 states.
Choose Your Level
All plans include core features. Upgrade for advanced AI and priority support.
| Feature | Free $0/mo | MOST POPULAR Plus $9/mo | Premium $19/mo |
|---|---|---|---|
| Cipher AI Messages | 10/day | 50/day | 200/day |
| AI Model | Haiku (Fast) | Sonnet (Advanced) | Sonnet (Advanced) |
| Voice Transcription | - | ✓ Whisper API | ✓ Whisper API |
| AI Resume Analysis | Basic | Full Analysis | Full + Priority |
| Resume Exports | - | 10/month | Unlimited |
| ATS Optimization | ✓ | ✓ | ✓ |
| Federal Resume Format | - | ✓ | ✓ |
| Cover Letter Generator | - | ✓ | ✓ |
| Badge Automation | - | ✓ | ✓ |
| TryHackMe Sync | Manual | Auto-sync | Auto-sync |
| Credly Integration | Manual | Auto-sync | Auto-sync |
| LinkedIn Optimization | - | ✓ | ✓ |
| Career Roadmaps | ✓ | ✓ | ✓ |
| Resource Library | ✓ | ✓ | ✓ |
| Job Description Analysis | 3/month | Unlimited | Unlimited |
| Saved Jobs | - | 100 max | Unlimited |
| Community Access | ✓ | ✓ | ✓ |
| Priority Support | - | Email + Chat | |
| Early Feature Access | - | - | ✓ |
Free
$0/mo
Plus
$9/mo
Premium
$19/mo
Ready to Accelerate Your Career?
Join veterans, military spouses, and career changers who've launched their cybersecurity careers with Cyber Wingman.
Free to start. No credit card required.