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Trusted Cybersecurity & Managed IT Services in Chicago
Reachout It is a cybersecurity-first managed service provider headquartered in Chicago, delivering structured IT systems to protect operations, ensure compliance, and build trust for SMBs nationwide. Our approach combines licensed cybersecurity protection with proactive IT support, designed to scale with businesses while maintaining audit readiness and resilience against evolving threats. Founded on the principle that structured systems outperform reactive models, we prioritize protection from the outset, offering predictable pricing and eliminating surprises. Our team of experts, led by industry-recognized leader Rick Jordan, has maintained client relationships for over a decade through operational stability and a commitment to resolving issues before they escalate. We specialize in reducing recurring IT issues by 95% within 90 days, achieving rapid resolution times under 20 minutes, and providing seamless transitions by buying out existing contracts.

Our services include 24/7 monitoring, data protection, employee security training, and compliance readiness for frameworks like HIPAA and CMMC. By focusing on process-driven solutions rather than reactive ticketing, we rebuild trust for businesses burned by traditional IT models. Our proven systems have earned recognition in cybersecurity documentaries and partnerships with law firms, healthcare providers, and enterprises seeking reliable infrastructure. With a foundation built on transparency and accountability, we ensure clients maintain control over their operations while preparing for both current and future threats.
Services
Managed IT Services Cybersecurity Protection Cloud Solutions IT Consulting Data Backup 24/7 Monitoring Employee Training Compliance Readiness Dark Web Monitoring Unified Communications
Highlights and features
  • We implement a patented cybersecurity-first approach that prevents 95% of recurring IT issues within 90 days.
  • Our team includes experts trained by the CIA, NSA, and White House consultants.
  • We guarantee 20-minute resolution times for most IT issues.
  • Clients stay with us for over a decade due to our structured, transparent systems.
  • We buy out existing contracts up to 12 months to ensure seamless transitions.
What people say
Quick response Proactive issue resolution Maintains professionalism Structured systems work Expert cybersecurity support
Services
Managed IT Services
Our Managed IT Services combine proactive monitoring with cybersecurity-first infrastructure to reduce downtime by 95% within 90 days. We provide dedicated success managers, hybrid office support, and 24/7 network monitoring without hourly rates. Clients benefit from predictable pricing, compliance readiness, and rapid resolution times under 20 minutes for most issues.
Cybersecurity Services
Cybersecurity Services include 24/7 threat hunting, breach recovery, and AI-driven protection to prevent 95% of human-error-related breaches. We offer employee training, dark web monitoring, and compliance solutions for HIPAA and PCI standards. Our team, trained by intelligence agencies, ensures businesses withstand and recover from attacks with minimal disruption.
Cloud Solutions
Cloud Solutions focus on secure, seamless transitions to cloud infrastructure with 24/7 system availability. We optimize costs, enhance collaboration through hybrid workplace tools, and provide data protection with disaster recovery. Our approach eliminates hardware expenses while ensuring secure file sharing and compliance with industry standards.
IT Consulting
IT Consulting offers co-managed solutions and fractional CIO services to address critical infrastructure gaps. We provide cybersecurity audits, server support, and project management tailored to businesses lacking internal resources. Our consultants bring corporate IT experience to design scalable systems aligned with long-term business goals.
Unified Communications
Unified Communications enable seamless connectivity through cloud-based phone systems with 98% open-rate text messaging. Features include remote deskphones, call routing, and real-time reporting. Businesses maintain communication during outages while improving customer interactions through presence indicators and mobile app integration.
People
Rick Jordan
Founder & CEO
Rick Jordan founded ReachOut after decades in tech, including congressional testimony on cybersecurity. He led high-performance teams and advised national security policy, creating structured IT systems that scale. His leadership drives the company's operational standards and client retention.
Ryan Luering
Director of Operations
Ryan Luering has served ReachOut for 10 years, rising from technician to Director of Operations. With prior experience at BestBuy's Geek Squad since 1997, he oversees daily operations and ensures delivery of structured IT systems that meet client needs.
Ashley Kedra Johnson
Executive Director
Ashley Kedra Johnson manages communications and internal operations at ReachOut. She strengthens industry relationships, oversees M&A activities, and connects the company with the Channel Community through strategic media engagement and operational leadership.
Lisa Lively
Community Engagement Manager
Lisa Lively coordinates industry events and podcast guest logistics for ReachOut. She builds relationships through small-town outreach and ensures smooth execution of community initiatives while managing event correspondence and guest onboarding.
Questions
What cybersecurity frameworks do you support?
We provide compliance readiness for HIPAA, CMMC, ITAR, and PCI standards with tailored protection systems.
How fast is your average response time?
Our average response time is 9 minutes or less for most IT issues.
Do you offer contract exit assistance?
Yes, we buy out existing contracts up to 12 months to ensure seamless transitions.
What happens during a data breach?
Our 24/7 threat hunting and incident response teams contain breaches and implement recovery plans immediately.
Can you support hybrid work environments?
Yes, our unified communications and cloud solutions enable seamless remote and office collaboration.
How do you prevent human error breaches?
We combine AI monitoring, employee training, and behavior analysis to reduce human-error-related breaches by 95%.