Richard Rick Olsen

About Richard Rick Olsen

Visionary, business-driven IT Executive with 20+ years of leadership spanning infrastructure, operations, cybersecurity, and enterprise IT strategy in dynamic, high-growth, and post-M&A environments. Expertise aligning technology initiatives with business objectives, scaling systems for 10x workforce growth, and enhancing operational resilience and cost efficiency. Trusted partner to executive leadership and audit committees, specializing in IT governance, SOC/SOX compliance, and digital transformation. Renowned for fostering innovation, building high-performance teams, and positioning IT as a strategic enabler of organizational success.CORE COMPETENCIESIT Strategy & Road mapping · Enterprise Infrastructure · Digital Transformation · IT Governance & Compliance · Cloud Computing (AWS, Azure) · Disaster Recovery & BCP · Budgeting & Cost Optimization · Cybersecurity & Risk Management · Executive Stakeholder Engagement · ITIL & Service Management · SOC 1/2, SOX Compliance · Vendor Negotiation · M&A Integration · Leadership & Team Development

Experience

1. Senior Director of Information Technology

   Lessen

   Jun 2013 — Present · Chicago, IL, US

   Executive leader responsible for infrastructure, IT operations, cybersecurity, and compliance for a private equity-backed property services platform. Guided IT through multiple growth phases, including merger and integration with SMS Assist, and enterprise scale-up from 100 to users.• Cloud Strategy: Architected and executed a full cloud-first strategy, modernizing infrastructure for 24/7 scalability and resiliency.• Technical Infrastructure Management: Oversaw the design and implementation of robust IT infrastructure, including data centers, networking, and storage solutions, to support business operations.• Support Operations: Established a centralized IT support structure, improving incident response times and user satisfaction through effective ticketing systems and ITIL-based processes.• Risk & Compliance: Chaired the Enterprise Risk Committee, leading SOC 1/2 Type II readiness and audits.• IAM Deployment: Implemented Okta enterprise IAM, streamlining user provisioning and enhancing security across SaaS and cloud platforms.• Disaster Recovery & BCP: Designed and operationalized a company-wide business continuity program, ensuring minimal disruption and rapid recovery.• Financial Stewardship: Achieved multimillion-dollar cost savings through strategic vendor negotiations and modernization of legacy infrastructure.• Corporate Social Responsibility: Founded “Computers for Kids,” providing refurbished laptops to underserved families.

Education

• DeVry University

  B.S., Computer Information Systems

  1986 — 1990

• Keller Graduate School of Management of DeVry University

  Master of Business Administration - MBA

  2002 — 2004

Skills

• Vmware
• System Administration
• Microsoft Exchange
• Networking
• Budgets
• Contract Negotiation
• Checkpoint
• Data Center
• Citrix
• Infrastructure
• Project Management
• Cisco Technologies
• Leadership
• Team Leadership
• Facilities Management
• Active Directory
• Windows Server
• Disaster Recovery
• Process Improvement
• Cisco Routers
• IT Operations
• Management
• Servers
• Vendor Management
• Saas
• Security
• Enterprise Software
• Information Technology
• Technical Support
• Wan
• Virtualization
• Sdlc
• Blackberry Enterprise Server
• Sharepoint