Rocky Vienna

About Rocky Vienna

I created the Outcome-First AI Methodology, designed to guide executive and mid-management teams how to anchor AI and RPA within measurable business transformation outcomes, not just technology adoption.Technology and operations executive with 20+ years in CIO, CTO, and COO roles, driving transformation, scalability, and risk reduction across PE-backed and mid-market companies. I specialize in aligning technology and business operations strategy with investment theses to improve EBITDA, accelerate exit readiness, and create enterprise value.Across multiple M&A events and four successful SMB and PE-backed exits, I’ve delivered 5 to 15 percent valuation uplifts by implementing process transformation, financial reporting discipline, and cybersecurity programs that bring clarity and control to operational and regulatory complexity.IMPACT HIGHLIGHTS Built and led a $2M-revenue (first year) digital transformation and cybersecurity practice from inception, managing P&L, utilization, and client relationships across multiple PE firms. Delivered $15M in cost savings by launching hybrid cloud infrastructure across 4 global regions in under 6 months. Implemented a cybersecurity oversight program for PE firm and 28 of their portcos that included security assessments and roadmaps. Created product strategy for IT Managed Services. Led go-to-market planning, branding, pricing, channel creation, and customer support planning. Moved company from -7% EBITDA to +3% EBITDA in 14 months through process reengineering and strict compliance to pricing/margin tactics. Positioned the company for a positive exit. Reorganized and right-sized a healthcare technology organization of 284 personnel, including migration off a legacy platform and introduced CI/CD and Dev/Sec/Ops. Saved $3.6 million by transitioning software development back in-house to regain control, enhance integration, and increase agility.Led two companies through successful initial SOC2 Type II certifications.CORE COMPETENCIES• Board & C-Suite Stakeholder Engagement • Global Technology Architecture and Strategy• Outcome-First methodology for Digital Transformation & AI Integration• M&A Tech Due Diligence & Integration• Cybersecurity & Risk Management Program Implementation• Data Governance & Analytics • Service Delivery & Vendor Management• Organizational Restructuring & Turnaround• Change Management & Cross-Functional Leadership

Experience

1. CIO Consultant

   Innovation Vista

   Jun 2025 — Present · Bend, OR, US

   Partnering with midsize organizations to provide strategic IT leadership and guidance.• Delivering expert insights in IT assessments, strategic roadmaps, fractional/virtual CIO services, M&A/interim CIO services, information security consulting, AI strategy & governance, and board & C-suite IT advisory.• Focusing on transforming IT into a strategic asset that drives business results and enhances enterprise value.

Skills

• Analysis
• Cobit
• Pmo
• Leadership
• Business Strategy
• Contract Negotiation
• Start-Ups
• IT Strategy
• Software Documentation
• Sdlc
• Program Management
• IT Operations
• Business Continuity
• Outsourcing
• Saas
• IT Audit
• Business Analysis
• Software Project Management
• Erp
• Cloud Computing
• Software as a Service (Saas)
• Sarbanes-Oxley Act
• IT Governance
• Data Center
• Integration
• Consulting
• Project Management
• Sox
• Project Planning
• Governance
• Business Process Improvement
• Disaster Recovery
• Executive Management
• Operations Management
• Information Technology
• Testing
• Compliance
• Strategy
• E-Commerce
• Product Management