Open to opportunities

Ryan Howland

@ryanhowland

I lead enterprise transformations, portfolio governance, and technology modernization from strategy through successful delivery.

United States

Message

What I'm looking for

I'm open to remote work, travel, and relocation, and seek opportunities to lead strategic transformation, enterprise portfolios, governance, technology modernization, and operational improvement.

I've led statewide Salesforce Government Cloud modernization for the Colorado Division of Vocational Rehabilitation, recovering a high-risk approximately $4M program through production deployment while managing complex requirements, integrations, governance, vendors, and delivery risk.

I've built governed portfolios, operating models, and PMO practices that turn strategy into executable outcomes. My work has improved governed project success from approximately 10% to 90% at Tacoma Public Schools, supported statewide enterprise implementations, and equipped leaders to make clearer decisions on priorities, capacity, risk, and investment.

Experience

Work history, roles, and key accomplishments

Chief Management Officer

Outlook Insight LLC

Mar 2025 - Aug 2026 (1 year 5 months)

Promoted to executive leadership of a seven-person consulting firm while remaining accountable for the Colorado Division of Vocational Rehabilitation statewide transformation. Orchestrated 90+ contributors, managed $2.5M subcontract scope, and advised the CEO on strategy and operations.