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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 targeting Director and senior leadership roles focused on strategic initiatives, enterprise transformation, PMO and portfolio leadership, technology modernization, and operational improvement. Open to remote work, travel, and relocation for the right opportunity.

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

Apr 2024 - Aug 2026 (2 years 4 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.

Program Management Portfolio Governance Executive Leadership Contract Management Risk Management Stakeholder Management Smartsheet Power BI Agile Scrum Waterfall UAT Vendor Management

Owner & Principal Consultant

RAK Systems LLC

Jul 2023 - Aug 2026 (3 years 1 month)

Advised organizations on transformation roadmaps, portfolio intake and prioritization, initiative sequencing, capacity and resource planning, PMIS and workflow design, executive dashboards, governance, program recovery, and operating process improvement. Designed practical delivery systems connecting strategy, proposed initiatives, dependencies, timing, resources, financial considerations, decision rights, risk, and measurable outcomes.

Transformation Advisory Portfolio Management Prioritization Resource Planning PMIS Design Workflow Design Executive Dashboards Governance Program Recovery Process Improvement Generative AI Structured Reviews

Director of Projects & Grants

Olympia School District

Sep 2021 - May 2023 (1 year 8 months)

Directed a 12-initiative strategic portfolio and introduced an organization-wide operating model connecting priorities, resources, governance, executive accountability, adaptive delivery & change, and outcome measurement. Trained 24 district and cabinet leaders to use consistent intake, prioritization, planning, risk, stakeholder communication, and performance practices.

Strategic Portfolio Management Operating Model Design Governance Executive Accountability Adaptive Delivery Change Management Stakeholder Communication Performance Measurement Coaching Leadership Development

Sr. Project Manager Enterprise PMO

Tacoma Public Schools

Feb 2017 - Sep 2021 (4 years 7 months)

Managed an estimated $4M portfolio of enterprise technology, facilities, student-success, and operating-model initiatives. Standardized intake, prioritization, governance, and reporting practices, raising governed project success from approximately 10% to 90% and contributing to a 2018 PMI PMO of the Year finalist selection.