Kyle Bradshaw

About Kyle Bradshaw

I lead Portfolio Management for one of the largest customer support organizations in the world, driving transformation across dozens of strategic programs that impact nearly support engineers globally. Over 20 years, I\'ve built a career at the intersection of strategy, execution, and innovation—translating complex business needs into scalable frameworks, governance structures, and enterprise systems.My approach combines strategic program leadership with technical fluency. I design and deploy portfolio planning frameworks, data architectures, and AI-first tooling platforms that improve visibility and decision-making across organizational boundaries. As a certified Prosci Change Management Practitioner, I build Centers of Excellence that standardize how teams execute programs and navigate change, publishing playbooks and delivering training that equip hundreds of program and change managers with practical, reusable standards.I thrive in environments where ambiguity meets scale—where the challenge is not just what to build, but how to align cross-functional teams, integrate execution models, and create the systems and rhythms that make enterprise transformation sustainable. Whether I\'m designing data models for real-time portfolio reporting, leading AI adoption across program management functions, or coaching teams through complex stakeholder landscapes, I focus on enabling others to execute with clarity, confidence, and impact.

Experience

1. Portfolio Manager, Customer Service & Support

   Microsoft

   Jun 2021 — Present · Redmond, WA, US

   I lead Portfolio Management for Customer Service & Support (CSS), one of the largest customer support organizations in the world, enabling transformation across dozens of business and technology-led transformational programs impacting nearly Support Engineers worldwide.Key Responsibilities• Program Strategy & Enablement: Build and execute long range strategic planning and prioritization frameworks, establish program taxonomies, maturity roadmaps, charters, and integrate execution models into dozens of teams.• Cross Functional Leadership & Governance: Drive alignment across support delivery, product engineering, change management, business management, and executive teams through structured governance and rhythm of business interactions.• Process & Framework Design: Create and deploy enterprise wide program and change management frameworks, including quarterly workshops and training across program teams to establish and maintain standards for sequencing, planning, and change readiness.• Program & Change Management Centers of Excellence: Publish playbooks outlining change management standards and program management best practices to standardize execution across strategic programs.• Program Reporting & Tooling: Partner with business teams, data stewards, Program and Change Managers to design portfolio reporting data architecture and create new apps supporting enterprise planning, program and change management workflows. Designed and implemented tool + reporting systems capturing 600+ real-time data updates, improving visibility, predictability, and decision making across program and change management inputs.• AI Innovation: Lead and execute Portfolio, Program and Change Management Office (PCMO) AI training and design of new AI-first PCMO tooling platform.

Education

• Gonzaga University

  BA, Communications/Music

  1994 — 1998

• Pendleton High School

  High School

  1990 — 1994

Skills

• Telecommunications
• Product Development
• Leadership
• Marketing Communications
• Market Research
• Marketing
• Crm
• Management Consulting
• Human-Centered Design
• Program Management
• Brand Development
• Management
• Advertising
• Account Management
• Change Management
• Budget
• Project Management
• Strategic Planning
• Brand Architecture
• Competitive Analysis
• Creative Direction
• Business Development
• Analytics
• Business Strategy
• Go-to-Market Strategy
• Budgets
• Marketing Research
• Persona Development
• Product Management
• Strategy
• Cross-Functional Team Leadership
• Retail
• Marketing Strategy
• Training
• Customer Satisfaction
• Product Marketing
• Consulting
• New Business Development
• Strategic Partnerships