Principal, Technology Strategy Advancement

About the role

The Principal, Technology Strategy Advancement plays a critical role in shaping, connecting, and activating technology strategy across a large, complex, high-visibility business segment. This role brings together business strategy, technology strategy, product roadmaps, investment planning, portfolio performance, modernization priorities, execution risks, and value realization into one clear and actionable leadership view.

Primary Responsibilities

• Create and maintain a clear technology strategy view that connects business priorities, enterprise goals, product roadmaps, technology capabilities, modernization needs, investment plans, portfolio performance, and execution outcomes.
• Translate business strategy into technology roadmap implications, investment themes, capability needs, sequencing considerations, risks, dependencies, and leadership decision points.
• Develop executive-level strategy materials, including technology strategy narratives, roadmap updates, investment alignment views, business cases, value realization views, scorecards, strategic risk summaries, tradeoff recommendations, and decision packages.
• Establish and maintain a 360-degree view of the technology organization, including strategic alignment, roadmap progress, investment health, modernization progress, technology risk, delivery confidence, dependencies, capacity, and measurable value.
• Partner with business, product, engineering, architecture, finance, cybersecurity, data, portfolio, and delivery leaders to identify gaps, overlaps, risks, dependencies, sequencing issues, investment tradeoffs, and roadmap alignment opportunities.
• Evaluate whether current and planned investments are aligned to business strategy, technology strategy, product lifecycle needs, modernization priorities, OKRs, and measurable business value.
• Support annual and quarterly planning by developing strategic inputs, roadmap alignment insights, investment framing, scorecard themes, value narratives, and leadership-ready recommendations.
• Facilitate cross-functional strategy-to-execution discussions that clarify priorities, frame tradeoffs, resolve ambiguity, align stakeholders, and convert strategic direction into actionable plans.
• Translate portfolio, roadmap, financial, OKR, delivery, and technology health information into concise insights that help leaders understand what is working, what is at risk, what decisions are needed, and where focus should shift.
• Monitor external market trends, emerging technologies, healthcare technology shifts, digital capability trends, and internal performance signals to inform technology strategy and investment recommendations.
• Drive follow-through on strategic decisions by ensuring leadership decisions are translated into clear actions, owners, milestones, scorecard measures, and execution checkpoints.

Key Deliverables

• Technology strategy narrative that clearly communicates priorities, direction, risks, and expected outcomes.
• Integrated business-to-technology roadmap view connecting business priorities, product roadmaps, technology capabilities, modernization work, investment timing, and major dependencies.
• Investment alignment view showing how funded work maps to enterprise goals, business priorities, OKRs, roadmap priorities, technology strategy, and measurable outcomes.
• Technology strategy scorecard covering roadmap progress, investment health, modernization progress, delivery confidence, technology risk, value realization, and key leadership decision points.
• Quarterly strategy-to-execution readout for senior leadership.
• Executive decision packages for major roadmap, investment, sequencing, modernization, prioritization, or tradeoff decisions.
• Strategic tradeoff memos that clarify options, risks, value, financial impact, timing, dependencies, and recommended path forward.
• 360-degree organizational health view across strategy, investments, roadmap, execution, risks, dependencies, technology health, capacity, and outcomes.
• Capability gap assessment identifying where business ambition, technology readiness, funding, capacity, or execution plans are misaligned.
• Roadmap risk and dependency assessment for major technology and business priorities.
• Value realization framework for major investments, including success measures, expected benefits, baseline metrics, and progress indicators.
• Executive briefing materials for leadership forums, business reviews, technology planning discussions, governance meetings, and investment reviews.

Required Qualifications

• Bachelor's degree in Business, Technology, Engineering, Finance, Strategy, Operations, or a related field.
• 15+ years of experience in technology strategy, enterprise strategy, portfolio management, technology transformation, strategic planning, consulting, business operations, or executive advisory roles.
• Experience supporting large, complex technology organizations with multi-year roadmaps, substantial investment portfolios ($350M+), strategic initiatives, and senior executive stakeholders.
• Proven ability to translate business strategy into technology strategy, roadmaps, investment priorities, OKRs, governance processes, and measurable business outcomes.
• Experience developing executive-level strategy deliverables, including business cases, strategic roadmaps, investment narratives, scorecards, value realization frameworks, capability assessments, and leadership decision packages.
• Strong experience aligning technology investments to business value through financial analysis, ROI modeling, benefit tracking, portfolio analytics, investment prioritization, and value realization methodologies.
• Experience partnering with senior business, technology, product, architecture, finance, data, delivery, and portfolio leaders within complex, matrixed organizations.
• Experience supporting CIO, CTO, SVP, Technology Strategy, Enterprise Strategy, Transformation Office, or Office of the CIO functions.
• Deep knowledge of technology roadmaps, strategic portfolio management, investment governance, technology modernization, technology business management, and multi-year planning.
• Strong analytical, strategic thinking, executive communication, storytelling, facilitation, and stakeholder influence skills.
• Able to synthesize complex information, develop strategic recommendations, frame executive decisions, and translate strategy into actionable plans and measurable outcomes.
• Experience facilitating executive planning sessions, investment reviews, governance forums, roadmap discussions, and strategy-to-execution operating routines.