Principal, Technology Strategy Advancement

This is a fully remote position, open to applicants in Florida, +4 more states.

📋 Description

• Design, connect, and implement technology strategy across a vast, intricate, and highly visible business segment.

• Integrate business strategy, technology strategy, product roadmaps, investment planning, portfolio performance, modernization priorities, execution risks, and value realization.

• Develop and sustain technology strategy perspectives that align business priorities with enterprise goals, product roadmaps, technology capabilities, modernization requirements, investment plans, portfolio performance, and execution outcomes.

• Convert business strategy into implications for roadmaps, investment themes, capability needs, sequencing considerations, risks, dependencies, and leadership decision points.

• Create executive-level strategy narratives, roadmap updates, investment alignment perspectives, business cases, value realization views, scorecards, strategic risk summaries, tradeoff recommendations, and decision packages.

• Establish a comprehensive view of the technology organization’s health, encompassing strategic alignment, roadmap advancement, investment health, modernization progress, technology risk, delivery confidence, dependencies, capacity, and measurable value.

• Collaborate with business, product, engineering, architecture, finance, cybersecurity, data, portfolio, and delivery leaders.

• Assess the alignment of existing and planned investments with business strategy, technology strategy, product lifecycle requirements, modernization priorities, OKRs, and measurable business value.

• Develop value frameworks, success metrics, baseline measurements, financial assumptions, and value realization perspectives for significant initiatives.

• Assist in annual and quarterly planning with strategic inputs, roadmap alignment insights, investment framing, scorecard themes, value narratives, and leadership-ready recommendations.

• Facilitate cross-functional discussions to translate strategy into execution, clarify priorities, frame tradeoffs, resolve ambiguities, align stakeholders, and convert strategy into actionable plans.

• Transform portfolio, roadmap, financial, OKR, delivery, and technology health information into succinct leadership insights.

• Keep abreast of market trends, emerging technologies, healthcare technology shifts, digital capability trends, and internal performance indicators.

• Ensure follow-through by transforming leadership decisions into actions, responsibilities, milestones, scorecard measures, and execution checkpoints.

• Report to a Director of IT Portfolio Management.

• Function as an individual contributor without direct reports.

⛳️ Requirements

• Bachelor's degree in Business, Technology, Engineering, Finance, Strategy, Operations, or a related field, or equivalent work experience.

• Over 15 years of experience in technology strategy, enterprise strategy, portfolio management, technology transformation, strategic planning, consulting, business operations, or executive advisory roles.

• Proven experience supporting large, complex technology organizations with multi-year roadmaps and significant investment portfolios exceeding $350M.

• Experience working with strategic initiatives and senior executive stakeholders.

• Capability to translate business strategy into technology strategy, roadmaps, investment priorities, OKRs, governance processes, and measurable business outcomes.

• Experience in producing executive-level strategy deliverables, including business cases, strategic roadmaps, investment narratives, scorecards, value realization frameworks, capability assessments, and leadership decision packages.

• Proficiency in aligning technology investments with business value through financial analysis, ROI modeling, benefit tracking, portfolio analytics, investment prioritization, and value realization methodologies.

• Experience collaborating with senior leaders in business, technology, product, architecture, finance, data, delivery, and portfolio within complex, matrixed organizations.

• Background supporting CIO, CTO, SVP, Technology Strategy, Enterprise Strategy, Transformation Office, or Office of the CIO functions.

• Comprehensive 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.

• Ability to synthesize complex information, develop strategic recommendations, frame executive decisions, and convert strategy into actionable plans and measurable outcomes.

• Experience facilitating executive planning sessions, investment reviews, governance forums, roadmap discussions, and strategy-to-execution operating routines.

• Must reside near one of the specified market locations.

• This position is not eligible for work visa sponsorship.

• Must meet home internet requirements: minimum 25 Mbps download and 10 Mbps upload speeds.

• Must work from a designated space free from interruptions to protect PHI/HIPAA information.

🏝️ Benefits

• Bonus incentive plan based on company and/or individual performance.

• Medical benefits.

• Dental benefits.

• Vision benefits.

• 401(k) retirement savings plan.

• Paid time off.

• Company holidays.

• Personal holidays.

• Paid parental leave.

• Paid caregiver leave.

• Short-term disability.

• Long-term disability.

• Life insurance.

• Remote work arrangement.

• Occasional travel to Humana offices for training or meetings.