Boston, Massachusetts, United States
Onsite
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.
Connect technology investments to business outcomes by developing value frameworks, success measures, baseline metrics, financial assumptions, and value realization views for major initiatives.
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.
Strategic Focus Areas
Technology Strategy
Support the development, refinement, and activation of technology strategy by connecting business priorities, technology capabilities, modernization needs, product direction, investment choices, and execution realities into a coherent plan.
Business Roadmap to Technology Roadmap Alignment
Ensure business roadmaps and technology roadmaps are connected, sequenced, and understood together. Identify where business demand creates technology implications, where technology constraints affect business timing, and where leadership decisions are required.
Investment Strategy and Value Realization
Evaluate whether investments are aligned to strategy, OKRs, product lifecycle needs, modernization priorities, technology health, and measurable business value. Recommend where investment focus should continue, shift, pause, accelerate, or be reframed.
Technology Scorecards and Organizational Health
Develop and maintain leadership-facing scorecards that provide a clear view of technology strategy health, roadmap progress, investment alignment, execution confidence, modernization progress, delivery risk, technology health, and value realization.
Multi-Year Planning and Roadmap Strategy
Support multi-year planning across platforms, products, capabilities, modernization efforts, data, digital, security, and enabling technology investments. Help leaders understand sequencing, dependencies, funding implications, and tradeoffs required to deliver long-range outcomes.
Strategy Activation and Execution Follow-Through
Activate technology strategy by engaging business and technology leaders, aligning stakeholders, establishing follow-up mechanisms, tracking progress, and ensuring strategic decisions translate into execution plans and measurable outcomes.
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.
Ability 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.
Additional Information
This role is not eligible for work visa sponsorship.
This position falls within our Individual Contributor career pathway, and it will not manage any direct reports.
Reporting Structure: You will report to a Director, IT Portfolio Management.
Work Style: This position's work style is remote from any of the locations listed below. You must reside in close proximity to one of these locations.
Market Location Options:
Louisville, KY
Dallas/Frisco, TX
Washington, DC (Arlington, VA)
Chicago, IL
Fort Lauderdale, FL
Tampa, FL
New York, NY
Boston, MA
Atlanta, GA
Nashville, TN
Charlotte, NC
Travel: While this is a remote position, occasional travel to Humana's offices for training or meetings may be required.
Scheduled Weekly Hours
40Pay Range
The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.
Description of Benefits
Humana, Inc. and its affiliated subsidiaries (collectively, “Humana”) offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities.
Equal Opportunity Employer
It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.
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