Principal, Technology Strategy Advancement

Humana • Boston, MA

1d • Remote

About The Position

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. This role will partner across business, product, engineering, architecture, finance, portfolio, and delivery teams to translate business priorities into technology roadmap implications, investment themes, capability needs, scorecards, leadership decision points, and measurable outcomes. The ideal candidate brings experience working across large-scale, multi-year technology portfolios of $350M+ with multiple initiatives, platforms, products, stakeholders, and cross-functional dependencies. You must be able to operate at a strategic level, synthesize complex information, influence senior stakeholders, and turn ambiguity into clear recommendations and action.

Requirements

• 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.

Nice To Haves

• 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.
• You must reside in close proximity to one of these locations: 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.
• To ensure Home or Hybrid Home/Office employees’ ability to work effectively, the self-provided internet service of Home or Hybrid Home/Office employees must meet the following criteria: At minimum, a download speed of 25 Mbps and an upload speed of 10 Mbps is required; wireless, wired cable or DSL connection is suggested.
• In certain roles, the minimum recommended internet speed required by Humana may not be sufficient for business needs.
• Humana reserves the right to require associates to upgrade their internet service if necessary.
• Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information.
• While this is a remote position, occasional travel to Humana's offices for training or meetings may be required.

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.

Benefits

• medical
• dental
• vision
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Principal