Strategy Director

The Enterprise Strategy Director is the lead in-house strategy advisor to one of GuideWell’s business segments, partnering directly with its leadership to solve the enterprise’s most important and most complex problems. Operating like an internal engagement lead, the Director owns discrete, time-bound engagements from start to finish - framing the question, directing a small team of analysts, and turning analysis into clear, decision-ready recommendations for senior leaders and, where relevant, the Board. Working across business-unit peers, segment subject‑matter experts, finance, and corporate development, the Director connects internal and external insight to sharpen GuideWell’s view of the market dynamics shaping strategy, growth, and operations.

GuideWell is standing up its Enterprise Strategy team - an in-house strategy and internal-consulting group - and we are looking for a Director to help build it from the ground up. You will be the trusted strategy advisor to the leaders of a GuideWell business, own strategic engagements end to end (from framing the problem to delivering the recommendation), and present your thinking directly to senior leadership. Because the team is being purpose-built, you will have unusual influence over how it works: the engagement model, the playbooks and tools, and the analysts you develop along the way.

You will thrive here if you love turning ambiguous, cross‑functional problems into clear recommendations, are energized by working shoulder to shoulder with senior leaders, and want the intellectual challenge and variety of consulting without the constant travel - all in service of a mission you believe in.

What makes GuideWell different:

• A not‑for‑profit, mission‑driven company - one of the nation’s largest health insurers and a Fortune 500 organization - whose purpose is helping people and communities achieve better health.
• Core Blue Cross Blue Shield health plans in Florida (Florida Blue) and Puerto Rico (Triple‑S), with deep ties to government‑sponsored health care and the members who rely on it.
• A diversified portfolio that reaches well beyond insurance - including GuideWell Health care delivery (Sanitas Medical Centers, GuideWell Emergency Doctors, and Florida Health Care Plans), GuideWell Source, WebTPA, and Lucet - serving tens of millions of people across all 50 states, Puerto Rico, and the U.S. Virgin Islands.
• A policyholder‑owned, long‑term orientation and a strong balance sheet that let us invest in health‑care‑defining capabilities rather than chase quarterly results.
• Deep community trust and a genuine focus on impact in everything we do.

Why join the Enterprise Strategy team:

• Build something that lasts. As one of the first Directors, you will help set the engagement model, the standards, and the culture of a purpose‑built team, and leave your fingerprints on both the work and the people.
• Work on problems that matter - helping GuideWell get the whole concept of health care right, not just run a health plan - during a period of real growth and transformation.
• Grow a full strategy career here, with clear levels, a transparent competency model, and mentorship built into every engagement, all the way to Head of Enterprise Strategy.
• Or use the team as a launchpad into the business: at defined points you can move into an operating (P&L or functional) role, supported by optional 6‑12 month secondments with a guaranteed path back and sponsored placements that keep the move a step up, never a step down. People who move on stay part of the strategy alumni network - and we count that as a win.

Above all, this is a chance to put sharp strategic thinking behind a mission worth believing in: helping the people and communities we serve achieve better health.

Key Requirements

Own the Strategy Agenda for a Business Segment

• Own the strategy agenda for an assigned P&L or group of support‑services functions, serving as the embedded strategy advisor to that unit’s leadership team.
• Frame the strategic questions that matter most before the analysis begins, and shape the major bets and investment choices that follow.
• Translate GuideWell’s enterprise strategy into a clear roadmap for the segment, and keep it current as markets, competitors, and regulation evolve.
• Act as the single point of accountability for the segment’s strategy work, driving alignment across business partners in a matrixed environment.

Lead Strategic Engagements End to End

• Run discrete, time‑bound engagements from start to finish - scoping the problem, structuring the analysis, and setting the workplan.
• Direct a team of analysts drawn from the shared team pool, owning quality, pace, and the balance between rigor and speed.
• Turn analysis into decision‑ready recommendations and a practical roadmap, and secure the buy‑in of the leaders who must act on it.
• Present findings directly to business‑unit and enterprise leaders, tailoring the message to the audience.

Inform the Executive and Board Strategy Process

• Provide the data, market intelligence, frameworks, and facilitation that help executives define, align on, and refresh enterprise, business‑unit, and functional strategy.
• Develop scenarios and test current and proposed strategies against them, anticipating how traditional and non‑traditional competitors alike could reshape the market.
• Prepare clear, decision‑ready materials for executive leadership and, where relevant, the Board, supporting the enterprise strategy‑refresh cycle.

Develop Talent and Build the Practice

• Coach and develop the analysts staffed to your engagements - setting direction, reviewing their work, and giving direct, timely feedback as part of the Enterprise Strategy team.
• Strengthen the team’s shared methods, tools, and intellectual property, raising the bar for how engagements are run.
• Help the team scale by contributing to recruiting and onboarding and by developing the analysts you lead, both directly and indirectly.

Build Cross‑Enterprise Relationships and Outside‑In Thinking

• Build durable, trusted relationships with peers across business units, finance, and corporate development, and respond to inbound requests for strategic analysis.
• Introduce new ideas and frameworks that embed long‑term, outside‑in thinking into everyday business decisions.
• Partner with subject‑matter experts to assess what federal and state health care legislation, policy, and regulation mean for GuideWell’s strategy.

Qualifications

• 12-16 years of experience.
• 12+ years in management consulting, corporate strategy, or a comparable role, including significant experience leading engagements and senior relationships.
• Demonstrated experience owning the strategy agenda for a business or major function, and advising its leadership team.
• Per the team’s leveling map, an experienced Engagement Manager, Project Leader, or Manager from a top‑tier firm slots in at this level.

Required Management Experience

• 5+ years leading teams and developing talent, including indirect leadership in a matrixed environment.

Required Education

• Bachelor’s degree
• Quantitative, analytical, business, or health‑related field preferred (e.g., economics, finance, statistics, data or analytics, engineering, or public health); other majors welcome where the analytical toolkit is demonstrated.

Preferred Education

• MBA or other relevant advanced degree
• MBA, or a master’s degree in a quantitative, analytical, business, or health‑related field (e.g., economics, finance, statistics, data science, engineering, or public health).

Additional Qualifications

• Demonstrated experience owning the strategy agenda for a business or major function, including framing the questions before the analysis begins.
• A track record as a trusted advisor to a leadership team, with real influence over major bets and investment choices.
• The ability to run engagements end to end while also carrying a standing coverage relationship.The ability to translate an enterprise strategy into a unit‑level roadmap, and to keep it current as markets, competitors, and regulation move.
• Experience preparing and delivering decision‑ready material for executive leadership and, where relevant, a Board.
• The ability to build bench strength - developing talent and sponsoring careers, directly and indirectly.
• Command of a market: its competitors, its regulation, and the economics that drive it.
• Executive presence, and the ability to frame strategy in the language of the leaders who have to act on it.
• The ability to act as a single point of accountability and drive alignment in a matrixed environment.

Preferred Qualifications

• Experience at engagement‑manager level or above at a top‑tier strategy consultancy, or experience leading an in‑house strategy function.
• MBA or other relevant advanced degree.
• Deep health care experience; payer experience strongly preferred.
• Experience with scenario planning and with an enterprise strategy‑refresh cycle.
• Experience with corporate development, M&A, or partnership strategy.
• Experience building a team’s shared methods, tools, and intellectual property.

General Physical Demands
Sedentary work: Exerting up to 10 pounds of force occasionally to move objects. Jobs are sedentary if traversing activities are required only occasionally.

Physical/Environmental Activities
Must be able to travel to multiple locations for work (i.e. travel to attend meetings, events, conferences). Occasionally

What We Offer:

As a Florida Blue employee, you will be at the heart of GuideWell’s vision - to lead the nation in transforming health through compassionate, connected, and technology‑enabled care that delivers personalized value and empowered living.

To support your wellbeing, comprehensive benefits are offered. As an employee, you will have access to:

• Medical, dental, vision, life and global travel health insurance;
• Income protection benefits: life insurance, short- and long-term disability programs;
• Leave programs to support personal circumstances;
• Retirement Savings Plan including employer match;
• Paid time off, volunteer time off, 10 holidays and 2 well‑being days;
• Additional voluntary benefits available; and
• A comprehensive wellness program

Employee benefits are designed to align with federal and state employment laws. Benefits may vary based on the state in which work is performed. Benefits for intern, part‑time and seasonal employees may differ.

To support your financial wellbeing, we offer competitive pay as well as opportunities for incentive or commission compensation. We also conduct regular annual reviews with pay for performance considerations for base pay increases.

Annualized Salary Range: $180,000 - $292,500

Typical Annualized Hiring Range: $180,000 - $225,000

Final pay will be determined with consideration of market competitiveness, internal equity, and the job‑related knowledge, skills, training, and experience you bring.

We are an Equal Employment Opportunity employer committed to cultivating a work experience where everyone feels like they belong and can perform at their best in pursuit of our mission. All qualified applicants will receive consideration for employment.