Enterprise Strategy Principal

The Enterprise Strategy Principal runs a full engagement end to end — scope, plan, team, timeline, and quality — for one of GuideWell’s in-house strategy projects. The Engagement Manager owns the analytic approach and the engagement storyline, balancing rigor against speed, and turns findings into an actionable roadmap that the leaders who must act on it will back. Day to day, they hold the executive-sponsor relationship, manage and develop a team of Associates and Analysts, and are deep enough in one or more segments to anticipate the regulatory and market shifts that could change the answer. This is the first level accountable for a whole project and its outcome: the priority is to deliver engagements that change decisions, and to prepare for Senior Engagement Manager, where scope grows to multiple concurrent engagements or a complex program.

GuideWell is standing up its Enterprise Strategy team — an in-house strategy and internal-consulting group — and we are hiring Engagement Managers to help build it. As an Engagement Manager, you run a full engagement end to end: you scope the problem, set the approach, build and lead the team, own the storyline, and land a recommendation and roadmap that senior leaders act on. You hold the executive-sponsor relationship day to day, and you are accountable for the outcome — the intellectual challenge and variety of consulting, without the constant travel.

You will thrive here if you like owning a whole problem and a whole team, are comfortable sitting across from an executive sponsor and telling them something they may not want to hear, and want your recommendations to be implemented rather than filed.

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 team as an Engagement Manager:

• Own the whole thing — the problem, the plan, the team, and the answer — on questions that matter to a Fortune 500 health company.

• See your work through to a decision. Because we are in-house, you stay for the roadmap and the follow-through rather than handing off at the final read-out.

• Build something that lasts — as an early hire you will help set the engagement model, the playbooks, and the standards of a purpose-built team.

• 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: leadership brokers moves into functional lead and director roles against real openings, with sponsorship and a published leveling equivalence.

If you want to run real strategy work end to end in service of a mission you believe in, and help build the team that does it, we would like to meet you.

Key Requirements

Run a Full Engagement End to End

• Run a full engagement from start to finish — scope, workplan, team, timeline, and quality — and be accountable for the outcome.

• Scope the problem with the sponsor, define what is in and out, and reset scope openly when the facts change.

• Staff and structure the team from the shared pool, allocate the work, and manage pace and capacity across the engagement.

• Own delivery risk — anticipate what could derail the engagement and act before it does.

Own the Analytic Approach and Balance Rigor Against Speed

• Own the analytic approach for the whole engagement, deciding which questions get depth and which get a directional answer.

• Balance rigor against speed deliberately, and be explicit with the sponsor about the trade-off being made.

• Review and challenge the team’s analysis, and take personal responsibility for the integrity of the numbers.

Own the Storyline, the Roadmap, and the Buy-In

• Own the engagement storyline, tailoring the message to the audience without softening the conclusion.

• Turn findings into an actionable roadmap — sequenced moves, owners, and the decisions required to start.

• Secure the buy-in of the leaders who must act, working the recommendation through in advance rather than unveiling it at the read-out.

Manage and Develop the Engagement Team

• Manage and develop a team of Associates and Analysts — set direction, give direct feedback, and hold a clear standard.

• Create the conditions for people to do their best work: clear roles, useful coaching, and protection from unnecessary churn.

• Drive recruiting and shape how engagements are run, contributing to the team’s playbooks, tools, and onboarding.

Own the Executive-Sponsor Relationship and Deepen Segment Expertise

• Own the day-to-day executive-sponsor relationship for the engagement, keeping them ahead of both progress and problems.

• Go deep in one or more segments, and anticipate the regulatory and market shifts that could change the recommendation.

• Build the cross-functional relationships — business units, finance, corporate development — that the engagement depends on.

Qualifications

• 7-10 years of experience.

• 7+ years in management consulting, corporate strategy, or a comparable role, including demonstrated experience leading project teams.

• Demonstrated experience running projects end to end — scope, workplan, team, timeline, and quality — with accountability for the outcome.

• Per the team’s leveling map, post-MBA consultants with demonstrated project leadership enter at this level or as a Senior Associate.

Required Management Experience

• 2+ years leading project teams; formal people-management experience preferred

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

Additional Qualifications

• Demonstrated experience running projects end to end — scope, plan, team, timeline, and quality — and being accountable for the outcome.

• The ability to scope an ambiguous problem with a sponsor, define what is in and out, and reset scope openly when the facts change.

• The ability to own the analytic approach for a whole engagement and to balance rigor against speed deliberately and explicitly.

• A track record of owning a storyline and turning findings into an actionable roadmap that the leaders who must act on it will back.

• Experience managing and developing a team, including giving direct feedback and holding a clear standard.

• The ability to hold a senior-sponsor relationship day to day, including telling a sponsor something they may not want to hear.

• Executive-level written and verbal communication, and the ability to tailor a message without softening the conclusion.

• Depth in one or more health care segments, and an eye on the regulatory and market shifts that could change a recommendation.

• The ability to build the cross-functional relationships — business units, finance, corporate development — that an engagement depends on.

Preferred Qualifications

• Experience at engagement-manager level or equivalent at a top-tier strategy consultancy, or comparable in-house strategy leadership.

• MBA or other relevant advanced degree.

• Health plan or payer experience.

• A record of recommendations that were implemented, not just presented.

• Experience contributing to the playbooks, tools, or onboarding of a strategy team.

• Recruiting and interviewing experience.

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: $126,000 - $204,800

Typical Annualized Hiring Range: $126,000 - $157,500

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.