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GuideWell Mutual

Nonprofit mutual health insurance group in Florida

Principal Cybersecurity Architect AI

Full-TimeUpdated on 10/23/2026
$153.8k - $249.9k/yr
Expert
Bachelor's
United States
HybridHybrid arrangement; travel to corporate offices may be required.
CybersecuritySecurity Engineering & Architecture

About the job

Requirements
  • At least 8 years of related work experience as an architect on progressively complex IT and cybersecurity projects, including enterprise-wide initiatives with significant size, scope, and risk.
  • At least 1 year of hands-on experience designing, securing, assessing, or governing production AI/ML, generative AI, or agentic systems, including personally defining controls for model or agent access to sensitive regulated data in at least one implementation.
  • A related bachelor's degree in an IT-related field, or additional related equivalent work experience. Computer science, cybersecurity, information systems, data science, or engineering are preferred fields.
  • CISSP certification is required.
  • Expert knowledge of information security procedures and controls, including defense in depth, trust levels, privileges, and permissions.
  • Expert proficiency in creating architectural designs for progressively complex environments and translating security principles into enforceable technical controls.
  • Working knowledge of modern AI architecture, including large language models, prompt and context engineering, embeddings and vector stores, retrieval-augmented generation, fine-tuning and model customization, inference serving, orchestration frameworks, and single- and multi-agent designs.
  • Working knowledge of the Model Context Protocol, including its trust model, tool discovery and invocation flow, transport and authorization patterns, and security implications of connecting an agent to multiple MCP servers.
  • Understanding of AI-specific attack techniques and mitigations, including direct and indirect prompt injection, jailbreaks, tool and function abuse, excessive agency, insecure output handling, training-data and memory poisoning, model inversion and extraction, membership inference, embedding inversion, adversarial examples, and AI supply chain compromise.
  • Expert knowledge of identity and access management for non-human and machine identities, including workload identity, OAuth 2.0 and OpenID Connect authorization flows, token scoping and lifetime management, secrets management, just-in-time and just-enough access, and privileged access management.
  • Expert knowledge of HIPAA Privacy, Security, and Breach Notification Rules as applied to automated and AI-driven access to Protected Health Information, including the minimum necessary standard, audit controls, encryption, risk analysis, and Business Associate obligations; ability to explain why a system prompt or model instruction is not an access control.
  • Working knowledge of the NIST AI Risk Management Framework, NIST Cybersecurity Framework, ISO/IEC 42001, MITRE ATLAS, and OWASP GenAI, agentic, and MCP security projects, and ability to apply them as design and assessment tools.
  • Extensive knowledge of data security and data governance practices, including classification, lineage, de-identification, tokenization, encryption in transit and at rest, key management, data loss prevention, and data security posture management, and their effects when a non-deterministic system is in the data path.
  • Expert knowledge of application and API security, including authentication and authorization patterns, input validation, secure integration design, and API gateway controls.
  • Extensive knowledge of secure software development practices and ability to embed controls into CI/CD and MLOps pipelines; ability to read code and infrastructure-as-code well enough to independently review an AI or agent implementation.
  • Mastery of distributed platforms, mainframe, container and Kubernetes environments, desktops, mobile devices, and a variety of operating systems.
  • Consulting, negotiating, communicating, consensus-building, presentation, and facilitation skills, including ability to clearly communicate complex technical information to varied audiences and provide business owners with defensible, timely answers on AI use cases.
  • Ability to understand overall IT strategy and apply and implement it in assigned projects and initiatives, including architecture and design decisions.
  • Ability to reason about controls for systems whose behavior is probabilistic and only partially specified.
  • Ability to learn from mistakes and apply constructive feedback to improve performance.
  • Leadership skills demonstrated through project or technical leadership experience, and knowledge of project management methodologies.
  • Expert knowledge of common information management systems.
Responsibilities
  • Lead project management through the venture design process and deliver projects on time and within budget.
  • Drive cross-functional collaboration with legal, medical, procurement, business units, and project or program managers of connected efforts to advance projects through the venture design process.
  • Recruit and schedule customers and experts, and interface with vendors for research and co-creation activities.
  • Ensure Stage-Gate preparations are complete and manage Gate submissions for executive and steering committee review.
  • Organize and document project knowledge and develop best practices for the innovation team.
  • Design technical controls to keep Protected Health Information within HIPAA boundaries during AI and agent use, including field-level classification before agent access, minimum-necessary enforcement at a centralized context-delivery layer, chunk-level access control in retrieval-augmented generation, de-identification and tokenization, prompt and output redaction, preventing Protected Health Information persistence in model weights, embeddings, caches, memory stores, prompt logs, and observability tooling, and tenant and workload isolation.
  • Design runtime protection for AI and agentic workloads, including AI and MCP gateway mediation of model and tool traffic, input and output guardrails, prompt-injection and jailbreak defenses, tool-call authorization and rate limiting, sandboxed code execution, egress filtering, context and memory scoping, and behavioral anomaly detection tailored to agent actions.
  • Establish AI and agent observability and auditability that satisfy HIPAA Security Rule audit controls at the operation level, including tamper-evident immutable logs of agent access to Protected Health Information, actions, authorization, and represented party, plus decision traces linking AI-influenced outputs to source data, policies, and logic.
  • Establish and maintain an enterprise AI asset inventory and AI Bill of Materials covering models, agents, prompts, datasets, embeddings, MCP servers, tools, and AI-enabled vendor features.
  • Partner with Security Operations to detect and govern shadow AI and unapproved AI usage across the enterprise and software development lifecycle.
  • Lead governance processes for intake, review, and lifecycle management of AI and non-AI technologies and solutions.
  • Serve as the senior security voice on the enterprise AI governance body and set risk-tiering criteria, pre-deployment assessment requirements, approval conditions, monitoring obligations, and decommissioning standards.
  • Embed security into the AI and agentic development lifecycle and partner with data science, MLOps, platform, and DevOps teams to shift controls into CI/CD, including model and dependency scanning, secrets detection, prompt and configuration review, evaluation gates, policy-as-code enforcement, and continuous posture assessment and remediation workflows.
  • Own security architecture requirements for AI-related third-party and supply-chain risk; define pre-contract AI vendor and model security requirements; ensure Business Associate Agreements and security addenda are in place before Protected Health Information reaches AI services; evaluate AI frameworks, agents, vector databases, and AI platforms for enterprise readiness; and influence vendor roadmaps and product releases.
  • Ensure AI and agentic architectures align with applicable regulations and frameworks, including HIPAA rules and anticipated Security Rule amendments, HITECH, NIST AI Risk Management Framework and generative AI profile, NIST Cybersecurity Framework, HITRUST, SOC 2, state AI and health-data statutes, and CMS and payer program requirements; produce architecture evidence for auditors and regulators.
  • Serve as security architecture subject matter expert to business areas, project teams, client groups, and vendors, especially for AI-enabled utilization and prior authorization, claims and payment integrity, care management, member and provider service, appeals and grievances, coding, and enterprise productivity copilot workflows; lead examination of technology vision, opportunities, and challenges.
  • Build consensus around security architecture principles, including least privilege and least agency for autonomous systems, and interpret and clarify these principles for technical and business audiences.
  • Participate in evaluating, selecting, and implementing technology solutions, including AI security tooling such as AI and MCP gateways, AI security posture management, data security posture management, model and agent scanning, guardrail engines, and AI red-team platforms; provide pros-and-cons, build-versus-buy analysis, and total cost of ownership assessment.
  • Maintain operational, architectural, and design documentation, including procedures, task lists, architecture blueprints, agent and data-flow diagrams, control mappings, and reusable design components and patterns.
  • Establish and lead an AI red-teaming and adversarial evaluation program; define enterprise AI security assessment methodology across applications, agents, tools, and multi-step workflows; commission and oversee internal and third-party engagements that cover agentic and MCP attack patterns; and drive remediation of findings to closure.
  • Investigate and report security threats and incidents involving AI and agentic systems; develop and maintain AI-specific incident response playbooks addressing prompt-injection compromise, agent credential abuse, rogue and drifted agent behavior, poisoned memory or tooling, and Protected Health Information exposure through prompts, logs, or non-Business-Associate-Agreement services, including breach-assessment triggers; conduct post-event reviews and drive corrective action.
  • Provide technical leadership, coaching, and oversight to less experienced Cybersecurity Architects and engineering and data science partners, promoting knowledge-sharing and professional growth.
  • Enhance own breadth and depth of knowledge, benchmark technology strategies and architectures against peer payers and industry, monitor and anticipate trends, and prepare benchmarking reports and presentations for leadership.
Desired Qualifications
  • Health plan, payer, or other health care industry experience, including familiarity with Protected Health Information-bearing workflows such as claims, enrollment, prior authorization and utilization management, care management, appeals and grievances, provider data, and member service.
  • Hands-on experience with enterprise AI platforms and agent frameworks, including Microsoft Azure AI Foundry, Azure OpenAI, Azure API Management, Microsoft Copilot and Copilot Studio, AWS Bedrock, Google Vertex AI, Databricks Unity Catalog and MLflow, and LangChain, LangGraph, AutoGen, CrewAI, or Google ADK.
  • Hands-on experience deploying or evaluating AI gateways, MCP gateways or proxies, large-language-model firewalls and guardrail engines, AI security posture management, and data security posture management.
  • Experience with AI red-teaming and evaluation tools such as Microsoft PyRIT, Garak, or equivalent, and experience running or commissioning adversarial testing of agentic workflows.
  • Identity and access management experience spanning workforce, consumer, and non-human or agent identity, including consumer identity security for member-facing digital experiences.
  • Experience securing APIs at enterprise scale, including health care interoperability standards and interfaces such as FHIR, HL7, and X12 EDI, and their risks when exposed to AI agents.
  • Working proficiency in Python and familiarity with common data science and AI libraries sufficient to prototype controls and validate implementations.
  • Experience with privacy-enhancing technologies, including differential privacy, synthetic data generation, and confidential computing.
  • Experience preparing AI systems for external assurance, including HITRUST and SOC 2.
  • Experience using Agile methodology and operating inside a formal enterprise architecture review or governance board.
  • At least 2 years of cloud security experience.

About the company

GuideWell Mutual Holding Corporation is the not-for-profit, policyholder-owned parent of Florida Blue, the Blue Cross and Blue Shield health insurer for Florida. Its family of companies also includes Triple-S, which runs the Blue plans in Puerto Rico, and GuideWell Source, which processes Medicare claims for the federal government through Novitas Solutions and First Coast Service Options. Most income comes from health plan premiums paid by employers, individuals and Medicare members, plus fees for running claims for others. As a mutual, it has no shareholders, and Florida Blue policyholders control it. GuideWell was formed in 2013 and is based in Jacksonville, Florida.

Company Size

10,001+

Company Stage

N/A

Total Funding

N/A

Headquarters

Jacksonville, Florida

Founded

2011

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Simplify Jobs

Simplify's Take

What believers are saying

  • Brian Pieninck became CEO October 1, 2025, bringing CareFirst operating discipline.
  • AM Best affirmed GuideWell's long-term issuer rating at a- on July 30, 2026.
  • GuideWell earned Great Place to Work certification in 2026, aiding recruiting.

What critics are saying

  • GuideWell cut workforce 3% in January 2025, signaling continued margin pressure.
  • Broward Health sued Florida Blue in April 2026 over emergency-room underpayments exceeding $750,000.
  • Florida Blue's MIHC filing risks regulatory delay and policyholder revolt after approval.

What makes GuideWell Mutual unique

  • GuideWell remains a policyholder-owned, not-for-profit health solutions platform across 50 states.
  • Florida Blue gives GuideWell a dominant Florida payer base and integrated delivery footprint.
  • GuideWell Innovation Center, launched in Jacksonville, anchors payer-provider experimentation and partner access.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • Disability Insurance
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Paid Vacation
  • Unlimited Paid Time Off
  • Wellness Program

Company News

Miami's Community Newspapers
Oct 19th, 2026
Fortune Media and Great Place To Work name GuideWell to 2026 Best Workplaces in Health Care List, ranking no. 21.

Fortune Media and Great Place To Work name GuideWell to 2026 Best Workplaces in Health Care List, ranking no. 21. Great Place To Work(R) and Fortune magazine have selected GuideWell for the 2026 Fortune Best Workplaces in Health Care(TM) List. This is GuideWell's first time being named to this prestigious list, this year coming in at 21st place in the large category. Earning a spot means that GuideWell is one of the best companies to work for in the country. The Best Workplaces in Health Care award is based on analysis of survey responses from nearly 222,000 employees at Great Place To Work Certified(TM) companies in the health care industry. "This recognition belongs to our people," said Brian Pieninck, President and CEO of GuideWell. "Culture is built one action at a time, and our teammates bring those actions to life every day. I am grateful to every person who shows up for each other and for the people we serve. This honor reflects what our people have built, and it reminds us how much more there is to build." The Best Workplaces in Health Care list is highly competitive. Great Place To Work, the global authority on workplace culture, determines its lists using its proprietary Trust Index(TM) Survey to evaluate and certify thousands of organizations in America's largest ongoing annual workforce study, based on over 1.3 million survey responses and data from companies representing more than 7.3 million employees. Survey responses reflect a comprehensive picture of the workplace experience. Honorees were selected based on their ability to offer positive outcomes for employees regardless of job role, work status, or other demographic factor. "Congratulations to the Fortune Best Workplaces in Health Care," says Michael C. Bush, CEO of Great Place To Work. "People are at the heart of work in every industry, and health care is no exception. These companies show how delivering for your people drives financial performance and turns fear of the future into the confidence to win." In May 2026, GuideWell also earned a Great Place To Work(R) Certification for the first time in its more than 10-year history. About GuideWell GuideWell comprises Florida's Blue Cross Blue Shield plan, Florida Blue, the leading health insurer in Florida and Triple-S Management, Puerto Rico's Blue Cross Blue Shield plan and a leading healthcare services company on the island. The GuideWell portfolio of care delivery organizations provides primary and urgent care at nearly 80 care centers and affiliate clinics in Florida, including Sanitas Medical Centers, GuideWell Emergency Medical Doctors, and Florida Health Care Plans. Other GuideWell subsidiaries include GuideWell Source, which provides administrative services to federal healthcare programs, and WebTPA, a market leading administrator of self-funded employer health plans. GuideWell also has a majority stake in several health solutions companies, including Lucet, a behavioral healthcare company that offers tech-enabled support to payers, providers, and health plan members, as well as home-based, whole-person care for high-risk patients. GuideWell serves nearly 36 million customers across 50 states, Puerto Rico and the U.S. Virgin Islands, including more than 6 million customers in Florida. For additional information visit GuideWell.com. For details regarding the company's community and sustainability efforts, read the GuideWell Impact Report. For the latest news and content, visit the GuideWell Newsroom, and follow GuideWell on Facebook, LinkedIn, Instagram @LifeAtGuideWell, and X @_GuideWell. About the Fortune Best Workplaces in Health Care List Great Place To Work selected the 2026 Fortune Best Workplaces in Health Care by analyzing confidential survey responses from more than 1.3 million employees, representing the experiences of more than 7.3 million employees in 2025 and 2026. Of those responses, nearly 222,000 were from employees at Great Place To Work Certified companies in the health care industry, and this ranking is based on that feedback. Companies with 10 to 999 employees competed in the small and medium category. Companies with 1,000 or more employees were considered for the large category. Read the full methodology. About Great Place To Work As the global authority on workplace culture, Great Place To Work, a UKG company, brings 30 years of groundbreaking research and data to help every place become a great place to work for all. Its proprietary platform and Great Place To Work Model help companies evaluate the experience of every employee, with exemplary workplaces becoming Great Place To Work Certified and receiving recognition on a coveted Best Workplaces list. About Fortune Media Fortune is a global multi-platform media company built on a legacy of trusted, award-winning reporting and information for those who want to make business better. Independently owned, Fortune tells the stories of the world's biggest companies and their leaders as well as a new generation of innovators who are moving business forward. Digitally and in print, Fortune measures corporate performance through rigorous benchmarks, and holds companies accountable, in regions around the world. Its iconic rankings include Fortune 500, Fortune Global 500, Most Powerful Women, and World's Most Admired Companies. Fortune builds world-class communities by convening industry thought leaders for exclusive summits and conferences, including the Fortune Global Forum, Fortune Brainstorm Tech, and Fortune Most Powerful Women. For more information, visit fortune.com. Connect To Your Customers & Grow Your Business

DistilInfo
Aug 20th, 2026
Health Net taps CEO from Nevada plan.

Health Net taps CEO from Nevada plan. Table of contents. Centene's Health Net named Eric Schmacker as plan president and CEO, confirming the Eric Schmacker Health Net CEO appointment following his tenure as the health plan's interim leader. How the Eric Schmacker Health Net CEO appointment came together. Schmacker most recently held the same role at Silver Summit Health Plan, another Centene plan in Nevada, a LinkedIn announcement said. Leading up to his official appointment, he has been Health Net's interim plan president. This progression from interim leadership to permanent appointment suggests Centene opted for continuity, promoting a leader already familiar with Health Net's operations rather than conducting an external search from scratch. Why his Nevada background matters. Having previously led another Centene-owned plan in Nevada gives Schmacker direct experience navigating the same corporate structure and operational expectations he'll now apply at Health Net, a factor that may have streamlined his transition into the permanent role. Schmacker's background before this Health Net CEO appointment. Before Centene, Schmacker held executive roles at Tenet Healthcare's San Antonio, Texas-based Baptist Health System, including CEO of St. Luke's Baptist Hospital, CEO of Mission Trail Baptist Hospital, and COO of North Central Baptist Hospital. He is also a 21-year U.S. Army veteran. Why this combination of experience stands out. Schmacker's background spanning multiple hospital COO roles within a major health system, combined with more than two decades of military service, gives him a leadership profile shaped by both large-scale healthcare operations and the discipline associated with a long military career, a combination that may prove valuable as he takes on the operational demands of leading a Medicaid-focused managed care plan. Why this Health Net CEO transition matters. Former Health Net CEO Brian Ternan left the company in July to serve as GuideWell's executive vice president of commercial business. This departure created the leadership vacancy Schmacker has now filled, following a relatively swift transition from Ternan's exit to Schmacker's confirmed permanent appointment. How this fits a broader wave of payer executive turnover. This appointment adds to a broader pattern of health plan C-suite transitions in 2026, with Becker's separately tracking 22 health plan C-suite exits this year alone, spanning regional plans and large, for-profit insurers alike. The same week also brought news of Cambia Health Solutions naming a new CEO for its third-party administrator subsidiary and a CVS Health board appointment. What this Eric Schmacker Health Net CEO appointment means going forward. With Schmacker's transition from interim to permanent CEO now complete, Health Net has resolved its leadership uncertainty following Ternan's July departure, giving the plan stable, confirmed leadership as it continues operating within Centene's broader managed care portfolio. Given Schmacker's prior experience leading another Centene plan in Nevada, his approach to Health Net's operations may reflect lessons and strategies carried over directly from his time at Silver Summit Health Plan. What to watch going forward. As Schmacker settles into his permanent role, industry observers will likely watch how his hospital operations background and military leadership experience shape Health Net's strategic priorities going forward. Given the broader wave of health plan executive turnover occurring across the industry in 2026, this Eric Schmacker Health Net CEO appointment may offer one more data point in understanding how insurers are approaching leadership transitions amid a year marked by significant C-suite change across the payer sector.

Port Arthur News
Aug 4th, 2025
GuideWell appoints Brian D. Pieninck president & CEO

JACKSONVILLE, Fla., Aug. 4, 2025 /PRNewswire/ - GuideWell Mutual Holding Corporation has appointed Brian D. Pieninck as its next president and chief executive officer (CEO), effective Oct. 1.

PR Newswire
May 2nd, 2025
Florida Blue Foundation Honors Nine Nonprofits From Across The State For Innovation And Community Impact During 20Th Annual Sapphire Awards

ORLANDO, Fla., May 2, 2025 /PRNewswire/ -- The Florida Blue Foundation, the philanthropic affiliate of Florida Blue, is proud to announce the nine finalists for the 2025 Sapphire Awards, recognizing outstanding programs, organizations, and individuals making a significant impact in community health across Florida.2025 Sapphire Award WinnersAt its annual Community Health Symposium and Sapphire Awards on May 1 in Orlando, the Florida Blue Foundation announced the winners who will share $525,000 to continue their local impact work. This year's symposium theme highlighted the power of technology, innovation, and AI in improving health outcomes for many in the state."We are thrilled to celebrate the 20th anniversary of the Sapphire Awards and recognize the outstanding contributions of these programs, organizations and individuals," said Florida Blue Foundation Executive Director, Susan Towler. "Each of the honorees is dedicated to innovation that improves the lives of Floridians, and we are honored to support their inspiring work."Below are the programs that were honored:The Family Navigator program, led by Alzheimer's Community Care ( West Palm Beach , Palm Beach County ) provides a lifeline of support, tools, and resources to family caregivers, empowering them to care for their loved ones at home. The program has served 3, 846 patients and caregivers and has achieved an 85% success rate. The Family Navigator program received a first-place award and $100,000. Watch their video., ) provides a lifeline of support, tools, and resources to family caregivers, empowering them to care for their loved ones at home

PR Newswire
Mar 31st, 2025
Guidewell / Florida Blue Ceo Pat Geraghty To Step Down At Year End

Tenure Marked by Dramatic Growth, Industry Leadership, and Statewide Community ImpactJACKSONVILLE, Fla., March 31, 2025 /PRNewswire/ -- Pat Geraghty will retire from his role as president and chief executive officer of GuideWell and Florida Blue on December 31, 2025, after serving since 2011, the company announced today. During his tenure, Geraghty, 65, led the transformation of Florida's largest health insurer into GuideWell, a comprehensive health solutions enterprise, with a significant presence in Puerto Rico and across the country while also expanding Florida Blue's reach and impact across the state.GuideWell & Florida Blue President & CEO, Pat GeraghtyThomas G. Kuntz, Chairman of the GuideWell and Florida Blue Boards of Directors, stated, "Pat Geraghty's visionary leadership has transformed our organization and positioned us as a national leader in the evolution of health care. His commitment to members, employees, and the communities GuideWell serves has been extraordinary. Under his guidance, the company has grown from $8 billion to $32 billion in revenue while maintaining a strong mission focus. He has strengthened the company immeasurably and his dedication to our values and to helping people and communities achieve better health has had a profound impact on our culture, the health insurance industry, and the communities where GuideWell and its companies operate.""Being entrusted with the leadership of GuideWell / Florida Blue has been the highlight of my career," said Geraghty