Full-Time

Senior IT Systems Engineer

macOS and iOS Management

Posted on 8/20/2026

GuideWell Mutual

GuideWell Mutual

201-500 employees

Mutual holding company enabling integrated health

Compensation Overview

$100.4k - $163.2k/yr

+ Incentive compensation + Commission

Jacksonville, FL, USA

Hybrid

Hybrid work requires in-office engagement in Jacksonville; candidates should live within 50 miles or be open to relocation.

Bachelor's

Category
Software Engineering (1)
Required Skills
PowerShell
Bash
LDAP
SOC 2
iOS/Swift
HIPAA

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Requirements
  • Five years of experience managing and supporting Apple macOS, iOS, and iPadOS devices in an enterprise environment.
  • Prior experience working in healthcare, health insurance, or financial environments involving HIPAA, PCI, SOC 2, HITRUST, and CMS compliance.
  • A bachelor's degree in an information technology-related field or equivalent work experience.
  • Extensive working knowledge of multiple technologies and their interfaces and integration.
  • Competence working in one or more environments highly integrated with an operating system.
  • Extensive experience implementing and administering or managing technical solutions in major, large-scale system implementations.
  • Ability to evaluate alternatives and present solutions consistent with business objectives and strategy.
  • Ability to manage tasks independently and take ownership of responsibilities.
  • Ability to communicate technical information clearly and articulately.
  • Ability to adapt to a rapidly changing environment.
Responsibilities
  • Perform installation, monitoring, testing, configuration, migration, maintenance, and troubleshooting of assigned technology.
  • Manage system and application environments and ongoing operations.
  • Ensure technologies are updated with current, stable, and compliant architectures and applications that meet enterprise standards.
  • Research, design, implement, and test technology solutions.
  • Monitor and report the performance and utilization of assigned technologies.
  • Troubleshoot software and hardware issues and failures.
  • Resolve alerts and perform remediation activities.
  • Manage problems, escalated tickets, tasks, and out-of-cycle requests from system and software owners.
  • Collect and present data for reporting and planning.
  • Assist with developing tactical strategies, processes, and procedures related to systems and application administration.
  • Determine migration and upgrade impacts and diagnose and resolve complex technology and application errors.
  • Collaborate with IT and business-area partners on work groups and initiatives.
  • Determine the best course of action for meeting business needs.
  • Write programming and scripting.
  • Ensure execution and alignment with architectural standards and blueprints.
  • Perform on-call activities as needed for the environment and technologies.
Desired Qualifications
  • JAMF Certified Administrator certification or a higher-level JAMF certification.
  • Advanced experience managing JAMF Pro, including policies, configuration profiles, smart groups, patch management, extension attributes, and API-based scripting automation.
  • Advanced experience with Apple Business Manager, Automated Device Enrollment, and Apple's Volume Purchase Program.
  • Advanced experience with macOS imaging, PKG and DMG packaging, Jamf Composer, and scripted software deployment.
  • Experience designing and administering zero-touch deployment and mobile-device-management enrollment workflows for Mac, iOS, and iPadOS devices.
  • Experience implementing Declarative Device Management alongside traditional mobile-device-management payloads.
  • Knowledge of macOS security and compliance baselines, including FileVault, Gatekeeper, System Integrity Protection, and Center for Internet Security benchmarks.
  • Experience integrating Apple devices with identity and single sign-on providers such as Okta or Microsoft Entra ID, including Platform Single Sign-On.
  • Experience with patch and software deployment automation using AutoPkg, Installomator, or Munki.
  • Experience deploying and maintaining endpoint security and endpoint detection and response agents on macOS.
  • Experience with Apple Configurator for supervised device workflows.
  • Experience supporting multiple sites and environments with more than 10,000 users.
  • Working knowledge of Active Directory and Lightweight Directory Access Protocol for device binding and authentication integration.
  • Experience installing, managing, and administering SSL certificates through JAMF Pro and external enterprise tools.
  • Working knowledge of Secure Sockets Layer/Transport Layer Security protocols, standards, and methodologies.
  • Working knowledge of networking fundamentals related to endpoint deployment, including VPN, 802.1X, proxy, and DNS/DHCP for zero-touch enrollment.
  • Strong PowerShell and Bash or shell scripting experience, including JAMF API scripting for automation.
  • Knowledge of Apple device implementation and management in a clinic environment.
  • Experience evaluating procedures and processes and implementing improved practices.
  • Experience with escalation, communication, and management of production system problems.
  • Experience contacting vendors for problem and incident resolution.

GuideWell Mutual Holding Corporation is a not-for-profit mutual holding company that acts as the parent to a family of companies focused on transforming health care. It builds an integrated ecosystem of health-related products and services, collaborates with partners, and advocates for better health to help people navigate the changing health landscape and enjoy a better experience. Its approach emphasizes improving efficiency and delivering high-quality care rather than pursuing profit. The goal is to shape the future of health by coordinating services and innovations that improve outcomes and access across the health system.

Company Size

201-500

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

  • Pat Geraghty exits December 31, 2025, after scaling revenue from $8 billion to $32 billion.
  • Brian D. Pieninck starts October 1, 2025, preserving leadership continuity into 2026.
  • GuideWell Chat reduced employee time on coding, writing, summaries, and status reports.

What critics are saying

  • GuideWell cut 3% of staff in January 2025, signaling margin pressure and restructuring.
  • Trademark litigation against Guidewell Education, LLC exposes brand and legal costs.
  • Florida concentration makes a sustained Florida Blue share loss existential by 2027.

What makes GuideWell Mutual unique

  • Florida Blue covers all 67 Florida counties, giving GuideWell statewide distribution.
  • GuideWell's mutual, not-for-profit structure supports member-owned positioning and community reinvestment.
  • Triple-S Puerto Rico and Florida Blue diversify revenue beyond a single state.

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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

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

South Florida Hospital News
Mar 12th, 2025
GuideWell and Florida Blue Appoint Julia M. Brown to Board of Directors

GuideWell and Florida Blue appoint Julia M. Brown to board of directors.