IT Operations Engineer

Who We Are At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision. As both a franchise platform and direct insurance provider, We Insure empowers like‑minded entrepreneurs to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results. Your Impact The IT Operations Engineer is a hands‑on, highly motivated technical leader who thrives at the intersection of technology, people, and continuous improvement. You proactively seek friction, inefficiency, and risk – then fix it. You bring creative problem‑solving and a relentless drive to elevate the IT experience for both corporate teammates and franchise partners, the vast majority of whom are non‑technical and depend on IT to be a trusted, patient, and proactive guide. You use AI as a practical toolkit, build automations, surface insights, and mitigate security risks. You operate comfortably in ambiguity, make thoughtful decisions with incomplete information, and adjust quickly as circumstances evolve. You are as comfortable sitting with a frustrated franchisee as you are architecting a cloud identity solution. Your diplomacy is sharp; you translate complex problems into clear, empathetic communication, leaving people feeling supported, capable, and confident in IT. Key Responsibilities DevSecOps & Infrastructure Serve as the Tier3 escalation point for complex infrastructure issues across cloud and on‑prem systems, providing thorough root‑cause analysis and permanent fixes. Own and operate the organization’s AWS environment, architecting secure, scalable infrastructure, enforcing cloud security guardrails, and embedding security controls into CI/CD pipelines. Manage access controls, cost governance, and partner with development teams to integrate security scanning, policy‑as‑code, and automated compliance checks. Design, implement, and optimize system environments; enforce configuration standards and change‑management discipline. Fix inefficiencies without being asked. Lead OS, firmware, and security patching programs—define cadence, oversee execution, validate outcomes, and report status to management. Architect and maintain backup, disaster recovery, and business continuity systems; regularly test recovery procedures and drive improvements based on results. Manage Active Directory, AzureAD, and identity/authorization platforms at an advanced level, including group policy design, role‑based access, and lifecycle automation. Evaluate and recommend infrastructure improvements, new technologies, and vendor solutions aligned with business needs and security posture. Communicate infrastructure risk and status clearly to IT leadership; prepare concise written summaries and impact assessments – no jargon, all clarity. Intelligent Automation & AI Enablement Actively identify repeatable, manual, or error‑prone IT processes and build AI‑assisted or scripted automations to eliminate them. Evaluate and deploy AI tools that improve IT operations, user support, and infrastructure management; document outcomes and evangelize successful approaches. Stay current on AI capabilities and their practical applications in an IT operations context; present concrete proposals regularly. Proactively identify, document, and remediate security risks introduced by AI tools, including data exposure and prompt‑injection vulnerabilities. Partner with leadership to establish AI governance guardrails that protect the organization while enabling innovation; balance security rigor with practicality. Serve as an internal resource for the broader team on responsible AI usage – educate colleagues on both opportunities and risks. Franchisee & End‑User Support Excellence Handle Tier2–3 escalations from corporate staff and franchise partners, meeting users where they are and ensuring genuine support. Translate complex technical problems into plain language—verbally and in writing—for non‑technical audiences. Proactively identify recurring pain points and address root causes before they become widespread, using trend data and user feedback. Design and deliver user‑facing documentation, training materials, and knowledge‑base articles written for non‑technical audiences. Manage the full user account lifecycle—provisioning, access reviews, privilege management, and deprovisioning—with accuracy and clear communication. Champion a culture of digital safety and IT best practices among franchisees and corporate users, making security understandable and actionable. Partner with SaaS vendors and application providers to resolve issues impacting user productivity, advocating fiercely on behalf of users while maintaining professional vendor relationships. Department Leadership & Strategic Contribution Identify technology opportunities that improve IT delivery, reduce cost, or enhance user experience; build the case, gain alignment, and execute. Lead and coordinate technology projects from requirements through deployment; communicate status proactively to stakeholders at all levels. Author and maintain comprehensive IT documentation: architecture diagrams, runbooks, project plans, and process guides for both technical and non‑technical readers. Mentor junior IT Operations staff—provide guidance, constructive feedback, and development support. Lead the Disaster Recovery and Business Continuity Planning program; schedule and facilitate exercises, documenting outcomes with clear improvement actions. Review and audit systems for compliance with security policies and industry frameworks; prepare findings and remediation plans for leadership. Assist management with vendor evaluations, RFP processes, and technology roadmap planning; provide data‑driven recommendations. Your Experience Relentless innovation: never satisfied with ‘good enough,’ constantly seeking smarter, faster, or more reliable solutions. Bias toward action: make decisions with available information, move quickly, and course‑correct as needed. Comfort in ambiguity: thrive where definitions are incomplete, creating clarity for others. People‑first technical thinking: design solutions with the end user, especially non‑technical users, in mind. Customer diplomacy: handle frustrated, confused, or overwhelmed users with patience and clear communication. AI fluency with security maturity: use AI while rigorously addressing security questions and implementing solutions. Ownership mentality: take personal responsibility for problems, communicate, and see them through. Preferred Experience Experience with cloud infrastructure (AWS, Azure, or GCP) and hybrid identity environments. Familiarity with service‑management platforms (ServiceNow, Jira Service Management, Zendesk). Experience supporting compliance audits (SOC2, ISO27001, HIPAA, or similar). Experience deploying or administering AI productivity tools (Microsoft Copilot, ChatGPT Enterprise, or similar) in an enterprise context, including governance and security configuration. Experience working in or supporting franchise business models, distributed retail, or field‑based operations. Relevant certifications: Microsoft 365 / Azure Administrator, CompTIA Security+, ITIL Foundation, or equivalent. Our Values: The We Way Personalize protection at a price you can trust. Hustle to find opportunity. Care authentically. Thrive in ambiguity. Own our results. Have fun along the way. Our Total Rewards Medical, Dental, Vision, Life, Pet; Flexible Spending Account. Competitive salaries. 401K match. Work‑life balance: Personal Days, PTO Days, 12 paid holidays, two paid days for volunteer service, paid parental leave. Short‑ and long‑term disability. Employee support programs, including mental health. Tuition reimbursement. Matching charitable gift program. Lucrative referral program. Location Restrictions This position is not able to be performed in California, Colorado, New York, or Washington. EEO We Insure Group is an equal‑opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics. Disability We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at View email address on click.appcast.io. We will work with you to provide the necessary accommodations. Note to Applicant It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment. Please know that our company does not use lie detector tests in our hiring process. #J-18808-Ljbffr