Cloud & AI-Driven 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 with the opportunity 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. What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We’re building something meaningful and looking for purpose-driven individuals to help lead the way. 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. This is not a role for someone who waits to be told what to do. You actively seek out 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 see artificial intelligence not as a buzzword but as a hands‑on toolkit. You identify repeatable processes, build automations, and leverage AI to surface insights and accelerate delivery—while simultaneously recognizing the very real security risks AI introduces and taking personal ownership of mitigating them. You operate comfortably in ambiguity, making thoughtful decisions with incomplete information and adjusting quickly as circumstances evolve. You are as comfortable sitting with a frustrated franchisee who cannot get their system to work as you are architecting a cloud identity solution. Your diplomacy is as sharp as your technical skills. You translate complex problems into clear, empathetic communication—and you leave every interaction making people feel supported, capable, and confident in IT. Key Responsibilities: DevSecOps & Infrastructure Serve as Tier 3 escalation point for complex infrastructure issues across cloud and on‑prem systems, providing thorough root cause analysis and permanent fixes—not band‑aid. Own and operate the organization’s AWS environment, architecting secure, scalable infrastructure, enforcing cloud security guardrails, and embedding security controls directly into CI/CD pipelines, while managing access controls, cost governance, and partnering with development teams to integrate security scanning, policy as code, and automated compliance checks throughout the software delivery lifecycle so that security is built in, not bolted on. Design, implement, and optimize system environments; own configuration standards and enforce change‑management discipline. When something is broken or inefficient, you fix it 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, Azure AD, 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 scripted automations to eliminate them— not as a future initiative, but as an ongoing personal practice. Evaluate and deploy AI tools that improve IT operations, user support, and infrastructure management; document outcomes and evangelize successful approaches across the team. Stay current on AI capabilities and their practical applications in an IT operations context; bring concrete proposals—not just ideas—to the team on a regular basis. Proactively identify, document, and remediate security risks introduced by AI tools—including data exposure, shadow AI usage, and prompt injection vulnerabilities. Take personal ownership of implementing protective controls rather than waiting for a policy to be written. Partner with leadership to establish AI governance guardrails that protect the organization while enabling innovation; balance security rigor with practical usability. Serve as an internal resource for the broader team on responsible AI usage—educating colleagues on both the opportunities and the risks of AI in the enterprise. Franchisee & End‑user Support Excellence Most of our franchisees are fully non‑technical. They depend on IT to be clear, patient, empathetic, and effective. This section is not a footnote—it is core to the role. Handle Tier 2–3 escalations from corporate staff and franchise partners—always meeting users where they are, never talking down, and leaving every interaction with the user feeling genuinely supported. Translate complex technical problems into plain language—both verbally and in writing—for franchisees and non‑technical business stakeholders. Your explanations should empower, not overwhelm. Proactively identify recurring pain points and address root causes before they become widespread issues. Use trend data and user feedback—not just tickets—to inform your priorities. Design and deliver user‑facing documentation, training materials, and knowledge‑base articles written specifically for non‑technical audiences. Assume no prior IT knowledge. Manage the full user account lifecycle—provisioning, access reviews, privilege management, and deprovisioning—with accuracy, speed, and clear communication to affected users. Champion a culture of digital safety and IT best practices among franchisees and corporate users—making security understandable, approachable, and actionable for all skill levels. Partner with SaaS vendors and application providers to raise and resolve issues impacting user productivity; advocate fiercely on behalf of users while maintaining professional, constructive vendor relationships. Department Leadership & Strategic Contribution Identify technology opportunities that improve IT delivery, reduce cost, or improve the user experience—then build the case, get alignment, and execute. Bias toward action over analysis paralysis. Lead and coordinate technology projects from requirements gathering through deployment; communicate status clearly and proactively to stakeholders at all levels. Author and maintain comprehensive IT documentation: architecture diagrams, runbooks, project plans, and process guides—written for both technical and non‑technical readers as appropriate. Mentor junior IT Operations staff—provide technical guidance, constructive feedback, and professional development support. Model the behaviors and mindset this team values. Lead the Disaster Recovery and Business Continuity Planning program; own DR test scheduling, facilitate exercises, and document 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; bring data‑driven recommendations rather than anecdotal opinions. Your Experience. Relentless innovation: You are never satisfied with “good enough.” You constantly ask whether there is a smarter, faster, or more reliable way to solve a problem—and you act on the answer. Bias toward action: You make decisions with the best available information, move quickly, and course‑correct as needed. You do not wait for perfect conditions or perfect instructions. Comfort in ambiguity: You thrive in environments where not everything is defined. You create clarity for others rather than needing it handed to you. People‑first technical thinking: You recognize that technology serves people. You design solutions with the end user in mind—especially when that user has no technical background. Customer diplomacy: You handle frustrated, confused, or overwhelmed users—including non‑technical franchisees—with patience, empathy, and clear communication. You de‑escalate, not inflame. AI fluency with security maturity: You are excited about AI capabilities and actively use them— but you are also the person in the room who raises the hard security questions and follows through with real solutions. Ownership mentality: If you see a problem, you own it. You do not pass it to someone else or wait for someone to notice. You communicate, escalated when needed, and see it 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 (SOC 2, ISO 27001, 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. We personalize protection at a price you can trust. We hustle to find opportunity. We care authentically. We thrive in ambiguity. We own our results. We have fun along the way. And—we’re just getting started. 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. 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. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, contact our HR department at View email address on click.appcast.io. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process. 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