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 handson, 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 problemsolving and a relentless drive to elevate the IT experience for both corporate teammates and franchise partners, the vast majority of whom are nontechnical and depend on IT to be a trusted, patient, and proactive guide.
You see artificial intelligence not as a buzzword but as a handson 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.
Your Impact.
Key Responsibilities:
DevSecOps & Infrastructure
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, policyascode, 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.
Manage Active Directory, Azure AD, and identity/authorization platforms at an advanced level - including group policy design, rolebased access, and lifecycle automation.
Intelligent Automation & AI Enablement
Actively identify repeatable, manual, or errorprone IT processes and build AIassisted or scripted automations to eliminate them - not as a future initiative, but as an ongoing personal practice.
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.
Franchisee & End-user Support Excellence
Most of our franchisees are fully nontechnical. 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.
Manage the full user account lifecycle - provisioning, access reviews, privilege management, and deprovisioning - with accuracy, speed, and clear communication to affected users.
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.
Author and maintain comprehensive IT documentation: architecture diagrams, runbooks, project plans, and process guides - written for both technical and nontechnical readers as appropriate.
Beyond technical qualifications, the right person for this role brings a distinct mindset:
Customer diplomacy: You handle frustrated, confused, or overwhelmed users - including nontechnical franchisees - with patience, empathy, and clear communication. You deescalate, not inflame.
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, escalate when needed, and see it through.
Preferred Experience.
Experience deploying or administering AI productivity tools (Microsoft Copilot, ChatGPT Enterprise, or similar) in an enterprise context, including governance and security configuration.
Relevant certifications: Microsoft 365 / Azure Administrator, CompTIA Security+, ITIL Foundation, or equivalent.
Our Values. The We Way.
At We Insure, Group our values shape how we work, how we lead, and how we grow together. They’re more than just words, they guide every interaction, every decision, and every customer experience.
We Way Reflects Our Commitment to.
Our Total Rewards.
Medical, Dental, Vision, Life, Pet; Flexible Spending Account
Work-Life Balance: Personal Days, PTO Days, 12 Paid Holidays, Two Paid Days for Volunteer Service, Paid Parental Leave
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, please contact our HR department at [email protected]. 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.
