Remote Windows Administrator Jobs in Connecticut

Overview
At Banner Life Insurance Company, we lead with heart and ambition. Every day, we transform purpose into progress, guided by our unwavering commitment to be better for our customers, clients, and communities, not just today but long-term as well. Our people are the driving force behind everything we achieve. Their passion, purpose, and pursuit of innovation empower us to deliver cutting-edge solutions that support those we serve, ensuring we are here for you, here for good and striving for better.
We're a forward-thinking company energized by our work and how we show up for one another. Our culture is built on meaningful impact and genuine enjoyment, because we believe great work and great experiences should go hand in hand.
By offering career development opportunities, comprehensive benefits, and programs that support your wellbeing, we help you thrive personally and professionally. We are here for you, here for good and here for better.
This role is a part of our Retirement division
Banner Life is a leader in Pension Risk Transfer (PRT) with over a decade of experience in the industry. The retirement business has grown steadily since its inception in 2015, and we have written over $14 billion in total PRT premium as of year-end 2025. Known for customer service excellence, Banner Life retirement secures the retirement of over 200,000 annuitants annually.
Purpose and Objective
The Senior Systems Administrator is responsible for ensuring the reliability, security, performance, and continuous improvement of Banner Life Retirement's technology infrastructure across Microsoft Azure, Microsoft 365, and on-premises environments. This role serves as a senior technical expert and thought leader for infrastructure, identity, security, and operational challenges, helping to maintain a resilient, secure, and highly available technology environment that supports business objectives and regulatory requirements.
As a hands-on technical leader, the Senior Systems Administrator is responsible for system administration, infrastructure engineering, troubleshooting, automation, implementation, and documentation activities. The role drives operational excellence through proactive monitoring, continuous improvement, and a security-first approach to technology management. Working closely with managed service providers, vendors, and internal stakeholders, the Senior Systems Administrator ensures that services are delivered in accordance with Company standards, security policies, compliance obligations, and operational expectations.
This is an individual contributor role with no direct people management responsibilities. Success is achieved through deep technical expertise, ownership, sound judgment, effective collaboration, and the ability to independently design, implement, and support technology solutions while serving as a trusted escalation resource and technical advisor to the organization.
Responsibilities

• Administer and support Azure infrastructure services including Entra ID, Conditional Access, RBAC, PIM, networking, compute, and storage.
  • Manage and support Microsoft 365 services including Exchange Online, Teams, SharePoint, and OneDrive.
  • Support on-premises infrastructure including Windows Server, Active Directory, DNS/DHCP, Group Policy, and file services.
  • Design and maintain hybrid integration between on-premises systems and Azure.
  • Lead incident resolution, root cause analysis, and preventative remediation.
  • Work closely with managed service providers (MSPs) to oversee service delivery, validate work quality, enforce standards, and address performance or compliance issues.
  • Implement and maintain security controls aligned with SOC 2 and NIST principles.
  • Support audits, risk assessments, and evidence collection activities.
  • Define, maintain, and improve operational runbooks, monitoring, backup, and recovery processes.
  • Mentor and provide technical guidance to system administrators and service desk staff.
  • Partner with IT leadership on platform improvements, standardization, and roadmap planning.

Qualifications
Required Qualifications

• 7+ years of experience in systems administration or infrastructure engineering.
  • Strong hands-on experience with Azure, Microsoft 365, and Windows Server / Active Directory.
  • Experience supporting hybrid cloud environments.
  • Knowledge of identity and access management concepts.
  • Experience operating in regulated or audit-driven environments.
  • Experience coordinating with or overseeing managed service providers.
  • Strong troubleshooting, documentation, and communication skills.

Preferred Qualifications

• Experience in financial services, insurance, or pension administration environments.
  • Familiarity with SOC 2, NIST, or ISO security frameworks.
  • Relevant Microsoft or Azure certifications.

Benefits

• 10 - 25 vacation days, depending on experience level and years of service
• 4 floating holidays, 2 personal days, & 2 wellness days
• 10 - 15 sick days, depending on years of service
• 2 paid volunteering days
• Health benefits, including medical, dental, and vision coverage
• Supplemental health benefits and life insurance
• 6 weeks of paid parental and maternal leave
• Immediate vesting into a 401 (k) savings plan with up to 6% company match
• 100% employer-contributed Pension Plan - Cash Balance Plan after 1 year of service
• Flexible Workspace and Arrangements
• Tuition and Certification reimbursements
• Infertility and domestic partner benefits

The expected hiring compensation range for this position is $137,000 - $160,000 USD annually. Base pay offered may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. The current bonus target for the position is 20% of the base salary with a stretch to twice the target, modified for corporate and individual performance.
**This role is hybrid located in Stamford, CT**
We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.