We are a healthcare technology company that provides platforms and solutions to improve the management and access of cost-effective pharmacy benefits. Our technology helps enterprise and partnership clients simplify their businesses and helps consumers save on prescriptions.

As a leader in SaaS technology for healthcare, we offer innovative solutions with integrated intelligence on a single enterprise platform that connects the pharmacy ecosystem.  With our expertise and modern, modular platform, our partners use real-time data to transform their business performance and optimize their innovative models in the marketplace.

Position Summary

We are seeking an experienced and motivated Senior IT Support Analyst to join our Boston office. This role is built for a technically well-rounded professional who can own complex, multi-system problems independently, serve as the escalation point for challenging support issues, and apply AI and automation to improve how the team operates and supports end users. You will be the primary IT presence in the Boston office—resolving advanced end-user issues, contributing to infrastructure and cloud initiatives, and actively driving tool improvements and AI integrations alongside the global IT team.

Must be aware of and comply with all aspects of the RxSense Information Security Program and the policies contained therein. Must always understand the importance of maintaining Information Security.

Key Responsibilities

End-User & Office Support

• Serve as the primary on-site IT resource for Boston office staff, delivering prompt, high-quality technical assistance in person and remotely.
• Provide dedicated on-site and remote technical support to executives and office staff, ensuring responsive, and high-quality assistance for time-sensitive needs.
• Manage and own the IT support ticket queue, ensuring timely resolution in accordance with SLA targets; serve as the escalation point for complex and non-standard issues, engaging senior engineers or specialized teams only where scope requires it.
• Provision, configure, and support Windows and macOS endpoints, including laptops, desktops, printers, scanners, and mobile devices.
• Support A/V and conferencing equipment, including video conferencing systems, microphones, and display technology for meetings and presentations.
• Assist with user account management, including password resets, MFA configuration, and access provisioning.
• Manage hardware and software inventory, ensuring accurate and up-to-date asset records.
• Recover and validate assets upon employee separations.
• Assist with physical office equipment moves and workspace setup as needed.
• Administer physical access control systems, including badge provisioning, door reader troubleshooting, and coordination with facilities for access changes.

Cloud & Systems Support

• Support day-to-day administration tasks across AWS, Azure, and GCP environments, partnering with the systems engineering team on complex changes.
• Perform day-to-day administration of Windows 365 and Google Workspace.
• Support identity and access management tasks across Okta, Entra ID, and Active Directory, including account lifecycle, group membership, and SSO troubleshooting.
• Write, own, and maintain automation scripts in PowerShell and Python; manage and version all scripts and tools via GitHub.
• Maintain clear and accurate documentation for all systems, configurations, and procedures.
• Leverage AI tools (e.g., Claude, Microsoft Copilot) to accelerate automation scripting, documentation generation, and workflow improvements across IT operations.
• Conduct deep-dive evaluations of current and prospective IT tools; document findings and present integration and improvement recommendations to the team.
• Develop and deliver internal training sessions and reference materials to improve team proficiency with key platforms and AI-powered capabilities.

Networking & Connectivity

• Support and perform basic configuration of office network hardware including switches, firewalls, and wireless access points; escalate complex network engineering tasks to senior network staff.
• Troubleshoot common connectivity issues across wired LAN, Wi-Fi, and VPN; identify root cause and escalate infrastructure-level problems appropriately.
• Perform cabling, patching, and physical network infrastructure tasks as required.

Compliance & Security

• Ensure compliance with SOC1, SOC2, HIPAA, HITRUST, and ISO 27001 standards in all IT activities.
• Enforce Information Security policies and IT procedures; report suspected policy violations promptly.
• Protect all information in any form and assist with end-user security awareness and training.
• Maintain confidentiality and use sound judgment when handling technical or sensitive matters.

Documentation & Continuous Improvement

• Document all support interactions and resolutions in the IT ticketing system.
• Create and maintain end-user guides, runbooks, and process documentation.
• Apply AI tools to accelerate the creation and maintenance of documentation, runbooks, and self-service knowledge base content; continuously assess output quality and accuracy.
• Identify gaps in process or documentation and take initiative to close them.
• Stay current with technology trends through ongoing training and self-development.
• Contribute actively to team projects and initiatives by sharing technical knowledge, providing hands-on assistance, and helping to raise the collective capability of the IT team.

Required Skills & Qualifications

• 3+ years of IT experience centered on end-user support, with hands-on exposure to systems administration and networking.
• Proficient with Windows and macOS operating systems and enterprise endpoint management tools (Intune, JAMF).
• Hands-on experience with Google Workspace, Okta, Windows 365, and Active Directory.
• Working knowledge of AWS, Azure, and GCP for systems administration tasks; foundational understanding of cloud networking concepts (DNS, VPNs, TCP/IP, RBAC, SAML, OIDC) sufficient for troubleshooting and cross-team collaboration.
• Basic familiarity with network hardware (firewalls, managed switches, wireless access points) including routine support tasks such as port configuration, AP troubleshooting, and firmware updates.
• Demonstrated scripting proficiency in PowerShell and/or Python; ability to independently build, maintain, and document automation solutions for IT administration tasks.
• Hands-on experience using AI productivity and coding tools (e.g., Claude, Microsoft Copilot, GitHub Copilot) in a professional IT context; comfort applying AI to real workflows, not just experimentation.
• Excellent communication skills with a strong customer-service orientation.
• Ability to work independently, prioritize effectively, and manage multiple responsibilities and projects in a fast-paced environment.
• Strong organizational skills and attention to detail.
• Proficiency with Jira and Confluence for ticket management, documentation, and internal knowledge management.
• Familiarity with physical access control platforms (e.g., Brivo), including badge provisioning and basic troubleshooting.

Nice to Have

• IT certifications such as CompTIA A+, Network+, AWS, Cisco, or Azure.
• ITIL certification or familiarity with ITIL practices.
• Experience in regulated industries such as health tech or finance.
• Familiarity with prompt engineering or LLM-powered workflow automation; experience building or integrating AI agents or assistants into IT processes.
• Experience with unified communications or telephony systems.

Work Environment

• Hybrid role – required to be in the Boston office a minimum of 3 days per week; must maintain a professional home office setup including reliable internet for remote work days.
• Occasional physical tasks such as moving equipment, running cables, or configuring hardware in server/network closets.
• Ability to lift and move items weighing up to 30 pounds occasionally.
• Travel required is less than 20%.
• Professional business casual attire is required when working on-site; candidates must be comfortable presenting themselves professionally in an environment that includes executives and business stakeholders.

Salary Range: $80,000 - $100,000

RxSense believes that a diverse workforce is a more talented and productive workforce. As such, we are an Equal Opportunity and Affirmative Action employer. Our recruitment process is free from discriminatory hiring practices and all qualified applicants are considered for employment without regard to race, color, religion, sex, gender, sexual orientation, gender identity, ancestry, age, or national origin.  Neither will qualified applicants be discriminated against on the basis of disability or protected veteran status.  We believe in the strength of the collaboration, creativity and sense of community a diverse workforce brings.