Senior IT Administrator

Forward Financing is a financial technology company based in Boston, Massachusetts with team members throughout the United States, Dominican Republic, and Canada. The company is on a mission to unlock the capital that fuels small businesses across America. Recognized as a Best Place to Work by Built In Boston and certified as a Great Place To Work®, Forward is investing in its employees, technology, and customer experience – with long-term success in mind every step of the way.

In the Senior IT Administrator role, you will assume ownership over the configuration and optimization of our corporate technology infrastructure. This role requires a deeply technical and strategic leader who can successfully design, manage, and scale environments built on SaaS-based infrastructure and cloud services. You will lead the configuration and maintenance of critical IT endpoints, core systems, and networking infrastructure, acting as a top-tier escalation point for complex technical issues. This includes performing advanced root cause analysis and engineering solutions to enhance organizational technology, as well as serving as the subject matter expert (SME) for various systems.

Why you should apply:

• Meaningful work. Each day, you will solve interesting problems at our rapidly growing company. There is a strong technical foundation and a commitment to ongoing improvement.

• Mission-driven company. Forward is a trusted source of fast, flexible funding for small businesses that have often been underserved by traditional financing options. When you join the team, you will help ensure all small businesses have access to the financial support they need to succeed.

• Flexibility is a top priority. Our employees are empowered to choose where they want to work (whether that’s from home, in the office, or a combination of both) with flexible hours.

In this role, you will:

• Serve as the definitive technical escalation point (Tier 3/Expert), solving complex, systemic support issues that require advanced diagnostic expertise and cross-platform investigation across Windows, macOS, and ChromeOS environments for both onsite and remote users.

• Design, implement, and govern endpoint deployment strategies using MDM platforms (Kandji, JumpCloud, Google Workspace), focusing on reducing deployment time, maximizing security posture, and establishing configuration standards for all Windows and Mac endpoints.

• Act as a main point of contact for employee lifecycle events, responsible for administering and executing the technical workflows for both employee onboarding and off-boarding.

• Oversee and ensure the reliability and high performance of all in-office technology. This includes leading the configuration, proactive maintenance, and expert troubleshooting of complex conference room systems (Zoom Rooms), Audio/Visual (A/V) equipment, digital signage, copiers, and core networking components (switches, access points, and localized network connectivity).

• Drive security enhancements by continuously identifying, designing, and implementing configuration changes and governance policies to harden the security of all core SaaS software.

• Lead technical collaboration with business stakeholders to define requirements, configure, and continuously improve critical information systems for business functions.

• Manage and execute major upgrades to both physical and virtual network infrastructure, ensuring scalability and robust performance.

• Proactively identify, design, and take ownership of implementing strategic enhancements to IT Support service processes to significantly drive operational efficiency and measurable improvements in employee experience.

• Own and execute large-scale, complex IT projects from conception through successful completion and transition to operations.

• Independently manage time effectively and prioritise issues/problems that arise via our ticketing system

• Mentor and empower the IT support team by creating and maintaining high-quality, actionable technical documentation and leveraging ticketing system data to identify training needs and common failure points.

• Strategically manage time and competing priorities stemming from both the ticketing system and long-term project roadmaps, ensuring alignment with organizational goals.

Requirements:

(Even if you don’t check every box, but see yourself contributing, please apply.)

• 4+ years supporting macOS, Windows, iOS/Android, ChromeOS

• Bachelor’s degree (technical preferred) or equivalent work experience

• Ability to solve complex technical issues independently

• Expert troubleshooting skills for devices (laptops, work-from-home hardware, mobile devices, printers, etc.)

• Advanced proficiency in managing and deploying endpoints (Windows, Mac) using a major Mobile Device Management (MDM) solution (e.g., Intune, Jamf, Kandji).

• Experience troubleshooting and configuring a wide variety of SaaS applications (Google Workspaces, Atlassian, Slack, etc.).

• Extensive, hands-on experience managing and securing identities using SSO (SAML), SCIM provisioning, and Multi-Factor Authentication (MFA) with Identity Providers (IdP) like Okta, Azure AD, or JumpCloud.

• Success in solving IT problems by writing custom scripts in Python, Bash, PowerShell, or leveraging low-to-no-code automation tools.

• Hands-on experience in maintaining and monitoring corporate network infrastructure

• Excellent verbal and written communication skills (Fluent English)

• Creative thinking and a genuine desire to challenge yourself every day

• A drive for continuous improvement