IT Operations Manager

About the Company

At Drake & Associates, we’re not looking for the average or the expected. We’re looking for THE EXCEPTION. Thank you for your interest in making an impact with us. This opportunity plays a meaningful role in supporting our mission and delivering the ultimate client experience, and our hiring process reflects that. Please take a moment to watch our video and learn why we approach hiring with such intention. Drake & Associates: Make an Impact!

We are a well-established and rapidly growing financial planning firm in Waukesha, WI, with a strong focus on helping individuals and families navigate their retirement planning with confidence and clarity. As our firm continues to scale, technology plays a critical role in delivering an exceptional client experience and supporting our internal operations.

About the Role

We are seeking a proactive and hands-on IT Operations Manager who has experience developing or scaling an IT function within a financial or professional services environment. This individual will oversee all aspects of technology for our growing financial planning firm. They will also have the opportunity to build and shape the IT department as a new strategic function, ensuring our systems are secure, efficient, and scalable as we continue to expand. The ideal candidate combines strong technical expertise with leadership skills and enjoys balancing day-to-day support with long-term Technology Strategy and planning.

Responsibilities

• Establish, manage, and grow the IT function, building foundational systems, processes, and best practices to support firmwide operations.
• Maintain and troubleshoot computer systems, networks, and software applications to ensure reliability and performance.
• Provide responsive technical support to team members and resolve IT issues promptly.
• Manage and administer Google Workspace, user accounts, and security permissions.
• Support key firm technology systems—including CRM, project management, communication, and training platforms—to ensure seamless functionality and integration.
• Set up, configure, and maintain hardware and software across office and remote environments.
• Document IT inventory, processes, and procedures in internal systems.
• Supervise and mentor the IT Intern, assigning tasks and providing hands-on training and feedback.
• Implement and monitor cybersecurity policies, backups, and data protection measures.
• Develop and maintain IT policies, best practices, and compliance standards.
• Lead technology improvement projects, upgrades, and rollouts that align with firm goals.
• Oversee conference room A/V systems, video conferencing platforms, and collaboration tools.

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, or a related field.
• 5+ years of progressive IT experience, including at least 1–2 years in a leadership or management role.
• Proficiency with Mac OS and Google Workspace administration.
• Experience with CRM and project management systems and other cloud-based business tools.
• Understanding of cybersecurity best practices and compliance requirements in financial services.
• Strong analytical, problem-solving, and documentation skills with a high attention to detail.
• Excellent communication and interpersonal skills.
• Proven ability to lead IT initiatives, mentor, and train junior staff to build a strong, collaborative team environment.