Annex Wealth Management – Know the Difference

Join Our Growing Team at our Headquarters in Brookfield - (on-site gym)!

Are you in search of an employer that prioritizes a positive culture and encourages outstanding teamwork? ‘Know the Difference’ applies to our employees too. We are a proud seven-time recipient of the Milwaukee Journal Sentinel's Top Workplaces Award. Our employees list our vibrant culture and engaged teams as two of our best features!

Annex Wealth Management is a privately held, full-service registered investment advisor acting as a fiduciary for individuals, families, and businesses. Our team approach means our clients consistently interact with a group of experienced professionals boasting key credentials, certifications, and achievements in investment, tax, insurance, estate planning, and more.

Communication and Education are key to Annex Wealth Management’s growth. Check us out on YouTube, our multiple podcasts, “Money Talk” on WTMJ; “The Investment Show” on WISN; and “The Annex Wealth Management Show” on WHBY and WFSX.

At Annex Wealth Management, our values aren’t just words – they guide how we work every day:

• Knowledge
• Accountability
• Integrity
• Courage
• Respect
• Ownership

Does this resonate with you? We're looking for positive, talented individuals who naturally embody these principles in their work and interactions. If you're ready to join a culture where these values are the foundation of everything you do, we’d love to hear from you.

What You’ll Do

The purpose of the Director of Information Technology is to lead the firm’s technology strategy and operations, ensuring secure, reliable, and scalable systems that support growth, productivity, and excellent client experience. This role oversees enterprise applications, data systems, cybersecurity, and digital workflow modernization while driving innovation and developing a high-performing IT team for a multi-location, enterprise-scale RIA.

• Technology Strategy & Roadmap: Develop and maintain a multi-year technology roadmap, identify opportunities to automate and modernize firmwide processes, and partner with senior leaders to ensure technology decisions align with business strategy.
• Cybersecurity, Risk & Compliance: Maintain a strong cybersecurity posture, oversee data protection and vendor risk, and ensure compliance with SEC and RIA regulatory expectations.
• Data, Reporting & Integration: Manage data governance and integrity, ensure high-quality data flows across key systems, and lead integration and API strategies that support real-time insights and efficient workflows.
• User Experience, Support & Change Management: Ensure team members have reliable tools and timely support, oversee help desk and onboarding/offboarding processes, and drive adoption of new systems through effective change leadership.
• Vendor Management & Technology Finance: Manage vendor selection, contracts, and performance, ensure technology investments deliver ROI, and oversee IT budgeting.
• Business Continuity & Resilience: Maintain and test disaster recovery, continuity plans, and backup strategies to ensure operational resilience.
• Team Leadership & Development: Lead and develop a high-performing IT team, fostering a culture of accountability, collaboration, and continuous improvement with clear roles and career paths.

What You’ll Need to Succeed

• Experience: 7+ years of progressive IT leadership in complex, security-sensitive or regulated environments, with experience supporting multi-office or multi-state operations and a strong preference for backgrounds in wealth management, financial services, or other SEC-regulated settings.
• Technical Expertise: Strong understanding of enterprise applications, systems architecture, cloud platforms, device management, and identity/security frameworks, with experience across core RIA technologies including CRM, planning and portfolio systems, custodial integrations, reporting tools, and a solid foundation in cybersecurity, vendor risk, and data protection best practices.
• Strategic & Operational Skills: Ability to build, communicate, and execute a clear technology roadmap, with strong project management and cross-functional leadership skills, plus the analytical ability to identify opportunities for efficiency, automation, and process improvement.
• Leadership & Communication: Skilled in coaching and developing teams, communicating technical concepts to non-technical audiences, and building trust across departments.

Comprehensive Benefits

We deeply value your leadership, talent, time, and commitment. In return, we offer a total rewards package designed to recognize and appreciate your contributions.

This includes a comprehensive suite of:

• Benefits: Our benefits package includes medical, dental, and vision insurance, as well as a 401(k) plan to help you secure your financial future
• Life & Disability Insurance
• Paid Time Off (PTO)
• 401(k) Retirement Plan: Build your future with our 401(k) plan and employer contribution
• Company Events: We believe in celebrating wins and creating connections – whether it’s through get togethers, our Annual Picnic, or company milestones
• Opportunities for professional growth and development
• Summer hours
• Casual Friday’s!

We are committed to providing an environment where you can thrive and achieve your full potential.

Equal Employment Opportunity: Annex Wealth Management is an equal opportunity employer. We are committed to providing a work environment free from discrimination and harassment. All employment decisions are based on qualifications, merit, and business needs. We do not discriminate based on race, color, religion, national origin, sex, age, disability, genetic information, or any other protected status. We encourage applicants of all backgrounds to apply.