Telecommute Director Technology Strategy Jobs in Wisconsin

Medical Associates Clinic & Health Plans is seeking an innovative, strategic, and collaborative Director of Information Technology & Digital Strategy to lead our organization's technology strategy and operations. This is a key leadership role responsible for advancing technology, cybersecurity, data and analytics, digital transformation, and artificial intelligence initiatives across the organization.

Reporting to the Chief Financial Officer, the Director will serve as a trusted technology advisor to executive leadership, physicians, and operational leaders. This individual will develop and execute an enterprise technology roadmap while ensuring our technology environment is secure, reliable, efficient, and aligned with organizational priorities.

The ideal candidate is a forward-thinking technology leader who can balance strategic vision with operational execution, build strong relationships across a complex healthcare organization, and identify opportunities to use technology and innovation to improve patient care, operational performance, member experience, and organizational growth.

What You'll Do: Strategic Technology Leadership

• Serve as a strategic advisor to executive leadership on technology investments, risks, opportunities, and emerging trends.
• Develop and maintain an enterprise technology strategy and roadmap aligned with organizational priorities.
• Evaluate emerging technologies and recommend solutions that improve performance, security, efficiency, and patient experience.
• Partner with physicians and operational leaders to understand business needs and translate them into effective technology strategies.

Technology Portfolio, Governance & Project Execution

• Lead enterprise technology governance, prioritization, and resource allocation.
• Establish clear project expectations, including scope, ownership, milestones, budgets, timelines, and measurable outcomes.
• Oversee technology initiatives and hold teams accountable for successful execution.
• Monitor project performance and provide regular updates, recommendations, and risk assessments to senior leadership.

Data Management, Application Development & AI

• Lead organizational strategies for data management, software development, automation, integration, and artificial intelligence.
• Establish and maintain data governance practices that promote data quality, consistency, security, and accessibility.
• Advance modern development practices, technologies, and automation opportunities.
• Identify and implement responsible AI solutions that create measurable clinical, operational, financial, or patient/member experience improvements.

Cybersecurity, Risk Management & Compliance

• Provide leadership for a comprehensive cybersecurity and technology risk management program.
• Ensure compliance with HIPAA, privacy and security requirements, organizational policies, and applicable standards.
• Oversee disaster recovery, business continuity, incident response, access management, and third-party technology risk.
• Develop and maintain technology, cybersecurity, data governance, and AI policies and standards.

IT Operations & Service Delivery

• Ensure reliable, secure, and efficient operation of infrastructure, applications, networks, communications systems, and end-user technology services.
• Establish service levels, performance metrics, and accountability measures that support organizational needs.
• Drive continuous improvement to enhance reliability, user satisfaction, and operational efficiency.
• Build and maintain strong vendor relationships and oversee technology contracts and service agreements.

Leadership & Financial Stewardship

• Recruit, develop, coach, and retain a high-performing technology team.
• Foster a culture of accountability, innovation, collaboration, customer service, and continuous learning.
• Develop and manage departmental operating and capital budgets.
• Ensure technology investments deliver measurable value and support organizational objectives.

What You'll Bring: Required Qualifications

• Bachelor's degree in Information Technology, Computer Science, Information Systems, Business Administration, Healthcare Administration, or a related field.
• 10 or more years of progressive technology leadership experience.
• 5 or more years of experience leading multiple technology disciplines, such as infrastructure, applications, cybersecurity, data, software development, or analytics.
• Demonstrated success developing and executing technology strategy, managing complex projects, leading teams, and overseeing budgets.
• Strong written, verbal, interpersonal, and executive communication skills.
• Experience developing technology policies, governance processes, and organizational standards.
• Ability to collaborate effectively with executive leaders, physicians, operational leaders, employees, and external partners.

Preferred Qualifications

• Experience within a healthcare provider, payer, or integrated healthcare organization.
• Experience with electronic health records, data warehouses, analytics platforms, artificial intelligence, and Microsoft technologies.
• Master's degree in a related field.
• Professional certification in healthcare IT, cybersecurity, project management, or a related discipline preferred.

Why Join Medical Associates?

This is an opportunity to make a meaningful impact within a long-standing, physician-owned healthcare organization. You will have the opportunity to shape the future of technology across both healthcare delivery and health plan operations, working directly with executive and clinical leadership to advance innovation, security, efficiency, and the overall patient and member experience.

If you are a strategic technology leader who is excited about the intersection of healthcare, technology, cybersecurity, data, digital transformation, and AI, we invite you to apply.

Benefits Package Includes:

• Single or Family Health Insurance with discounted premium rates for wellness program participation.
• 401k with immediate matching (50% on the dollar up to 7% of pay) + additional annual Profit Sharing
• Flexible Paid Time Off Program (29 days off/year)
• Medical and Dependent Care Flex Spending Accounts
• Life insurance, Long Term Disability Coverage, Short Term Disability Coverage, Dental Insurance, etc.

Why Dubuque, Iowa?

Located along the Mississippi River in the heart of the Tri-State region, Dubuque, Iowa offers the best of both worlds—an exceptional quality of life with easy access to larger metropolitan areas. Dubuque is a vibrant, growing community with a rich history, beautiful natural surroundings, and a strong sense of community.

• Exceptional quality of life: Enjoy a welcoming community, affordable cost of living, excellent schools, and a variety of housing options.
• Outdoor recreation: Take advantage of the Mississippi River, scenic bluffs, parks, trails, golf courses, and year-round recreational opportunities.
• Thriving community: Experience a growing downtown, locally owned restaurants and shops, arts and cultural attractions, community events, and a strong local business environment.
• Convenient location: Dubuque is approximately 70 miles from Madison, Wisconsin, and 80 miles from Cedar Rapids, with Chicago and Milwaukee within a few hours' drive.
• Family-friendly environment: Dubuque offers excellent opportunities for families, including quality schools, youth activities, parks, recreation, and community programs.
• Healthcare leadership: Join a respected, physician-owned healthcare organization that has served the region for more than 100 years and plays an important role in the health and well‑being of the Tri-State community.
• Small-city advantages: Enjoy the accessibility and community feel of a smaller city while benefiting from a diverse economy, professional opportunities, and amenities typically associated with larger communities.

Join us in shaping the future of healthcare through technology and innovation!