Remote Software Engineer Apprenticeship Jobs in Wisconsin

What We Do
Milliman IntelliScript is a group of a few hundred experts in fields ranging from actuarial science to information technology to clinical practice. Together, we develop and deploy category-defining, data-driven, software-as-a-service (SaaS) products for a broad spectrum of insurance, health IT and life sciences clients. We are a business unit within Milliman, Inc., a respected consultancy with offices around the world.
Candidates who have their pick of jobs are drawn to IntelliScript's entrepreneurial and collaborative culture of innovation, excellence, exceptional customer service, balance, and transparency. Every single person has a voice in our company, and we challenge each other to push the outer limits of our full, diverse potential. And, we've shown sustained growth that ensures you'll have room to grow your skillset, responsibilities, and career.
Our team is smart, down-to-earth, and ready to listen to your best ideas. We reward excellence and offer competitive compensation and benefits. Visit our LinkedIn page for a closer look at our company, and learn more about our cultural values here.
Milliman invests in skills training and career development and gives all employees access to a variety of learning and mentoring opportunities. Our growing number of Milliman Employee Resource Groups (ERGs) are employee-led communities that influence policy decisions, develop future leaders, and amplify the voices of their constituents. We encourage our employees to give back to their varied professions, including leadership in professional organizations. Please visit our website to learn more about Milliman's commitments to our people, diversity and inclusion, social impact, and sustainability.
What this position entails
IntelliScript's Information Technology organization is critical to our ability to deliver secure, reliable, and scalable SaaS products to insurance, health IT, and life sciences clients. As the Manager of Software Engineering for the Data Curation team, you will lead the engineers responsible for designing, delivering, and modernizing the backend services and data pipelines that power next-generation Insurtech products and support IntelliScript's most-used offerings built on prescription, health, and medical record data. You will manage a team of software engineers while serving as the technology lead for a cross-functional Scrum team, balancing people leadership with technical expertise to deliver scalable, secure, and compliant solutions. Partnering closely with Product Management, Architecture, and Engineering, you will maintain the technical roadmap for your product area, align delivery to business outcomes, and drive modernization initiatives within a SAFe Agile environment. As IntelliScript expands its use of GenAI in the software development lifecycle, you will help your team adopt AI-assisted development practices to responsibly improve productivity and quality while maintaining strong engineering standards, security, and compliance.
What you will be doing

• Lead and develop a team of software engineers through hiring, onboarding, coaching, performance management, and career development

• Serve as technical lead for your Scrum team by guiding architecture and design decisions, setting engineering direction, and ensuring delivery of high-quality outcomes
• Own software delivery accountability for your product area operating in SAFe Agile, managing dependencies, and driving predictable execution
• Partner with Enterprise Architecture to define and maintain a technology roadmap which balances feature delivery, reliability, scalability, and technical debt reduction
• Partner with Product Management to define and maintain a product roadmap which balances business value, technical approach, and resource capacity
• Provide level 3 support production systems including incident response, root-cause analysis, and continuous improvement
• Establish and enforce engineering best practices across the team such as code review, secure coding, unit test automation, CI/CD, documentation, and operational readiness
• Collaborate across engineering, architecture and platform teams to align architecture patterns and ensure cohesive platform evolution
• Drive adoption of GenAI-enabled engineering practices with appropriate governance, security, and quality controls

What we need

• 10+ years of professional software engineering experience, including 3+ years managing multiple software engineers

• Demonstrated ability to balance people management with technical leadership
• Experience leading teams that build and operate scalable backend services, data pipelines, and data processing systems
• Strong experience building and operating modern applications using:


• C# / .NET
• Relational and non-relational databases
• React or comparable modern front-end framework
• API and service development including REST and event-driven integrations


• Extensive cloud experience with AWS, including designing scalable, reliable, secure, and cost-effective solutions for both application and data workloads
• Experience with microservice architecture, domain-driven design, and event-driven architecture patterns
• Strong understanding of data modeling, data integration, data lifecycle management, and designing resilient, observable data systems
• Strong understanding of DevOps and operational excellence: CI/CD, infrastructure-as-code concepts, observability, incident management, and SRE-minded practices
• Experience delivering in Agile environments using Scrum and/or SAFe
• Excellent technical judgment, problem solving, debugging, and ability to make pragmatic tradeoffs
• Strong written and verbal communication skills and the ability to influence across engineering and product stakeholders
• Hands-on experience implementing GenAI-enabled development practices and establishing team guidelines for appropriate usage

What you bring to the table

• Aligns team objectives with organizational priorities, drives performance by setting ambitious goals, and ensures resources are used effectively to achieve results while upholding quality and integrity
• Leads teams in identifying opportunities for improvement, implementing new ideas, and fostering a culture of innovation
• Models empathy, resilience, and self-awareness, supporting team well-being and navigating challenges effectively
• Ensures clear, transparent communication within and across teams, influencing others to achieve objectives
• Actively coaches and mentors team members, creating opportunities for development and career progression

• Operates as a technical leader by facilitating sound architecture decisions, raising the engineering bar, and ensuring long-term maintainability and operability of systems
• Champions the responsible adoption of GenAI in engineering workflows, ensuring appropriate controls for security, privacy, IP, and quality

Wish list

• Continued education and/or advanced degree(s)
• Experience leading engineering teams responsible for healthcare, prescription, medical record, or other regulated data solutions
• Experience with production data pipelines using AWS data services
• Experience with real-time or streaming data architecture
• Familiarity with data warehouse, lakehouse, or modern data platform architectures
• Experience implementing data observability, lineage, and governance practices
• Experience in environments subject to HIPAA and/or PCI regulations
• Experience modernizing legacy on-premises applications and data platforms to AWS
• Experience in software-as-a-service, actuarial science and/or insurance underwriting industry
• AWS certifications or advanced cloud engineering training

Location
The expected application deadline for this job is September 30, 2026. This position is open to remote work. Applicants must be willing to travel to the Milliman office in Brookfield, WI as needed and travel nationwide for meetings, conferences, and team events.
Compensation
The overall salary range for this role is $117,500 - $222,985. For candidates residing in:

• Alaska, California, Connecticut, Illinois, Maryland, Massachusetts, New Jersey, Pennsylvania, Virginia, Washington, the District of Columbia, New York City, Newark, San Jose, or San Francisco the salary range is $135,125 - $ 222,985.
• All other locations the salary range is $117,500 - $193,000.

A combination of factors will be considered, including, but not limited to, education, relevant work experience, qualifications, skills, certifications, etc.
Benefits
We offer a comprehensive benefits package designed to support employees' health, financial security, and well-being. Benefits include:

• Medical, Dental and Vision - Coverage for employees, dependents, and domestic partners
• Employee Assistance Program (EAP) - Confidential support for personal and work-related challenges
• 401(k) Plan - Includes a company matching program and profit-sharing contributions
• Discretionary Bonus Program - Recognizing employee contributions
• Flexible Spending Accounts (FSA) - Pre-tax savings for dependent care, transportation, and eligible medical expenses
• Paid Time Off (PTO) - Begins accruing on the first day of work. Full-time employees accrue 15 days per year, and employees working less than full-time accrue PTO on a prorated basis
• Holidays - A minimum of 10 paid holidays per year
• Family Building Benefits - Includes adoption and fertility assistance
• Paid Parental Leave - 11 weeks of paid leave for employees who meet eligibility criteria
• Life Insurance & AD&D - 100% of premiums covered by Milliman
• Short-Term and Long-Term Disability - Fully paid by Milliman

Equal Opportunity
All qualified applicants will receive consideration for employment, without regard to race, color, religion, sex, sexual orientation, national origin, disability, or status as a protected veteran.
#LI-REMOTE
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.