Chief Learning Officer Remote Jobs in Illinois (NOW HIRING)

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 clients. We’re 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 has been a key part of business success and is critical to future performance. The Chief Technology Officer (CTO) will be crucial in leading the implementation and operations of IntelliScript’s technology. This will involve aligning technology initiatives with the overarching business objectives, ensuring the company’s technology adequately supports its operations, objectives, and customers. This person will have oversight of the technology strategy, software development, resource management, team leadership, vendor management, IT governance, stakeholder collaboration, and business continuity.

As the most senior technology executive, the CTO will oversee engineering, IT operations, and AI initiatives, leveraging technology to drive growth capabilities, safeguard data and systems, and support organizational objectives. It will be important for the CTO to drive collaboration throughout the organization and specifically with product stakeholders to successfully deliver innovative, flexible, cost-effective, and reliable technology services. The CTO will play a central role in advancing business performance, unlocking new growth capabilities, and ensuring the organization can operate efficiently, securely, and at scale.

What you will be doing

The Chief Technology Officer will be responsible for:

• Technology Management: Oversee the selection, implementation, and maintenance of all technology systems, including hardware, software, networks, and enterprise applications.
• Innovation and Digital Transformation: Identify opportunities for digital transformation and innovation to enhance business processes, customer experiences, and competitive advantage.
• IT Strategy and Leadership: Develop and implement the organization’s IT vision and strategy in alignment with overall business goals. Lead the IT department and provide direction for technology investments and initiatives.
• Cybersecurity and Risk Management: Establish and enforce policies to protect the organization’s digital assets, ensure data privacy, and manage IT-related risks and compliance with relevant regulations.
• Drive AI/ML adoption, automation, and cloud modernization to enhance product innovation and operational efficiency.
• Budgeting and Resource Allocation: Develop and manage the IT budget, allocate resources efficiently, and ensure cost-effective technology solutions.
• Vendor and Partner Management: Negotiate contracts and manage relationships with technology vendors, service providers, and consultants.
• Team Leadership and Development: Recruit, mentor, and develop IT staff; foster a culture of continuous learning and high performance within the technology team.
• Stakeholder Collaboration: Collaborate with other executives and departments to identify technology needs and deliver solutions that support business objectives and company goals.
• Business Continuity and Disaster Recovery: Develop and maintain plans to ensure the continuity of IT services during emergencies or disruptions.
• Drive the development of enterprise technology standards, governance processes and performance metrics to ensure IT is delivering value to the enterprise
• Lead the development of our infrastructure and application systems to ensure that business processes are supported now and for the future
• Ensure information and technology capabilities and services within his/her scope are adaptable to changing business needs and delivered reliably, sustainably, securely and cost-effectively
• Stay current on modern technologies and provide direction on which emerging technologies should be introduced and integrated within the enterprise to ensure IT capabilities respond to the needs of the enterprise’s business strategy
• Establish active relationships with the company’s executives, business leaders, and members of their teams.
• Lead complex, major change initiatives with demonstrated skills in change management.

What we need

• Bachelor's degree in Computer Science, Information Systems, or related field (Advanced Degree preferred)
• 15+ years of relevant technology experience
• 10+ years of experience in leadership roles, including 3+ years of prior experience in a CTO role demonstrating the ability to effectively lead teams and drive strategic initiatives
• Proven track record of developing and executing IT strategies aligned with business objectives.
• In-depth knowledge of IT systems, infrastructure, cybersecurity, and emerging technologies.
• Strong leadership, communication, and interpersonal skills.
• Experience managing large-scale technology projects and budgets.
• Ability to build and lead high-performing teams.
• Experience with compliance, risk management, and operations for technology product organizations
• Proven experience leading large, complex, and transformative initiatives and taking advantage of opportunities to innovate business models and digitalization of the organization
• Experience leading cloud transformations with AWS and/or Azure
• Sound business acumen and strategy execution
• Strong written and verbal presentation skills, with adeptness to distill technical complexity for non-technical executives

What you bring to the table

• Shapes organizational strategy, sets performance targets for departments or large teams, and ensure alignment with long-term business goals and ethical standards
• Sets the direction for departmental learning and improvement, ensuring that systems and processes enable ongoing growth
• Cultivates emotionally intelligent leadership throughout the organization, mentoring others and shaping a supportive culture
• Communicates and influences at the departmental level, ensuring alignment with vision and strategy
• Develops organizational strategies for growth and development, mentoring other leaders and investing in leadership pipelines

Location

The expected application deadline for this job is September 15, 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 range for this role is $254,900 - $498,295. For candidates residing in:

• Alaska, California, Connecticut, Illinois, Maryland, Massachusetts, New Jersey, New York City, Pennsylvania, Virginia, Washington, or the District of Columbia the range is $293,135 - $498,295. 
•  All other locations the range is $254,900 - $433,300. 

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 – Up to 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