Senior Learning and Development Specialist

Overview Company Overview Who We Are Established over 70 years ago, we are two of the largest Taft-Hartley trust funds in the United States. With over $50 billion in assets and $7 billion in benefits paid each year, we provide critical health insurance and lifetime retirement benefit services to nearly one million Teamster participants and family members. At Central States/TeamCare we jointly administer two trusted organizations: TeamCare, a Central States Health Plan Central States Southeast and Southwest Areas Health and Welfare Fund was founded in 1950 and was one of the first non-profit labor health funds in the United States. Since 2014, the Fund has done business under the tradename TeamCare. Today, TeamCare covers the lives of 550,000 members, from 1,100 different employers, making it the largest labor healthcare fund in the country. Central States Pension Fund Central States Southeast and Southwest Areas Pension Fund was founded in 1955 and has blazed a trail to retirement security. Paying over $90 billion in lifetime pension benefits for 690,000 retirees and beneficiaries to-date and has revolutionized the pension world of American workers. Position Summary This hybrid Senior Learning & Development Specialist role, based out of our O'Hare office, designs and facilitates impactful leadership and capability‑building learning experiences that support enterprise‑wide priorities for employees at all levels, including senior leaders. The role may partner with HR, Talent Management, and select business leaders to translate development needs into effective learning solutions and contribute to execution of the enterprise learning strategy. The Senior L&D Specialist models high‑quality facilitation, drives continuous improvement through evaluation and feedback, and supports learning effectiveness through LMS implementation and reporting. Responsibilities Key Responsibilities Facilitate high-impact learning experiences for managers, leaders, senior leaders, and broader employee populations, strengthening leadership effectiveness, manager capability, and core behavioral skills in support of enterprise-wide priorities. Design, adapt, and continuously improve leadership and capability building learning experiences, partnering with learning colleagues and stakeholders to align solutions to learner needs and enterprise priorities. Partner with HR, Talent Management, and select business colleagues to understand development needs, translate themes into learning priorities, and tailor learning design and facilitation approaches accordingly. Contribute to the development and implementation of the enterprise learning strategy, ensuring learning efforts are aligned with business needs and organizational priorities. Create and facilitate customized leadership experiences for leadership teams, addressing bespoke needs such as trust building, strategic alignment, and team effectiveness. Support evaluation and continuous improvement efforts by gathering qualitative and quantitative feedback, identifying patterns, and recommending enhancements to learning experiences. Model high quality facilitation practices and support continuous skill development among facilitators through feedback, coaching, and shared learning. Partner on Learning Management System (LMS) implementation and adoption, and may contribute hands on to system setup, course and evaluation configuration, and reporting. Qualifications Qualifications Bachelor’s degree in Human Resources, Education, Organizational Development, Psychology, or a related field preferred; advanced certifications or coursework in facilitation, leadership development, or organizational effectiveness a plus, or equivalent professional experience. 7+ years of progressive experience as a learning facilitator with demonstrated credibility delivering leadership and manager development programs, including senior leaders. Strong consulting and partnership skills, with experience working with HR, Talent Management, and business stakeholders to diagnose development needs, translate themes into learning priorities, and tailor learning solutions accordingly. Experience creating and facilitating customized leadership experiences for intact teams, addressing complex dynamics such as trust building, strategic alignment, and team effectiveness. Experience contributing to the development, refinement, and ongoing support of a Learning & Development strategy. Demonstrated comfort using qualitative and quantitative feedback to evaluate learning effectiveness, identify patterns, and recommend improvements to learning design, content, and facilitation practices. Experience supporting or mentoring other facilitators, modeling strong facilitation practices, sharing design insights, and reinforcing quality and consistency across learning programs. Familiarity with Learning Management Systems (LMS) or learning platforms, including experience contributing to system implementation, course or evaluation setup, or reporting; Workday experience preferred. Strong written, verbal, and facilitation communication skills, with the ability to clearly convey concepts, guide meaningful dialogue, and adapt messaging for diverse audiences and leadership levels. Compensation Annual Salary Range: $85,000 - $100,000 ( The posted range of pay represents the anticipated pay scale for this position. Final pay will be determined based on a variety of job-related factors, including, but not limited to, skills, experience, education, certifications, internal equity, and organizational needs.) Benefits* We’re proud to offer one of the most competitive total rewards packages in the nonprofit and benefits administration sectors, including: 100% company-paid family insurance benefits including health, dental, RX & vision (comprehensive coverage with low deductibles) 100% company-funded pension plan (at no cost to the employee) Health care and dependent care Flexible Spending Accounts (FSAs) 401(k) retirement plan with company match Paid vacation and PTO days Flexible start times & hybrid work-from-home schedule Lunch stipend for onsite café Tuition reimbursement * Please note that, though uncommon, the benefits described above are subject to change at the company’s discretion. Equal Opportunity Employer We are committed to providing equal employment opportunities to all employees and applicants for employment. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other characteristic protected by law.