Demo

Senior Learning and Development Specialist

Central States Funds/TeamCare
Chicago, IL Full Time
POSTED ON 5/22/2026
AVAILABLE BEFORE 6/18/2026
Position Summary

The Senior Training Specialist 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 Training 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.

Salary.com Estimation for Senior Learning and Development Specialist in Chicago, IL
$100,459 to $126,502
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