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Training Lead, Manager; Workday Financial

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Apex Systems
Apprenticeship/Internship position
Listed on 2026-02-16
Job specializations:
  • IT/Tech
  • Education / Teaching
    Training Consultant
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below
Position: Training Lead, Manager (Workday Financial)

Training Manager, Program Far Side (Contract)

At Colibri, culture is a critical part of our collective success, and we live our values everyday:
Love, Joy, Boldness, Teamwork and Curiosity. These values guide our interactions with each other, our customers, and the community as a whole.

Far Side Program is Colibri Group’s enterprise-wide transformation program, driving modernization across systems, processes, and operations. Anchored in platforms like Workday and Salesforce, the program spans multiple ecosystems and brands, with the goal of enabling scalability, integration, and operational excellence.

Role Overview

The Training Lead will play a critical role in enabling successful adoption of Colibri’s Far Side Program by ensuring employees are informed, equipped, and confident in using new systems, tools, and processes (e.g., Workday, Salesforce, Adaptive). Reporting to the Organizational Change Management (OCM) Lead, this role will oversee end-to-end training strategy, design, and delivery across program phases.

This individual will coordinate with workstream leads, system owners, and functional subject matter experts to develop training plans, materials, and delivery mechanisms that support readiness and sustainment. Success in this role requires strong facilitation, stakeholder engagement, and a learner‑centric mindset focused on outcomes and adoption.

Key Responsibilities Training Strategy & Planning
  • Develop and maintain the Far Side training strategy and roadmap across Workday, Salesforce, and supporting tools.
  • Define training scope, approach, and delivery model (e.g., train‑the‑trainer, virtual instructor‑led, self‑paced).
  • Collaborate with the OCM and Program Management teams to align training activities with the overall change and communication plans.
Content Development & Coordination
  • Partner with functional leads and SMEs to create, review, and validate training content.
  • Leverage standardized templates and tools (e.g., SharePoint, Viva Engage, or KnowBe4) for consistent delivery and access.
  • Curate and maintain a central training repository with version control and intuitive navigation for end users.
Delivery & Readiness
  • Coordinate and execute end‑user and super‑user training sessions, ensuring materials are tailored by audience and role.
  • Manage the training calendar, logistics, and registration process across business units and program phases.
  • Support readiness and testing activities (e.g., UAT, dry runs) to ensure a seamless learning experience.
Measurement & Sustainment
  • Establish KPIs and feedback mechanisms to measure training effectiveness and adoption.
  • Partner with OCM and HR to transition materials into ongoing enablement or LMS channels post go‑live.
  • Drive continuous improvement through evaluations, surveys, and lessons learned sessions.
Team Collaboration
  • Work closely with Change Management, Communications, PMO, and Product Owners to ensure consistent engagement and enablement experiences.
  • Act as the primary liaison between system owners, workstream leads, and business stakeholders for all training‑related activities.
  • Support alignment with Far Side engagement, recognition, and readiness initiatives.
Qualifications
  • 7+ years of experience in learning and development, instructional design, or training delivery within complex organizations.
  • Experience designing and leading role‑based training for enterprise systems such as Workday, Salesforce, or Adaptive.
  • Strong facilitation and communication skills, with the ability to translate complex concepts into clear, engaging learning.
  • Proven track record managing end‑to‑end training programs — from needs assessment through delivery and evaluation.
  • Skilled in developing a variety of learning formats (instructor‑led, virtual, self‑paced, and blended).
  • Strong organizational skills and attention to detail; able to manage multiple priorities and stakeholders.
  • Knowledge of adult learning principles and familiarity with digital learning tools or learning management systems (LMS).
  • Bachelor’s degree in a related field (e.g., Education, Instructional Design, Communications, or HR Development).
Success in This Role Looks Like
  • Training plans and materials are clear, current,…
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