Senior Training Manager - Chicago, IL

OneDigitalChicago, IL
$70,000 - $90,000Onsite

About The Position

The Senior Training Manager - Medicare reports to the Sr. Program Manager and works closely with Sales, Quality Assurance, and other cross-functional teams to identify, develop, and support training initiatives that ensure new sales hires are prepared to successfully engage with clients. In addition to overseeing a team of Training staff, this role is responsible for the ongoing development of current agents by designing, delivering, and maintaining continuous learning programs, refresher training, and curriculum updates to support evolving products, processes, compliance requirements, and organizational initiatives throughout the year. This position plays a key role in driving employee performance, knowledge retention, and operational excellence through strategic learning and development initiatives.

Requirements

  • Curriculum development, instructional design, and content creation
  • Strong facilitation and presentation skills with the ability to engage audiences of all sizes
  • Ability to translate complex concepts into clear, engaging, and actionable learning experiences
  • Strong interpersonal skills with the ability to build trust, credibility, and influence at all levels of the organization
  • Excellent written, verbal, and presentation communication skills
  • Proven leadership, coaching, and team development skills
  • Strong organizational and project management skills with the ability to manage multiple priorities and deadlines
  • Adaptable and able to thrive in a fast-paced, changing environment
  • High degree of professionalism, accountability, and attention to detail
  • Bachelor’s Degree or equivalent experience; required
  • 1+ years of leadership or people management experience; required
  • Demonstrated experience delivering presentations and facilitating training for audiences of varying sizes and organizational levels

Nice To Haves

  • Experience in the Medicare or health insurance industry; preferred
  • Experience leading training operations within a high-volume contact center or customer service environment; preferred
  • Proven ability to manage multiple training programs, projects, and competing priorities in a fast-paced environment

Responsibilities

  • Design, develop, and maintain comprehensive company training programs, onboarding, curricula, and learning content that align with business objectives, organizational priorities, and employee development needs
  • Lead curriculum strategy and program design, ensuring training content remains current, effective, and aligned with company goals and industry best practice
  • Partner with executive leadership, operations, quality assurance, sales team, and HR to identify performance gaps and implement learning solutions.
  • Utilize a variety of training methodologies, techniques, concepts, learning tools, and practices to ensure maximum effectiveness of training programs
  • Monitor and measure effectiveness of all training programs
  • Lead, mentor, and develop a team of training managers and training leads
  • Relay training effectiveness to OneDigital Advanced Health Senior Leadership

Benefits

  • health, wellbeing, retirement, and other financial benefits
  • paid time off
  • overtime pay for non-exempt employees
  • robust learning and development programs
  • reimbursement of job-related expenses
  • employee perks and discounts
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