Senior Training Manager - Chicago, IL

OneDigital Medicare Services, LLC; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Job summary

OneDigital is seeking a Senior Training Manager – Medicare to lead the design, development, and delivery of comprehensive training programs for new sales hires and cross-functional teams. This role reports to the Sr.

Program Manager and collaborates with Sales, QA, HR, and Operations to close performance gaps and elevate learning outcomes. The ideal candidate will have experience in curriculum development, strong facilitation and presentation skills, and a proven track record in leading training

Qualifications

• 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.
• 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 training programs, onboarding, curricula, and learning content that align with business objectives and employee development needs.
• Lead curriculum strategy and program design, ensuring training content remains current and effective.
• Partner with executive leadership, operations, quality assurance, sales, and HR to identify performance gaps and implement learning solutions.
• Utilize various training methodologies and tools to maximize 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.

Skills

Curriculum design

Facilitation

Communication

Leadership

Project management

Interpersonal skills

Adaptability

Professionalism

Education

Bachelor's degree

Job description

Job Overview

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.

Essential Duties & 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.

Qualifications & Skills

• 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.

Education & Experience

• 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.
• 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.

Compensation & Benefits

Base Pay Range: 70,000-90,0000. The base pay depends on skill, education, qualifications, professional experience, and location. Variable compensation, commission, and/or annual bonus may be available based on individual and company performance.

Benefits include health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non‑exempt employees, and robust learning and development programs. Job‑related expenses may be reimbursed, and employees may receive perks and discounts.

Equal Employment Opportunity Statement

OneDigital is an equal‑opportunity employer committed to a culture that celebrates diversity, insists on equity and inclusion, and connects our people. We provide equal employment opportunities to all employees and applicants for employment regardless of veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information, or any other category protected by federal, state or local law. A copy of the Federal EEO poster is linked here. Pursuant to local Fair Chance Ordinances, qualified applications with arrest or conviction records for employment will be considered. For applicable candidates, relevant ordinances are linked to inform you of your rights as an applicant. Employment decisions shall comply with all other applicable federal, state, and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal‑history‑inquiry (or ‘ban the box’) laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont, and Washington. This posting will remain live while we actively accept applications.