Senior Training Manager - Chicago, IL

Insight Performance Inc

Chicago, IL

JOB DETAILS
SALARY
SKILLS
Artificial Intelligence (AI), Best Practices, Call Centers, Communication Skills, Content Development, Cross-Functional, Customer Support/Service, Detail Oriented, Health Insurance, Instructional Design, Insurance Sales, Interpersonal Skills, Leadership, Medicare, Mentoring, Multitasking, Onboarding, Operational Strategy, Organizational Skills, People Management, Presentation/Verbal Skills, Product Support, Project/Program Management, Quality Assurance, Recruiting/Staffing Agency, Regulatory Compliance, Sales, Staff Development, Staff Training, Time Management, Training Program, Training Program Evaluation, Training/Teaching Curriculum, Training/Teaching Materials, Writing Skills
LOCATION
Chicago, IL
POSTED
3 days ago

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that's making a bigger impact on the world? At OneDigital, we are on a mission to help people do their best work and live their best lives. From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other's truest selves.

We understand that pursuing a new job is a big deal. Maybe you're afraid you won't fit in. Well, here's the good news. For us, the days of "fit in to get in" are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot. Your best life awaits.

Must be eligible to work in the United States without the need for work visa or residency sponsorship.

We kindly ask that external recruiters, agencies, and search firms do not contact our hiring managers or employees directly regarding open positions. All candidate submissions must go through our official application process and must be made aware to our internal Talent Acquisition team to verify candidate ownership.

Unsolicited resumes or candidate profiles sent to OneDigital without a prior signed agreement will be considered the property of OneDigital. In such cases, OneDigital reserves the right to pursue and hire those candidates without any financial obligation to the agency or recruiter.

Our Newest Opportunity:

Summary:

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.

Essential Duties and Responsibilities (include but are not limited to):

The Senior Training Manager - Medicare will lead the OneDigital Advanced Health Training team and carry out the following 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 and 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

Education, Training and 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

Other:

Base Pay Range: 70,000-90,0000

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company's performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.

To learn more, visit: www.onedigital.com/careers

OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.

OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: 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 (including testing and characteristics) or any other category protected by federal, state or local law (collectively, "protected characteristics"). A copy of the Federal EEO poster is linked here.

Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant:

City and County of San Francisco

City of Los Angeles

County of Los Angeles

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.

In short, we believe in hiring the most qualified applicant for the position, regardless of background.

This posting will remain live while OneDigital is actively accepting applications. Once candidates have been selected, the posting will be removed.

OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow.

If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you.

Thank you for your interest in joining the OneDigital team!

About the Company

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Insight Performance Inc