Enter a job title or keyword

Training Manager Chicago, IL

OneDigital


Job Location:

Chicago, IL - USA

Yearly Salary: $ 55000 - 65000
Posted: 11 July 2026 (30+ days ago)
Application Deadline: 8 October 2026
Vacancies: 1 Vacancy

Job Summary

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you A career thats 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 others truest selves.

We understand that pursuing a new job is a big deal. Maybe youre afraid you wont fit in. Well heres 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 best life awaits.

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

Our Newest Opportunity:

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

The Training Manager Medicare will lead the OneDigital Advanced Health Training team and carry out the following responsibilities:

  • Create and facilitate onboarding training programs for direct new hires in sales-focused roles
  • Facilitate company training schedules and curriculum focused on meeting the needs for the specific time of year
  • Work in partnership with sales managers to identify knowledge/skill gaps and bridge those gaps through training to enhance overall results for the overall team
  • Partner closely with the Quality Assurance team to ensure newly onboarded hires are training according to compliance standards
  • Utilize a variety of training methodologies techniques concepts learning tools and practices to ensure maximum effectiveness of training programs
  • Maintain database of reference materials for ongoing access by staff to include training manuals binders best practices etc.
  • Monitor and measure effectiveness of all training programs
  • Continuously update and enhance training materials and programs for maximum impact
  • Manage a team of assigned Training staff
  • Relay training effectiveness to OneDigital Advanced Health Senior Leadership

Qualifications Skills and Requirements:

  • Confident and comfortable speaking to audiences of all sizes
  • Adept at conveying complex information in a way that is easy to understand and engaging
  • Ability to garner and foster trust and credibility
  • Excellent written and verbal communication skills
  • Self-starter who is committed to making a positive impact on the organization
  • Team player with selfless attitude

Education Training and Experience:

  • Bachelors Degree or equivalent experience; required
  • 2year of management experience; required
  • 2 years of experience in a training coaching or instructional design role (preferably in a call center or sales environment)
  • Medicare or other Insurance experience preferred not required
  • Experience speaking to audiences of all sizes; required
  • Demonstrated experience developing and delivering training programs
  • Current Health Insurance Producer License preferred or willingness to obtain one within a specified timeline
  • Proven ability to coach and develop sales agents including call coaching performance feedback and skills development
  • Experience using performance metrics (e.x: conversion rates QA scores compliance audits) to evaluate training effectiveness and drive continuous improvement)

The typical base pay range for this role nationwide is $55000 to $65000 per year.

Your base pay is dependent upon your skills education qualifications professional experience and addition to base pay some roles are eligible for variable compensation commission and/or annual bonus based on your individual performance and/or the companys 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: 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.

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 such cases OneDigital reserves the right to pursue and hire those candidates without any financial obligation to the agency or recruiter.

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!


Required Experience:

Manager


About Company

Company Logo

Access insurance, financial services, employee benefits, and PEO solutions on one platform through local advisors.

View Profile View Profile