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Medicaid Instructional Designer and Trainer - Remote US

March 5, 2026

Great companies need great teams to propel their operations. Join the group that solves business challenges and enhances the way we work and grow. Working at Gainwell carries its rewards. You’ll have an incredible opportunity to grow your career in a company that values your contributions and puts a premium on work flexibility, learning, and career development. Summary Gainwell Technologies is seeking an Medicaid Instructional Designer and Trainer – Remote US to join our Training and Development team supporting the Wisconsin Medicaid program. In this role, you will design, develop, and deliver engaging learning programs that enhance performance, ensure compliance, and promote continuous learning for teams supporting Wisconsin Medicaid operations. Your role in our mission <ul><li>Design, develop, and facilitate engaging training programs across virtual, classroom, and on-the-job environments. </li><li>Develop learning content aligned with Wisconsin Medicaid program requirements, policies, and procedures. </li><li>Create eLearning and digital training materials using authoring tools such as Articulate, Captivate, or similar authoring tool. </li><li>Partner with subject matter experts and cross-functional teams to assess training needs and ensure effective learning outcomes. </li><li>Evaluate and refine training effectiveness through learner feedback, assessments, and performance metrics. </li><li>Provide post-training support and resources to reinforce knowledge retention and skill development. </li></ul>What We're Looking For <ul><li>5–7 years of experience as an instructional designer, trainer, or facilitator in a learning and development environment. </li><li>1–3 years of experience designing computer-based training or eLearning modules using authoring tools (Articulate, Captivate, or similar). </li><li>Strong knowledge of adult learning principles and instructional design methodologies (ADDIE, SAM, or equivalent). </li><li>Proficiency with Microsoft Office Suite and virtual learning platforms (Teams, WebEx, Zoom). </li><li>Excellent presentation, communication, and collaboration skills. </li><li>Experience supporting Medicaid or government healthcare programs preferred. </li></ul>What You Should Expect In This Role <ul><li>Full-time, remote position (40 hours per week). </li><li>Reliable broadband internet connection required (minimum 24 Mbps download / 8 Mbps upload). </li><li>Flexibility to conduct both virtual and in-person training sessions as needed. </li><li>Collaboration with cross-functional teams and subject matter experts across Gainwell and client organizations. </li><li>Opportunities for professional growth through Gainwell University and career advancement programs. </li></ul>The pay range for this position is $51,700.00 - $73,800.00 per year, however, the base pay offered may vary depending on geographic region, internal equity, job-related knowledge, skills, and experience among other factors. Put your passion to work at Gainwell. You’ll have the opportunity to grow your career in a company that values work flexibility, learning, and career development. All salaried, full-time candidates are eligible for our generous, flexible vacation policy, a 401(k) employer match, comprehensive health benefits, and educational assistance. We also have a variety of leadership and technical development academies to help build your skills and capabilities. We believe nothing is impossible when you bring together people who care deeply about making healthcare work better for everyone. Build your career with Gainwell, an industry leader. You’ll be joining a company where collaboration, innovation, and inclusion fuel our growth. Learn more about Gainwell at our company website and visit our Careers site for all available job role openings. Gainwell Technologies is an Equal Opportunity Employer, where all qualified applicants will receive consideration for employment without regard to race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical condition), age, sexual orientation, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Gainwell Technologies defines “wages” and “wage rates” to include “all forms of pay, including, but not limited to, salary, overtime pay, bonuses, stock, stock options, profit sharing and bonus plans, life insurance, vacation and holiday pay, cleaning or gasoline allowances, hotel accommodations, reimbursement for travel expenses, and benefits.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...