Training Lead (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The Training Lead is a strategic learning partner responsible for delivering high-impact training experiences and developing best-in-class learning programs. This role combines expert facilitation skills with strong instructional design capabilities to support new hire onboarding, continuous development, and performance improvement across teams. This role leads the design and delivery of learner-centered programs aligned to business objectives, using data-driven insights and proven learning methodologies. They also collaborate with cross-functional stakeholders to identify skill gaps, recommend targeted interventions, and help drive operational excellence.

• Deliver engaging, inclusive training sessions across onboarding, upskilling, and refresher programs using best practices in adult learning and facilitation.
• Design and develop training materials (e.g., guides, decks, videos, eLearning) using structured to enhance knowledge retention and application.
• Conduct needs assessments and performance analysis in collaboration with leaders to identify gaps and recommend targeted training solutions.
• Maintain and update all training documentation, including SOPs, job aids, and process maps, ensuring accessibility and version control.
• Collaborate with internal teams on UAT testing, tool rollouts, and process changes by providing feedback and enabling just-in-time training.
• Evaluate training effectiveness using feedback, assessments, and key performance indicators; iterate programs based on learner and business input.
• Mentor facilitators and model best practices in training delivery and learner engagement.
• Support operations during high-volume periods by assisting with escalated calls and integrating real-time insights into training improvements.
• Promote a culture of learning that is inclusive, performance-focused, and aligned with company values.
• Contribute to other strategic initiatives and department-wide projects as assigned.

Department hours are 7 a.m. CT to 9 p.m. CT. Applicants should be available to work an 8-hour shift falling within this daily window. Up to 20% nationwide traveling for conferences and department meetings.
Preferred Qualifications
Education & Experience

• Bachelor's degree in Instructional Design, Education, Business, or related field preferred
• 3-5 years of experience in training, instructional design, or learning and development.
• Professional certification in instructional design or training (e.g., CISP) preferred.

Skills & Abilities
Facilitation & Communication

• Exceptional facilitation skills with the ability to lead dynamic, learner-centered sessions across in-person, virtual, and hybrid environments.
• Clear, engaging communicator with strong verbal and written communication skills.

Instructional Design & Learning Science

• Deep understanding of adult learning theory, instructional frameworks (ADDIE, Bloom's), and learner engagement strategies.
• Demonstrated experience designing inclusive, effective learning content.

Client Service & Relationship Management

• Builds trust and rapport with internal and external stakeholders.
• Maintains professionalism and a client-focused mindset in all interactions.

Critical Thinking & Problem Solving

• Applies sound judgment, analytical thinking, and creative solutions to training challenges.
• Manages competing priorities in fast-paced environments.

Organization & Reliability

• Highly organized, dependable, and detail-oriented with excellent time management skills.
• Follows through on commitments and adapts well under pressure.

Technical Proficiency

• Proficient in Microsoft Office Suite (Excel, PowerPoint, Outlook, etc.).
• Skilled in content creation tools such as Articulate Rise/Storyline, Camtasia, and Canva.
• Working knowledge of Salesforce, Service Cloud, and InContact preferred.

Collaboration & Teamwork

• Contributes to a positive, high-performing team culture.
• Mentors peers and supports knowledge sharing across teams.

Continuous Learning & Innovation

• Proactively explores new training methods, technologies, and tools to enhance learning experiences.
• Demonstrates adaptability in evolving training environments.

Industry & Platform Knowledge

• Familiarity with trust accounting systems is a plus.
• Bilingual language proficiency preferred.

Additional Requirements

• Primarily computer-based role; may require extended periods of screen time.
• Occasional lifting of training materials up to 25 lbs.
• Flexibility to work overtime during program launches or peak periods.

Compensation & Benefits
$25.25/hr-$30.75/hr ($52,520/yr-$63,960/yr)