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ezICHRA Customer Success Manager

Oswald Companies

Oswald Companies

Sales & Business Development, Customer Service
Richfield, OH, USA
Posted on Nov 19, 2025

Would you like to take ownership in a dynamic, high-growth business that truly walks the talk?

Oswald Companies seeks goal-driven professionals ready to take their career to the next level.

Job Overview: We are seeking a dynamic and customer-focused ICHRA (Individual Coverage Health Reimbursement Arrangement) Customer Success Manager to join our team. The ideal candidate will be responsible for ensuring a smooth and positive experience for our ezICHRA customers as they navigate the implementation and ongoing management of their ICHRA plans. This role involves building strong relationships with customers, providing strategic guidance, and offering support to ensure their satisfaction and success in utilizing the ICHRA model.

Key Responsibilities:

  • Customer Onboarding & Implementation: Guide customers through the process of setting up and launching their ICHRA plans. Ensure smooth integration with customers’ internal management systems, helping customers understand the features, compliance requirements, and best practices. Ensure that customers are provided with appropriate plan advisory assistance during the employee plan selection process.
  • Timely Enrollment & Payment Processing: Ensure that employee enrollments are processed accurately and on time, and that all payments related to the ICHRA program are made promptly. Address any issues related to delays in enrollment or payment and ensure timely resolution.
  • Customer Education & Training: Deliver training and informational sessions to customers and their teams, educating them on ICHRA plan features, regulations, and optimization strategies to maximize the value of their plans.
  • Ongoing Customer Support: Serve as the primary point of contact for all ICHRA-related inquiries. Proactively address any issues, troubleshooting problems, and offer solutions to ensure customers' success with their plans.
  • Renewal & Retention: Manage the renewal process with customers, including collaboration with the ezICHRA Analyst team ensuring ICHRA contributions are updated within the customer’s ezICHRA Platform Tech and proactively preparing customers for annual renewals. Address any renewal-related questions or concerns to facilitate a smooth renewal process.
  • Strategic Account Management: Develop deep, trusted relationships with key customer stakeholders. Regularly check in with customers to assess their satisfaction and identify opportunities for improvement or growth.
  • Plan Optimization & Problem Solving: Collaborate with customers to review usage data, suggest improvements, and implement changes to increase efficiency and cost-effectiveness of their ICHRA plans.
  • Collaboration with Cross-Functional Teams: Work closely with Sales, ezICHRA Platform Tech, Analyst, Marketing, and Compliance teams to relay customer feedback, recommend improvements, and ensure the delivery of exceptional customer experience.
  • Compliance & Regulatory Guidance: Keep customers informed about changes in healthcare regulations and ICHRA-related compliance requirements. Provide guidance to ensure customers' plans remain compliant with federal, state, and local laws.
  • Performance Reporting: Track and report on customer success metrics such as engagement, retention, and overall satisfaction. Utilize data to proactively identify opportunities for improvement.

Qualifications:

  • Education & Experience:
    • Bachelor’s degree in business, Healthcare Administration, or a related field (or equivalent experience).
    • 3+ years of experience in customer success, account management, or customer-facing role, preferably in the health insurance or benefits industry.
    • Life & Health Insurance License (company paid if not already licensed)
  • Knowledge & Skills:
    • Strong understanding of ICHRA, healthcare benefits, and individual health insurance plans.
    • Proven ability to manage customer relationships and deliver exceptional service.
    • Excellent communication and interpersonal skills, with the ability to explain complex concepts in a clear, concise manner.
    • Strong problem-solving skills with a solution-oriented mindset.
    • Ability to work in a fast-paced, dynamic environment and manage multiple priorities effectively.
    • Proficiency with CRM systems, customer management tools, and data analysis.

Preferred Qualifications:

  • Experience with ICHRA administration platforms or benefits management software.
  • Knowledge of healthcare regulations such as ACA, ERISA, HIPAA, and other relevant compliance frameworks.

Why Join Us?

  • Be part of a growing team at the forefront of transforming how organizations manage healthcare benefits.
  • Competitive salary and benefits package.
  • Opportunities for career growth and development.
  • Collaborative and supportive work environment.

Who is Oswald?

Oswald is a 129-year-old company that creates a world of protection around the lives and businesses of our clients.

We are an independent, employee-owned company. So, essentially, you own your own success in a personally and financially rewarding opportunity.

Inclusivity is a priority. We foster an environment of collaboration and belonging where our Employee-Owners thrive on their unique path. Our diverse talent reflects the communities and clients we serve, while driving unmatched risk and insurance innovations.

Our people-first culture and client service excellence have built our reputation of integrity, resourcefulness, and a relentless care for our clients and employees. Don’t believe us? Ask your friends, colleagues, and mentors about Oswald. There’s a reason Oswald has been named a Top Workplace for nine consecutive years.

What you’ll get...

At Oswald, you will have the opportunity to build a long-term career with unlimited growth potential. Aim high, work hard and we’ll help you achieve your goals.

At Oswald, you will experience our caring work environment. We care about our Employee-Owners, we care about our customers, and we care about the world around us. Our caring personality comes to life in the form of volunteering in the community. We even give employees paid time off to volunteer with an organization of their choice.

At Oswald, you will achieve a work-life balance. We care about your physical and emotional well-being, so work-life balance is encouraged and practiced. We understand you have a life outside of work, and we want you to live it.

At Oswald, you will have access to a world-class Total Rewards package. We truly value our people, which shows in our compensation, benefits, and perks.

  • In addition to competitive pay, we have designed a performance-based annual incentive program. All employees are eligible to earn a bonus by meeting performance objectives.

  • Comprehensive medical, dental and vision plans and numerous supplemental benefit offerings.

  • Paid time off annually and a sabbatical at every 10-year service anniversary.

  • Ownership in the company in the form of company stock (discretionary profit-sharing and 401(k) match contribution)

  • Assistance with parking expenses, discount programs for area services/experiences, and financial support for professional development and licensure/designations

  • Access to specialized leadership development programming designed to take your career to the next level.

  • And so much more!

To learn more about Oswald, our culture and everything we have to offer, visit us on LinkedIn.

Oswald, a Unison Risk Advisors company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic.