Cynthia Kowalski
Highland
Summary
Founder of a Medicare advisory firm, innovating an education-first model that empowers seniors in 22 states. Successfully guided clients through complex enrollment periods, ensuring clarity in communications and adherence to CMS regulations, while establishing a comprehensive resource library for continued client support.
Overview
40
40
years of professional experience
1
1
Certification
Work History
Founder & Principal Advisor
Eligry LLC
12.2025 - Current
- Founded independent Medicare advisory serving seniors across 22 states, focusing on Florida, Texas, Indiana, and Illinois.
- Developed education-first advisory model, providing side-by-side Medicare Advantage and Medigap comparisons.
- Guided clients through initial, annual, and special enrollment periods, enhancing their understanding and confidence in Medicare options.
- Managed all member communications personally, ensuring compliance with CMS documentation standards and fostering strong client relationships.
- Established business infrastructure, creating website, content library, CRM, and marketing funnel to support client engagement and education.
- Authored Medicare education ebook and maintained ongoing client resource library.
Licensed Health Insurance Agent
Health Plan One
08.2025 - 12.2025
- Completed six-week Aetna certification program in Medicare Advantage, Medicare Supplement, and Part D prescription drug plans to enhance expertise in health insurance offerings.
- Transitioned from role to focus on health recovery, demonstrating commitment to personal well-being.
- Educated clients about various health insurance options and benefits.
- Assisted clients in selecting suitable health plans based on individual needs.
- Analyzed client information to determine eligibility for specific health insurance programs.
Owner & Principal
Adaptechs
01.2009 - 01.2025
- Founded and ran an IT support firm serving small and mid-sized businesses across multiple industries for 16 years.
- Provided strategic IT consulting to optimize client technology solutions.
- Served as single point of contact for client escalations, diagnosing technical issues, setting clear expectations, and ensuring resolution.
- Simplified technical concepts for non-technical clients, fostering long-term relationships through patience, responsiveness, and follow-through.
Sales Director
AT&T
01.1986 - 01.2009
- Led team of six account managers serving Fortune 500 enterprise customers; coached and mentored to enhance team effectiveness and exceed performance targets.
- Managed relationships with enterprise accounts, ensuring high levels of client satisfaction and retention.
- Owned executive-level client escalations, de-escalating high-pressure situations and keeping complex, multi-party issues moving toward resolution.
- Trained the team on consultative selling, relationship building, and customer advocacy.
Education
B.S. - CRIMINAL JUSTICE
Illinois State University
Normal, ILSkills
- Health insurance strategy
- Medicare Advantage and Supplement
- Regulatory compliance
- Medical terminology
- Client onboarding process
- Multi-system navigation
- CRM proficiency
- Documentation management
- Team management
- Training and mentorship
- Conflict resolution
- Documentation management
Years Of Client Advocacy
25+
AHIP Certified
2026
References
Available on request.
States Licensed
22
Licensing
Life & Health, 22, IN, NPN 21601670, AHIP, Aetna, BCBS/HCSC, Humana, UHC, Wellcare, CMS-compliant annually
Certification
- Life & Health Licensed in IN, CA, FL, GA, IL, KS, KY, LA, MA, MI, MN, MO, NC, NJ, NY, OH, PA, SC, TX, VA, WA
Timeline
Founder & Principal Advisor
Eligry LLC
12.2025 - Current
Licensed Health Insurance Agent
Health Plan One
08.2025 - 12.2025
Owner & Principal
Adaptechs
01.2009 - 01.2025
Sales Director
AT&T
01.1986 - 01.2009
B.S. - CRIMINAL JUSTICE
Illinois State University