Samuel Rosenwinkel
Chaska,MN
Summary
Results-driven sales and client advisory professional with a strong track record in healthcare and employee benefits technology. Experienced in scaling early-stage organizations, advising employers and employees on ICHRA and individual market strategies, and building durable broker and client relationships. Thrives in entrepreneurial, fast-paced environments with a focus on revenue growth, customer satisfaction, and long-term partnerships.
Overview
12
12
years of professional experience
Work History
Regional Sales Manager
zizzl health
Minnesota & Wisconsin
09.2021 - Current
- Own regional sales strategy and execution across Minnesota and Wisconsin, managing full-cycle sales through broker, agency, and employer channels.
- Personally sold, closed, and onboarded over 20% of the company’s existing clients, representing over $2M in annual recurring revenue (ARR).
- Achieved individual quota every year since 2022, consistently contributing to company-wide growth targets.
- Built and manage relationships with 200+ brokers across ~30 agencies, driving sustained pipeline and platform adoption.
- Maintained a 14% closing ratio in 2025 through disciplined qualification and consultative selling.
- Serve as a subject-matter expert on ICHRA, and individual market benefit strategies, advising brokers and employers on compliant, cost-effective solutions.
- Manage and mentor a District Sales Manager in Wisconsin; introduced him to 100+ brokers across 15 agencies and coached him to double quota attainment in 2025.
Senior Advisor; Producer
Gravie, Inc.
07.2018 - 09.2021
- Advised eligible employees and employers on ICHRA, QSEHRA, and taxable contribution models, supporting adoption of modern health benefit strategies.
- Assisted with individual health insurance policy enrollment across federal and state exchanges, including MNsure and Covered California.
- Played a key role in early ICHRA premium payment implementation programs, contributing to scalable client operations.
- Managed high-touch, high-visibility client relationships in a dynamic startup environment.
- Recognized as a consistent top performer in customer satisfaction and quality scoring.
- Licensed Health and Life Insurance Producer in 36 U.S. states.
Inventory Control Clerk
Apex International
Chaska, MN
01.2017 - 01.2017
- Developed inventory control processes and supported raw materials receiving and quality sampling.
Bartender / Server / Trainer
Mexico Lindo
Duluth, MN
01.2014 - 01.2017
- Led front-of-house operations, trained new staff, and managed inventory during high-volume service periods.
Education
B.A. - Economics
University of Minnesota, Duluth
01.2015
Skills
- Regional & Channel Sales Leadership
- ICHRA & Individual Market Expertise
- Broker & Client Relationship Management
- Revenue Growth & Quota Attainment
- Customer Satisfaction & Retention
- Training, Coaching & Presentation
- CRM & Sales Documentation
ADDITIONAL
Interests: Health & fitness, outdoor recreation, travel, music, golfing, fishing, and camping
Timeline
Regional Sales Manager
zizzl health
09.2021 - Current
Senior Advisor; Producer
Gravie, Inc.
07.2018 - 09.2021
Inventory Control Clerk
Apex International
01.2017 - 01.2017
Bartender / Server / Trainer
Mexico Lindo
01.2014 - 01.2017
B.A. - Economics
University of Minnesota, Duluth