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Remote Stop Loss Insurance Jobs in Cascade, WI (NOW HIRING)

Remote Stop Loss Insurance information

See Cascade, WI salary details

$16

$31

$63

How much do remote stop loss insurance jobs pay per hour?

As of Aug 1, 2026, the average hourly pay for remote stop loss insurance in Cascade, WI is $31.80, according to ZipRecruiter salary data. Most workers in this role earn between $19.47 and $47.93 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Stop Loss Insurance Specialist, and why are they important?

To excel as a Remote Stop Loss Insurance Specialist, you need expertise in health insurance underwriting, risk assessment, and policy analysis, often supported by a background in insurance or finance. Familiarity with industry-standard claims management systems, CRM platforms, and regulatory compliance tools is essential. Strong analytical thinking, attention to detail, and effective written communication are crucial soft skills for success in a remote environment. These abilities ensure accurate risk evaluation, regulatory adherence, and clear client interactions, which are critical for managing high-value stop loss insurance contracts.

What is remote stop loss insurance?

Remote stop loss insurance is a type of coverage designed to protect self-funded employers from large or catastrophic claims, but managed and administered through digital or remote platforms. This insurance reimburses employers for claims that exceed a predetermined limit, helping them manage risk and avoid significant financial loss. The 'remote' aspect refers to the use of online tools and services for policy management, claims processing, and communication, allowing for flexible and efficient administration without the need for in-person meetings. This is particularly beneficial for companies with distributed teams or those seeking streamlined, technology-driven solutions.

What is the difference between Remote Stop Loss Insurance vs Remote Underwriter?

AspectRemote Stop Loss InsuranceRemote Underwriter
CredentialsInsurance licenses, actuarial knowledgeInsurance licenses, underwriting certifications
Work EnvironmentInsurance companies, brokers, remoteInsurance companies, remote or office
Industry UsageHealth and self-funded plansInsurance policy assessment and risk evaluation

Remote Stop Loss Insurance professionals focus on providing coverage for self-funded health plans, managing risk, and setting policy terms. Remote Underwriters evaluate insurance applications, assess risks, and determine policy eligibility. While both roles require insurance knowledge and licenses, Stop Loss Insurance specialists concentrate on risk management for health plans, whereas Underwriters focus on evaluating individual applications. Understanding these differences helps clarify career paths and job expectations in the insurance industry.

What are some common challenges faced by professionals working in remote stop loss insurance roles?

One common challenge in remote stop loss insurance roles is maintaining clear and effective communication with underwriters, brokers, and clients, since much of the collaboration happens virtually. Additionally, staying updated on changing regulations and market trends requires proactive self-learning and digital resourcefulness. Managing sensitive data securely and ensuring timely turnaround on complex claims or policy analysis can also be demanding when working remotely. Building strong relationships with team members and clients, despite the lack of in-person interaction, is key to long-term success in this field.
What cities near Cascade, WI are hiring for Remote Stop Loss Insurance jobs? Cities near Cascade, WI with the most Remote Stop Loss Insurance job openings:
Infographic showing various Remote Stop Loss Insurance job openings in Cascade, WI as of July 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $66,146 per year, or $31.8 per hour.

LLM Optimization & Agentic Commerce Manager

Sargento Foods

Plymouth, WI • On-site, Remote

Full-time

Medical, Dental, Vision, Retirement

Re-posted 11 days ago


Sargento rating

9.2

Company rating: 9.2 out of 10

Based on 23 frontline employees who took The Breakroom Quiz

3rd of 434 rated food and drinks producers


Job description

The LLM Optimization & Agentic Commerce Manager is responsible for ensuring Sargento's brand, products, and claims are accurately represented, discoverable, and competitively positioned across large language models (LLMs), AI assistants, and agent-based commerce platforms. This role works across brand, media, eCommerce, analytics, and technology in areas where standards and best practices are still emerging. Beyond protecting brand integrity and improving AI visibility, this role is expected to drive business impact by shaping brand positioning, influencing how Sargento appears across the media ecosystem, and capturing consumer sentiment and coverage across AI surfaces, social environments, and agentic commerce experiences.

Your Story.

The LLM Optimization & Agentic Commerce Manager is responsible for ensuring Sargento’s brand, products, and claims are accurately represented, discoverable, and competitively positioned across large language models (LLMs), AI assistants, and agent-based commerce platforms. This role works across brand, media, eCommerce, analytics, and technology in areas where standards and best practices are still emerging. Beyond protecting brand integrity and improving AI visibility, this role is expected to drive business impact by shaping brand positioning, influencing how Sargento appears across the media ecosystem, and capturing consumer sentiment and coverage across AI surfaces, social environments, and agentic commerce experiences.

Your Passion. Our Culture.

At Sargento, you work for a company you believe in, with a family of people who believe in you.  Our culture stems from a simple premise: Hire good people and treat them like family.  At Sargento, you can make decisions based on how they affect people as well as the long-term health of our company.  You will be encouraged to make a meaningful difference in the community, in the company and in your career.  With diverse experiences and tools to learn and develop, you can transform your aspirations into reality.  If you’re ready for the right place to belong and grow your career, you can find it here.

Benefits that set us apart.

  • Comprehensive medical including Fertility, Adoption benefits, Dental, and Vision Insurance
  • Remote ½ day Fridays
  • Onsite Health & Wellness Center
  • Employer 401K contribution in the top 1% of the nation
  • Relocation Assistance
  • Tuition Assistance
  • Access to Employee Store

What You Do.  

  • LLM & AI Visibility Strategy
    • Own & evolve the Sargento’s brand strategy for LLM discoverability, accuracy, and brand representation rapidly changing AI ecosystem.
    • Monitor how Sargento products, claims, nutrition, and brand stories appear across major LLMs and AI assistants.
    • Identify gaps, risks, and opportunities related to misinformation, hallucinations, or loss of share of voice in AI-driven discovery.
    • Adapt strategy as platforms, models, and behaviors evolve.
  • AI Agent & Media Enablement
    • Partner with Media, Omni-Channel, and Analytics teams to evaluate how AI agents can support or optimize media planning, activation, and performance analysis, as LLMs increasingly function as media and commerce environments.
    • Translate emerging AI agent capabilities into practical, test-and-learn use cases (planning efficiency, optimization signals, reporting acceleration).
    • Stay ahead of platform changes that affect how media, commerce, and content are surfaced in AI environments, proactively adjusting approaches as rules, capabilities, and signals shift.
  • Data, Content & Signal Management
    • Partner with Brand, Omni, Legal, IT, and Analytics to ensure structured, authoritative, and up-to-date data signals (product info, FAQs, claims, imagery, content) are AI-ready.
    • Help define evolving best practices for content creation and governance that improve AI interpretation and reuse.
    • Collaborate on schema, feeds, APIs, and other inputs that influence AI outputs.
  • Governance, Risk & Brand Protection
    • Establish guardrails and governance for AI usage related to brand, media, and commerce.
    • Proactively identify reputational, legal, or consumer trust risks associated with AI-generated outputs.
    • Partner closely with Legal and PR on escalation paths and response protocols when inaccuracies surface.
  • Measurement & Learning
    • Define success metrics for LLM visibility and accuracy (share of voice, sentiment, citation quality, accuracy benchmarks).
    • Build ongoing reporting and learning loops to inform brand, media, and eCommerce strategy.
    • Share insights with leadership to guide investment, prioritization, and capability development.
    • Serve as the primary owner of Sargento’s AI/LLM visibility platform responsible for day-to-day usage, monitoring brand presence and accuracy, interpreting insights, managing vendor partnership, and translating results into clear actions for Brand, Media, Omni-Channel, PR, and Analytics teams.
    • Partner with Brand Strategy & Analytics to evolve brand equity tracking to include AI-driven discovery and recommendation environments.
    • Translate LLM visibility signals into leading indicators of brand equity shifts (early signals vs. lagging survey data).
  • External Partnerships & Thought Leadership
    • Lead evaluations and partnerships with AI/LLM visibility platforms, measurement vendors, and tech partners.
    • Represent Sargento as a knowledgeable, credible voice in evolving AI-driven marketing and commerce conversations
    • Stay current on platform, and industry shifts related to AI and marketing.

Your Education and Experience.

  • Bachelor’s degree required  
  • 5+ years of experience in marketing, media, analytics, digital strategy, or marketing technology
  • Strong understanding of search, media ecosystems, and data signals, with curiosity and fluency in AI/LLMs
  • Ability to translate complex technical concepts into clear business implications
  • Proven cross-functional leadership experience (Brand, Media, Analytics, IT, Legal, PR)
  • Comfort operating in ambiguity and building new processes from scratch
  • Preferred experience with AI platforms, LLM tools, marketing automation, or advanced analytics
  • Preferred familiarity with retail media, eCommerce content, and digital shelf dynamics
  • Preferred background in governance, risk management, or platform standards is a plus
  • CPG or regulated-category experience preferred

Our Story.

With over 2,400+ employees and net sales of nearly $1.8 billion, Sargento is a family-owned company that has been a leader in cheese for more than 70 years.  We created the world’s first, successful pre-packaged sliced and shredded natural cheeses.  Sargento is based in Plymouth, Wisconsin, where we manufacture and market shredded, sliced and snack natural cheese products, as well as ingredients and sauces.  Sargento is known for the exceptional quality of our products and for product design, packaging and merchandising innovations that have transformed our industry.

To learn more about our culture and values, please visit our website at https://careers.sargento.com/us/en.

#LI-KJ1

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.Employment Type: FULL_TIME

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About Sargento

Sourced by ZipRecruiter

Industry

Food and drink manufacturing

Company size

1,001 - 5,000 Employees

Headquarters location

Plymouth, WI, US

Year founded

1953