ZipRecruiter

Log In

1

We Insure Jobs in Chicago, IL (NOW HIRING)

We Insure

Senior Financial Analyst

Chicago, IL · On-site

$88K - $109K/yr

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client ...

We Insure

Senior Financial Analyst

Chicago, IL

$88K - $109K/yr

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client ...

We Insure

Financial Operations Manager

Chicago, IL · On-site +1

$91K - $120K/yr

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client ...

Insure Online

Insurance Sales Agent

Chicago, IL · On-site

$40K - $60K/yr

We represent over 50 insurance companies, ranging from the largest and most recognizable carriers to the most reliable regional carriers, enabling us to write any risk with a quality product. DUTIES ...

Insure Online

Insurance Sales Agent

Bedford Park, IL

$40K - $60K/yr

We represent over 50 insurance companies, ranging from the largest and most recognizable carriers to the most reliable regional carriers, enabling us to write any risk with a quality product. DUTIES ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

We insure both nonprofit and for-profit social service organizations, such as child daycare, sheltered workshops, group homes, senior citizen centers, senior independent living, schools, counseling ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

We insure both nonprofit and for-profit social service organizations, such as child daycare, sheltered workshops, group homes, senior citizen centers, senior independent living, schools, counseling ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

We insure both nonprofit and for-profit social service organizations, such as child daycare, sheltered workshops, group homes, senior citizen centers, senior independent living, schools, counseling ...

Brookfield

Sr. Business Analyst

Chicago, IL · On-site

$105K - $125K/yr

This approach helps those we insure drive down their ultimate cost through prevention and aggressive claims handling. Simply stated, our products and services help keep businesses in business. Argo ...

Hiscox

Underwriter - Terrorism

Chicago, IL · Hybrid

Here are some of the requirements we would ideally like to see: * Experience in sales is ideal, and experience in insurance with established relationships with wholesale property and general ...

Peak6 Investments LLC

Office Manager

Chicago, IL · On-site

PEAK6's core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets. ABOUT THIS ROLE As a ...

next page

Showing results 1-20

All JobsWe Insure JobsWe Insure Jobs in Chicago, IL

We Insure information

See Chicago, IL salary details

$11

$22

$32

How much do we insure jobs pay per hour?

As of Jul 26, 2026, the average hourly pay for we insure in Chicago, IL is $22.60, according to ZipRecruiter salary data. Most workers in this role earn between $17.84 and $27.26 per hour, depending on experience, location, and employer.

What do We Insure agents do?

We Insure agents are licensed insurance professionals who work with clients to help them find the best insurance coverage for their needs. They represent multiple insurance carriers, allowing them to offer a variety of products, including home, auto, business, and life insurance. We Insure agents guide clients through the process of comparing policies, selecting appropriate coverage, and handling claims. Their goal is to make insurance shopping simple and to provide personalized service to each client.

What are the key skills and qualifications needed to thrive as an Insurance Agent at We Insure, and why are they important?

To thrive as an Insurance Agent, you need in-depth knowledge of insurance products, state licensing, and strong sales abilities. Familiarity with CRM systems, quoting software, and relevant insurance certification courses is typically required. Outstanding interpersonal skills, active listening, and resilience help build client trust and manage relationships effectively. These skills ensure agents can match clients with appropriate coverage, maintain compliance, and grow their book of business in a competitive industry.

What is the difference between We Insure vs Insurance Agent?

AspectWe InsureInsurance Agent
CredentialsVaries by employer, often requires licensingRequires state licensing and certification
Work EnvironmentTypically office-based, with some remote optionsOffice, client meetings, and fieldwork
Industry UsageBrand or franchise name for insurance servicesProfessionals selling insurance products
Job RoleBrand representing insurance servicesSales and customer service in insurance

We Insure is a brand or franchise offering insurance services, often employing licensed agents. Insurance Agents are licensed professionals who sell insurance policies and provide client consultations. While We Insure may employ Insurance Agents, the two are distinct: We Insure is a company name, whereas Insurance Agent is a job role. Understanding this difference helps job seekers and customers clarify whether they are applying for a position or seeking insurance services.

What are some common challenges faced by Insurance Agents at We Insure, and how can new hires overcome them?

Insurance Agents at We Insure often encounter challenges such as building a strong client base, staying current with industry regulations, and effectively managing multiple policies and client needs simultaneously. New hires can overcome these challenges by leveraging the company's robust training programs, utilizing provided sales tools, and actively seeking mentorship from experienced team members. Consistent networking, strong organizational skills, and a proactive approach to client relationship management are key to long-term success in this role.
What are popular job titles related to We Insure jobs in Chicago, IL? For We Insure jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching We Insure jobs in Chicago, IL look for? The top searched job categories for We Insure jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for We Insure jobs? Cities near Chicago, IL with the most We Insure job openings:
We Insure jobs near you
Infographic showing various We Insure job openings in Chicago, IL as of July 2026, with employment types broken down into 100% Full Time. Highlights an 86% In-person, and 14% Remote job distribution, with an average salary of $47,009 per year, or $22.6 per hour.
Senior Financial Analyst

Senior Financial Analyst

We Insure

Chicago, IL • On-site

$88K - $109K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 4 days ago

Job description

Who We Are.
At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client's unique needs, ensuring they feel confident and supported in every decision.
As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.
What sets us apart? We're data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.
We Insure is building a lean, high-leverage finance organization to power both organic growth and mergers and acquisitions.
Your Impact.
As a Senior Financial Analyst, you will independently own and manage the full cycle of FP&A activities from start to finish, including budgeting, forecasting, financial reporting, variance analysis, and financial modeling. This role is responsible for connecting business performance to financial outcomes by providing data-driven analysis and insights that support operational and strategic decision-making. You will partner with cross-functional teams to evaluate initiatives, monitor financial performance, and identify opportunities to improve reporting, efficiency, and profitability.
Key Responsibilities
FP&A Ownership & Financial Strategy
  • Independently own and manage the full FP&A function from start to finish, including budgeting, forecasting, financial reporting, variance analysis, and long-range planning.
  • Lead monthly, quarterly, and annual financial reporting processes, delivering actionable insights on business performance, trends, and operational drivers.
  • Develop and maintain financial models, dashboards, and forecasting tools that connect operational performance to financial outcomes.
  • Partner with leadership to support strategic planning, capital allocation, profitability improvement, and business decision-making.
  • Build ROI analyses and evaluate the financial impact of new initiatives, investments, and growth opportunities.
Financial Analysis, Modeling & Risk Management
  • Analyze revenue, expense, and operational performance data to identify risks, trends, and opportunities for improvement.
  • Develop scenario, sensitivity, and "what-if" models to evaluate assumptions, forecast outcomes, and assess business risk.
  • Quantify the financial impact of sales performance, market conditions, operating costs, and strategic initiatives.
  • Deliver concise reporting packages, dashboards, and executive-level presentations to support informed decision-making.
  • Proactively identify financial gaps, performance issues, and operational inefficiencies, while recommending data-driven solutions.
Process Improvement & Cross-Functional Leadership
  • Drive continuous improvement initiatives across FP&A processes, including automation, reporting efficiency, and scalability.
  • Own optimization and ongoing enhancement of financial systems and planning tools, including NetSuite and Adaptive Insights.
  • Identify process gaps and implement improvements that strengthen reporting accuracy, workflow efficiency, and financial visibility.
  • Serve as a strategic business partner to Sales, Marketing, Operations, and Technology teams by providing financial guidance, ad hoc analysis, and performance insights.
  • Independently manage priorities, reporting deliverables, and cross-functional initiatives with minimal oversight.

Qualifications
Required
  • Bachelor's degree in Finance, Accounting, Economics, or related field.
  • 5-8 years of experience in FP&A, corporate finance, or a similar analytical role.
  • Advanced Excel and strong financial modeling skills.
  • Excellent communication and presentation abilities.

Preferred
  • Experience with ERP or planning tools (NetSuite, Adaptive Insights).
  • Familiarity with SQL, Python, Tableau, or Power BI.
  • Background in insurance or financial services.

Our Values. The We Way.
At We Insure, Group our values shape how we work, how we lead, and how we grow-together. They're more than just words-they guide every interaction, every decision, and every customer experience.
We Way Reflects Our Commitment to.
  • We personalize protection at a price you can trust
  • We hustle to find opportunity
  • We care authentically
  • We thrive in ambiguity
  • We own our results
  • We have fun along the way
  • And-we're just getting started

Our Total Rewards.
  • Medical, Dental, Vision, Life, Pet; Flexible Spending Account
  • Competitive Salaries
  • 401K Match
  • Work-Life Balance: Personal Days, PTO Days, 12 Paid Holidays, Two Paid Days for Volunteer Service, Paid Parental Leave
  • Short and Long-Term Disability
  • Employee Support Programs, Including Mental Health
  • Tuition Reimbursement
  • Matching Charitable Gift Program
  • Lucrative Referral Program

This position is not able to be performed in California, Colorado, New York or Washington.
EEO
We Insure Group is an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.
Disability
We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hrinfo@peak6insurtech.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.
Note to applicant: It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment. Please know that our company does not use lie detector tests in our hiring process.
Base Salary Range:
$88,000-$110,000

Apply