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Insurance Startup Jobs in Chicago, IL (NOW HIRING)

ISG Partners

Customer Support Specialist

Evanston, IL · On-site

$55K - $65K/yr

Health, Dental, and Vision Insurance: 85% coverage for employees, 60% for dependents. * Flexible ... startup. * Because of the close collaboration with our team, we prefer candidates based in the ...

blueStone

Ruby Developer

Chicago, IL · On-site

Company Description Our client is an enterprise startup that is disrupting the outdated auto insurance claims settlement process and turning a $120B market on it's head. Client is growing rapidly and ...

atom.com

Broker

Hoffman Estates, IL

In person (hybrid) Come build something real at a fast-growing tech startup, where your work on day ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

atom.com

Broker

Hoffman Estates, IL · On-site

In person (hybrid) Come build something real at a fast-growing tech startup, where your work on day ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

atom.com

Sales Representative

Hoffman Estates, IL · On-site

In person (hybrid) Come build something real at a fast-growing tech startup, where your work on day ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

atom.com

Sales Representative

Hoffman Estates, IL · On-site

In person (hybrid) Come build something real at a fast-growing tech startup, where your work on day ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

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All JobsInsurance Startup JobsInsurance Startup Jobs in Chicago, IL

Insurance Startup information

What is an insurance startup?

An Insurance Startup job typically involves working for a newly established company in the insurance industry, focusing on innovation and disruptive solutions. Roles can range from product development and underwriting to sales, marketing, and technology-driven initiatives like insurtech. Employees in these roles often work in a fast-paced environment, helping to build new products, automate processes, or improve customer experiences. Since startups are growth-oriented, employees may take on diverse responsibilities and have opportunities for rapid career progression.

What does a typical workday look like at an insurance startup?

Working at an insurance startup involves a mix of tasks, from developing and refining insurance products to liaising with partners, clients, and regulators. Your day may include market research, pitching new solutions to prospective clients, managing tech integrations, and collaborating closely with a small, agile team. Expect a fast-paced environment where you'll juggle multiple responsibilities and contribute directly to the company's direction and success. You'll also have opportunities to learn from industry experts and take on increasing responsibility as the business grows.

What are the key skills and qualifications needed to thrive in an insurance startup, and why are they important?

To thrive in an Insurance Startup, you need a blend of entrepreneurial drive, industry knowledge, and strong business development skills, often supported by experience in insurance, finance, or related fields. Familiarity with insurtech platforms, CRM systems, and compliance regulations is highly valued. Exceptional problem-solving, adaptability, and networking abilities set top performers apart in dynamic startup environments. These skills are essential for navigating regulatory complexity, identifying growth opportunities, and building a successful insurance business from the ground up.

What are popular job titles related to Insurance Startup jobs in Chicago, IL?

For Insurance Startup jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Insurance Startup jobs in Chicago, IL look for?

The top searched job categories for Insurance Startup jobs in Chicago, IL are:

Insurance Startup jobs near you
Infographic showing various Insurance Startup job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 89% In-person, and 11% Remote job distribution.

Customer Support Specialist

ISG Partners

Evanston, IL • On-site

$55K - $65K/yr

Full-time

Medical, Dental, Vision, PTO

Posted 10 days ago

Job description

Position: Support Specialist

Division: Customer Operations

Location: Chicago, IL (Hybrid, 3 days onsite/week)

Salary: $55–65K


What Goose Offers

  • Great working environment with a family oriented culture.
  • Health, Dental, and Vision Insurance: 85% coverage for employees, 60% for dependents.
  • Flexible PTO (vacation, sick, personal days) plus 5 company holidays.
  • Opportunities for professional development and career growth.
  • A collaborative, inclusive, and supportive team environment.


Work Environment

  • This role is ideal for someone who genuinely enjoys helping people and wants to grow within a fast-moving startup.
  • Because of the close collaboration with our team, we prefer candidates based in the greater Chicago area who can work onsite three days per week. 


About the Role

  • Goose is hiring a Support Specialist to join their growing Customer Operations team.
  • You’ll be on the front lines of the customer experience — resolving issues, deepening product expertise, and helping shape the systems that make great support scalable.
  • You’ll report to our Senior Support Specialist and work closely with teams across Customer Success and Implementation.
  • This is a net-new role with clear early KPIs (time to respond, time to close, DSAT) and the opportunity to help define future success metrics as you grow.


What You’ll Do

  • Manage and resolve inbound support tickets across chat, email, and additional channels with accuracy, empathy, and care.
  • Become a product expert, developing a deep understanding of Goose’s platform to guide customers through issues and workflows.
  • Partner with our offshore support team to ensure smooth handoffs and consistent customer experiences across time zones.
  • Identify recurring issues and customer friction points, escalating trends to senior team members and leadership.
  • Collaborate with Customer Success and Implementation on cross-functional customer needs.
  • Participate in weekend support rotation and shared team coverage schedules.
  • Maintain internal documentation, support playbooks, and training materials.


Necessary Skills Needed

  • 1–3 years in customer support, customer success, or another customer-facing role.
  • Clear, empathetic communication skills — written and verbal — with the ability to simplify complex concepts.
  • A problem-solving mindset and curiosity about root causes, not just quick fixes.
  • Strong organizational habits and comfort managing multiple open issues.
  • Ability to thrive in a fast-paced startup environment where processes evolve.
  • Familiarity with support tools (Intercom, HubSpot, Zendesk, etc.) or a willingness to learn quickly.


Bonus Points if You Have…

  • Experience in pet services, hospitality, or other service-based industries.
  • Background in SaaS support at an early-stage startup.
  • Interest in growing into a senior or lead support role over time.