Underwriting Assistant New Chicago, IL

Resilience; Chicago, Northern (IL, KY); Hybrid; USD 48,000 - 66,000; Full time

Benefits offered by this job

Flexible work schedule

Flexible paid time off

Healthcare for employees

Family paid leave

401k/Pension

Professional development

Job summary

Resilience is at the forefront of integrating cyber risk, insurance, and technology from Chicago. As an Underwriter Assistant on our Operations team in Chicago, you will take full ownership of the administrative velocity and transactional accuracy that enables our underwriting process to scale.

You will learn from leaders across Underwriting, Claims, Marketing, Finance, and Security Operations, handling applications, broker/client communications, policy issuance, and cross-functional

Qualifications

• Excellent analytical skills and detail orientation.
• Exceptional written and verbal communication with a customer-first approach.
• Ability to multi-task and thrive in a fast-paced environment.
• Interest in cybersecurity, tech, and cyber risk.
• Prior experience in customer service, support, or administrative role.
• Familiarity with productivity software and basic insurance operations.

Responsibilities

• Process and review incoming insurance applications for completeness and accuracy.
• Own front-line communication with brokers and clients to ensure smooth placement of business.
• Coordinate policy and endorsement issuance and maintain file compliance.
• Bridge underwriting with Claims, Security Sales, Security Engagement, and PAS to optimize regional portfolio.

Skills

Analytical skills

Communication skills

Multi-tasking

Customer service experience

G-Suite & Salesforce

Tools

G-Suite

Salesforce

Job description

At Resilience, we’re creating a new category that integrates cybersecurity, cyber insurance, and cyber risk management. Founded in 2016 by experts from across the highest tiers of the US military and intelligence communities – and built by prominent leaders and innovators from the insurance, technology, and cybersecurity industries – Resilience is rewriting the rules of how cyber risk is assessed, measured, and managed.

Our integrated cyber risk solutions connect risk quantification software, cybersecurity experts, and A+ rated cyber insurance, all purpose-built for middle and large organizations. We are a cybersecurity company, a Cyber and Tech E&O-focused MGA, a fintech startup, and a data science powerhouse, all purposefully built into one.

Resilience is proud to be backed by leading technology investment firms, including General Catalyst, Lightspeed Venture Partners, Intact Ventures, Founders Fund, CRV, and Shield Capital.

The Hook: Why this role matters now

Launch your career at the high-velocity intersection of cyber risk, insurance, and technology. As an Underwriter Assistant on our Operations team, you won’t just be filing paperwork or sitting on the sidelines. You will take complete ownership of the administrative velocity and transactional accuracy that enables our underwriting team to evaluate cyber and tech E&O applications at scale. This is a foundational, high-visibility role where you will learn from seasoned leaders across Underwriting, Claims, Marketing, Finance, and Security Operations, serving as a critical operational pillar of our growth.

The Mission: What you will achieve in the first 6 months

In your first six months, you will take full accountability for processing and reviewing incoming insurance applications, ensuring every file is complete, accurate, and ready for deep underwriting. You will own the front-line communication loop, actively managing transactional relationships with brokers and clients to guarantee smooth, frictionless placement of business. Beyond basic execution, you will coordinate policy and endorsement issuance, maintain meticulous file compliance, and bridge the gap between our Underwriting team and cross-functional partners in Claims, Security Sales, Security Engagement, and Policy Administration Services (PAS) to keep the regional portfolio highly optimized.

The Toolkit:

• Excellent analytical skills with a relentless attention to detail.
• Exceptional written and verbal communication skills, with a customer-first approach to solving problems.
• A proven ability to multi-task, stay organized, and thrive in a fast-paced, highly dynamic environment.
• A genuine interest in cybersecurity, tech, and cyber risk.(This role is perfect for ambitious recent graduates and early-career professionals).
• Prior experience in a customer service, support, or administrative role.
• Familiarity with modern productivity software (such as G-Suite or Salesforce) and basic insurance operations.

The Culture: How we work

We move fast, operate with zero ego, and embrace a bias to action. We are guided strongly by our four core values: transparency, excellence, grit, and humility. You will work in a highly collaborative, cross-functional environment where you will be expected to raise your hand, ask questions, and take real pride in the precision of your work.

The Benefits: Standardized perks

You will work alongside prominent leaders and innovators from the insurance, technology, and cybersecurity industries, as well as experts from the highest tiers of the US military and intelligence communities. Comprehensive perks include a flexible work schedule, flexible paid time off, paid healthcare for employees, family paid leave, a 401k/Pension, and robust professional development advancements.

Compensation range

$48,000 - $66,000 USD

What Resilience Offers You

Innovative company culture

Family paid leave

Paid healthcare for employees

401k/Pension

Professional development & career advancements

Flexible paid time off

Employee referral bonus

Accommodations and Accessibility

We want to ensure you're able to perform as well as possible in your interview. As part of that, if you have any accessibility-related needs to ensure a comfortable visit, please let us know. We'll do our best to provide reasonable accommodations to suit your working style during your interview and if you join our team.

If you require a reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please let your recruiter contact know.