Underwriter CL - Associate

WHO WE ARE

We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. 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

The Underwriter Associate CL-I provides high-quality, concierge-level service to insureds and agents by managing and multi-tasking across a broad range of servicing functions for workers’ compensation accounts, including complex billing matters, payroll adjustments, audit payment plans, and the coordination of loss runs and experience modification factors. This role handles a high volume of incoming calls, emails, and chats related to policy servicing, renewals, billing inquiries, cancellations, audits, and account maintenance, while effectively prioritizing multiple requests simultaneously. The Underwriter Associate CL-I plays a critical role in supporting the full policy lifecycle by delivering timely, accurate communication, maintaining regulatory compliance, and ensuring operational efficiency and service quality standards are consistently met. 

Position Description 

Customer & Agent Servicing (Calls, Emails, and Chats) 40%

• Receive and manage a high volume of incoming calls, emails, chats, and service tasks related to workers’ compensation policies, including:

• Policy document and endorsement requests

• Complex billing inquiries and audit-related questions

• Renewal reviews and policy status updates

• Claims inquiries by directing customers to the appropriate claims resources and adjuster contacts

• Cancellation and reinstatement inquiries

• Communicate professionally and effectively with insureds, agents, and underwriting partners to:

• Confirm renewal processing and binding status

• Provide timely billing, audit, and service request updates

• Review potential cancellations and explain policy status

• Address general workers’ compensation coverage questions within authority

• Support agents by preparing policy documentation, coordinating service requests, and managing service needs for both voluntary and assigned risk policies, ensuring a consistent, high-quality customer and agent experience.

Policy Processing & Account Management 35%

• Process and manage workers’ compensation policies, including new business, renewals, voluntary, and assigned risk accounts, ensuring accuracy, completeness, and timely delivery to policyholders and agents.

• Review policy information for correctness, including payroll, classifications, billing setup, and endorsements, and resolve discrepancies as needed.

• Maintain thorough and compliant documentation of all servicing activity, ensuring clear audit trails and adherence to regulatory and service standards.

• Proactively follow up on outstanding items, coordinating across teams as needed to ensure all service requests are resolved within established timelines while effectively managing multiple priorities.

Compliance, Quality & Continuous Improvement 15%

• Ensure all workers’ compensation servicing activities (including voluntary and assigned risk policies) are completed in accordance with regulatory requirements, carrier guidelines, and internal service standards.

• Maintain high quality and accuracy across calls, chats, emails, and task processing while effectively multi-tasking and prioritizing competing requests.

• Identify trends, recurring issues, or process gaps and escalate appropriately to support continuous improvement.

• Actively participate in training, updates, and cross-functional collaboration to remain current on product knowledge, billing practices, audits, and service expectations.

Claims Support & Coordination 10%

• Assist callers with claims-related inquiries by providing adjuster contact information and directing them to available resources for claim status and bill payment.

• Document claim-related inquiries and guidance provided, ensuring accurate records and timely communication as needed.

• Participates as a member of the Service Center Flex Team; can expect to be cross-trained in other units/areas and should be prepared to assist with workload in those areas throughout the workday as business needs require.

Education  

• Licensing:

• Not required

Work Experience  

•  Experience:

• 3–5 years of progressive experience within the workers’ compensation insurance industry.

• Prior call center and or high-volume customer service experience is a plus.

• Experience handling customer inquiries via chat, providing timely, accurate, and professional responses while maintaining engagement and service quality.

• Technical Skills:

• Proficient in Microsoft Office Suite (Word, Excel, Outlook, PowerPoint).

• Experience with management systems such as ImageRight or similar platforms.

• Ability to operate office equipment: scanners, copiers, fax machines, calculators.

Knowledge, Skill and Abilities  

• Accountability: Owns outcomes and meets expectations with integrity.

• Client Service Orientation: Acts promptly and professionally to resolve client needs and improve satisfaction.

• Communication: Communicates clearly in verbal and written formats; bilingual (English/Spanish) preferred.

• Problem Solving: Gathers relevant information and proposes practical, timely solutions.

• Technical Acumen: Understands and applies technical knowledge of P&C insurance in client-facing discussions.

• Sales Insight: Applies consultative selling and identifies opportunities to offer additional value.

• Organization: Manages multiple priorities in a fast-paced environment while meeting deadlines.

• Professionalism: Exhibits respect, tact, and accountability under pressure.

• Team Support: Fosters collaboration and assists team members as needed.

OUR REWARDS

We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week depending on the role. The base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits.

PEAK6 is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to 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.

PEAK6 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 hrpeak6@peak6.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

#PEAK6

Application data may be reviewed, including through automated tools, for security and fraud-prevention purposes. This review is conducted by our information security team and is separate from hiring decisions

About Us

We're In The Business Of What Ought To Be The business of doing, creating, and building the world the way we see fit. We seek out the transformational opportunity, making it better, more useful, more valuable. At PEAK6, we activate what is into what ought to be through world-class technology, operational excellence and purposeful design. Headquartered in the Chicago Board of Trade Building, PEAK6 is not your typical investment firm. While trading got us our start and still powers our center, we quickly realized that our vision was to embrace and empower today’s consumer through technology, simplifying processes, improving performance and creating new wealth.