Remote Director Technical Operations Jobs in Chicago, IL

Job Type:

Build a brilliant future with Hiscox

**Please Note: This position is primarily hybrid and requires in-office attendance at least two (2) days per week for candidates that are located near one of our office locations. However, qualified remote candidates will also be considered**

The Position Can Be Based In:

• Boston, MA

• Chicago, IL

• Manhattan, NY

• West Hartford, CT

About Hiscox USA:

Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2026, gross written premiums for the segment will represent over $1bn. Circa 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners including Professions, Crisis Management and Specialist lines such as Media & Entertainment. Hiscox USA has built the digital business since 2010 through ongoing investment in the brand, technology and operational capabilities. The business has pursued an omni-channel approach since inception, and so are less constrained by the channel conflict which affects some competitors. Customers have a choice of buying policies online end-to-end, by connecting with a Hiscox agent over the telephone, or alternatively through a third-party broker or insurance carrier partner. The business follows an 'all roads lead to Hiscox' philosophy, ensuring it is available to do business with target customers whichever way they choose.

The Role:

The Technical Director plays a key role within the Claims organization and is tasked with providing technical expertise in assisting and overseeing Hiscox's larger and more complex claims within the Specialty Claims organization, including Allied Healthcare, A&E, Miscellaneous Professional Liability, Cyber, Crime, and Media and Technology claims, with an emphasis on all aspects of the life of a claim, including reserving and reserving behaviors, implementation and execution of complex claim resolution strategies and partnering with Senior Leadership in Claims, Actuary, Underwriting, Legal and Risk Control.The Technical Director role does not directly handle claims but instead provides oversight and is a deep technical resource to the entire Specialty Claims organization.

Key Responsibilities:

• Partner with claims professionals and their managers in providing both coverage and liability insights and oversight of the claims handled by the Specialty Claim team.Such work includes involvement in all aspects of the life of a claim with an emphasis on developing and implementing claim resolution strategies. This includes working directly with Claims Professionals and their managers.

• Act as a coverage resource for the Specialty Claims team, including identifying and addressing coverage issues, developing a coverage strategy, coordinating and directing coverage counsel and overseeing coverage litigation.

• Drives technical excellence through mentoring, education, training, and assisting in the creation and execution of technical guidelines and governance.

• Active partnership with Senior Claim Leadership, Underwriting and Actuary on claims, litigation developments, coverage trends, reserve movements and loss mitigation efforts, with ability to address both micro and macro developments.

• Identifies emerging legal and claims trends and shares that information (along with their impacts) with Senior Claims Leadership.

• Manages and maintains claims Watchlist and implements resolution strategies for claims on that list.

• Effective engagement in reserve and trial roundtables.

Relevant Experience and Skills:

• 7+ years of insurance and/or law firm practice/litigation experience.

• JD degree strongly preferred.

• 3+ years of claims or law firm leadership experience preferred.

• Deep technical expertise in all aspects of Specialty claims.

• Self-starter who manages efficiently and oversees claims across various lines of business with varying degrees of complexity all while partnering and collaborating with others in Claims.

• Experience in handling complex/high severity claims is required.

• Strong working knowledge of insurance coverage and coverage litigation and experience in working with coverage counsel in achieving strategic results aligned with overall claims strategy.

• Excellent leadership, communication, and interpersonal skills with ability to engage and influence across all levels of the organization.

Hiscox Values:

At Hiscox our spirit is in Challenging Convention and everything we do is guided by our Values.

• Courage: Dare to take a risk

• Ownership: Passionate, commercial and accountable

• Integrity: Do the right thing, however hard

• Connected: Together, build something better

• Human: Clear, fair and inclusive

What Hiscox USA Offers:

• Competitive salary and bonus (based on personal & company performance)

• 401(k) with competitive company matching

• Comprehensive health insurance, vision, dental and FSA plans (medical, limited purpose, and dependent care)

• Company paid group term life, short- term disability and long-term disability coverage

• 24 Paid time off days, 2 Hiscox Days, 10 paid holidays, and ability to purchase 5 PTO days

• Paid parental leave

• 4 week paid sabbatical after every 5 years of service

• Financial Adoption Assistance and Medical Travel Reimbursement Programs

• Annual reimbursement up to $600 for health club membership or fees associated with any fitness program

• Company paid subscription to Headspace to support employees' mental health and wellbeing

• Recipient of 2024 Cigna's Well-Being Award for having a best-in-class health and wellness program

• Dynamic, creative and values-driven culture

• Modern and open office spaces, complimentary drinks

Salary Range: $180-$220k

The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment

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