1

Insurance Surety Jobs in Chicago, IL (NOW HIRING)

AVP, Commercial Surety

Chicago, IL · On-site +1

$133K - $206K/yr

Job Summary Assist in overseeing surety production and underwriting activities within the region ... July 09, 2026 14400 Arch Insurance Group Inc.

AVP, Commercial Surety

Chicago, IL · On-site +1

$133K - $206K/yr

Job Summary Assist in overseeing surety production and underwriting activities within the region ... July 09, 2026 14400 Arch Insurance Group Inc.

Berkley Corporation member company Berkley Insurance Company, which has an A.M. Best rating of A ... surety solutions. Company URL: www.berkleysurety.com Manage, produce and underwrite new and renewal ...

Broker I, Surety

Chicago, IL · Hybrid

$100K - $130K/yr

We're seeking an Broker to join our Surety Group in Chicago. This is an exciting opportunity to ... Lead, monitor, and report on ongoing insurance or risk retention programs, ensuring they meet ...

Berkley Corporation member company Berkley Insurance Company, which has an A.M. Best rating of A ... surety solutions. Company URL: www.berkleysurety.com Responsibilities Manage, produce and ...

Broker I, Surety

Chicago, IL · On-site

$100K - $130K/yr

We're seeking an Broker to join our Surety Group in Chicago. This is an exciting opportunity to ... Lead, monitor, and report on ongoing insurance or risk retention programs, ensuring they meet ...

Berkley Corporation member company Berkley Insurance Company, which has an A.M. Best rating of A ... surety solutions. Company URL: www.berkleysurety.com Responsibilities Manage, produce and ...

next page

Showing results 1-20

Insurance Surety information

See Chicago, IL salary details

$38.6K

$85.3K

$126.2K

How much do insurance surety jobs pay per year?

As of Aug 1, 2026, the average yearly pay for insurance surety in Chicago, IL is $85,294.00, according to ZipRecruiter salary data. Most workers in this role earn between $68,500.00 and $102,000.00 per year, depending on experience, location, and employer.

How does an Insurance Surety professional typically collaborate with underwriters and clients during the bonding process?

As an Insurance Surety professional, you will frequently work alongside underwriters to assess the risk and eligibility of applicants seeking surety bonds. This collaboration involves gathering and reviewing financial statements, analyzing project details, and ensuring all underwriting criteria are met. Additionally, you’ll be in regular contact with clients to clarify requirements, collect necessary documentation, and explain the bonding process. Effective communication and relationship-building skills are essential, as you’ll serve as a key liaison between the client and the underwriting team throughout the lifecycle of the bond.

What are insurance surety bonds?

Insurance surety bonds are legally binding agreements that involve three parties: the principal (the party required to obtain the bond), the obligee (the party requiring the bond), and the surety (the company guaranteeing the principal’s obligations). These bonds ensure that the principal will fulfill specific obligations or perform tasks as agreed, such as completing a contract or adhering to legal requirements. If the principal fails to meet these obligations, the surety steps in to cover losses or ensure completion. Surety bonds are commonly used in construction, licensing, and court-related matters. They are different from traditional insurance in that they protect the obligee rather than the principal.

What are the key skills and qualifications needed to thrive as an Insurance Surety professional, and why are they important?

To thrive as an Insurance Surety professional, you need a strong understanding of risk assessment, financial analysis, and contract law, often supported by a bachelor's degree in finance, business, or a related field. Familiarity with underwriting software, financial modeling tools, and regulatory compliance systems is typically required. Excellent negotiation, attention to detail, and relationship-building skills help establish trust and maintain client partnerships. These skills and qualities are crucial to accurately assess risks, ensure compliance, and deliver tailored bonding solutions in a highly regulated industry.
What job categories do people searching Insurance Surety jobs in Chicago, IL look for? The top searched job categories for Insurance Surety jobs in Chicago, IL are:
Infographic showing various Insurance Surety job openings in Chicago, IL as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $85,294 per year, or $41 per hour.

Senior Counsel, Surety

Berkshire Hathaway Specialty Insurance

Chicago, IL • On-site

$180K - $240K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 10 days ago


Job description

Who are we?
A strategic and trusted insurance partner, Berkshire Hathaway Specialty Insurance (BHSI), provides a broad range of commercial property, casualty and specialty insurance coverages and outstanding service to customers and brokers around the world. Part of Berkshire Hathaway’s insurance operations, we bring our solutions to market with our stellar brand name, top-rated balance sheet, and the expertise of our global team of professionals, who exude excellent capabilities and strong character.

We are a values-based organization where respect, integrity, excellence, collaboration, and passion define who we are and how we do business. We value diversity of backgrounds, experience, and perspectives and strive to foster an inclusive environment that enables all our team members to bring their best selves to work. We are one team committed to building a culture where every teammate has the opportunity to contribute and be recognized. Want to be part of the team building the finest property, casualty and specialty lines insurance company in the world?

Learn more about our unique culture and history.

Job Opportunity:

BHSI has an exciting opportunity for a Senior Counsel - Surety. This position will be part of the Legal Department and will interact with the entire Surety team to support BHSI’s business goals and contribute on a strategic level to our growing global surety business. The role will report to Vice President and Chief Counsel - Surety, and participate in managing all facets of underwriting support for BHSI’s contract and commercial surety business. The ideal candidate values working in a highly collaborative environment; simplicity over complexity and thinking outside of the box in providing practical solutions for underwriters, brokers, and customers. This position affords the opportunity to make significant and lasting contributions across all facets of our growing surety organization.

The desired location of the position is one of our offices in Atlanta, Boston, Chicago, Houston, Los Angeles New York, Philadelphia, or San Franciso, but remote candidates will be considered.

Duties & Responsibilities:

  • Provide input and advice on risk and legal issues to surety underwriters and senior management to assist with risk assessment concerning all aspects of the surety business, including complex project delivery methods, contracts and bond forms, indemnity agreements, and other related underwriting documents and agreements.
  • Assist in the negotiation with brokers, bond customers, obligees, and other related parties in surety transactions.
  • Active involvement in Co-Surety relationships and responsible for Co-Surety Agreements and related documents.
  • Research laws and regulations that impact the underwriting of surety products.
  • Monitor legal and regulatory developments impacting the surety, construction business and commercial surety business.
  • Participate in developing and implementing training, resource materials and underwriting guidance for all surety professionals within the organization.
  • Assist in the development of business documents for Global surety growth, including new international surety markets.
  • Provide input and participate in new product development.

Qualifications, Skills and Experience:

  • Law degree required. Business, engineering, or finance undergraduate degree a plus.
  • 10+ years’ experience in surety claims, surety and construction law, or surety underwriting support. National account and international surety experience a plus.
  • Admission to practice as a licensed attorney in the applicable jurisdiction required.
  • Time management, prioritization, and ability to balance competing priorities required.
  • Ability to function without significant oversight, and while navigating uncertainty.
  • Effective communication and interpersonal skills.
  • Ability to travel up to 30% of the time.
  • Ability to work within a team environment.
  • Must have strong verbal and written communication skills with the confidence and ability to collaborate with senior executives both internally and externally.
  • Strong negotiation, analytical and decision-making skills required.
  • Ability to identify and resolve problems to achieve strategic business results.


BHSI Offers:

  • A competitive package and exciting growth opportunities for career-oriented teammates.
  • A dynamic, action oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and our other stakeholders.
  • A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework.
  • Benefits that support your life and well-being, which include:
  • Comprehensive Health, Dental and Vision benefits
  • Disability Insurance (both short-term and long-term)
  • Life Insurance (for you and your family)
  • Accidental Death & Dismemberment Insurance (for you and your family)
  • Flexible Spending Accounts
  • Health Reimbursement Account
  • Employee Assistance Program
  • Retirement Savings 401(k) Plan with Company Match
  • Generous holiday and Paid Time Off
  • Tuition Reimbursement
  • Paid Parental Leave


The base salary range for this position is $180,000 to $240,000, along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates – both their capabilities and character – as demonstrated by our amazing culture.

NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.