Careers


CapSpecialty is always looking for ambitious, curious, fun and hardworking candidates who are driven by creative problem-solving and excited by new challenges. 

We value the experiences of our employees both in the office and outside of work, which is why we offer generous salary, benefits, and extras including:  open vacation, nine paid holidays, paid parental leave, bonus opportunities, fully vested 401k from the start with a 100% match up to 5%, flexibility, paid continuing education, volunteer opportunities, relaxed attire, accessible management team, opinions and ideas welcomed, and so much more!

Client & Policy Servicing Specialist

Middleton, WI or Glastonbury, CT

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including generous paid time off, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking experienced, business-focused Client & Policy Servicing Specialists to assist with their Property & Casualty, Errors & Omissions and Healthcare Underwriting teams.

While delivering service excellence, this position will be responsible for processing new and renewal quotes and policies, with high productivity and 100% quality to our agents. The Specialist will also assist Underwriters in achieving service standards through process improvements and team communications.

Education & Experience:

  • College degree or high school diploma with prior experience.
  • Prior customer service a plus but not required.

Essential skills:

  • Excellent interpersonal and communication skills.
  • Ability to be a positive, team player, able to work within a dedicated, hardworking environment.
  • Self-directed and innovative.
  • Detail- and Service-orientated.
  • Highly productive and accurate.
  • Technically competent in all standard business software applications, including Excel, Word, PowerPoint.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Professional Liability Underwriter

Chicago, IL

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking a Professional Liability Underwriter to join our Professional Lines team in Chicago. This position will be responsible for new business production and renewal business servicing, with an emphasis on providing quality and service to our wholesale production partners. The Underwriter will be expected to work in a team environment to achieve premium production goals of the department, as well as expected to build and maintain relationships with our wholesale production partners.

Education & Experience:

  • Bachelor’s degree, or equivalent
  • 1+ years of insurance experience preferred but not required
  • Completed or continuing work towards industry certification (RPLU, CIC, CPCU, etc.) preferred but not required.

Essential skills:

  • General familiarity with lawyer's professional liability and insurance agents professional liability preferred but not required.
  • Basic understanding of financial evaluation tools.
  • Effective written and oral communication skills with the ability to interact well with internal resources at all levels.
  • Ability to develop familiarity with a wide variety of businesses and organizations, the services they provide, as well as the regulatory, legislative, legal and economic factors that affect them.
  • Skills with using personal computers, the internet and multiple software programs.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Commercial Liability Underwriter - Environmental

Middleton, WI, Chicago, IL, or New York, NY

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking an experienced, business-focused Commercial Liability Underwriter. With an emphasis on providing quality service to our wholesale production partners, this underwriter will be responsible for renewal and new business production. Other expectations will be to work in a team environment to achieve premium production goals of the department, build and maintain relationships with our wholesale production partners, and develop marketing and distribution strategies. Must interact well with internal resources.

Education & Experience:

  • Bachelor’s degree or equivalent.
  • Minimum 3 years of professional underwriting experience with strong emphasis in environmental liability: site pollution liability, contractor’s pollution liability, professional liability, general liability, and excess liability.
  • Completion or continuing work towards industry certification (RPLU, CIC, CPCU, etc.) preferred.
  • Recent college graduates with a concentration in Risk Management will also be considered.

Essential skills:

  • General familiarity with environmental liability and knowledge of insurance and underwriting technical basics obtained working within the small business and middle market segments.
  • Basic understanding of financial evaluation tools and rating models.
  • Excellent interpersonal and communication skills with the ability to interact well with internal and external resources at all levels.
  • Ability to develop familiarity with a wide variety of businesses and organizations, the services they provide, as well as the regulatory, legislative, legal and economic factors that affect them.
  • Must be highly organized, detail-oriented, accurate and timely.
  • Forward-thinking capability, with problem-resolution and analytical skills required.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Billing & Collections Specialist

Middleton, WI

Full and Part-time opportunities available

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including generous paid time off, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking an experienced, business-focused Billing & Collections Specialist. With exceptional service to agents and policyholders, this role’s primary goal is delivering billing ease through all payment channels. While delivering service excellence, this position will be responsible to receive or post cash as required, reconcile financial statements, pursue collection activity, perform daily report analysis to ensure quality and accuracy, proactively identify billing system and internal process improvements, and collaboratively work in a team environment.

Education & Experience:

  • Associates Degree in Accounting, or equivalent.
  • 1-3 years of experience in accounting (reconciliation, spreadsheet creation, etc.) preferred.
  • Previous property & casualty insurance experience preferred.

Essential skills:

  • Excellent interpersonal and communication skills.
  • Ability to be a positive, team player, able to work within a dedicated, hardworking environment.
  • Self-directed and innovative.
  • Detail- and Service-orientated.
  • Highly productive and accurate.
  • Technically competent in all standard business software applications, including Excel, Word, PowerPoint.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

System Owner

Middleton, WI

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty®, a fast-paced, growing Insurance Carrier in Middleton/Madison, WI seeks an experienced, customer-focused System Owner for its Information Technology & Operations Unit. The System Owner is responsible for the overall procurement, development, integration, modification, operations, maintenance and retirement of the system s/he owns. A key contributor in developing system design specifications to ensure strategic fit of the system(s) and that stakeholder needs are documented, developed, tested and implemented.

Responsibilities include: End-to-end responsibility for technology assets s/he owns, which includes project delivery, production support, vendor management, and total cost of ownership. System Owner will be responsible for helping shape the organization through the implementation of best practice, ensuring technology solutions are aligned with architectural standards and the broader Business/IT strategy, collaborating with other System Owners, proactively identifying ways we can improve the IT service model, and proactively managing expenses associated to the technology assets. * Responsible for managing direct reports as well as working in a matrixed environment to execute against organizational goals. The system owner will have responsibility for project delivery, assessing and implementing small enhancements, and production support/maintenance activities. * Maintain currency on technical assets s/he owns. As such, the System Owner will be responsible for developing and executing on strategies that align the business strategy, technology roadmap, and total-cost of ownership. * Manage vendor relationships, negotiating contracts, and ensuring the services provided are in line with the Business/Operational needs and aligned to IT best practices. * Ensure the application is compliant with all legislative/regulatory requirements. * Design application measurement, assessment and quality improvement options/programs to continuously raise the performance and effectiveness of the system.

Education & Experience:

  • Bachelor’s degree in Management Information Systems, Computer Science or equivalent
  • 5+ years of systems development management experience with increasing levels of responsibility.
  • Proven experience in implementing systems in area(s) of responsibility (e.g. Policy Administration, Claims, Billing).
  • Demonstrable experience in system quality improvement, efficiency improvement and cost reduction projects.
  • Experience with WYDE eWAM development tools or the WYNSURE Insurance application highly desirable.
  • Experience managing vendor relationships and contract negotiations is a plus.

Essential skills/aptitude:

  • Solid understanding of business processes and how stakeholders use, manage and analyze information from the system s/he owns.
  • Excellent communications skills; able to convey information effectively, responsibly and with accountability.
  • Resourceful at assembling information needed to make decisions.
  • Ability to handle multiple projects, work independently, excellent follow-up skills.
  • System view, understanding of integration and interdependencies issues.
  • Excellent analytical and problem-solving abilities along with the ability to deal effectively with change.
  • Strong presence and ability to establish and maintain relationships at all levels of the organization to be known as the go-to person for the system(s) responsible for.
  • Excellent interpersonal skills, collaboration and team building skills.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Commercial Liability Underwriter - Construction

New York, Chicago, or Telecommuting Opportunity

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking an experienced, business-focused commercial liability underwriter. With an emphasis on providing quality and service to our wholesale production partners, this position will be responsible for new business production and renewal business servicing. Other expectations will be to work in a team environment to achieve premium production goals of the department, build and maintain relationships with our wholesale production partners, and develop marketing and distribution strategies. The underwriter will also assist in crafting policy language and must be able to interact well with internal resources. Senior level available commensurate with experience.

Education & Experience:

  • Bachelor’s degree, or equivalent
  • 2+ years of professional liability underwriting experience, environmental or construction focus preferred.
  • Completed or continuing work towards industry certification (RPLU, CIC, CPCU, etc.) preferred.

Essential skills: * General familiarity with intellectual property, privacy, personal injury, security exposures and issues and knowledge of insurance technical basics.
* Basic understanding of financial evaluation tools. * Effective written and oral communication skills with the ability to interact well with internal resources at all levels. * Ability to develop familiarity with a wide variety of businesses and organizations, the services they provide, as well as the regulatory, legislative, legal and economic factors that affect them.
* Technically competent in all standard business software applications.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Senior Claims Specialist - Casualty

Middleton, WI or Glastonbury, CT

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking an experienced Senior Claims Specialist to join its Casualty Claims team. This highly motivated individual will investigate, evaluate and resolve third-party property damage, construction defect and environmental claims. The claims may be litigated and non-litigated, potentially in all 50 states. Some claims may be handled directly with the claimant while others will involve managing the defense of complex litigation. The ideal candidate will possess advanced technical skills, highly refined verbal and written communications skills, and have a proven track record of delivering solid claim outcomes on third party property claims, including those with complex coverage issues. This position also requires interaction with our underwriting staff and agent partners to advise on claim issues in general and assigned claim files in particular.

Education & Experience:

  • A Bachelor’s Degree or higher. JD or industry certifications strongly preferred.
  • A minimum of 10 years of casualty insurance claims handling or related litigation defense experience. Expertise in property damage, construction defect, and/or environmental claims desired.
  • Adjuster license in at least one state.

Essential skills:

  • Strong written and verbal communication, negotiation, and organizational skills.
  • Analytical problem solver.
  • Resilient, resourceful, and able to operate with a moderate to high volume claim load.
  • Ability to respond rapidly to changing work conditions and expectations.
  • Ability to travel when necessary (approximately 6-10 times a year for settlement conferences and/or mediations).

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Commercial Underwriter - P&C Portfolio Management

Middleton, WI

Want to join an exciting and collaborative company that offers competitive compensation and benefits packages – including an innovative open vacation plan, fully vested matching 401k, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance?

CapSpecialty® is seeking a business-focused Commercial Underwriter for their Property & Casualty Underwriting team in Middleton, WI. This position will minimize risk by accepting and rejecting insurance applications and modifying insurance coverage in accordance with company underwriting guidelines. Implementation of CapSpecialty Underwriting Strategy in business development and growth and applying sound decision-making to underwrite business that contributes to a profitable portfolio.

Education & Experience:

  • Bachelor's degree, or equivalent
  • Some commercial underwriting experience is preferred, but willing to train the right candidate.
  • Completion or continuing work towards industry certification (i.e. CIC, IIA, CPCU) is preferred.

Essential skills:

  • Strong underwriting and marketing skills.
  • Solid analytical-reasoning skills, methodical problem-solving skills and ability to focus on execution.
  • Excellent interpersonal and communication skills.
  • Knowledge of specified territory including agency plant, accounts, competition and general business climate.
  • Ability to be a team player.
  • Technically competent in all standard business software applications, including Excel, Word, PowerPoint.

CapSpecialty is a leading provider of specialty insurance for small- to mid-sized businesses in the U.S., offering Commercial Property and Casualty, Professional Liability, Surety and Fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty’s creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty’s carriers have an A (“Excellent”) rating from A.M. Best, writing both admitted and non-admitted policies on the paper of Capitol Indemnity Corporation, Capitol Specialty Insurance Corporation and Platte River Insurance Company – subsidiaries of Alleghany Insurance Holdings LLC, part of Alleghany Corporation (NYSE: Y).

Apply today!

Equal Employment Opportunity Employer

CapSpecialty is an equal opportunity employer.

Get In Touch

GET IN TOUCH

CALL US: 800-475-4450

EMAIL US

BILL PAYMENT

1600 Aspen Commons
Suite 300                          
Middleton, WI 53562