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).

Underwriter, Specialty Casualty Excess

New York, NY

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 Specialty Casualty Excess Underwriter, with a focus on the build out, marketing, training, monitoring, and growth of our DragonX Excess Liability product. This role will select profitable risk and manage Large Account Book of Business by underwriting assigned territory and building working relationships with agents and coworkers.

Education & Experience:

  • Bachelor’s degree or equivalent
  • 3+ years commercial casualty underwriting experience
  • Experience with internal and broker facing underwriting portals preferred
  • Completion or continuing work towards CIC, IIA, CPCU or other programs preferred

Essential skills:

  • Knowledge of primary and excess commercial casualty insurance contracts
  • Risk management
  • 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
  • Ability to think clearly and quickly, work independently and in a team to analyze and problem solve

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). For more information please visit our website.

Underwriter, Misc. Medical

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 a Misc. Medical Underwriter to join our team. This position will be responsible for 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, developing marketing and distribution strategies.

Education & Experience:

  • Bachelor’s degree, or equivalent
  • 1-3 years’ experience in Healthcare/Human Services, familiarity with standard and E&S underwriting 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). For more information please visit our website.

Bond Assistant

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, a fast-paced, growing Commercial Lines Insurance/Surety Company seeks an experienced, customer-focused Bond Assistant for their Commercial Fidelity & Surety Underwriting team in Glastonbury, Connecticut. The Bond Assistant administratively assists the Underwriters and Assistant Underwriters by keeping files current, generating correspondence, answering questions, and processing new and renewal bonds, endorsements and notices of cancellation and POA administration. The Bond Assistant will also provide special project support – often systems related – as needed to enhance automated processing.

Education & Experience:

  • High School diploma or equivalent.
  • 3+ years experience in customer service/office setting.

Essential Skills:

  • Great interpersonal, communication and organizational skills.
  • Basic math skills are a must.
  • Ability to be a team player and work independently.
  • 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). For more information please visit our website.

Head of Marketing

Arlington, VA

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 proven leader to head our marketing team for our Professional Risk Management Services, Inc.® (PRMS) company in Arlington, VA. This role will be responsible for the marketing strategy, direction, and organization for a small dynamic department and will partner with appropriate vendors and team members to implement and align company goals and objectives.

Education & Experience

  • Bachelor’s Degree in Marketing or equivalent.
  • 7 + years marketing, advertising or communications experience.
  • Experience leading a team.
  • Experience in insurance and/or behavioral healthcare preferred.

Essential Skills

  • Excellent organizational skills to establish efficient systems.
  • Must demonstrate proactive problem-solving skills.
  • Excellent communication skills, both verbally and written, are essential, with a proven ability to write and edit original copy.
  • Ability to manage multiple projects and prioritize with the ability to meet deadlines and adapt.
  • Ability to adapt to an ever-changing work environment.
  • Proven ability to build connections and partner with employees at all levels of the Company.

Professional Risk Management Services, Inc., a CapSpecialty company, is a leading provider of psychiatric malpractice insurance in the U.S. with a strong dedication to customized and highly relevant products, valuable educational resources, and outstanding customer service. For over 30 years, PRMS has been committed to serving the needs of behavioral healthcare professionals through our comprehensive program and support of the mental healthcare community at large. For more information, please visit PsychProgram.com.

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). For more information please visit our website.

Senior Claims Specialist - Professional Liability

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 seeks a dynamic, versatile claims professional to add to its experienced, team-oriented staff. This claims professional will investigate, evaluate and resolve claims made against the company’s professional liability insurance policies including: insurance agents E&O, lawyers professional liability, miscellaneous E&O, insurance company E&O and D&O including employment practices liability, media liability, cyber-liability and privacy, and asset managers’ policies. This position also requires frequent interaction with our underwriting staff and agent partners to advise on claim issues in general and assigned claim files in particular. This position requires travel approximately 15% - 25% of the time.

Education & Experience:

  • Bachelor’s degree, or equivalent
  • 7+ years of claims handling experience
  • Current adjuster license
  • Juris Doctorate or industry certifications (i.e. RPLU, CPCU, AIC) are strongly preferred

Essential skills:

  • Advanced technical knowledge of insurance coverage and polices, insurance law, employment law, tort law, and claims handling practices for one or more lines of business
  • Highly refined verbal and written communications skills
  • A proven track record of delivering solid claim outcomes on PL claims
  • Ability to multi-task and seamlessly maneuver from a set of issues in one jurisdiction to completely different matters in other jurisdictions
  • Forward-thinking capability, including the ability to formulate a strategy and proactively move a claim toward resolution
  • Excellent analytical, problem-solving, and organizational 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). For more information please visit our website.

CapSpecialty is an equal opportunity employer.

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1600 Aspen Commons
Suite 300                          
Middleton, WI 53562