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).

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.

Litigation Specialist - PL Healthcare

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 Litigation Specialist for our Healthcare Claims team. This highly motivated individual will investigate, evaluate and resolve behavioral health, human services, miscellaneous medical and other healthcare professional and general liability claims.

The ideal candidate will possess advanced technical knowledge of insurance coverage and policies, insurance law, tort law, and claims handling practices for healthcare professional and general liability, and have highly refined verbal and written communications skills.

Education & Experience:

  • A Bachelor’s Degree.
  • A minimum of 5 years of claims or litigation experience in healthcare professional and general liability.
  • A J.D. and/or R.N. strongly preferred.

Essential skills:

  • Strong communication, negotiation, and organizational skills.
  • Analytical problem solver.
  • Resilient and able to operate under pressure in high complexity, high risk situations.
  • Ability to respond rapidly to changing work conditions and expectations.
  • Ability to travel up to 25% of the time.

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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CALL US: 800-475-4450

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1600 Aspen Commons
Suite 300                          
Middleton, WI 53562