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

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; media liability, cyber-liability and privacy, asset managers, and management liability (D&O and EPL) 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 may require travel approximately 15% - 20% 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).

Developer/Analyst - ImageRight

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 seeks an energetic and skilled Developer/Analyst to perform as a technical lead and application administrator of our document management system, ImageRight. The successful candidate will be required to maintain and support the system on a daily basis and work directly with project managers and business analysts to build our requirements for enhancements and projects. This role is responsible for the planning, testing and deployment of any needed system upgrades and will work directly with Infrastructure to validate technical designs and performance of the system.

Education & Experience:

  • Bachelor's degree in Business, Information Systems, Management Information Systems or related field.
  • 3+ years experience developing in Microsoft Technologies (C#, WCF, MVC, VBScript) and working with relation databases (Oracle, Microsoft SQL Server).
  • 2+ years administering, maintaining, enhancing, and integrating a document management system. Experience with ImageRight v5.0 or higher is preferred.
  • Knowledge or experience in P&C insurance and surety domains is preferred but not required.

Essential Skills:

  • Excellent interpersonal and communications skills with a customer service mindset.
  • Solid understanding of the Software Development Life Cycle (SDLC).
  • Program Management skills to build our technical requirements for enhancements and projects.
  • Solid and measured experience in Application Support of multi-tier applications.
  • Ability to work independently and as part of a team in a highly dynamic environment.
  • Solid organizational and time management skills is a must.
  • A positive attitude, strong problem-solving skills and the ability to think critically is highly desired.
  • Demonstrated ability and ardent desire to grasp new technologies 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).

Budget & Expense Specialist

Middleton, WI

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 a Budget & Expense Specialist that will assist in the processing and reporting of expenses, employee expense reports, and assist in the payables process. The Specialist will also assist in the training of other employees, to ensure that they understand & follow company processes and policies; and assist in in other Finance Department and reporting tasks and requirements as necessary.

Education & Experience:

  • Associates degree in Accounting (Bachelor’s preferred), or equivalent work experience.
  • 2-4 years of accounts payable or general accounting systems experience preferred.

Essential skills:

  • Strong communication skills, with the ability to assist others both in person and in other locations.
  • Organizational and prioritization skills are essential.
  • Ability to work in a fast-paced, high volume environment while maintaining a high level of quality and service.
  • Must be able to effectively apply general processes & guidelines in different situations.
  • Ability to work independently to resolve outstanding issues and suggest process improvements, while contributing towards team goals.
  • Intermediate experience using Microsoft Word and Excel preferred.

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 Systems Engineer

Middleton, WI Relocation considered for the right candidate

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 looking for a skilled senior level systems engineer to provide IT architecture design and planning, installation, configuration, documentation, training and day-to-day support of IT services related to the operation, performance, security, and availability of data, application and voice communications systems. Successful candidates will have experience building servers, analyzing system performance, recommending adjustments and preparing proposals while ensuring cost effective performance. Availability to work flexible hours and be a part of a 24/7 on call rotation is required.

Education & Experience:

  • Bachelor’s Degree in computer science or equivalent.
  • 5+ years of systems administration and network engineering experience in a corporate environment.
  • 3+ years in an enterprise environment supporting business critical application in mixed operating system environment.
  • Knowledge or experience in P&C insurance is a plus.

Essential Skills:

  • Excellent working knowledge of Windows Server, Linux, VMWare vSphere and Active Directory.
  • Strong working knowledge of AWS, Azure, WebSphere and Compellent preferred
  • Excellent interpersonal and communications 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.
  • Demonstrated ability and ardent desire to grasp new technologies 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).

Senior Support Analyst

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 an energetic and skilled support analyst to perform technical support to end users on a variety of IS related issues. The successful candidate will identify, analyze, research, and resolve technical issues related to computer hardware and software, network devices, network security, phone and remote computing. The position will provide training and documentation relating to software and hardware usage, policies, procedures and employee orientation.

Education & Experience:

  • Associate’s Degree in computer related field or equivalent.
  • 4+ years of related experience in a corporate Information Technology help desk role.
  • Knowledge or experience in P&C insurance is a plus.

Essential Skills:

  • Excellent interpersonal and communications skills with a customer service mindset.
  • 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.
  • Demonstrated ability and ardent desire to grasp new technologies 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).

Underwriter - MPL/Tech/Cyber

Kansas City, Chicago, New York City, or Glastonbury

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 professional liability underwriter to manage the Technology/Cyber book of business within the PL Division’s MPL platform. With an emphasis on providing quality service to our wholesale production partners, this underwriter 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 partners, and develop marketing and distribution strategies. Senior level available commensurate with experience.

Education & Experience:

  • Bachelor’s degree or equivalent.
  • 5 + years as a commercial underwriter working with MPL, Tech and/or Cyber experience strongly preferred.
  • Established relationships within the wholesale community.
  • Completion or continuing work towards industry certification (RPLU, CIC, CPCU, etc.) preferred.

Essential skills:

  • Proven analytical underwriting, reasoning, and methodical problem-solving skills and ability to focus on execution.
  • 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.
  • Excellent interpersonal and communication skills.
  • Self-directed and innovative.
  • Detail and Service orientated.
  • Ability to be a positive, team player, able to work within a dedicated, hardworking environment.

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