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).

Assistant Underwriter - Commercial Surety & Fidelity

Houston, TX, Glastonbury, CT or 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 a self-motivated, adaptable underwriting assistant to add to its experienced, team-oriented staff. These individuals will assist Underwriters in all aspects of the underwriting process.

While delivering service excellence, this position will be responsible for gathering, screening, analyzing and evaluating information on new and existing accounts; making underwriting decisions within letter of authority; and making recommendations to the underwriters for accounts outside authority.

Education & Experience:

  • One to two years’ surety or corporate financial analysis experience
  • Associate in Fidelity & Surety Bonding (AFSB) designation, or working towards one is desirable.
  • Associates degree or equivalent preferred.

Essential Skills:

  • Adaptable underwriting and marketing skills.
  • Solid analytical-reasoning skills, methodical problem-solving skills and ability to focus on execution.
  • Great interpersonal, communication and organizational skills.
  • Knowledge of bonds, procedures and rates.
  • 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).

Commercial Liability Underwriter

Middleton

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 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.
  • Risk management and underwriting background preferred. Recent college graduates with a concentration in Risk Management are encouraged to apply.
  • Completion or continuing work towards industry certification (RPLU, CIC, CPCU, etc.) preferred.

Essential skills:

  • General familiarity with environmental liability and/or 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).

Commercial Underwriter - Surety & Fidelity

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 seeks a self-motivated, adaptable Commercial Underwriter to add to its experienced, team-oriented staff. The primary purpose of this position is to ensure underwriting growth and profitability by underwriting new and renewal business and manage agency relationships. This is position is located in our Chicago Office. Senior level is available commensurate with experience.

Responsibilities include:

  • Underwrite and approve risks with appropriate pricing through review & analysis of financials.
  • Generate leads & independently develop business relationships through industry networking, strong customer service and participation in agency functions and general sales calls.
  • Demonstrate leadership skills by leading, developing & motivating team members through our service standards, technological tools and house system, CapEx.
  • Determine what underwriting guideline changes are needed by investigating and reporting on bond claims and losses.

Education & Experience:

  • Bachelor’s Degree or equivalent.
  • 3+ years’ surety experience is required.
  • AFSB designation or working towards one is preferred.

Essential Skills:

  • Adaptable underwriting and marketing skills.
  • Solid analytical-reasoning skills, methodical problem-solving skills and ability to focus on execution.
  • Great interpersonal, communication and organizational skills.
  • Knowledge of bonds, procedures and rates.
  • Knowledge of specified territory including agency plant, accounts, competition and general business climate.
  • Ability to be a team player.

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).

CapSpecialty is an equal opportunity employer.

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1600 Aspen Commons
Suite 300                          
Middleton, WI 53562