Nick Chiariello

Insurance professional with 10+ years of experience in property underwriting, pricing analysis, and program development, combined with hands-on work in AI training and data modeling. Proven track record building rating engines, pricing tools, and analytical frameworks from scratch. Brings deep insurance domain expertise that InsurTech teams can deploy immediately to develop smarter products, better data pipelines, and more accurate models.

Technical Task Writer, Insurance Expert at Fleet AI (2026-05 – 2026-08)

• Developed synthetic data worlds for AI training, applying deep insurance domain knowledge to ensure model accuracy.
• Crafted prompts and grading guidance for tasks to train AI models.
• Evaluated model output and peer work for quality and domain correctness.
• Assumed ownership of orphaned tasks vacated by offboarded subject matter experts.

Recreation Supervisor at City of Melbourne, Parks and Recreation (2023-10 – Present)

• Manage a team of 8 part-time and 2 full-time staff to run daily operations and special events at a community center.
• Plan, organize, and coordinate all activities, field trips, and experiences for a 10-week summer camp serving 130 campers daily.
• Recruit and supervise 20+ seasonal camp counselors each summer.

Recreation Leader (Part-Time) at City of Melbourne, Parks and Recreation (2023-01 – 2023-10)

• Supervised gym activities and ensured safe participation for local youth.
• Reconciled daily cash transactions.

Vice President, Property Underwriting at Blue Sky Risk (2020-03 – 2021-06)

• Managed a hybrid team responsible for underwriting and company-wide data collection, analysis, and submission of bordereaux reports.
• Designed and built a rating engine and quote letter generator using SQL query language within Google Sheets as core components of the Mobile Home Park Program launch.
• Grew the Entertainment Risk Program's commercial property book from zero to $1 million in premium in approximately 12 months.
• Launched the Mobile Home Park Program through a nationwide market assessment, comprehensive underwriting guideline authorship, and property and general liability pricing derivation; program reached over $25 million in written premium.
• Trained colleagues in underwriting practices and data analysis techniques.
• Provided underwriting and pricing support for large accounts across all programs within the Blue Sky umbrella.

Senior Pricing Analyst, Property Department at Berkshire Hathaway Homestate Company (2016-03 – 2019-08)

• Developed a Gross Linear Model to estimate residential building replacement costs for all zip codes nationwide; outputs were prefilled into insurance limits across all property quotes.
• Researched, developed, and implemented a property insurance product for cannabis operations.
• Built summary dashboards in Excel using data from Berkshire's online rating system to surface user experience insights for management.
• Proposed future rate levels by analyzing loss and premium experience.
• Led implementation of Berkshire's new online quoting system for appointed agents, coordinating across multiple internal departments and third-party vendors.
• Collaborated with the legal department to draft proprietary coverage forms.
• Served as cross-departmental liaison to improve communication throughout the product development process.

Senior Commercial Property Underwriter at Berkshire Hathaway Homestate Company (2013-01 – 2016-03)

• Underwrote coverage for over $1B of property across 40+ states, generating over $4M in revenue.
• Performed ad hoc rate, building valuation, and process analyses to improve underwriting loss results.
• Trained dozens of new hires on the technical aspects of the underwriting process.
• Represented the company at career fairs to identify and recruit quality collegiate candidates.

Package Staff and Cashier, Front End Customer Service at Publix Supermarkets (2006-02 – 2012-12)

• Delivered front-end customer service while managing cash handling responsibilities.
• Maintained consistent performance while balancing full-time academic coursework.

BA in Dual Major: Actuarial Science and Risk Management & Insurance – Florida State University (2012-12)