HH Insurance scaled commercial operations and reduced E&O risk while empowering producers with Cara

About HH Insurance

Founded in 2018, HH is a fast-growing independent P&C agency headquartered in St. Petersburg, Florida. The agency specializes in coastal and lifestyle-focused risks, including residential coastal property, watercraft, condo associations, restaurants, charter captains, and other marine-adjacent commercial exposures.

HH operates with a modern, process-driven mindset, combining a large onshore team with offshore support across South Africa and the Philippines. As the agency matured, HH invested heavily in systems, automation, and internal tooling to support scale, reduce risk, and improve operational consistency.

HH is headquartered in St. Petersburg, Florida, employs approximately 70 onshore team members with an additional offshore support team, was founded in 2018, and has grown rapidly while transitioning into a more mature operating stage.

Problems

As HH scaled its commercial business, the team faced a growing challenge around training, consistency, and risk management. Commercial insurance is complex, and onboarding new team members—especially those without deep insurance backgrounds—introduced E&O exposure and heavy reliance on senior staff for reviews.

Critical workflows such as E&O checks, policy consistency reviews, ACORD form completion, and nuanced client communication were highly manual. Team leads often had to personally review submissions, quotes, certificates, and forms to ensure accuracy, creating bottlenecks and limiting how quickly newer team members could operate independently.

At the same time, producers and account teams spent a significant portion of their day in Outlook—drafting detailed emails, explaining coverage nuances, and locating policy data across systems—slowing response times and pulling senior talent away from higher-value work.

HH needed a way to reduce risk, speed up execution, and empower less experienced team members, without increasing review overhead or adding complexity to its tech stack.

Solution

HH partnered with Cara, an AI platform purpose-built for insurance agencies, to serve as a flexible assistant across commercial workflows.

Initially, Cara was introduced as an E&O safeguard—running consistency and accuracy checks across quotes, renewals, certificates, and policies by analyzing multiple PDFs at once. Over time, the team expanded Cara’s use across additional high-impact workflows.

Today, key workflows powered by Cara include:

• E&O and consistency checks across quotes, renewals, and certificates

• ACORD and supplemental form generation directly from source documents

• Email drafting for nuanced client communications

• Coverage lookups and explanations to support faster client responses

Cara allowed newer and mid-level team members to take on more responsibility, while senior leaders shifted from hands-on execution to quick review and approval. Importantly, Cara fit seamlessly into HH’s environment—no downloads, minimal onboarding, and a clean, intuitive interface that the team adopted quickly.

What HH Says

“Cara works as a really flexible assistant that can lighten the load for your best producers.”

— Mike, Project Manager, HH Insurance

Results

By using Cara as a first pass across commercial workflows, HH significantly reduced reliance on senior team members for routine reviews. Tasks like ACORD form completion and document validation that previously required hands-on involvement from team leads can now be completed by other team members, with senior staff providing only a final review. This shift freed up leadership capacity and reduced operational bottlenecks.

Cara also improved onboarding and trust in newer hires. With built-in consistency checks and document validation, HH was able to confidently empower less experienced team members and even bring on more senior producers who could “hit the ground running” without overwhelming existing infrastructure. This flexibility changed how the agency approached hiring and role design.

Operationally, Cara delivered meaningful time savings across email communication, form generation, and data retrieval. By accelerating response times and reducing rework, Cara helped HH improve efficiency, reduce E&O exposure, and support continued growth—without adding friction or complexity to day-to-day operations.

Why It Matters

For HH, Cara is more than a point solution—it’s a force multiplier.

By embedding insurance-native AI directly into core workflows, HH reduced risk, empowered its team, and enabled producers to focus on higher-value work. The result is a more resilient, scalable operation that supports growth while maintaining quality, consistency, and speed.