Mastering Growth: Transparency, Leadership, and Taking Risks in the Insurance Industry – A Conversation with Aron Robertson

The middle market commercial insurance landscape is evolving at a rapid pace. Agencies that once relied solely on traditional property and casualty products are now discovering untapped revenue streams by embracing surety bonds and specialty coverages. By understanding how to position niche products—such as drone insurance for contractors—alongside licensing and permit bonds, agencies can capture high-intent leads, accelerate earned premium, and foster deeper client relationships.

In this post, we’ll explore a comprehensive bonding-first growth strategy: from the fundamentals of surety bonds to advanced marketing funnels, partner ecosystems, and actionable implementation checklists. Whether you’re a seasoned producer or a rising agency principal, you’ll walk away with a playbook to maximize revenue, differentiate your brand, and become the go-to resource for contractor clients.

In the world of independent insurance agencies, servicing existing policies often overshadows the pursuit of new business. It’s estimated that 80% of agency time is spent servicing renewals rather than generating new opportunities. With the average cost of servicing a policy renewal totaling around $135 per policy, agencies are dedicating significant resources simply to maintain the status quo.

This servicing burden presents a major scalability problem. For every thousand policies on the books, agencies are effectively employing two full-time account executives just to keep up. The result is a “tyranny of insurance” where agency growth becomes harder as success increases. This challenge is even more pronounced for agencies focused on the middle market or attempting to backfill their books with small commercial insurance and personal lines.

Scaling a book of business while trapped in administrative quicksand isn’t just inefficient; it’s unsustainable. Agencies need a way to break free if they hope to thrive in today’s competitive and evolving market.

Middle-mazrket businesses face unique challenges when it comes to managing their workers’ compensation programs. Unlike large enterprises, they often lack dedicated in-house resources for safety, compliance, and claims oversight; yet unlike small businesses, their scale subjects them to more sophisticated regulatory scrutiny and larger potential losses. In this environment, commercial insurance producers who master an integrated approach—combining precise prospecting data, impactful compliance applications, and exceptional claims handling—can both win new accounts and build lasting client relationships.

In the most challenging insurance market many of us have ever seen, independent agencies are grappling with a familiar foe: limited carrier access. Whether you’re a former captive agent trying to break into the independent space or a small agency trying to grow your commercial book, the obstacles are real. Direct appointments are hard to come by, especially for shops under $5 million in revenue, and wholesale markets can feel intimidating or like a last resort.

But they don’t have to be. With the right partner, wholesale and brokerage relationships can become a strategic advantage, not just a stopgap. This post explores how agencies can leverage smart market access to grow confidently, preserve profitability, and position themselves for long-term success.

The insurance industry is undergoing a profound transformation as middle-market agencies recognize the benefits and challenges of embracing a fully remote workforce. No longer viewed as a temporary workaround, remote models offer the potential to tap into nationwide and offshore talent pools, reduce overhead, and increase flexibility in an increasingly digital world. Yet, flipping the switch to virtual operations can expose gaps in documentation, dilute corporate culture, and strain traditional oversight mechanisms. In this post, we’ll explore the four pillars essential to building a high-performing remote insurance team—core values, hiring practices, onboarding processes, and KPI strategies—while also delving into best practices for managing domestic versus offshore employees, ensuring data security, leveraging productivity tools, and fostering trust and autonomy.

In today’s hard commercial insurance market, middle market business owners are more open than ever to solutions that give them greater control over their insurance costs. While guaranteed cost programs remain the default option, they often lack the flexibility and long-term savings that high-performing businesses crave. That’s where captive insurance comes in—a powerful but often misunderstood tool that enables clients to turn insurance from a sunk cost into a strategic asset.