It’s never been easier to get a quote for Directors & Officers (D&O) insurance. A few clicks, a few forms, and you’re bound. But in today’s unusually soft D&O market, that ease of access can be misleading. Policies might look comprehensive at face value, but when financial events or company shifts occur, many insureds (and their agents) discover too late that key protections are missing.
Michael De Feo, Executive Vice President at Jencap, sees this trend firsthand. “It’s so easy right now for retailers to go online, complete a submission form, and get a quote,” says De Feo. “But many of our insureds, whether it’s a public company, a private company, or a nonprofit, will run into changes throughout their policy term that aren’t always addressed with the carrier.” In other words, just because it’s easy to get coverage doesn’t mean it’s the right coverage. And that’s a problem for clients—and for the agents representing them.
A Soft Market with Sharp Edges
In insurance, a “soft market” refers to conditions where carriers compete aggressively for business. There’s more capacity, more lenient underwriting, and lower pricing across the board. Right now, the D&O insurance market is squarely in that category. On the surface, that sounds like good news. For companies looking to secure D&O liability coverage, the process is fast and affordable.
But De Feo cautions that speed and savings can come at a cost. “In a soft market, underwriting can get watered down,” he says. “There’s not always the deep analysis that’s needed to align a policy with what the company is actually doing—or about to do.” That’s especially problematic in D&O insurance, where the exposures are highly nuanced. This isn’t like insuring a fleet of trucks or a warehouse. D&O protects against complex risks tied to management decisions, governance, and fiduciary responsibility—issues that evolve with every fundraising round, merger conversation, or pivot in business strategy.
And yet, in the current environment, it’s easy to bind a policy without ever bringing those looming changes to the surface.
The Coverage Gaps You Don’t Know You Have
De Feo has worked with agents who assumed their client’s policy would cover a pending acquisition, only to discover the policy didn’t contain the right change-in-control language. He’s seen nonprofits with D&O policies that didn’t contemplate decisions made by volunteer boards. He’s reviewed coverage for private companies raising capital that failed to account for investor litigation risk. None of these coverage gaps were due to bad intentions. They were the result of insufficient due diligence during the application process.
“Due diligence will ensure clients aren’t caught off guard by exclusions, policy misapplications, or biases from underwriters,” De Feo says. “You need someone who knows what to ask before you go to the underwriter, because that’s where things get missed.”
He points to a recent case where a company was preparing for an ESOP conversion—selling ownership of the business to an employee stock ownership plan. On paper, their D&O policy was up to date. But no one had flagged the shift in ownership structure to the carrier. When it came time to file a claim related to that transition, the coverage was murky, and the company ended up absorbing losses it thought were insured.
“These are not rare cases,” De Feo adds. “They’re happening all the time.”
Why Agents Need Backup in D&O Insurance
Retail agents are often excellent at understanding their clients’ needs and navigating traditional coverages. But D&O insurance is a different animal. The risks are tied not just to the business model but to its financial strategy, governance framework, and future trajectory. That makes D&O one of the most dynamic and specialized lines to place correctly. And in a soft market, where it’s tempting to take the quickest path to binding coverage, that specialization becomes even more critical.
“D&O coverage requires a specialized focus when the client is partaking in financial transactions such as refinancing their initial investors, mergers or acquisitions, raising capital via private placements or IPO, ESOP conversions, and so on,” says De Feo. “Those aren’t things every agent is used to digging into, and frankly, they shouldn’t have to do it alone.” This is where wholesale brokers like Jencap become essential allies.
What a Strategic Directors and Officers Partner Actually Does
Jencap’s team of professional lines experts operates like a risk strategy partner, helping agents and their clients think through what’s ahead and whether their coverage can support it. “Our job is to ask the uncomfortable questions early,” De Feo explains. “We look at where the company is now, where it’s going, and what that means for the policy language. That’s how you protect your client—not just with limits and premiums, but with insight.”
By getting involved before the application goes out the door, Jencap helps avoid coverage gaps, policy mismatches, missing endorsements, and vague exclusions that create claim disputes down the line. It’s a proactive approach that turns the soft market’s speed into an advantage, without sacrificing rigor. “You don’t want to wait until there’s a claim to realize the policy wasn’t built for what the company actually needed,” says De Feo. “That’s avoidable, but only if you slow down and bring in the right people.”
In today’s D&O landscape, it’s tempting to lean into convenience. But not everyone can build a policy that’s actually ready for what’s ahead. Contact Jencap today to see how we can support your clients.
