Every D&O broker I've talked to says they specialize in startups. Most of them are stretching that claim, and the only way to find out before you're locked into a year of coverage is to ask questions a generalist can't fake the answers to.
The policy itself matters, but the broker matters more than founders think. A good one catches a bad exclusion before you sign it. A bad one hands you whatever the first carrier quotes and moves on to the next deal. Here's what separates them, and the exact questions that surface the difference on a single call.
"How many carriers are you actually quoting?"
A broker who says "startup specialist" on their website but only has appointments with two or three carriers isn't shopping your risk, they're placing it wherever they have a relationship. Real specialists in venture-backed D&O typically hold appointments with eight to ten carriers that actively underwrite early-stage companies.
Ask for the carrier list by name. If they hesitate or give you a vague answer like "we work with all the major ones," that's your answer. A broker who's actually done this a hundred times will rattle off five or six names without checking notes.
"Walk me through Side A, B, and C without me asking"
This is the single fastest filter. A D&O policy has three components, and a broker who works with startups daily brings this up unprompted because it's the first thing that determines whether the policy actually protects the individual founder or just the company's balance sheet.
If you have to ask what Side A even means, or the broker explains it like it's a niche add-on rather than the core of the product, you're talking to someone who sells general commercial policies and added D&O to their product list. That's not necessarily disqualifying, but it means you'll need to do more of the vetting yourself instead of trusting their judgment.
"What happens 90 days before my renewal?"
D&O is a claims-made policy, which means the binding is the easy part and renewal is where brokers earn their fee or don't. If a carrier hardens terms or raises premium at renewal, a broker who isn't already remarketing your policy 90 days out will hand you a take-it-or-leave-it increase with no time to shop alternatives.
Ask specifically: "At what point before renewal do you start remarketing, and how many alternative quotes do I typically see?" A good answer names a timeline and a number. A vague "we handle renewals for you" answer means you'll find out how they handle it the hard way, during a premium spike with three weeks of runway.
"What happens to my coverage if we get acquired or shut down?"
This is the question most founders never think to ask until it's too late. Claims-made policies stop covering new claims the moment the policy lapses, even for decisions made while it was active. If your company is acquired, merges, or shuts down, you typically have a narrow window, often 60 to 90 days, to buy an extended reporting period, sometimes called tail coverage, that keeps you protected for claims that surface later about decisions made while you were still operating.
Ask your broker to quote the tail cost now, before you need it. Tail coverage can run one to three times your annual premium as a one-time cost, and a broker worth keeping will flag this during the original sale, not wait for you to ask during a rushed acquisition close.
"How do you get paid on this policy?"
Most brokers work on commission from the carrier, typically 10 to 15 percent of premium, which is standard and not a red flag by itself. What matters is whether they'll tell you plainly when you ask. A broker who gets evasive about how they're compensated, or claims they're "just helping you find the best option" without naming a structure, may be steering you toward whichever carrier pays them the most rather than whichever policy fits your risk best.
"Can I talk to two other startup clients you've placed D&O for?"
This is the question that ends the conversation fastest if the specialization claim is fiction. A broker who's genuinely placed dozens of venture-backed D&O policies can produce two references within a day, usually founders happy to spend five minutes vouching for someone who caught a bad exclusion or negotiated a better retroactive date for them. A broker who deflects, stalls, or only offers a generic testimonial page hasn't done this enough times to have real relationships to point to.
What to do this week
Get on calls with three brokers before you get a single quote. Ask all six questions on every call, in the same order, and write down the answers side by side. The differences show up fast: one broker will have crisp, specific answers to all six, and the other two will start hedging by question three. Pick based on the answers, then compare price and exclusions between your top two. A broker who's excellent at vetting a policy but expensive is worth more than a cheap one who sells you whatever the first carrier offers.
Frequently asked questions
Should I use the same broker as my competitors or portfolio peers?
It's a reasonable starting point since a referral from another founder confirms the broker has actually closed startup D&O deals, but still run all six questions yourself. A good referral shortens the search, it doesn't replace the vetting.
Is it worth using a broker at all instead of buying direct from a carrier?
For most first-time buyers, yes. D&O underwriting is negotiable in ways that aren't obvious from a direct application, and a specialist broker who's placed dozens of these policies knows which exclusions to push back on. The commission is baked into the premium either way, so going direct rarely saves you money, it just removes the person who would have caught the retroactive date gap.
How long should the broker search take?
Three calls, one to two days total. Each broker's application takes 15 to 20 minutes once you've picked one, and most carriers return quotes same-day, so the vetting is the only part of this process that actually takes deliberate time.
What's the biggest tell that a broker isn't a real specialist?
They lead with price instead of coverage design. A broker who opens the conversation with a number before asking about your board composition, funding stage, or prior claims history is selling a commodity product, not underwriting your specific risk.