CEO Sean O'Keefe, an army veteran, emphasizes responsiveness, clear communication, and trade-specific knowledge
The general contractor insurance business in the country is undergoing a major expansion, and one man is leading the change with military precision, literally. Sean O'Keefe, CEO, Founder & Principal Broker, Affordable Contractors Insurance, who is also an army veteran, has been helping general contractors navigate the complex insurance landscape for the past 15 years, and claims to have cracked the code for offering insurance for growth, not just risk-covering.
Asserting that military training is at the heart of his operations, Sean draws a comparison, saying that in both the army and the construction insurance business, risk mitigation makes the difference between success and disaster. “You’re trained to identify threats early, prepare for worst-case scenarios, and always have a contingency plan. That mindset translates directly into construction insurance,” he says.
“I run ACI and UCI the same way: understand the risk, prepare for it properly, and make sure nothing blindsides you,” says Sean. “Contractors get into trouble when they underestimate exposures or when an inexperienced agent misses critical endorsements. That’s why my team and I take a consultative approach. We break down the risk, explain it clearly, and structure coverage like mission planning — no assumptions, no shortcuts, no surprises. My military training taught me discipline, accountability, and the importance of ‘doing what you say you’re going to do.’ That’s the backbone of how we protect our clients’ businesses today.”
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Growth in construction insurance is being driven by more complex construction regulations and qualifications, increased liability exposure on commercial projects, and greater awareness of audit risks and contract compliance requirements. Sean believes contractors are realizing that insurance is a strategic part of bidding, winning, and delivering jobs, and those who don’t have proper coverage simply can’t compete. To address this shift, Sean is serving the price-sensitive “get me compliant today” contractors through ACI and the high-growth contractors who require ongoing consultation, endorsement management, audit support, and carrier negotiation through UCI. “The industry is moving toward specialization, and we’re already built for that,” he says.
Sean reasons that insurance is a strategic business tool rather than a mere legal obligation for contractors, because insurance determines what projects they qualify for, what revenue levels they can reach, and whether they stay protected when something goes wrong. “A properly structured insurance opens doors to higher-value contracts, reduces financial risk, builds trust with GCs and project owners, helps manage audits and cash flow, and protects against lawsuits that could shut a business down,” he says. “When done correctly, insurance becomes a growth engine. When done incorrectly, it becomes a liability.”
He adds that most contractors who avoid insurance do so because they don’t understand what they actually need, don’t trust insurance agents, have been burned by bad policies or surprise audit bills, or think “cheap” is good enough. “We solve that by making insurance clear, not just affordable,” Sean claims. “That means explaining why certain coverages matter, how audits work, what endorsements protect them from, and how the wrong policy can cost far more than the premium. Affordability gets them in the door. Education keeps them protected.”
Sean has tirelessly been educating his clients that generalist insurance agencies underserve contractors, because they simply don’t have the experience to understand state-specific construction laws, complex endorsements required by GCs, how audits can spike to $50k–$100k, what carriers are best for certain trades, and how commercial job qualifications actually work. “One mistake can cost a contractor their company. That’s why we only insure contractors. It’s all we do, and that focus protects our clients better than any generalist ever could,” Sean claims.
As founder of Affordable Contractor Insurance, Sean’s motto has been, “Do what you say you’re going to do.” He believes that a contractor should never be left guessing about what’s required and what it will cost, and should be informed of the “why” behind every coverage and endorsement. “We do this faster and clearer than anyone else in the industry. Contractors don’t have an hour to sit on the phone — they have 10 minutes between jobs. Our job is to be sharp, accurate, and reliable. That’s why we train agents for years, not weeks,” he says.
As contractor insurance becomes more specialized and more predictive due to climate risks, subcontractor chains adding more liability layers, and AI tools improving underwriting and fraud detection, Sean believes contractors will need more precise coverage, more education, and more support navigating qualifications and audits. “The days of ‘just give me the cheapest policy’ are ending. The winners will be agencies that specialize deeply and act as consultants — not order takers,” he says.
Taking pride in offering honest recommendations, no fluff coverage, and straightforward pricing, Sean says he always starts his conversation with, “Tell me what you’re trying to do, and I’ll tell you what you need — and what you don’t. Our ethical guidebook says don’t overpromise, don’t hide details, don’t string contractors along, always explain the plan upfront, and give them real numbers, not guesses. When you follow through every time, your clients trust you.”
Emphasizing that cheap coverage that doesn’t protect is expensive, Sean claims that they still manage to offer affordable insurance by placing contractors with the right carrier from the start. “Affordability comes from proper classification, buying only the coverages that are actually needed, avoiding costly audit mistakes, using carriers that specialize in their trade, and negotiating renewals aggressively.”
As a veteran leader who built a contractor-focused insurance agency around discipline, clarity, and real-world problem solving, Sean views his long-term customer relationships as the foundation of his business. “Contractors want you to fight for them during audits, show up when there’s a problem, answer the phone, save them money year after year, and keep them compliant so they can win bigger jobs. My goal isn’t a one-year policy — it’s a 10-year partnership that helps them grow,” he says.
Explaining how insurance coverage helps meet statutory requirements such as proper limits, endorsements, compliance documents, experience, and audit planning, Sean strongly believes the right insurance opens doors to bigger opportunities, whereas the wrong insurance blocks growth.
Claiming that contractors valuing honesty, clarity, and experience get the most benefit from working with them, Sean says small contractors ($0–$1M revenue) who need fast, affordable policies to stay compliant, and growing and established contractors ($1M–$20M+) who need consultative guidance, endorsements, audit management, and commercial job qualification, can benefit the most from their services.
Educating the clients has been Sean’s priority because he believes it makes the conversation easy. “Educating them using real examples like claims being denied because of wrong endorsements, audits spiking up to $80k+ because of misclassified payroll, contractors losing big commercial jobs because their policy didn’t qualify, and residential policies mistakenly being used for commercial work, helps them understand the risk of cheap coverage,” he says.
Today ACI operates across 50 states having different construction laws, different workers’ compensation rules, different carrier appetites, different endorsement requirements, and different auditing standards, besides every major builder and GC having their own qualification checklist. “To do this job well, an agent must know the state, trade, project type, carrier, and know the GC’s requirements. That level of complexity is why we train our agents for years, not weeks,” Sean claims.
