Let’s talk about the silent killer in construction - insurance.
Not the kind that protects your business, but the kind that eats your margins year after year.
Across the industry, premiums are rising faster than ever. In 2025, construction firms are seeing double-digit increases driven by rising insurance premiums, tighter underwriting guidelines, higher cost of claims, and more compliance scrutiny than ever. The result? Your insurance renewal has quietly become one of your biggest cost centers and you probably don’t even realize how much money you’re leaving on the table.
Here’s the hard truth: most firms don’t have an in-house risk manager. Their broker is a generalist juggling financial services, technology, and insurance . That means cookie-cutter coverage, blind spots in contracts, and zero proactive strategy. The outcome? Massive overpayment, coverage gaps, and lost margin disguised as “the cost of doing business.”
Our newest insurance partner WithCoverage
Our newest partner, WithCoverage, understands it doesn’t have to be this way.
WithCoverage pairs deep Construction risk expertise with a digital platform designed ground-up for contractors to manage all insurance aspects in one place. Their modern risk management platform makes more carriers compete for your business while centralizing insurance renewals, COI verification and compliance tracking. Unlike traditional brokers who spread their focus across multiple industries, WithCoverage exclusively serves construction companies with a dedicated team of contractor risk experts, bringing deep subject matter expertise from leaders who've worked with ENR Top 20 contractors and managed complex construction casualty claims.
Their clients - from street and road contractors to HVAC and electrical subs -save tens to hundreds of thousands of dollars annually, while gaining better coverage, a white glove team of Construction experts, and full operational visibility.
In today’s market, having a specialized risk manager isn’t a luxury - it’s a competitive advantage.
Technology-Driven Savings with Shepherd
While WithCoverage brings deep construction expertise and digital platform capabilities, they also leverage innovative carrier partnerships to maximize client savings. One of their key partners, Shepherd is the first technology-enabled insurance provider specifically for commercial construction - allowing WithCoverage to secure unprecedented savings for tech-forward contractors.
Here's what makes Shepherd unique: they're the first insurer to recognize that tech adoption directly reduces risk. With 67% of U.S. contractors now using software for critical functions like project management, reality capture, and safety tracking, the industry has fundamentally changed but traditional insurance pricing hasn't caught up.
The Shepherd Savings Program actually factors your technology stack into underwriting. By incorporating real time usage and activity data from platforms like Procore, Autodesk, OpenSpace, DroneDeploy, Raken, and Brickeye, Shepherd can offer what traditional insurers can't:
- Up to 25% lower premiums for tech-enabled contractors
- Improved coverage terms that reflect your actual risk profile
- Multi-year programs with rate renewal guarantees - predictability in an unpredictable market
For construction firms operating nationwide, this isn't just about lower premiums, it's about insurance that finally understands how modern construction actually works. Your investment in technology shouldn't just improve your operations, it should reduce your insurance costs too.
Certification Gets You Considered. Readiness Gets You Chosen.
For certified subcontractors - MBE, WBE, DBE, SDVOB - getting certified opens doors. But staying ready is what wins projects. General contractors are no longer just looking for a diverse roster; they’re looking for reliable, compliant, and insured partners who can deliver without delays.
A recent ENR survey found that 67% of GCs reject small or certified firms due to incomplete insurance documentation, and another 40% report project delays caused by compliance issues.
That gap between certification and readiness is where most opportunities are lost.
Insurance Is Paperwork - Until It Isn’t
Insurance may feel like paperwork, but to a GC, it’s proof. Proof that you can protect their jobsite, back your bid, and stay compliant when it matters.
Every project has different requirements: general liability, auto, umbrella, workers’ comp, and occasionally professional or pollution liability. But policies expire, limits vary, and paperwork gets buried in email threads.
Yet too often, policies expire mid-project, COIs get buried in email chains, and coverage limits don’t match contract requirements. That one missing endorsement can take a sub from “approved” to “disqualified” overnight. That’s why insurance lapses are one of the most common reasons certified subs lose eligibility mid-project.
That’s where WithCoverage comes in. Their platform centralizes every policy, renewal, and COI in one place - so you’re always current, always visible, and always ready.
For subs, it means less chasing paperwork and more winning bids.
For GCs, that means fewer compliance headaches.
Tough Leaf + WithCoverage: Turning “Bid Ready” into “Award Ready”
At Tough Leaf, we connect general contractors with qualified certified subs, not just by matching credentials, but by ensuring each firm meets the project’s specific requirements before bidding.
That includes:
- Confirming certifications and expiration dates
- Verifying that insurance coverage aligns with contract limits
- Helping subs update missing information before the GC ever sees the list
When that verification layer combines with WithCoverage’s digital risk platform and service, GCs see fewer compliance issues, and subs see more accepted bids.
In fact, on projects that use verified subcontractor lists, bid participation increases by an average of 3.5x, and award turnaround times drop by nearly 40%.
Practical Takeaways for Certified Subs
If you’re a certified sub looking to stand out, focus on what GCs actually check first: compliance, coverage, and communication.
- Keep your COI current and accessible. Don’t wait to be asked proactively share it with limits, expiration dates, and endorsements clearly listed.
- Match your limits to the job. Many GCs now require $2M+ per occurrence limits, up from $1M just five years ago.
- Track your certifications like invoices. Expired MBE/WBE/DBE status can cost both you and the GC the contract.
- Build a one-page “Readiness Sheet.” Include your certifications, coverage, safety rating, and contacts. Make it easy to say “yes.”
- Communicate early. If something changes, flag it, transparency builds trust faster than perfection.
The Bottom Line
In today’s market, insurance is no longer just protection, it’s positioning.
Certified subcontractors who manage risk and readiness win more work, move faster, and protect their margins.
WithCoverage makes risk management simple.
Tough Leaf makes matching and verification simple.
Together, we make it simple for certified subs to stand out and for GCs to build with confidence.
Email vin@withcoverage.com to get a free Risk Analysis of your insurance program from WithCoverage and see how much margin your insurance is really costing you.