If you run a startup, you already know how fast the ground can shift under you. Insurance is one of those things that founders set up early, then forget about until renewal season brings surprises.
As 2026 gets moving, it is a perfect moment to check whether the coverage you bought in calmer times still fits your team, your revenue, and your risk profile.
Here are six insurance areas worth revisiting this year, along with some fresh context from recent research and industry reports.
Recheck Your Key Person Cover Levels
Key person insurance is one of the most essential but most overlooked policies for early stage companies. If you or another core team member were suddenly unable to work, investors and customers would feel the ripple effect immediately. Policies bought in the first year of operations often no longer match reality by year two or three.
In a study by Businesswire, analysts noted that founders increased their reliance on structured protection as cyber and operational risks expanded. That same pattern applies to people risk. As your valuation, contracts, and team size change, your payout and premium expectations should shift too. If revenue has doubled since you first signed your policy, the original amount may not cover critical recovery periods.
2. Revisit Shareholder Protection Structures
Shareholder protection helps ensure that equity can be transferred smoothly if a cofounder dies or becomes critically ill. Yet many teams leave the structure too simple or outdated. For example, your original ownership stakes might not reflect new capital rounds or new cofounders. If the agreement does not match your current cap table, a crisis could freeze your business at the worst possible time.
Carriers also adjust underwriting rules every few years. Some have tightened medical review requirements, while others now bundle shareholder buyout protection with critical illness features. It is worth checking which structure best fits your team today, and having a shareholder agreement that prevents problems, not causes them.
3. Review Death in Service Arrangements
Death-in-service benefits are usually tied to payroll and team size. If you have hired aggressively over the last year, your policy may not cover everyone equally. Some companies also switch from fixed lump sum designs to salary based formulas as they scale.
In 2025, several brokers noted that group risk costs rose in industries with high burnout and turnover. You might see the same in your renewal this year. Keeping your census data accurate can prevent an unexpected jump in premiums.
A quick look at options
Check whether your benefit amount still makes sense
Confirm that new hires are included
Review whether your insurer has changed its group policy rules
4. Update Director Life and Critical Illness Coverage
Directors often have a unique mix of personal and business exposure. Life and critical illness policies bought when the company was small may not reflect your responsibilities today. This is also when you need to consider what insurance actually covers especially when families need to know what happens after an unexpected loss. For example, standard life insurance often pays out in a lump sum that can help with funeral costs, while certain burial focused policies offer more specific support.
Founders sometimes assume their company benefits alone will protect them, but personal policies can play an important role. Critical illness additions are also becoming more common, especially as workplace health expectations shift.
5. Reassess Income Protection for Owner Operators
Income protection for founders is one of the areas most likely to be outdated by 2026. You may now draw a salary instead of dividends, or your salary may have increased. If so, the payout amount on your policy could be out of sync with your real financial needs.
Small business insurance buyers are shifting toward more personalized risk mapping. That pattern suggests founders should take a closer look at how long they could realistically operate without income. Waiting periods, payout durations, and definitions of incapacity all deserve a second review.
6. Reevaluate Business Interruption and Cyber Dependencies
Business interruption insurance used to be about fires and floods. Now it is just as much about cloud outages, vendor downtime, and ransomware. In a report from Breached Company, researchers noted a rise in supply chain cyber incidents that cut off operations for days at a time. If your company relies on a single cloud platform or automation tool, you could face a serious interruption without ever being directly attacked.
Some insurers now exclude certain cyber linked events unless you buy a special endorsement. Others require proof of multi factor authentication across all apps. Checking for these changes can prevent a nasty surprise at renewal.
Final Thoughts
Most founders think of insurance as a background chore, but it is more like a living system. As your business evolves, your protection must evolve with it. Spending even one afternoon reviewing the six areas above can make your company far more resilient.
