In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Skylar from ATW Advisors to unpack how large CRE operators and syndicators can turn insurance from a deal-killing expense line into a strategic lever for protecting NOI and keeping closings on track.

Skylar shares how she spent 17 years as a commercial insurance broker serving real estate owners and developers before launching ATW as an owner’s rep and outsourced “CRO” for risk and insurance. She explains why she left the brokerage world, how ATW benchmarks programs across the country, and what sophisticated sponsors are doing differently to control premiums across entire portfolios instead of shopping one-off policies.

Skylar breaks down:

- Why insurance has become the fastest-growing expense line item in CRE and how 50–100%+ premium jumps can blow up deals at the closing table

- What’s really behind the recent hard market—replacement cost inflation, supply chain, labor, and reinsurance—and why a “softer” market doesn’t mean you can relax

- How portfolio-level strategy, data, and benchmarking beat chasing one-off quotes when you’re renewing across dozens of assets

- The liability squeeze in U.S. multifamily: crime scores, Fannie/Freddie requirements, and exclusions (assault & battery, firearms, animal bites, subsidence, and more) that can quietly wreck your coverage

- Why geography, crime, and local risk quirks (wildfires, hurricanes, tornadoes, mine subsidence, etc.) need to be underwritten up front—especially when you’re going out-of-market

- Practical ways operators are using technology—robot dogs, license plate readers, and other tools—to change the risk story they take to underwriters

- When to bring in an insurance advisor in the deal cycle (LOI, PSA, renewal) so your lender and carrier don’t surprise you at the eleventh hour


Skylar challenges operators to treat insurance with the same intentionality as debt and tax strategy: know your underwriters, understand your exclusions, review programs regularly, and either become your own advocate—or hire one—so you can protect NOI and keep deals alive in the next hard market.

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