Strategic legal leadership without the full-time commitment—nearly 20 years of in-house, regulatory, and appellate experience on a subscription basis

I provide fractional General Counsel services to companies that need sophisticated legal judgment but aren't ready for a full-time hire. My clients get access to nearly 20 years of experience spanning insurance regulation, government affairs, complex litigation, and startup operations—without the six-figure salary commitment. I run this practice through DM Legal Strategy LLC, which I founded in 2017.

I've served as General Counsel at two InsurTech startups (Amplify Life Insurance and Degree Insurance Co., which I co-founded), where I led legal, regulatory strategy, compliance, corporate governance, and government relations. Before that, I was General Counsel to Illinois Governor Bruce Rauner, supervising hundreds of attorneys and managing everything from constitutional litigation to multi-billion dollar labor negotiations.

I started my career clerking for two federal appellate judges and practicing appellate litigation at Jones Day. I'm also a trained actuary, which gives me an unusual ability to speak the language of risk, financial modeling, and data-driven decision-making.

What I offer:

• Strategic counsel on regulatory, compliance, and corporate governance
• Senior judgment without full-time overhead
• Flexible engagement models—monthly retainers designed for predictable budgeting
• Deep expertise in regulated industries, particularly insurance, government affairs, and complex commercial matters

I work with companies that have outgrown LegalZoom but aren't ready for BigLaw hourly rates or a full-time GC salary.

Based in the Chicago area. Father of four. Fluent in Russian. Passionate about pickleball and helping companies navigate the messy middle of growth.

Let's discuss whether fractional GC services are the right fit for your company. Visit dmlegalstrategy.com or email [email protected].