DM Legal Strategy - Fractional General Counsel for Growth Companies

Fractional General Counsel for Growth Companies

Strategic legal leadership on a subscription basis—backed by nearly 20 years of in-house, regulatory, government, and appellate experience

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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.

What Sets Me Apart

I've served as General Counsel at two InsurTech startups (Amplify Life Insurance Company 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 governanceNavigate complex regulatory environments with confidence

Senior judgment without full-time overheadGet experienced General Counsel-level guidance without the W-2 expense

Flexible engagement modelsMonthly retainers designed for predictable budgeting and guaranteed access

Deep expertise in regulated industriesParticular strength in insurance, government affairs, and complex commercial matters

Ideal for Companies That:

I work with companies that have outgrown LegalZoom but aren't ready for BigLaw hourly rates or a full-time GC salary.Typically, these are businesses in the $5M-$50M revenue range navigating regulatory complexity, preparing for fundraising, or scaling operations. You need strategic legal thinking, not just transactional execution—and you need it to be predictable and accessible.

Background and Credentials

Northwestern Law School (magna cum laude), federal appellate clerkships, Jones Day appellate practice, General Counsel to an Illinois Governor, General Counsel of two InsurTech startups, including one I co-founded, and actuarial training from my career before law school.Based outside Chicago. 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 Right for Your Company

Schedule a no-obligation conversation to explore whether this model works for your situation.

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