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

What Others Say

"Dennis has been an exceptional General Counsel for Amplify over the past three years. He brings strategic judgment and deep regulatory expertise in insurance—navigating complex compliance requirements across multiple states while keeping our business objectives front and center. What sets him apart is his pragmatic approach to risk. He doesn’t default to ‘no’—he helps leadership understand the trade-offs so we can make informed decisions and move quickly. He’s been a trusted partner in building Amplify, and I look forward to continuing to work with him."

— Hanna Wu, CEO, Amplify Life Insurance Company

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"Dennis navigated extraordinarily complex regulatory challenges at Degree Insurance with a combination of technical expertise and practical business judgment. He didn't just follow the traditional playbook—he thought creatively and strategically about how to structure the business to achieve regulatory approval while maintaining commercial viability. He's one of the most reliable and responsible partners we've worked with, and we'd collaborate with him on any deal. I'd highly recommend him to any growth-stage company navigating a regulated industry."

— Salen Churi, Founder & General Partner, Trust Ventures

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"Dennis is a gem to work with. He’s legitimately one of the smartest humans around, thoughtful in his approach and unlocks value in creative solutions. When you want to do something challenging—any lawyer can tell you, 'No.' Or that it can’t be done. Dennis will tell you how it can be done, what the risks are and how to mitigate them. That alone makes him a rare breed. He’s quick, responsive, endlessly patient, and comes to creative (and correct) solutions at the speed of business. I’m thrilled to have worked with him and would 10/10 recommend."

— Wade Eyerlly, Co-Founder & CEO, Degree Insurance

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"Dennis approaches legal risk with a structured, analytical mindset that made him an exceptional partner at Amplify. Unlike lawyers who default to extreme risk aversion, he contextualizes risk—helping leadership understand not just what the risk is, but the realistic probability and magnitude of impact. For companies in regulated industries, Dennis is a strategic enabler, not an obstacle."

— Tyler Sellers, VP of Data, Amplify Life Insurance Company

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

JD from Northwestern Law (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 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 Right for Your Company

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

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Or email directly: [email protected]