Corporate Counsel · Chicago

Practical Legal Counsel.
Built for Business.

Senior-level corporate counsel for businesses that need clear answers and practical strategy.

Oak & Hill, P.C. helps founders, growing companies, investment funds and established businesses navigate important decisions with responsive counsel, clearly defined services and transparent flat-fee pricing, without the traditional large-firm model.

30+
Years in Practice
5
State Bar Admissions
Flat Fee
Pricing Where Appropriate
Senior
Counsel on Every Matter
Why Clients Call Us

Legal Counsel That Moves
Business Forward.

Business moves quickly. Your legal counsel should help you keep pace. Oak & Hill, P.C. provides practical guidance for day-to-day legal needs, high-stakes transactions and the decisions that shape what comes next.

We offer ongoing outside general counsel support and focused assistance with corporate, transactional, employment, financing and technology matters. Our engagement structures are designed to provide clarity, accessibility and experienced legal judgment without the traditional large-firm model.

Ongoing Support

Outside General Counsel

Ongoing legal support for businesses that need senior legal guidance without adding a full-time in-house attorney. We work alongside owners, executives and internal teams on contracts, governance, employment, compliance, financing and strategic matters.

Learn About Outside General Counsel
Project and Transaction Work

Business and Transactional Services

Practical legal guidance for business formations, commercial agreements, mergers and acquisitions, securities matters, fundraising, fund formation, employment issues and other important transactions.

  • Business formation and governance
  • Commercial agreements
  • Employment matters
  • Mergers and acquisitions
  • Securities and fundraising
  • Fund formation
  • Contract drafting and negotiation
  • AI Legal Guidance
Explore Business and Transactional Services
Who We Serve

Counsel built around
the decision in front of you.

Oak & Hill, P.C. works with businesses at different stages of growth. What our clients have in common is a decision that carries legal consequence and a need for judgment they can act on quickly.

Startups and Emerging-Growth Companies

Founders come to us when they are ready to formalize what they have built: choosing an entity, papering equity, signing a first meaningful customer contract or preparing for a financing round.

Small and Midsize Businesses

Established companies engage us when growth outpaces their paperwork, when a contract demands real negotiation, or when an employment or governance question needs an answer the same week.

Founders and Entrepreneurs

We advise founders on ownership arrangements, co-founder terms, vesting, compensation and the personal-legal questions that surface when a business becomes valuable.

Technology and AI Companies

Companies building or deploying technology come to us over data rights, intellectual property ownership, platform and customer agreements, and the legal questions that AI adoption raises before anyone has settled answers.

Investment Funds and Sponsors

Sponsors engage us to form funds and special purpose vehicles, prepare offering and subscription materials, and support portfolio investments and governance from the first vehicle onward.

Companies in Acquisitions and Major Transactions

Buyers, sellers and management teams bring us in when a transaction becomes real: structure, letters of intent, diligence, definitive agreements and the coordination that gets a deal closed.

We are particularly well suited for organizations that need experienced legal leadership but may not require or want a full-time general counsel or a traditional large-firm relationship.

Representative Experience

Experience across
the business lifecycle.

Our experience spans the full business lifecycle, from formation and early-stage contracting through financing, growth, acquisitions and ongoing corporate governance. We have advised companies and investment sponsors on complex commercial agreements, strategic transactions, employment matters, securities offerings, fund structures and day-to-day legal operations.

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Why Oak & Hill, P.C.

Four reasons clients
stay with us.

Experienced Counsel

Senior-level legal guidance informed by decades of corporate and transactional experience.

Business-Minded Advice

Practical recommendations that account for legal risk, business priorities and the realities of implementation.

Flexible Engagement

Ongoing outside general counsel support or focused assistance for a specific project or transaction.

Clear Expectations

Clearly defined scopes, responsive communication and flat-fee pricing where appropriate.

Leonard Nannarone, Founder and Managing Partner of Oak & Hill, P.C.
Our Firm

Leonard Nannarone

Founder and Managing Partner

Leonard Nannarone has more than 30 years of experience advising startups, growing businesses, investment funds and established companies on corporate, transactional and strategic matters.

His practice includes general corporate law, mergers and acquisitions, outside general counsel services, contract drafting and negotiation, securities law, venture financing and employment matters. Before founding Oak & Hill, P.C., Leonard practiced at Kirkland & Ellis and worked at Intel Corporation.

About Our Firm
Get Started

Move Your Business Forward
With Confidence.

Whether you need an ongoing legal partner or focused counsel for an important matter, Oak & Hill, P.C. provides the judgment and practical direction to help you take the next step with confidence.

Legal guidance built around your business.

Schedule a Call

Start a conversation.

Tell us about your business and the legal support you are seeking. We will follow up to discuss whether the firm is a good fit for your needs.

Please do not send confidential or time-sensitive information through this form. Submitting this form does not create an attorney-client relationship.