Caitlin A. Donovan
Admitted: New York · Massachusetts · Arizona
Trained as a lawyer. Wired for business.
I built PPSC Counsel because I wanted more than the traditional law firm model offered: more access, more partnership, more efficiency, and far fewer obstacles. More genuine connection. More investment in the people, businesses, and ideas behind the work. I wanted to be closer to the client, closer to the business, and more involved in what happens next. The lawyering was never the problem. I love being a lawyer. I just wanted to practice with more ownership, more connection, and more investment in what happens next.
More than 14 years into practice, I have represented vendors and customers, startups and established companies, businesses buying technology and businesses building and selling it. I have litigated commercial disputes, negotiated complex transactions, navigated regulatory questions, and advised businesses on privacy, data, healthcare, technology, AI, risk, and operations.
I am admitted in New York, Massachusetts, and Arizona, and my practice has been shaped by working across different markets, industries, company stages, and legal disciplines. That range matters. It means I rarely look at a problem through only one lens.
A transaction is rarely just a transaction. It may also raise privacy, regulatory, operational, technology, data, product, or strategic questions. A new product, business model, partnership, or commercial relationship can touch several of those at once. And the right answer can look very different depending on the company, the industry, the stage of growth, and what the business is actually trying to accomplish.
I like the messy version. I like getting involved before everyone has decided exactly what the legal question is. I want to understand what the business is trying to accomplish, how the pieces fit together, what is getting in the way, and where I can make things work better.
Sometimes that means negotiating the agreement. Sometimes it means fixing the structure behind it. Sometimes it means building a process that should have existed years ago. Sometimes it means pressure-testing a new idea, finding another route through a regulatory constraint, or realizing that the thing everyone is calling a legal problem is really a business problem with a legal component.
That is what I love about being a business lawyer.
My litigation background is part of how I think. I have seen what happens when expectations diverge, incentives stop aligning, relationships deteriorate, and words that once seemed insignificant suddenly become very expensive. I carry that experience into transactional and advisory work. I think about how agreements will actually operate, where ambiguity can turn into conflict, and what happens when the relationship is no longer going according to plan.
It also means I am comfortable when things get complicated.
My job is not to deliver a list of risks and disappear. I want clients to understand what matters, what does not, what risk is worth taking, and what the actual decision looks like. Legal advice should create clarity and momentum. It should help the business make better decisions.
And I want clients to have real access to the lawyer doing the work.
Bring me the transaction. The regulatory question. The structure nobody quite loves. The process that stopped working. The new product. The difficult relationship. The idea that is not fully formed yet.
We will figure out what actually needs solving.
The work should be worth the investment. So should the relationship. I believe smart, kind, genuinely invested people do better work together, and clients should never have to choose between sophisticated legal judgment and genuine human connection.
Unexpected. Fearless. Seriously strategic. Just a hint of whimsy.
14+ years of practice
New York · Massachusetts · Arizona
Albany Law School, J.D., magna cum laude
Editor-in-Chief, Albany Law Journal of Science & Technology
Syracuse University
Best Lawyers: Ones to Watch®
Health Care Law, 2026
TGen Foundation Ambassador
2026
- International Association of Privacy Professionals (IAPP) — Professional Member
- American Health Law Association
- New York State Bar Association
- Arizona State Bar
The work behind the perspective.
Representative experience. Client identities and confidential details omitted.
High-stakes commercial deals
Led negotiations across complex SaaS, software licensing, data analytics, AI-enabled technology and strategic partnerships involving sophisticated, high-value commercial relationships.
From product to market
Counseled leadership, product, engineering, sales, finance and compliance teams through product launches, commercialization, enterprise expansion and market entry.
The deal behind the technology
Structured and negotiated enterprise SaaS, software licensing, professional services, vendor, reseller, referral, data-processing, platform, privacy/security, AI-enabled services and strategic partnership agreements.
Healthcare, without the silos
Advised digital health, health IT and healthcare organizations across commercialization, strategic partnerships, data strategy, privacy, security, AI governance, regulatory compliance and operational risk.
Strategic business counsel. Inside the business.
Served as general counsel and strategic commercial advisor to growth-stage and scaling companies, working directly with leadership on contracting, partner strategy, product implementation, data governance, compliance and day-to-day business risk.
Litigation-trained. Deal-focused.
Bring a disputes-informed lens to contract drafting and negotiation—including indemnity, limitations of liability, escalation paths, enforcement posture and designing agreements to hold up when things do not go according to plan.