Chief evangelist and general counsel | Leah

Jerry Levine
Chief evangelist and general counsel | Leah
What are the most significant cases, projects, or transactions that you and your legal team have recently been involved in?
The past year has been about building, which, frankly, is exactly where in-house legal should be spending its energy. We’ve taken the company through a complete rebrand, transforming from ContractPodAi to Leah. It’s a bit like renovating your house while still living in it, and everything needs to be touched, reviewed, and updated. Invigorating our partner ecosystem has been a big project over the past year, with consistent work on deal structures, collaboration frameworks, and how to build relationships that create real value for everyone involved. Finally, I really enjoyed the fact that numerous standardization projects I’ve been involved in have been successful. There’s a lot of satisfaction in turning the tools we help others use on ourselves.
How do you approach managing legal aspects during periods of instability or crisis to ensure the organisation’s resilience?
During periods of uncertainty, whether driven by financial volatility, regulatory change, or rapid technological shifts, organizational resilience comes from combining strong legal judgment with technology-enabled oversight. At Leah, I focus on identifying and mitigating risk early by working closely with business, product, and operations teams to ensure decisions balance compliance with commercial realities.
A collaborative and proactive approach is essential. As agentic AI scales across enterprises, legal, compliance, and technology functions are becoming deeply interconnected. Traditional boundaries between these disciplines are dissolving as shared challenges emerge around data governance, algorithmic transparency, and automated decision-making. In practice, this means legal teams must understand data flows and APIs, while technologists must account for regulatory and legal implications from the outset. By embedding legal into these conversations and leveraging AI-supported visibility into contracts, obligations, and compliance, we are able to reduce risk, adapt quickly, and support the business effectively—even under sustained pressure or uncertainty.
General counsel often speak of the need to be strategic to reach the pinnacle of the profession. What does being strategic mean to you?
“Strategic” has become one of those words that gets thrown around so often it’s at risk of meaning nothing at all. Being strategic means understanding that your job isn’t just to practice law — it’s to help the business succeed. It means knowing when to say yes, when to say no, and — most importantly —when to say “yes, if we do it this way.” It means being in the room when decisions are being made, not just when documents need signing. It means having the business acumen to understand what keeps your CEO up at night and the emotional intelligence to know how to talk about it.
For me, it also means being relentlessly curious about where things are headed. Strategic GCs are students of the future. They experiment. They ask uncomfortable questions about efficiency and automation — including about their own work. And perhaps most fundamentally, the best strategic move a GC can make is earning enough trust that people actually want you at the table.
What strategies do you employ to ensure the successful digital transformation of a legal department while maintaining compliance with your country’s data protection laws?
I’ll confess upfront: I work for a legal technology company, so take my enthusiasm for digital transformation with appropriate professional skepticism. That said, digital transformation isn’t really a technology project, it’s about trust (and therefore safety, privacy, compliance, and more). The fanciest platform in the world fails if your team doesn’t believe in it and your clients don’t trust the outputs. So, before we talk about tools, we have to talk about confidence: confidence that humans remain in control, that there’s accountability at every step, and that technology is enhancing legal judgment rather than attempting to replace it.
I’m a strong proponent of human-first AI. The goal isn’t to remove lawyers from the equation, rather it’s to make them faster, sharper, and more focused on work that actually requires their expertise. That means building systems where someone can always ask “why did it reach that conclusion?” and always intervene when judgment calls are needed.
In practice, we take a risk-based approach to delegation. Routine, low-stakes work can be automated with appropriate guardrails, while complex negotiations and high-value matters get human attention commensurate with the risk. This isn’t a revolutionary concept, but building trust-by-design (rather than focusing on speed) requires discipline.
From a data protection standpoint, explainable AI is critical. Systems must be able to articulate how decisions are made in a legally defensible way, enabling auditability, error detection, and accountability. Combined with strong access controls, data minimization, and clear governance over how data is used and retained, this approach allows us to modernize the legal function while remaining aligned with evolving data protection laws and regulatory expectations.
Based on your experiences in the past year, are there any trends in the legal or business world that you are keeping an eye on that you think other in-house lawyers should be mindful of?
One key trend I’ve been watching is how Agentic AI is transforming talent strategies. The legal profession is experiencing fundamental skills transformation. Lawyers now require proficiency in AI tools for research, contract analysis, and workflow automation as baseline competencies. Beyond technical skills, legal professionals will need enhanced critical thinking abilities to scrutinize AI outputs, identify hallucinations, and validate AI-generated work. Talent strategies will shift, with firms recruiting interdisciplinary expertise, seeking candidates with data literacy and technology fluency alongside legal knowledge.
Junior lawyers will transition from performing routine research and document review to validating AI outputs and handling complex analytical tasks that AI cannot yet master. This will fundamentally reshape the associate development model, with early-career lawyers focusing on judgment, strategy, and client relationship skills rather than volume-based tasks.
That said, in-house lawyers should take note: embracing AI is no longer an option. The legal profession will increasingly value professionals who can bridge legal expertise with technological understanding.
Chief Evangelist and General counsel | ContractPodAi
General counsel and corporate secretary | Ipsoft
1. ‘Jerry Levine has over 10 years of legal practice experience that ranges from working in a firm, owning his own firm and being in-house. Recently, Levine entered a company...