Will lead product strategy bringing proprietary contract intelligence into a new generation of Legal AI tools
As artificial intelligence becomes embedded in legal workflows, a clear reality is emerging across in-house Legal teams and law firms: legal AI fails in predictable ways when it is not grounded in context. SimpleDocs announced the appointment of Electra Japonas as Chief Product Officer, formalizing her leadership of a product strategy designed to address that limitation through proprietary contract intelligence.
Japonas, who formerly served as Chief Legal Officer of Law Insider (recently acquired by SimpleDocs), will lead the development of what the company describes as the most context-rich legal AI platform on the market. The strategy is underpinned by SimpleDocs’ unique access to proprietary contract intelligence and Japonas’ long-standing work at the intersection of legal judgment, standardization, and AI. For the past several years, legal AI has focused primarily on capability: faster drafting, quicker review, more fluent outputs. Yet in practice, these systems consistently break down when asked to support nuanced legal decisions. Across real contract reviews, the same patterns recur: AI proposes positions that are misaligned with a company’s risk appetite, flags issues that are acceptable under the circumstances, and struggles to distinguish between what is commercially acceptable and what is not, for the agreement in question.
These failures are not caused by a lack of capability. They are caused by a lack of structured context.
As Chief Product Officer, Japonas will lead SimpleDocs’ next phase of development: building AI-native legal systems that are explicitly designed to operate with context as a first-order input. The platform brings together three distinct and complementary sources of insight.
First, standards and best practice—including internal playbooks, templates, policies, and community-driven standards that reflect how Legal teams aspire to operate.
Second, market context—derived from Law Insider’s proprietary database of real-world contracts and clauses, capturing how terms are actually negotiated across industries, deal sizes, and geographies.
Third, organizational context—a Legal team’s own contracts, negotiated outcomes, fallback positions, and historical decisions, which collectively express that organization’s true risk appetite.
By collating these inputs, SimpleDocs enables AI to surface patterns that human lawyers rely on intuitively but have never been able to systematize at scale.
“Legal judgment has always been contextual,” said Preston Clark, CEO of SimpleDocs. “What’s changed is that we can now capture and operationalize that context. Electra is uniquely positioned to lead this because she understands both the theory and the reality of how Legal teams work—and we have the proprietary contract intelligence to make it real.”
Japonas’ approach is grounded in experience. She is the founder of oneNDA, a landmark standardization initiative that demonstrated how shared context and agreed baselines can remove friction from everyday contracting. She also founded and ran TLB, a legal operations consultancy that worked with hundreds of Legal teams to optimize how they operate.
Across those engagements, a consistent barrier emerged: Legal teams struggled not because of a lack of talent or effort, but because critical context—precedent, standards, and institutional knowledge—was fragmented, informal, and difficult to reuse. Decisions were made case by case, but without systems that captured patterns across those decisions, consistency and scalability remained elusive.
“Contract negotiation is nuanced, and it should be,” said Japonas. “We don’t believe in rigid rules or one-size-fits-all answers. Lawyers make decisions case by case. But those decisions are not random. They follow patterns—patterns in our precedent, in the standards we adopt, and in how the market behaves. Until now, we haven’t had the tools to surface and apply those patterns systematically.”
With AI, that constraint changes. SimpleDocs is building software that allows Legal teams to review contracts informed by their own historical decisions, their stated standards, and credible market insight. This enables lawyers to make decisions that are aligned with their risk appetite, consistent with best practice, and calibrated to positions that reduce unnecessary negotiation friction.
The goal is not simply faster contracting. It is better contracting: more consistent, more intelligent, and more aligned with how Legal teams want to operate.
Under Japonas’ leadership, SimpleDocs’ product roadmap will focus on transforming contracts into a living source of institutional memory—where past decisions, shared standards, and market intelligence actively inform future work. The appointment signals the company’s intention to define a new category of legal technology: contextual legal AI, built on proprietary contract intelligence and designed around how Legal judgment actually works.
