Chief Product Officer (CPO) / Co-Founder — Legal Engineer

Chief Product Officer (CPO) / Co-Founder — Legal Engineer

Company: Pleading.ai (parent of SueEasy)

Location: Hybrid / Remote

Reports To: CEO (Todd Lowdon)

About Pleading.ai

Pleading.ai is building the AI engine for civil litigation.

Our technology uses AI to interview users, structure facts, identify missing information, analyze claims and defenses, and draft high-quality complaints designed to withstand motions to dismiss. In reverse, it can analyze complaints for weaknesses and help draft motions to dismiss and other responses.

The engine powers two products:

Pleading.ai — professional litigation technology for lawyers and law firms.

SueEasy — our consumer and small-business platform, providing AI-guided self-service for lower-dollar disputes and AI plus attorney assistance for larger civil matters.

Our mission is to make civil justice faster, more accessible, and easier to navigate.

The Role

We are looking for more than a traditional CPO. We want a product leader who can also function as a Legal Engineer—someone who can translate litigation law, procedural rules, attorney judgment, and legal workflows into product logic that engineers and AI systems can execute.

You will own the product ecosystem from legal architecture and AI workflows through UX, commercialization, and scale.

That means understanding not merely what screen comes next, but what legal question the system should ask next, why it matters, what facts are missing, and what the software should do with the answer.

You should be able to think through questions like:

• What facts establish each element of a claim?
• What allegations are legally insufficient?
• What should AI ask to uncover missing facts?
• What defenses or procedural issues should be identified?
• When should documents or evidence be requested?
• What makes a complaint vulnerable to dismissal?
• How should jurisdiction-specific rules alter the workflow?
• When should AI hand the matter to a lawyer?

You don't need to write every line of production code. But you should be technically fluent enough to prototype, work directly with engineers, understand modern AI architectures, and translate legal reasoning into specifications, structured data, evaluations, prompts, agents, and workflows.

This is a builder role, not a product-management job centered around meetings and roadmaps.

Key ResponsibilitiesLegal Engineering

Translate substantive and procedural law into software.

Convert causes of action, elements, defenses, pleading standards, procedural rules, and litigation workflows into structured product logic.

Build systems that transform a client's story into legally relevant facts, claims, defenses, missing-information questions, supporting evidence, and litigation-ready work product.

AI Product Engineering

Design AI-native workflows rather than adding AI features to conventional software.

Determine where to use LLM reasoning, retrieval, deterministic rules, structured outputs, agents, and human review.

Work directly with engineering on prompts, schemas, evaluations, guardrails, and model behavior. Develop evaluations for legal accuracy, factual grounding, completeness, hallucination risk, and pleading quality.

Intelligent Legal Intake

Reimagine intake as an adaptive AI interview rather than a questionnaire.

The system should understand what a user has said, determine what legally material information is missing, ask intelligent follow-ups, request evidence, and progressively construct the factual and legal structure of the case.

The goal is to turn a client's story into structured litigation intelligence.

Pleading & Motion Intelligence

Build systems that analyze litigation from both sides.

For plaintiffs, identify weaknesses and strengthen factual allegations before filing.

For defendants, identify missing elements, procedural problems, and potential grounds for dismissal.

Lawyers should be able to understand, verify, modify, or reject the AI's reasoning.

Product Strategy

Own three related product motions:

1. Self-service SueEasy for small claims.
2. AI + attorney assistance for larger SueEasy matters.
3. Professional Pleading.ai tools for litigators and law firms.

Determine where these products should share technology and where their UX, risk tolerances, economics, and adoption strategies must differ.

UX, Product Marketing & Growth

Make complicated litigation workflows feel simple.

Own positioning for both sophisticated legal buyers and consumers. Personally map journeys, test prototypes, observe users, analyze funnels, and improve activation, conversion, retention, and adoption.

Design a seamless transition from AI self-service to attorney assistance where appropriate.

Hands-On Leadership

Write specifications. Map workflows. Prototype. Test prompts. Review AI output. Interview lawyers. Watch consumers use the product. Work directly with engineers.

As we scale, recruit and lead exceptional product, design, and legal-engineering talent while remaining close to the product.

What You Bring

Product Leadership

8+ years of product, technology, or related experience, including meaningful leadership responsibility in a startup or high-growth technology company.

We care more about what you have built than your title.

Legal Engineering Mindset

You naturally think about how law can be represented computationally.

You can take a cause of action, pleading standard, procedural requirement, or litigation workflow and break it into rules, facts, questions, dependencies, exceptions, evidence requirements, and decision points that can become software.

Legal + Technical Fluency

Our ideal candidate is an unusual hybrid: a litigator who became a technologist, product leader, developer, AI builder, or entrepreneur.

A JD and litigation experience are highly desirable, particularly experience with pleadings, motions, civil procedure, or plaintiff/defense litigation.

Alternatively, you may be an exceptional technologist or product leader with deep litigation and legaltech expertise.

Builder-Level Technical Fluency

You don't need to be a career software engineer, but you should be comfortable prototyping with AI coding tools, APIs, structured data, prompts, retrieval, agents, and modern development environments.

You should be able to sit beside an engineer and meaningfully participate in decisions about how the product works.

Genuine AI Fluency

AI is already part of your daily workflow.

You understand the capabilities and limitations of LLMs and have hands-on experience with prompting, retrieval, structured outputs, evaluations, agents, or AI-assisted development.

You actively follow AI-native legal technology and how lawyers are adopting it.

Litigation Curiosity

You want to understand why one complaint survives and another doesn't; why an experienced litigator asks a particular follow-up question; which facts change a claim; and how legal judgment can be translated into technology.

Startup Mentality

You thrive in ambiguity, move quickly, and are comfortable switching between strategy and execution.

You are low ego, intellectually curious, collaborative, and willing to change your mind when evidence changes.

Especially Interesting Backgrounds

We particularly want to hear from litigators who learned to code or became AI builders; attorneys who moved into product or technology; legaltech product leaders with hands-on AI experience; and engineers or founders with deep litigation knowledge.

An unconventional background is welcome. Show us what you have built.

Why Pleading.ai?

This is an opportunity to help define a new discipline at the intersection of law, product, and AI engineering.

We aren't building another legal chatbot. We want to build a legal reasoning engine that understands the structure of a dispute, identifies what matters, discovers what is missing, and helps people and lawyers produce stronger litigation work.

You will help architect that technology from the ground up, establish Legal Engineering as a core discipline, and ultimately build and lead the product organization.