Chief Product Officer (CPO) / Co-Founder

Chief Product Officer (CPO) / Co-Founder

Company: Pleading.ai (parent of SueEasy)

Location: Hybrid / Remote

Reports To: Chief Executive Officer (Todd Lowdon)

About Pleading.ai

Pleading.ai is building the AI engine for civil litigation. At our core is a pleadings engine that uses AI to streamline intake, gather and structure facts, and produce high-quality complaints built to withstand motions to dismiss — and, in reverse, motions to dismiss with a high likelihood of success against weaker complaints. That same engine powers two product lines: Pleading.ai, deployed directly to litigators and litigation law firms to accelerate and strengthen their drafting and motion practice, and SueEasy, our consumer and small-business product. On SueEasy, users with lower-dollar disputes (small claims) get a mostly self-serve, AI-guided path from intake through filing. For plaintiffs and defendants navigating limited and unlimited civil claims, that same AI-driven intake and drafting experience is paired with attorney assistance in select practice areas.

Our mission is to make the civil court system faster, fairer, and more navigable — for the people who represent themselves, the people who need some attorney support along the way, and the attorneys representing others.

The Role

As our Chief Product Officer, you will serve as the strategic visionary and hands-on architect of the Pleading.ai product ecosystem — the shared engine, and the experiences built on top of it. Reporting directly to the CEO, you will own the entire product lifecycle across both lines, from zero-to-one conceptualization through scalable execution and growth, and you will lead product marketing as a core part of the mandate — translating deep legal/technical capability into positioning and messaging for very different buyers.

You'll need to think in multiple registers at once: a largely self-serve, PLG-style experience for small-claims users on SueEasy; a hybrid experience for limited and unlimited civil claims on SueEasy, where self-serve AI tooling hands off cleanly to attorney assistance in select practice areas; and a more consultative, relationship-driven motion for Pleading.ai's litigator and law-firm customers. You bring deep expertise in modern product management, an obsession with friction-free UX, and a rigorous, data-driven approach to product analytics — balanced against the reality that legal buyers, and matters involving real attorney work, often need trust, proof, and a well-designed hand-off before self-serve is enough.

Key Responsibilities

• Multi-Motion Product Strategy: Define and execute a product roadmap across three motions — self-serve PLG for SueEasy's small-claims users, a hybrid self-serve-plus-attorney-assist journey for SueEasy's limited/unlimited civil users, and a firm-friendly adoption path for Pleading.ai's litigator and law-firm customers.
• Self-Serve + Assisted Hybrid Design: Design the product and triage logic that keeps small-claims users moving through a fast, clear, mostly self-serve journey, while building a smooth, well-timed hand-off to attorney assistance for limited and unlimited civil matters in select practice areas.
• Product Marketing Leadership: Own positioning and messaging across audiences — credible to litigators and law firms on Pleading.ai, and approachable and trustworthy to consumers and small businesses on SueEasy, whether they're self-serving a small claim or getting attorney support on a bigger one.
• AI & Legal Workflow Integration: Lead deployment of AI to automate intake, fact-gathering, and drafting — producing complaints built to survive motions to dismiss, and MTDs built to defeat weak complaints — while keeping legal quality and defensibility non-negotiable.
• Modern Product Execution: Champion agile, hypothesis-driven practices — rapid prototyping, continuous user research (with self-represented litigants, assisted users, and practicing attorneys), A/B testing, and full-funnel analytics across both products.
• UX & Design Leadership: Partner with design to make self-serve flows feel simple, make the self-serve-to-attorney hand-off feel seamless and trustworthy, and make Pleading.ai's litigator-facing tools feel indispensable.
• Hands-on & Executive Leadership: Write specs, map user journeys, and test builds yourself, while building and leading a high-performing product and design team as the company scales.
• Revenue & Commercial Alignment: Balance user delight and retention with monetization — optimizing SueEasy's self-serve and attorney-assisted tiers alongside Pleading.ai's firm- or seat-based commercial model.
• Cross-Functional Collaboration: Partner closely with the CEO, engineering, marketing, and legal advisors to keep product velocity, technical feasibility, and regulatory alignment in sync across both product lines.

What You Bring

• Product Leadership: 8+ years of product management experience, including executive-level leadership (VP, Head of Product, or CPO) in high-growth startup environments.
• Legal + Tech Fluency (ideal profile): A practicing attorney — ideally with litigation experience — who has made the leap into tech as a product manager, developer, or marketer. Comfortable in the law and comfortable building software.
• Or, Deep LegalTech Experience: If not an attorney, deep familiarity with the legaltech landscape — the players, the trends, how litigation and legal-services buyers actually evaluate and adopt software.
• Genuine AI Fluency: You actively use AI tools in your own daily workflow — this isn't conceptual for you. You also closely track how AI is reshaping the legal industry itself: the tools attorneys and firms are adopting, the AI-native legal tech landscape, and where the profession is headed.
• Multi-Motion GTM Fluency: Experience with product-led growth (activation funnels, self-serve conversion, viral distribution) and, ideally, exposure to hybrid self-serve/assisted-service models or more relationship-driven B2B adoption — you don't need to have run all three, but you understand why they differ.
• AI Product Experience: A demonstrated track record building and launching products that use modern AI/LLM capabilities to solve real, high-stakes user problems.
• Data-Driven & User-Centric: A clear, structured philosophy on product metrics, cohort retention, and qualitative user discovery — across multiple user bases and service models.
• Startup Agility: A builder's mindset — comfortable in ambiguity, moving fast, balancing strategic planning with hands-on execution.
• Character & Collaboration: Low ego, high EQ, and a team-first leadership style with a proven record of developing product talent.

Why Pleading.ai?

• Shape product strategy at the ground level of a platform built to change how civil litigation works — for self-represented people, people who need attorney support along the way, and the attorneys who litigate on others' behalf.
• Own a rare multi-motion mandate: self-serve, hybrid assisted-service, and professional-grade tooling, all powered by the same core AI engine.
• Meaningful equity ownership and competitive executive compensation.
• Direct partnership with executive leadership to build a category-defining legal AI company.