Co-Founder & CEO - AI LegalTech | AI-Native Litigation Defence Operations

FutureSight • Chicago, IL

7d

About The Position

FutureSight is seeking a Co-Founder & CEO to lead LucentAI, an AI-native litigation operations venture being built at FutureSight. This role offers meaningful founder equity, not a salary. LucentAI is designed to act as an autopilot for medical-records and discovery operations within small-to-mid insurance-defence firms. It integrates with case-management systems to retrieve and review records, flag key facts with confidence links, check billing reasonableness, and chronologically triage discovery. This system, while human-gated, aims to exclude legal drafting and externalize review capacity, enabling firms to scale case volume without increasing headcount. Market validation through FutureSight’s discovery interviews has confirmed strong demand for operations support, with the vision of an autopilot system. Buyers expressed a need for managed operations, and LucentAI provides end-to-end automation, building trust by handling routine work discreetly while maintaining human oversight for legal drafting. The primary pain point identified is financial, with significant costs associated with time and errors in the middle phase of litigation, and a substantial portion of medical bills being deemed unreasonable. Given the current lack of AI adoption in this area, the ROI is immediate. Manual partner review limits case capacity and revenue, and the proprietary dataset of defence records and billing patterns differentiates LucentAI from plaintiff-focused incumbents.

Requirements

• Previous founding experience at a venture-backed company.
• Demonstrated success in B2B AI or B2B SaaS go-to-market, including consultative, relationship-driven sales and customer engagement.
• Fundraising fluency, with the ability to develop investor narratives and close capital.
• Proven ability to attract, develop, and retain top talent.
• Clear-eyed understanding of the risks and demands of co-founding a venture-backed company.
• Deep domain expertise in insurance defence or claims operations, including pre-litigation records and discovery, legal billing review, and litigation case management.

Responsibilities

• Set the venture's direction and lead its execution.
• Refine the Ideal Customer Profile (ICP), size-tiered pricing model, and product positioning.
• Lead pilots with managing partners and claims/litigation-operations leads at small-to-mid insurance-defence firms.
• Convert design partners to paid engagements and build the go-to-market motion.
• Partner with the FutureSight product and engineering team to ship V1 (records retrieval, key-fact flagging, billing-reasonableness analysis, and discovery triage) and iterate based on user feedback.
• Sequence carrier reserving and prediction as a later phase.
• Lead the seed raise, supported by FutureSight's network and traction.
• Recruit and lead the founding team.
• Establish the cultural foundation of the company.

Benefits

• Meaningful founder equity
• Pre-seed capital committed by FutureSight for early hires and MVP development
• Potential for follow-on funding
• Venture building resources, including embedded design, engineering, growth, and fundraising support from day one
• Investor and advisor network across vertical AI and early-stage capital markets

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed