Litigation Case Manager Jobs in Toronto, ON (NOW HIRING)

FutureSight is seeking a Co-Founder & CEO to lead LucentAI, an AI-native litigation operations venture in build at FutureSight. This offers meaningful founder equity, not a salary.

LucentAI serves as an autopilot for medical-records and discovery operations in small-to-mid insurance-defence firms. Embedding in case-management systems, it retrieves and reviews records, flags key facts with confidence links, checks billing reasonableness, and chronologically triages discovery. This human-gated system excludes legal drafting, externalizing review capacity so firms can scale case volume without adding headcount.

Market validation through FutureSight’s discovery interviews confirmed strong demand:

• Operations is the wedge; autopilot is the vision. All buyers wanted managed operations. LucentAI provides end-to-end automation, earning trust incrementally by handling routine work silently while keeping legal drafting human.
• The pain is in the dollars, not the dashboards. One lead costs the middle phase at ~$1M/year in time and errors; a partner noted only ~$200K of a $1M medical bill was reasonable. With zero AI currently used, the ROI-driven payback case is immediate.
• Capacity is the ceiling, and the record is the moat. Manual partner review caps case capacity and revenue. Defence records and billing patterns form a proprietary dataset that plaintiff-focused incumbents lack.

We target underserved small-to-mid US insurance-defence firms.

The Phase-1 beachhead SAM is $150M–$600M across 1,500–3,000 firms; the full roadmap reaches a ≥$100M obtainable market (SOM ≈ $110M–$360M).

With 71% of legal AI funding flowing to plaintiff-focused companies, the defence market remains underserved, creating a need for technology purpose-built for litigation defence and risk management.

FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.

You’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth.

• Founder equity with meaningful ownership from inception
• Pre-seed capital committed by FutureSight for early hires and MVP development, with 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
• A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner

As Co-Founder & CEO, you will set the venture's direction and lead its execution.

• Strategy — Refine the ICP, size-tiered pricing model, and product positioning
• Customer Development — Lead pilots with managing partners and claims/litigation-operations leads at small-to-mid insurance-defence firms, starting from the confirmed design partner, convert them to paid engagements, and build the go-to-market motion
• Product — Partner with the FutureSight product and engineering team to ship V1 (records retrieval, key-fact flagging, billing-reasonableness analysis, and discovery triage) and iterate on user feedback; sequence carrier reserving and prediction as a later phase
• Capital — Lead the seed raise, supported by FutureSight's network and traction
• Team — Recruit and lead the founding team, and establish the cultural foundation of the company

• 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.

Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.