Technical Co-founder, CTO – AI Legal Front Desk

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FutureSight

WebsiteLinkedInAll Job Openings

11 - 50 employees

💼 Consulting

🏥 Healthcare

📚 Education

Consulting • Healthcare • Education

FutureSight is a venture studio that co-founds and funds B2B AI ventures, building scalable world-class businesses with values-driven leaders. Based in Toronto, New York, and San Francisco, FutureSight collaborates with entrepreneurs by providing a supportive community of experienced product leaders, business designers, engineers, marketers, and growth hackers. This 'Dream Team' aids in refining ideas from inception to scale, developing co-founders into transformational leaders. FutureSight focuses on various sectors, including health tech, education tech, and fintech, offering a rigorous process for validating ideas and investing in great talent and concepts.

📋 Description

• Harden Ava’s voice and workflow systems for in-production reliability • Establish core architecture, observability, and audit-trail standards • Build internal infrastructure for configuring, monitoring, and optimizing AI performance without scaling engineering headcount • Own trade-offs between AI quality and cost-per-call within the $499/month pricing model • Represent the company before lawyers, partners, and investors as the technical voice of the venture • Convert pilots into paying customers • Expand AI staff beyond the front desk • Begin a path toward custom and self-hosted models where legal and privacy requirements demand it • Recruit and lead the founding engineering team • Establish the company’s cultural foundation • Write the first lines of production code, set technical direction, and lead execution end-to-end

🎯 Requirements

• Shipped LLM-powered and voice systems into production environments where incorrect outputs carried real consequences • Full-stack confidence across applied LLMs, real-time voice and conversational AI, telephony, human-in-the-loop workflows, observability, and secure multi-tenant SaaS • Well-formed convictions about reliability engineering, edge-case management, and AI quality versus cost-per-call trade-offs • Experience building managed and service-heavy platforms while scaling delivery without scaling engineering headcount • Prepared to operate as a principal and challenge scalability or product readiness when product integrity requires it • Strongly preferred: prior founder or early-stage technical leadership experience • Strongly preferred: background in legal tech, healthcare, or another trust-sensitive vertical • Strongly preferred: capability to self-host custom models to meet legal and privacy needs • Submit a resume, LinkedIn profile, and brief note explaining venture alignment with founder goals

🏖️ Benefits

• Founder-level equity • Founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy • Genuine partnership with the CEO on every material decision • Diversity, equity, and inclusion commitment