Technical Co-founder, CTO – AI Staffing Platform for Law Firms

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🔥 0 minutes ago

🌽 Illinois – Remote

🌽 Illinois – Remote

⏰ Full Time

🔴 Lead

👨‍💼 Chief Technology Officer (CTO)

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FutureSight

WebsiteLinkedInAll Job Openings

11 - 50 employees

🤖 Artificial Intelligence

🤝 B2B

Venture Capital • Artificial Intelligence • B2B

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

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

🎯 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 the trade-offs between AI quality and cost-per-call • Experience building managed and service-heavy platforms, with the discipline to scale delivery without scaling engineering headcount • Prepared to operate as a principal — including saying "this won't scale" or "this isn't ready" when the integrity of the product requires it • Strongly preferred: prior founder or early-stage technical leadership experience; background in legal tech, healthcare, or another trust-sensitive vertical; capability to self-host custom models to meet legal and privacy needs