Technical Co-founder (CTO) - AI staffing platform

FutureSight • Chicago, IL

6h

About The Position

LexStaffing is building a managed AI staffing platform designed for solo practitioners and small law firms. Their flagship product, Ava, functions as an AI Front Desk, providing 24/7 call answering, structured intake capture, consultation booking, and outbound callbacks, all aimed at reducing operational burden for lawyers. The platform operates on a RaaS (Role-as-a-Service) model, where Ava is presented as a fully managed staff hire, with LexStaffing handling setup, training, monitoring, and continuous improvement. Lawyers evaluate the service based on outcomes such as time saved, calls answered, and consultations booked, rather than configuration effort. The company has completed problem and solution validation, and multiple live pilots are currently moving into production evaluation. The immediate focus is on establishing in-production technical reliability, delivery economics, and scalability, ensuring the product performs flawlessly in a live environment.

Requirements

• 6+ years of hands-on software engineering experience.
• Direct experience with voice systems, conversational AI, or real-time AI workflows.
• Experience deploying LLM-powered systems into production, not just prototypes.
• Capability to architect and implement the strategy for building and self-hosting custom models over time to meet legal/privacy needs.
• Strong understanding of: Reliability engineering
• Strong understanding of: Human-in-the-loop systems
• Strong understanding of: Edge-case management
• Experience building service-heavy or managed platforms, not just pure SaaS.
• Comfort working closely with business leadership and owning delivery outcomes.

Nice To Haves

• Experience in legal tech, healthcare, or other trust-sensitive verticals.
• Experience running production systems with real-world users under time pressure.
• Prior founder or early-stage leadership experience.

Responsibilities

• Commitment as a Strategic Co-Founder: The successful candidate will operate as a dedicated partner focused on sustainable equity appreciation and long-term organizational value, rather than prioritizing immediate high-level compensation.
• Lead with Reliability over Novelty: Architect and maintain "Ava’s" voice and workflow systems with an obsessive focus on uptime and latency. You value a system that works every time over a "clever" demo that fails in the field.
• Architect the RaaS Delivery Layer: Design the internal infrastructure that enables our team to configure, monitor, and optimize AI performance behind the scenes, ensuring we scale the service without increasing engineering headcount.
• Own the Technical Unit Economics: Directly manage the trade-offs between AI quality and cost-per-call. You are responsible for ensuring the technical architecture remains highly profitable within our $499/month pricing model.
• Exercise High-Stakes Judgment: Navigate technical uncertainty with a steady hand. You are expected to say "this won't scale" or "this isn't ready" when necessary to protect the integrity of the product and the trust of our users.
• Drive a Deep Ownership Mindset: Take full accountability for the end-to-end technical lifecycle—from the first line of code to the final outcome of a live pilot—motivated by building a tool that lawyers depend on for their livelihood.
• Master Scope & Feasibility: Partner with the Founder to define the product roadmap, aggressively cutting features that threaten delivery or economics while doubling down on those that solve the lawyer’s "operational burden."
• Scale the Engineering Culture: Build and lead a lean, high-leverage technical team. You will set the standard for code quality, logging, and audit trails so that every AI outcome is explainable and reviewable.
• Strategic Technical Storytelling: Act as the technical face of LexStaffing during fundraising and due diligence, translating complex voice AI and telephony architecture into a compelling vision for investors and partners.

Benefits

• A significant equity package: Participate in the upside of company growth as a co-founding member
• Opportunity to build, grow and develop a team as the company grows.
• Shape the culture and technical direction of a venture with your contributions.
• Collaborate with Talented Peers: Work with a passionate and experienced team of entrepreneurs dedicated to building something unique and transformative.
• Continuous Learning and Growth: Engage in professional development and constant learning opportunities, expanding your skills while tackling challenging, meaningful projects.

What This Job Offers

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