Technical Co-founder (CTO) - AI staffing platform

FutureSight
Chicago, IL

About Us

LexStaffing is building a managed AI staffing platform for solo practitioners and small law firms. Our first hire, Ava, is an AI Front Desk that answers calls 24/7, captures structured intake, books consultations, and performs outbound callbacks—without creating new operational burden for the lawyer.

LexStaffing is deliberately not a self-serve SaaS tool. It is a RaaS (Role-as-a-Service) model: Ava is positioned as a staff hire, fully set up, trained, monitored, and improved by LexStaffing. Lawyers evaluate us on outcomes—time saved, calls answered, consults booked—not configuration effort.

Problem and solution validation are complete. Multiple live pilots are entering production evaluation. The next phase is proving in-production technical reliability, delivery economics, and scalability.

The product is already validated conceptually. The challenge now is making it work flawlessly in production.

Role & 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.

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
    • Human-in-the-loop systems
    • Edge-case management
  • Experience building service-heavy or managed platforms, not just pure SaaS.
  • Comfort working closely with business leadership and owning delivery outcomes.
  • Good to have:
    • 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.

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.
Posted 2026-04-21

Recommended Jobs

FOOD SAFETY & QUALITY AUDITOR

Illinois

Company Description Ferrero is a family-owned company with a truly progressive and global outlook and iconic brands such as Nutella®, Tic Tac®, Ferrero Rocher®, Raffaello®, Kinder Bueno® and Kinde…

View Details
Posted 2026-02-09

Non-invasive Cardiologist needed in Matoon, IL

Mattoon, IL

HealthPlus Staffing is seeking a full-time Cardiologist to join a well-established hospital group in Mattoon, IL. This is a great opporutnity to join one of the nations leading healthcare organizati…

View Details
Posted 2026-01-29

Senior Manager, Deal Design

Cepheid
Chicago, IL

Bring more to life. Are you ready to accelerate your potential and make a real difference within life sciences, diagnostics and biotechnology ? At Beckman Coulter Diagnostics, one of Danahe…

View Details
Posted 2026-04-05

Vice President of Finance and Accounting

Exeter Group
Chicago, IL

: Reports To: Chief Financial Officer Responsibilities: Implement production, productivity, quality, and customer-service standards. Identify trends, determine system improvements, and imp…

View Details
Posted 2026-04-21

Installer Apprentice/Warehouse Assistant

Drapery Connection
Downers Grove, IL

Job Description Job Description   Drapery Connection is seeking a motivated, hands-on individual to join our team as a Window Treatment Installer Apprentice & Warehouse Assistant.  This role is …

View Details
Posted 2026-03-26

Product Manager - Veeva Labs

Veeva Systems
Illinois

Veeva Systems is a mission-driven organization and pioneer in industry cloud, helping life sciences companies bring therapies to patients faster. As one of the fastest-growing SaaS companies in histo…

View Details
Posted 2026-04-10

Energy Sales and Support - Ag-Land FS, Inc. - Princeville, IL

Ag Land FS Inc.
Princeville, IL

  The FS brand represents a standard of excellence for agricultural and energy-related products. It's the people who represent the FS brand that set it apart. As local cooperatives, FS Companies bel…

View Details
Posted 2026-04-21

IT (Information Technology) Manager - Behavioral Health

Skyway Behavioral Health
Chicago, IL

Job Description Job Description Skyway Behavioral Health is an innovative behavioral health center that goes beyond the treatment of psychiatric symptoms to address underlying biological, behavio…

View Details
Posted 2026-03-20

Electrical Test Technician

Scuttlebutt Services, LLC
East Peoria, IL

East Peoria, IL - Hourly Range 23-30   Job Brief Entry level Test Technician consisting of the ability to read and interpret electrical schematics and wire diagrams, basic concepts of electrica…

View Details
Posted 2026-03-23