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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Technical Co-founder (CTO) - AI Workforce for Solo Practitioners and Small Law Firms - **Company:** FutureSight Inc. - **Location:** Chicago, IL, United States - **Contract:** Permanent contract - **Skills:** AI Evaluation, Application Programming Interfaces (APIs), Artificial Intelligence, Software as a Service, Customer Data Management, Data Architecture, Open Source Technology, Reliability Engineering, Systems Integration, Workflow Management Systems, Core Voice Platform, Large Language Models, Agentic-AI, Low Latency - **Published:** October 26, 2026 - **Apply:** https://www.careerbuilder.com/job-details/technical-co-founder-cto-ai-workforce-for-solo-practitioners-and-small-law-firms-chicago-il--245677f8-416b-4df7-948b-313f520d6441 ## About the Role Artificial Intelligence (AI), Legal, Legal, Economics, Artificial Intelligence (AI), Marketing, Workforce Management, Sales Prospecting, Continuous Improvement, Demand Generation, * Shipped LLM-powered, agentic, voice, or automation systems into production environments where incorrect outputs and system failures carried meaningful consequences * Full-stack confidence across applied LLMs, conversational and real-time voice AI, APIs and integrations, workflow orchestration, observability, data architecture, and secure multi-tenant SaaS * Strong instincts around AI evaluation, reliability engineering, edge-case management, hallucination mitigation, human-in-the-loop design, and production monitoring * Well-formed convictions about the trade-offs among AI quality, latency, reliability, privacy, and cost * Experience building platforms that combine software with managed or service-heavy delivery, with the discipline to automate delivery rather than scale headcount linearly * The ability and willingness to work directly with customers and turn messy real-world workflows into reliable products * The mindset of a principal and owner - including the willingness to say "this won't scale," "this isn't ready," or "we need to rebuild this" when the integrity of the product requires it * The desire to remain deeply hands-on while building the team around you Strongly preferred: * Prior founder or early-stage technical leadership experience * Experience with production voice AI, telephony, agentic workflows, or AI evaluation infrastructure * Background in legal tech, healthcare, financial services, or another trust-sensitive vertical * Experience with security, privacy, and compliance requirements involving sensitive customer data * Experience deploying or self-hosting open-source/custom models where privacy, latency, control, or economics require it ## Description BloomLex is building an AI workforce for solo practitioners and small law firms, helping them win and serve more clients without adding headcount. We call the broader shift the Rise of the Solo: AI gives an individual lawyer or a small firm access to capabilities that historically required a much larger organization. Unlike self-serve software, BloomLex is fully managed. We configure, deploy, monitor, and continuously improve the AI workforce for each firm. Our customers evaluate us on outcomes - calls answered, prospective clients captured, consultations booked, demand generated, follow-up completed, and time saved - not on how much software they configure themselves. Our Bloomlex workforce starts with two teammates: Ava - AI Front Desk. Ava answers calls 24/7, handles structured intake, screens and routes inquiries, books consultations, performs outbound callbacks and follow-up, and integrates those interactions into the firm's workflow. Claire - AI Marketing Assistant. Claire helps firms generate and nurture demand through content, digital marketing, campaign management and optimization, lead nurturing, and ongoing marketing execution. Together, Ava and Claire address both sides of growth: Claire helps create demand; Ava helps ensure that demand is captured and converted. They are also the beginning, not the end, of the platform. Our roadmap expands the AI workforce across the operational side of the practice - including custom workflows and additional specialized AI roles - all delivered through the same managed model and coordinated around the lawyer. The Partnership The CEO co-founder is in place. The customer thesis is validated, design partners are engaged, live pilots are running, and the initial product architecture exists. What remains is to bring on the technical co-founder - a partner who will own product and engineering with the same conviction, urgency, and ownership as the CEO. This is a co-founder role, not a CTO hire. In return for that level of commitment, you receive founder-level equity, founder-level authority with decision collaboration on product, technology, hiring, fundraising, and strategy, and a genuine partnership with the CEO on every material decision. You will inherit working products and live deployments, but you will not inherit sacred architecture. Your job is to determine what should survive, what should be rebuilt, and what needs to exist for BloomLex to scale from pilots to thousands of firms., As Co-Founder & CTO, you will be a hands-on builder first and the architect of the technical organization that follows. * Product & Architecture - Own the technical architecture across Ava, Claire, and the broader BloomLex AI workforce. Make the build-versus-buy decisions that determine where BloomLex creates durable technical advantage. * Voice AI & Reliability - Harden Ava's real-time voice, telephony, intake, scheduling, routing, and workflow systems for production reliability. Establish observability, evaluation, escalation, and audit-trail standards appropriate for a trust-sensitive environment. * Agentic Workflows - Build reliable AI systems capable of executing multi-step operational and marketing workflows across voice, email, SMS, web, calendars, CRM and practice-management systems, with appropriate human oversight. * Managed AI Delivery Layer - Build the internal infrastructure that allows BloomLex to configure, deploy, monitor, evaluate, and continuously improve AI workers across hundreds and eventually thousands of firms without scaling engineering or implementation headcount linearly. * AI Quality & Economics - Own the trade-offs among model capability, latency, reliability, privacy, and inference cost. Build an architecture capable of delivering strong gross margins within the initial ~$499/month product model as usage scales. * Data, Security & Trust - Establish the security, privacy, tenancy, permissions, data-retention, and audit architecture required to earn the trust of law firms and their clients. * Customer & Market - Work directly with lawyers and design partners, translating real-world workflows and failure modes into product decisions. Represent BloomLex with customers, partners, and investors as the technical voice of the company. * Roadmap - Help convert pilots into repeatable commercial deployments, expand the AI workforce beyond Ava and Claire, deepen integrations into law-firm workflows, and establish a path toward custom and self-hosted models where economics, performance, privacy, or legal requirements justify them. * Team - Recruit and lead the founding engineering team and establish a culture of speed, accountability, technical rigour, and customer obsession.