Temporary Multi Engine Pilot Jobs in Chicago, IL

Compliance at U.S. RIAs, broker-dealers, and wealth fintechs still runs largely on manual review — analysts reading marketing materials line by line, scanning communications for keywords, and reviewing trades and trade requests by hand. Across more than 25,000 firms, operational costs are significant, and regulatory exposure is even greater.

Global RegTech spend is projected to grow from roughly $12B to more than $66B over the next decade, with the US growing to $32B. The teams that ship credible, audit-ready platforms in the next 18 months will define the category. We intend to be one of them.

The answer is not another rules engine. We are building an explainable AI platform that reasons like a senior compliance officer, cites firm policy and SEC/FINRA regulations for every decision, and produces audit-ready evidence on demand — across marketing, communications, trading, policy, audit, and filings.

The platform is designed to operate alongside the systems compliance teams already use, replacing manual review with explainable AI judgments that hold up to regulator scrutiny. The roadmap moves from marketing review into communications surveillance, policy and manuals, audit, and ultimately regulatory filings and enterprise integrations.

The CEO co-founder is in place. The customer thesis is validated, design partners are engaged, and the market work is complete. 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 stake.

This is a co-founder role, not a CPTO hire. In return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, a board or board-observer seat as appropriate to the cap table and stage, and a genuine partnership with the CEO on every material decision.

As Co-Founder & CPTO, you will write the first lines of production code, set the technical direction, and lead execution end-to-end.

• Architecture & Engineering Culture — Establish the core architecture, engineering culture, and security posture, including SOC 2 readiness, tenant isolation, encryption, and audit logging
• Product Build — Ship a marketing review prototype into production with a design partner early adopter, then deliver communications surveillance, trading oversight, audit-ready logs and reporting; release GA v1 covering all core modules except regulatory filings within 9 months, and expand into regulatory filings and enterprise integrations through 18 months
• AI/LLM Build — Own the training and constant evolution of the core AI/LLM model, delivering robust and highly reliable analysis
• Explainability & Reliability — Own the explainability layer that produces audit-ready evidence on demand, and the reliability engineering that ensures the platform performs consistently in the field
• Customer & Market — Represent the company in front of all customer constituencies and third-party interests, as well as investors, as the technical voice of the venture
• Capital — Convert pilots into ten paying customers and reach $1M ARR within 18 months, partnering with the CEO on conversion and fundraising
• Team — Recruit and lead the founding engineering and applied AI team, and establish the cultural foundation of the company

• Shipped LLM-powered systems into production environments where incorrect outputs carried real consequences — not prototypes or demonstrations
• Full-stack confidence across applied LLMs, RAG, retrieval, deterministic rules engines, human-in-the-loop workflows, observability, and secure multi-tenant SaaS (SOC 2, tenant isolation, encryption, audit logging)
• Well-formed convictions about explainability and reliability engineering, developed through direct production experience
• Preference for systems that perform consistently in the field over systems that demonstrate well in controlled settings
• Prepared to operate as a principal — setting the technical agenda, making decisive calls under uncertainty, and owning the outcomes that follow
• Strongly preferred: prior founder, founding engineer, or early-stage technical leadership experience; background in legal tech, RegTech, fintech compliance, healthcare, or another high-trust regulated vertical; familiarity with the U.S. wealth management ecosystem, including SEC and FINRA workflows, marketing review, communications surveillance, and trade monitoring; direct experience self-hosting or privately deploying foundation models

Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.