Trainee Multi Engine Pilot Jobs in Chicago, IL (NOW HIRING)

Finance teams at B2B companies lose cash the same way every month: an invoice ages past 45 days, someone sends an email, no reply, someone calls, voicemail, they call again next week, still nothing. AR teams spend 60-70% of their week on manual follow-up instead of posting cash, closing disputes, or analyzing aging. Adding headcount doesn't fix it; manual follow-up simply doesn't scale, and every ERP hits the same wall.

Problem and solution validation are complete. Live pilots are running with early design partners and entering production evaluation. The next phase is proving in-production reliability, delivery economics, and scalability. The teams that ship credible AI workers into finance-sensitive functions in the next 18 months will define the category. We intend to be one of them.

Argentl delivers an AI collections agent that handles outbound debtor follow-up automatically - trained, monitored, and continuously improved by our team. Rather than another self-serve SaaS tool, Argentl is evaluated on outcomes: DSO reduction, hours returned to the AR team, and cash commitments captured - not configuration effort.

Give us a list of overdue accounts and our voice agent calls each debtor, confirms invoice awareness, and captures exactly what they say - a payment commitment, a dispute, a request to split, or silence. The AR team gets a clean morning report: who's committed, who's disputing, who's gone silent, and what to do next. No ERP migration, no system credentials, no workflow overhaul - we're calling within a week of receiving the data. The roadmap expands from collections follow-up into adjacent AI finance-ops roles, all delivered through the same managed model.

The CEO co-founder is in place. The customer thesis is validated, design partners are engaged, and live pilots are running. 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 CTO 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, and a genuine partnership with the CEO on every material decision.

As Co-Founder & CTO, you will take over the production code and continue building the product (the first lines of production code), set the technical direction, and lead execution end-to-end.

• Architecture & Reliability - Harden the voice and workflow systems for in-production reliability. Establish core architecture, observability, and audit-trail standards for a product that speaks to customers' debtors on their behalf.
• Delivery Layer - Build the internal infrastructure that lets the team configure, monitor, and optimize agent performance without scaling engineering headcount. Mature the workflow engine so every call, intent classification, and next-action flows through reliably.
• Integrations & Distribution - Own the accounting and ERP integration layer (QuickBooks, Xero, and beyond) that turns Argentl from a CSV upload into an embedded part of the finance stack - the primary distribution unlock.
• Unit Economics - Own the trade-offs between AI quality and cost-per-call, and lock in unit economics within a productized monthly pricing model.
• Customer & Market - Represent the company in front of finance leaders, partners, and investors as the technical voice of the venture.
• Roadmap - Convert pilots into paying customers, expand the AI staff beyond collections, and begin a path toward custom and self-hosted models where data-privacy and financial-compliance requirements demand it.
• Team - Recruit and lead the founding engineering team, and establish the cultural foundation of the company

Must Have:

• 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
• A hands-on builder - you still write code and ship, and you're happiest close to the product

Great to Have:

• Finance, accounting, or FinOps background - you understand AR, DSO, aging, disputes, and how finance teams actually work
• Based in Los Angeles or the San Francisco Bay Area (or ready to be)
• Pragmatic and creative - a solution finder who gets to "working" fast and iterates from there
• Co-operative, strategic, and hands-on in equal measure
• Capable and willing to help in finding and closing early customer partnerships
• An active social media presence you can put to work for founder-led distribution

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.