FutureSight

Technical Co-founder (CTO) - AI Collections Agent

Canada full-time Executive Salary not listed
full-time Executive level Technology & IT Curated
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About the role

The Opportunity
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.
The Venture
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 Partnership
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.
What you'll own
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

Co-Founder Profile
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

How to Apply
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.
Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

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Executive
Technology & IT Accounting API integration Business Development Finance Sales Executive level

Likely questions

  1. Tell us about work you have done that is close to the Technical Co-founder (CTO) - AI Collections Agent role.
  2. How would you approach your first 30 days at FutureSight?
  3. Which of Accounting, API integration and Business Development have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Accounting, API integration and Business Development.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Technical Co-founder (CTO) - AI Collections Agent role because I can bring practical experience in Accounting, API integration and Business Development, learn the team quickly, and contribute to the outcomes FutureSight needs from this hire.

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