Job Title

CHIEF OF STAFFRobert.ai Toronto, ON Hybrid / Remote Flexible Full-Time---ABOUT ROBERT.AIRobert.ai is named after a man who never signed what he hadnt read line by line.We build mission-locked AI that turns source documents into institutional-grade deliverables with zero fabrication. Every claim cited to page and section. If its not in the source it doesnt appear in the output. If two documents contradict, Robert flags where and why.$80K ARR. Cashflow positive. 2 live pilots. 99% on OlmOCR-Bench.We are raising a $5M pre-seed to scale pilots into paid rollouts. This role exists because the CEO needs someone who can execute at the speed the company is moving.---THE ROLEYou are not an assistant. You are the person who makes sure the machine runs while the founders build it.You will operate as a direct extension of the CEO. You will touch fundraising, operations, investor communications, pilot coordination, hiring, and whatever else needs to happen that week. The scope is not fixed because the company is not fixed. It is moving fast and you move with it.This is not a role where you write strategy decks and present them in meetings. This is a role where you identify what needs to happen, figure out how to make it happen, and then make it happen. The difference matters.---WHAT YOU WILL ACTUALLY DO- Own the operating rhythm of the company. Weekly priorities, founder time allocation, pipeline tracking, investor follow-ups, pilot status. You keep the system running so the founders can build.- Coordinate across every function because at this stage there are no departments. You are the connective tissue between engineering, sales, legal, and finance.- Prepare investor materials, board updates, and fundraising documentation. You will learn how capital raising works at the pre-seed level by doing it, not by reading about it.- Manage pilot relationships and timelines. Our clients are a TSX-listed company and a Swiss financial services firm. You will communicate with their teams, track deliverables, and flag risks before they become problems.- Hire. You will help build the team from 3 people to whatever it needs to be. Source candidates, run screens, coordinate interviews, close offers.- Do the thing nobody else is doing that week. At a pre-seed company the Chief of Staff is the person who sees the gap and fills it without being asked.---WHAT WE CARE ABOUTWe dont care where you went to school. We dont care about your GPA. We dont care about your certifications.We care about:- Have you shipped something? Built something? Executed something that had real stakes and a real deadline? Tell us what it was and what happened.- Can you write? Not academic writing. Not corporate writing. Clear, direct writing that makes smart people act. If you cant communicate in writing you cant do this job.- Can you hold complexity? This company operates across AI, legal tech, financial services, capital markets, and patent law simultaneously. You dont need to be an expert in any of them. You need to be someone who can hold all of them in your head at once and not drop anything.- Are you fast? Not busy. Fast. There is a difference. Busy people do a lot of things. Fast people do the right thing quickly. We want fast.- Can you operate without instructions? If you need someone to tell you what to do every morning this is not the role. If you wake up and already know what needs to happen today because you were paying attention yesterday, keep reading.---WHAT WE OFFER- Equity. Meaningful. This is employee number 1 at a company valued at $20M. The math is not complicated.- Direct access to the CEO and CTO. You are not reporting to a middle manager. You are in the room.- The sharpest learning curve you will ever experience. Fundraising, enterprise sales, AI infrastructure, patent strategy, public company clients. In 12 months you will know more about how companies are actually built than most MBA programs teach in two years.- A company named after someone's father. The culture is not performative. The standard is real.---BONUS ROUNDWe believe the best people are relentlessly curious, resourceful, and unbothered by things that werent designed to be easy. If thats you, translate and answer the following. These are not trick questions. They are real questions about the role and the company, written in the languages of civilizations that understood what it means to build something that lasts.You are not expected to already know these languages. You are expected to figure it out. Use whatever resources you need. The quality of your answer matters more than the speed.I.Classical Latin (as written during the Republic, ca. 50 BC)'Duo in proelio maxime valent: consilium et celeritas. Si alterum tantum tibi sumere liceat, utrum capias? Dic causam.'Resources: Lewis & Short Latin Dictionary (logeion.uchicago.edu), Perseus Digital Library (perseus.tufts.edu), Caesar's Commentarii de Bello Gallico for stylistic context.II.Homeric Greek (epic Ionic dialect, ca. 8th century BC)' , ;'Resources: Autenrieth's Homeric Dictionary (logeion.uchicago.edu), Liddell-Scott-Jones Greek Lexicon, Cunliffe's Lexicon of the Homeric Dialect. Read Iliad Book II or Odyssey Book XIX for dialect examples.III.Vedic Sanskrit (Rigvedic register, ca. 1700 BC)'y vcam vadati antm, s vk km arth vahati? yth nad k, po n vahati.'Resources: Monier-Williams Sanskrit-English Dictionary (sanskrit-lexicon.uni-koeln.de), MacDonell's Vedic Grammar for Students, Jamison & Brereton's translation of the Rigveda for register and context.---HOW TO APPLYSend the following to with the subject line 'Chief of Staff':1. One page. Who you are, what youve shipped, why this role. No cover letter template. No 'Dear Hiring Manager.' Write like a person.2. Your answers to the three translation questions above. Include the translation and your response.3. One thing about Robert.ai that you would change or challenge if you were in the role today. Be specific.No resume required. Send one if you want. We will read the one-pager first.