Executive Assistant

Alloy River builds agentic applied AI for finance and accounting. Accounting today is fragmented, manual, and reactive. We believe it should be intelligent, structured, and operationally decisive. Our mission is to transform finance from a slow, labor-intensive, reporting function into a real-time, strategic engine for profit and control.

We re-architected the general ledger from first principles, and layered automation, workflow orchestration, and applied AI directly into its core. Instead of accountants moving data between tools and managing checklists, our system produces outcomes, surfaces exceptions, and compounds leverage over time. This is not incremental improvement. It is a ground-up redesign of financial infrastructure for an AI-native world.

We raised over $30m to date from Portage Ventures, Electric Capital, Elad Gil, and angels like Tobi Lütke, Balaji Srinivasan, and many more. We’re scaling what we do with the best builders, operators, and craftspeople in the world.

This role exists to take the day-to-day admin work off the CEO's plate - booking travel, managing office orders, supporting onboarding logistics, and the small things that add up - so the CEO can stay focused on the business. We’re looking for someone who runs their work with AI, but balances that output with human discernment. This role is a lot more about good judgement and high initiative over high effort or hours.

• Manage executive travel end-to-end.

• Keep the office running by managing keys, cleaners, supplies, etc.

• Coordinate team lunches, gifts, event bookings, and more.

• Represent the CEO well with everyone you deal with, internal and external.

• Strong relationship builder. You build trust and get things done because people respect you, not just who you work for.

• Excellent judgment. You know how long things should take, what matters, and when to just handle it.

• Reliable and trustworthy. You can be trusted with sensitive tasks and nothing slips.

• Fluent with AI, but you apply your own judgement to the output.

• Joy in supporting others. You enjoy the work and are looking to stay in it for the long run.

• Flexibility to respond outside normal hours in the occasional times it’s needed.

• Experience supporting a founder or senior executive.

• You work directly with the CEO, in a role built around making his day run smoothly.

• The CEO is a previously exited, Sequoia-backed founder. He is easy to work with, and someone the team is proud to have lead us.

• Most weeks are a steady amount of work, but there will be occasional weekend work required (once a quarter or so).

• We are in-person every day.

• Help create a category-defining product with a real impact on business owners.

• Work in-person with people who are excellent at what they do and fun to be around.

• Join early and shape the future of an industry.

• James makes everyone lunch at 12pm.

We hire high agency, AI-forward builders. The title or background matters less than the pattern underneath it.

• High agency. You don't wait to be pointed. You identify the problem, form a view, and act.

• AI-forward. You've changed how you work because of AI - not as a novelty, but because of how it lets you build. Your first instinct is to reach for the agent, not the keyboard.

• Strong opinions. You have a perspective and you share it - in writing, in meetings, in Slack. Strong opinions, loosely held. You're not afraid to be wrong.

• Ownership. You feel responsible for outcomes, not just doing your part. You've built something that didn't exist before you arrived, and you didn't let go until it was right.

• Curiosity. You go deep without being asked. You ask the questions others skip. You tinker.

• Optimistic. You believe that things can improve, problems can be solved, and people are generally trying their best. This is the foundation of how you work and how you treat people.

This role pays $60,000-$80,000 CAD base. This role is based in Toronto (in-person in Liberty Village).

• Competitive pay

• 100% covered health insurance

• Work laptop provided

• Flexible PTO

We may use AI to help review candidate applications, but the final decision is always made by a human.