Executive Assistant

Portage Ventures GP Inc.; Toronto; On-site; CAD 60,000 - 80,000; Full time

Benefits offered by this job

Competitive pay

100% covered health insurance

Work laptop provided

Flexible PTO

Job summary

Alloy River, a Toronto-based AI-driven finance and accounting platform, seeks an executive assistant to support the CEO’s day-to-day. You will manage travel, office operations, onboarding logistics, and other high-impact tasks with strong judgment and initiative.

You will work directly with the CEO, requiring a proactive, AI-aware approach, reliability, and discretion. This role is in-person at Liberty Village, with occasional non-standard hours.

Qualifications

• Experience providing executive support and handling travel arrangements.
• Strong judgment and ability to prioritize tasks effectively.
• Reliable, trustworthy and discreet with sensitive tasks.
• Comfort using AI in daily workflows and decision making.

Responsibilities

• Manage executive travel end-to-end.
• Keep the office running by coordinating facilities, supplies, and cleaners.
• Coordinate team lunches, gifts, event bookings, and related tasks.
• Represent the CEO professionally with internal and external contacts.

Skills

Relationship building

Judgment

Reliability

AI fluency

Tools

Office tools

Job description

About Alloy River

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.

Role Overview

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.

What You'll Work On

• 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.

What We're Looking For

• 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.

Bonus experience includes:

• Experience supporting a founder or senior executive.

How We Work

• 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.

Why Join Alloy River

• 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.

What We Look For

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.

Compensation & Location

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

Benefits

• Competitive pay

• 100% covered health insurance

• Work laptop provided

• Flexible PTO

AI Usage Policy

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