About UsGrayson AI is an early-stage startup based in Toronto. Grayson AI delivers AI-powered analytics agents to help engineers and operators in asset-intensive industries break through the cognition ceiling that limits how much data gets analyzed and acted on. Delivered through Microsoft Copilot, pre-certified for enterprise deployment. The RoleWe are looking for an Executive Assistant to support two senior leaders during a critical go-to-market phase. This is a full-time, 3-month contract role with the potential to become permanent based on company growth and campaign success.This role exists to help Grayson execute during a major go-to-market push.You will gain direct exposure to startup operations, executive leadership, investor relations, and AI-enabled business execution.You will report directly to the CEO and through this experience receive mentorship and exception experience in launching a startup.Location: Remote (Preference for GTA-based candidates, but open to broader North America)Hours: Full-TimeAvailability Required: Must be available for meetings between 09:00–17:00 EST This Is a High-Ownership RoleThis role requires exceptional attention to detail, strong judgment, and the ability to operate independently.There will not be heavy day-to-day oversight or micromanagement. You will receive mentorship, guidance, and context from leadership — but execution is expected to happen without someone constantly checking in behind you.Things need to be done:• correctly• professionally• proactively• and on time Primary Functions• Manage calendars across multiple time zones • Handle inbox triage by identifying what requires executive attention and resolving what does not• Prepare pre-meeting briefings and post-meeting follow-ups with clear owners and deadlines• Attend meetings, capture notes, create action items in Motion (or comparable project management tools), and follow up with stakeholders• Act as a central coordination point across leadership, investors, clients, and internal teams• Maintain daily CRM hygiene and management to ensure accurate reporting and pipeline visibility• Prepare and present daily CRM and project coordination updates to leadership• Build and improve workflows using AI tools to eliminate manual work and increase operational efficiency• Prepare weekly reports, dashboards, summaries, and operational briefings• Assist with investor relations coordination, meeting preparation, and follow-ups• Support go-to-market campaign execution during a high-growth startup phase Secondary Functions• Draft professional emails, summaries, meeting briefs, and operational documents• Coordinate timelines, priorities, and accountability across contributors About You (Education & Experience)• Experience managing calendars, meetings, communications, and operational workflows• Strong familiarity with AI tools and practical AI-assisted workflows• Comfortable working across CRM systems, operational dashboards, and project management tools• Previous startup (or similar) experience is highly valued (flat hierarchy, continually and rapidly changing environments)• Fluent in English with exceptional verbal and written communication skills• Must reside in North America About You (Skills & Attitude)• AI-fluent in practice — Claude, ChatGPT, Gemini, Grok, and Notion are already part of your workflow• Calm under pressure and comfortable managing multiple priorities• A strong writer capable of executive-level communication• Warm, discreet, and highly professional• Curious, growth-oriented, and eager to bring new tools and ideas to the team Technical SkillsRequired:• Working knowledge of Claude, ChatGPT, Gemini, Grok• Microsoft Office 365 (Teams, Excel, Word)• HubSpot• Motion or comparable project management toolsPreferred:• Experience building automations or AI-assisted workflows• Familiarity with startup operations and go-to-market execution• Exposure to investor communications or fundraising environments How to ApplyPlease send:1. Your resume.2. A 1–2 page document outlining how you would organize your day based on this job posting.3. A short video (5 minutes maximum) walking us through one workflow you have built or automated: - What was broken? - What did you build? - What changed? - Screen-sharing encouraged if possible. Please contact:Chad FordCEO, Grayson AIchad@grayson-ai.com Culture & Working StyleAt Grayson AI, we care deeply about how we work together — not just what we build.The primary goal of our culture is to foster a collaborative, high-performance environment where people can do meaningful work while treating others with professionalism and respect.We are committed to providing a welcoming environment for everyone, regardless of race, ethnicity, colour, nationality, gender identity or expression, sexual orientation, age, family status, disability, religion (or lack thereof), political belief or affiliation, socioeconomic background, or any other characteristic protected under applicable legislation.We believe diversity of background, experience, and perspective makes teams stronger. At the same time, we believe impact comes from focus, accountability, and collaboration.We Value:Being Welcoming — We strive to create an environment where people from all backgrounds feel supported, respected, and able to contribute meaningfully.Being Considerate — Your work impacts other people. We expect thoughtful decision-making, strong communication, and respect for teammates, customers, and partners.Being Respectful — Disagreement is normal — disrespect is not. We value constructive discussion, professionalism, and maturity, especially in fast-moving startup environments.Excellence, Impact & Growth — We believe sustained excellence comes from solving real problems, supporting one another, and building durable systems that create value for customers and stakeholders.Every person at Grayson contributes to the quality of our culture through: the quality of their work; how they communicate; how they collaborate; and how they represent the company internally and externally.This role is especially important because it sits at the operational center of the organization. Professionalism, discretion, accountability, and strong interpersonal judgment are essential.