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 RoleThis position serves as a central coordination function across leadership, sales, marketing, customer discovery, partnerships, and product initiatives. The successful candidate will help ensure priorities move forward, action items are completed, messaging remains aligned, and growth initiatives are executed efficiently.You will work directly with the CEO and leadership team, gaining exposure to startup operations, product strategy, customer validation, investor relations, partnerships, and AI-driven business execution. 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 FunctionsExecutive Operations & Leadership Support- Manage executive calendars, scheduling, priorities, and meeting coordination- Prepare leadership briefings, agendas, meeting notes, action items, and follow-up plans- Track accountability across projects and ensure action items are completed- Organize and maintain operational workflows, documentation, and reporting- Serve as a coordination point between leadership, team members, customers, partners, and investors- Support execution of go-to-market initiatives and growth campaigns- Coordinate customer discovery, outreach, pilot opportunities, and partnership discussions- Build, maintain, and improve outreach processes and prospect tracking- Research prospective customers, partners, and investors- Support pipeline development and relationship management activities- Reach out by call or email to potential clients and users CRM & Revenue Operations- Own HubSpot administration, CRM hygiene, contact management, and reporting- Maintain accurate sales, investor, customer, and partner records- Create dashboards, reports, and leadership updates- Identify opportunities to improve data quality and operational efficiency Website & Messaging Coordination- Coordinate website updates, content development, and messaging improvements- Translate leadership and customer feedback into clear implementation requirements- Maintain consistency across website, customer-facing materials, and outreach communications- Support product positioning, value proposition development, and customer education initiatives based on ongoing messaging and website work. Customer & Investor Relations Support- Coordinate follow-ups, communications, and meeting preparation with customers, strategic partners, and investors- Assist in preparing presentations, briefing materials, and meeting summaries- Support pilot projects, customer onboarding discussions, and market validation activities AI & Process Improvement- Design and improve AI-assisted workflows using tools such as ChatGPT, Claude, Gemini, Microsoft Copilot, and related platforms- Identify repetitive work suitable for automation- Improve organizational processes, reporting systems, and knowledge management practices Secondary Functions- Draft executive communications, outreach emails, customer correspondence, and operational documentation- Maintain tracking systems for strategic initiatives and key company projects- Support special projects as required by leadership- Coordinate cross-functional execution between product, growth, sales, and operations teams- Assist with research, market intelligence, and competitive analysis About You (Education & Experience)- Early career professional- 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)- Calm under pressure and comfortable managing multiple priorities- A strong writer capable of executive-level communication- Interested in entrepreneurship and start-ups- Curious, growth-oriented, and eager to bring new tools and ideas to the team- Ability to work independently with limited supervision- Comfortable managing ambiguity and shifting priorities- Ability to translate high-level discussions into actionable next steps- Strong stakeholder management and relationship-building skills Technical SkillsRequired:- Working knowledge of Claude, ChatGPT, Gemini, Grok- Microsoft Office 365 (Teams, Excel, Word)- HubSpot- Motion or comparable project management toolsPreferred:- AI workflow design and automation experience- Website content management experience- Sales operations and CRM reporting experience- Startup growth and go-to-market experience- Customer discovery and market validation experience 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:MariaOperations and Growth coordinatormaria@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 WelcomingWe strive to create an environment where people from all backgrounds feel supported, respected, and able to contribute meaningfully.Being ConsiderateYour work impacts other people. We expect thoughtful decision-making, strong communication, and respect for teammates, customers, and partners.Being RespectfulDisagreement is normal — disrespect is not. We value constructive discussion, professionalism, and maturity, especially in fast-moving startup environments.Excellence, Impact & GrowthWe 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.