Executive Operations Lead

TextLayer helps enterprises and funded startups deploy advanced AI systems. We work with organizations across fintech, healthtech, and other sectors to bridge the gap between AI potential and practical implementation. Our approach combines deep technical expertise with proven frameworks to accelerate development and ensure production-ready results. From bespoke AI workflows to agentic systems, we help clients adopt AI that actually works in their existing tech stacks. We're on a mission to help address the implementation gap that over 85% of enterprise clients experience in adding AI to their operations and products.

The Executive Operations Lead is part executive assistant, part operations owner, and part cultural force. You'll be a key member of the exec team, keeping leadership moving, keeping the business running smoothly, and making TextLayer a place people love working. This role is designed for an AI-native company. The routine work (drafting emails, scheduling, invoicing and follow-ups, account provisioning) should run on AI-assisted workflows that you build, monitor, and improve. That leaves your time for what most needs a person: relationships, judgment, and culture.

Key Responsibilities

• Support the executive team with scheduling, inbox and calendar management, meeting prep, and follow-through
• Draft leadership communication
• Manage invoicing end to end: sending invoices, tracking payment status, and following up on overdue accounts
• Handle account and tool provisioning for new hires and projects
• Identify repetitive tasks and build or configure AI-assisted workflows to handle them, working with our engineers where needed
• Document processes so the business keeps running consistently as the team grows

Culture And Team Experience

• Plan and host team meetups, socials, and offsites, including coordinating travel and logistics
• Own staff recognition: gifts, milestones, welcome experiences for new hires, and celebrations
• Help keep a distributed, project-based team feeling connected
• Gather feedback on what's working for the team and bring it to leadership

Business operations and exec-team partnership

• Support hiring operations & onboarding logistics
• Help leadership with operating cadence: meeting rhythms, planning cycles, and tracking priorities
• Manage vendors, tools, subscriptions, and light admin and compliance tasks
• Serve as a trusted, discreet partner to the leadership team on sensitive matters

What You'll Bring

• Experience as an executive assistant, chief of staff, operations manager, or office manager, ideally supporting senior leaders in a fast-moving company
• Excellent written communication and sound judgement, with the ability to draft in someone else's voice and know when to upscale
• Strong ownership: you spot gaps and fix them without being asked, and you follow things through
• Genuine enthusiasm for AI tools and automation, whether you've built workflows with tools like Zapier, Make, or n8n, used LLMs in your daily work, or are eager to learn quickly
• Warmth and energy for people: you enjoy bringing teams together and make others feel valued
• Discretion and professionalism with confidential information
• Comfort with Google Workspace and modern SaaS tools
• Willingness to travel for team events and company needs

Bonus Points

• Experience in a startup, consultancy, or professional services firm
• Experience coordinating events, offsites, or team programs
• Basic finance operations experience (invoicing, accounts receivable, bookkeeping tools)
• Light technical aptitude, such as scripting, APIs, or no-code automation
• Experience supporting a remote or distributed team

Compensation Range: CA$100K - CA$150K