About Textlayer
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. We're looking for sharp, curious people who want to meaningfully shape how we build, operate, and deliver.
If you're excited to work on foundational AI infrastructure, solve complex problems for diverse clients, and help define what agentic software looks like in practice, we'd love to meet you.
The Role
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.
TextLayer is an AI-native company, and this role is designed that way. 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
Executive support, automated where possible
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 judgment, with the ability to draft in someone else's voice and know when to escalate
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
Experience as an executive assistant, chief of staff, operations manager, or office manager; excellent written communication; strong ownership; enthusiasm for AI tools; discretion; comfort with Google Workspace and SaaS tools; willingness to travel.
Key Responsibilities
- managing executive support
- building AI workflows
- planning team events
Skills & Tools
Google Workspace, Zapier, Make, n8n
Job Details
- Category: Business Operations
- Seniority: Mid Level
- Commitment: Full Time
- Workplace: Remote — Ottawa or Canada
- Salary: CAD 100,000 – 150,000 / year
- Languages: English
About TextLayer
An AI-native company helping enterprises deploy advanced AI systems and bridge the gap between AI potential and practical implementation. — Industry: Information Technology