Executive Assistant III

About the role

The Executive Assistant III is a strategic business partner on both team-level and company-wide business operations who directly supports senior executives. In this role, you’ll customarily and regularly exercise a high degree of discretion and independent judgment on matters of significance, managing complex priorities, leading high-impact projects, and handling sensitive matters with discretion. You will operate only under general supervision and make independent decisions, recommendations, and prioritization calls on behalf of senior executives. You’ll partner closely with executives to improve workflows, drive cross-functional coordination, and help leaders stay focused on the most important business priorities. You’ll help shape how modern executive operations evolve at an AI-forward company by leveraging AI tools, automation, and scalable systems to create smarter, faster ways of working. Your work will directly enable leaders and teams to operate more effectively and maximize their impact.

What you’ll do

• Act as a strategic thought partner to senior executives to manage priorities, optimize workflows, and improve day-to-day operating effectiveness
• Strategically prioritize executive time, complex calendars, travel, meetings, operating rhythms, and exercising independent judgment on matters of significance to align with business priorities and strategic goals
• Own and lead high-priority and confidential projects requiring cross-functional coordination, strong judgment, and independent execution
• Build, manage, and improve systems, workflows, and AI-enabled processes that increase efficiency, scalability, and executive productivity
• Develop executive communications, presentations, briefing materials, and meeting content for leadership forums, planning cycles, and board-related activities
• Drive key deliverables, action items, and deadlines across leadership reviews, offsites, and operational planning processes to ensure strong follow-through and readiness
• Oversee executive-level budgets and operational reporting while exercising judgment to identify risks, resolve issues, and recommend cost optimization and process improvements
• Build trusted relationships across teams and act on behalf of senior executives as a key liaison for internal and external stakeholders, ensuring clear communication and alignment

In order to be successful, you must bring

• 5+ years of Executive Assistant or administrative experience, ideally supporting senior leaders or executives in fast-paced technology environments
• Experience supporting technical organizations such as Product, Engineering, or Marketing teams, with an understanding of how these organizations operate
• Strong project and operations management skills, with the ability to navigate ambiguity, balance competing priorities, and drive execution independently
• Proven ability to build or improve processes, systems, workflows, or operating mechanisms that increase team effectiveness and scalability
• Excellent written and verbal communication skills, including experience preparing executive-level communications, presentations, and briefing materials
• Strong organizational skills, attention to detail, business judgment, and discretion when handling sensitive or confidential information
• Experience managing budgets, vendor coordination, or operational reporting with accuracy and accountability
• Hands-on experience using AI tools such as ChatGPT, Claude, Gemini, Notion AI, or similar technologies to improve productivity, automate repetitive work, and enhance operational execution

Expected salary ranges

• For candidates living in Ontario and British Columbia, the expected salary range for the role is currently $97,800 - $126,500.

About the Executive Assistant Team

The Executive Assistant team at Thumbtack partners closely with senior leaders to help drive focus, execution, and business impact at scale. We operate at the center of critical initiatives — leading with strong judgment, seamless coordination, and proactive problem solving to keep teams moving forward. As an AI-forward company, we’re also redefining modern executive support by leveraging AI tools and automation to create smarter, faster, and more scalable ways of working.