Executive Assistant to the COO & CMO

Role Overview

The Executive Assistant (EA) provides proactive, high-caliber administrative and operational support to the Chief Operating Officer (COO) and Chief Marketing Officer (CMO). This role is a strategic partner who ensures both leaders can focus on their highest-value priorities by managing complex calendars, coordinating the executive operating rhythm, and serving as a central point of coordination across Operations, Marketing, and cross-functional partners.

This position is based in the Seattle area with a hybrid remote/in-office schedule (at least 3 days a week in our pet-friendly office).

Key Responsibilities

Calendar, Prioritization & Gatekeeping

• Own and manage complex, high-volume calendars for the COO and CMO, including triaging competing priorities and protecting focus time.
• Proactively assess trade-offs and recommend calendar decisions aligned to business priorities.

Meeting & Operating Rhythm Management

• Maintain visibility into recurring deliverables and key deadlines.
• Lead end-to-end preparation for executive meetings, including defining agendas, coordinating inputs, and producing high-quality presentation decks and briefing documents.
• Partner closely with leadership teams to synthesize complex information into decision-ready materials.
• Anticipate downstream needs by capturing decisions and action items.

Cross-Functional Coordination

• Serve as a connector between the COO, CMO, their leadership teams, and key partners (e.g., Finance, People Ops, Product, Communications).
• Support the flow of information across Operations and Marketing to help initiatives move forward efficiently.

Travel, Expenses & Logistics

• Coordinate domestic and international travel, itineraries, and expenses.
• Manage expense reporting and reconciliation accurately and timely.

Confidentiality & Judgment

• Handle highly sensitive and confidential information with professionalism, discretion, and sound judgment.

Process Improvement

• Identify opportunities to streamline workflows, standardize templates, and improve executive support processes.

Skills, Knowledge & Abilities

• Exceptional written and verbal communication skills.
• Strong organizational skills with the ability to manage multiple priorities.
• High emotional intelligence and confidence interacting with senior leaders.
• Excellent attention to detail and consistent follow-through.
• Proactive, solutions-oriented mindset.

Qualifications

• 10+ years of experience supporting senior leaders (VP-level or above); experience supporting multiple executives preferred.
• Advanced proficiency in Microsoft Office (Outlook, Word, PowerPoint, Excel).
• Demonstrated experience managing complex calendars and executive operating rhythms.

Compensation & Benefits

• Salary Range: $90,000 - $110,000.
• Eligibility for monthly bonuses and Restricted Stock Units (RSUs).
• Full medical, dental, and vision benefits at no cost.
• Four weeks of PTO and 9 paid float holidays.
• Five-week sabbatical after five years.
• Pet-friendly office with free pet medical insurance for one dog or cat.
• Seattle office amenities: Free gym, dog walking, parking, and ORCA cards.

Trupanion is an equal-opportunity employer. We provide reasonable accommodations for the application and interview process.