Executive Assistant to the COO & CMO

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. They will collaborate closely with other Executive Assistants across the company to ensure coordination and alignment of activities. The EA anticipates needs, brings structure and discipline to fast-moving agendas, and ensures leaders are prepared for key meetings, decisions, and communications. This role requires sound judgment, discretion, and the ability to operate independently in a dynamic, growing organization. This position is open to candidates in the Seattle area. You will have a hybrid remote/in-office schedule where you will work from our casual, pet-friendly office at least 3 days a week. Key Responsibilities Calendar, Prioritization & Gatekeeping Own and manage complex, high-volume calendars for the COO and CMO, including triaging competing priorities, protecting focus time, and sequencing meetings for decision readiness. Proactively assess trade-offs and recommend calendar decisions aligned to business priorities. Meeting & Operating Rhythm Management Maintain visibility into recurring deliverables and key deadlines (e.g., leadership cadences, planning milestones, major initiatives). Lead end-to-end preparation for executive meetings, including defining agendas, coordinating inputs, and producing high-quality presentation decks, briefing documents, and pre-read materials. Partner closely with the COO, CMO, and their leadership teams to synthesize complex information into clear, concise, and decision-ready materials. Apply strong judgment to shape materials for the intended audience, highlighting key insights, risks, and decisions required. Establish and manage timelines for material development, ensuring material quality and timely circulation. Anticipate downstream needs by preparing follow-up materials, capturing decisions and action items, and supporting next steps. Cross-Functional Coordination Serve as a connector between the COO, CMO, their leadership teams, and key partners (e.g., Executive Assistants, 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, including contingency planning as needed. Manage expense reporting and reconciliation accurately and timely. Confidentiality & Judgment Handle highly sensitive and confidential information with professionalism, discretion, and sound judgment at all times. Process Improvement Identify opportunities to streamline workflows, standardize templates, and improve executive support processes across Operations and Marketing. Skills, Knowledge & Abilities Exceptional written and verbal communication skills. Strong organizational skills with the ability to manage multiple priorities and shifting demands. High emotional intelligence and confidence interacting with senior leaders. Excellent attention to detail and consistent follow-through. Proactive, solutions-oriented mindset with strong judgment. Absolute discretion when handling sensitive information. 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. Experience partnering with other Executive Assistants and administrative professionals. Working Style & Expectations Highly proactive and anticipatory. Calm under pressure with the ability to manage ambiguity. Comfortable exercising judgment and diplomatically pushing back when appropriate. Reliable, trustworthy, and consistent in execution and follow-through. Demonstrates strong critical thinking and sound judgment, proactively anticipating potential challenges, evaluating options to ensure seamless execution Compensation: The salary range for this role is $90,000 - $110,000 on a full-time schedule. Along with base salary, Trupanion employees are currently eligible for monthly bonuses. We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years. Benefits and Perks: Full medical, dental, and vision benefits at no cost to the employee Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!) Five-week sabbatical after five years of employment Open, casual, pet-friendly, and fun office environment Free medical health insurance for your pet (1 dog or cat) Paid time off to volunteer at nonprofit organizations Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards. For more information about Trupanion, visit https://trupanion.com/about Learn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQ Trupanion is an equal-opportunity employer and embraces diversity. We are committed to building a team that represents a variety of backgrounds, abilities, perspectives, and skills. We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodations.