Trupanion
Insurance
ExecutiveAssistanttotheCOO&CMO
Neural analysis suggests this role is
optimal for mid candidates.
“Executive Assistant to the COO & CMO at Trupanion. Skills: Executive support, Calendar management, Meeting coordination. Manage complex calendars. Triage competing priorities”
Industry & Context.
Solutions-oriented mindset
What They're Looking For.
Must Have
10+ years supporting senior leaders, Advanced Microsoft Office proficiency, Manage complex calendars, Manage executive operating rhythms, Partner with other EAs
Nice to Have
Experience supporting multiple executives
What You'll Do.
Manage complex calendars
Triage competing priorities
Sequence meetings for decision readiness
Recommend calendar decisions
Maintain visibility into deliverables
Maintain visibility into deadlines
Lead meeting preparation
Define meeting agendas
Coordinate meeting inputs
Produce presentation decks
Produce briefing documents
Produce pre-read materials
Synthesize complex information
Shape materials for audience
Highlight key insights
Highlight decisions required
Establish timelines for material development
Manage timelines for material development
Ensure material quality
Ensure timely circulation
Prepare follow-up materials
Support information flow
Coordinate itineraries
Plan for travel contingencies
Manage expense reporting
Manage expense reconciliation
Handle confidential information
Identify workflow streamlining opportunities
Identify template standardization opportunities
Identify executive support process improvements
How You'll Work.
Team & Collaboration
Coordinate with EAs; Coordinate with Finance; Coordinate with People Ops; Coordinate with Product; Coordinate with Communications; Coordinate with leadership teams; Coordinate with cross-functional partners
Communication Scope
Written communication; Verbal communication
Full Job Description
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, highlig
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