Trupanion

Insurance

ExecutiveAssistanttotheCOO&CMO

$90–110k Seattle, Washington, United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for mid candidates.

The Brief

“Executive Assistant to the COO & CMO at Trupanion. Skills: Executive support, Calendar management, Meeting coordination. Manage complex calendars. Triage competing priorities”

Industry & Context.

Insurance
Problems you'll solve

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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