Executive Assistant to the COO & CMO

TrupanionSeattle, WA
$90,000 - $110,000Hybrid

About The Position

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.

Requirements

  • 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.
  • 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.
  • 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

Responsibilities

  • 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.
  • 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.
  • 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.
  • Coordinate domestic and international travel, itineraries, and expenses, including contingency planning as needed.
  • Manage expense reporting and reconciliation accurately and timely.
  • Handle highly sensitive and confidential information with professionalism, discretion, and sound judgment at all times.
  • Identify opportunities to streamline workflows, standardize templates, and improve executive support processes across Operations and Marketing.

Benefits

  • Full medical, dental, and vision benefits at no cost to the employee
  • Four weeks of paid time off
  • 9 paid float holidays
  • Five-week sabbatical after five years of employment
  • Free medical health insurance for your pet (1 dog or cat)
  • Paid time off to volunteer at nonprofit organizations
  • Free on-site gym
  • Free dog walking services for office pets during business hours
  • Free parking
  • Paid ORCA cards
  • Monthly bonuses
  • Restricted Stock Units (RSUs) that vest over 4 years
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