Executive Assistant to Co-CEO (Insurance Tech)

About You
Experienced Partner: 3-5+ years proven experience as an Executive Assistant supporting C-suite leaders or founders within a fast-paced startup or high-growth tech environment.
The “Forward-Looking” Mindset: A proven track record of anticipating needs. You don’t wait for instructions; you see a gap and fill it.
Proactive Self-Starter: Highly resourceful with strong time-management skills and a supernatural ability to anticipate needs, act quickly, and stay steps ahead.
Detail & Execution Focused: Exceptionally detail-oriented with masterful organizational and prioritization skills; able to juggle competing priorities seamlessly.
Adaptable & Composed: Comfortable navigating ambiguity and thinking quickly on your feet while maintaining sound judgment and confidentiality.
Master Communicator: Possesses excellent written and verbal communication skills, with a white-glove, professional approach to interfacing with internal and external stakeholders (investors, clients, board members).
Relationship-Driven: Skilled at asking thoughtful questions to deeply understand each executive’s specific preferences, working style, and pain points to deliver highly tailored support.
Collaborative: A team player who partners effectively across the leadership team, People team, and external partners.
Pet friendly: Enjoy being around dogs and are happy to help support a dog-friendly office environment (including our Co-CEO’s dog).

In This Role You Will
Calendar & Schedule Management: Own complex calendar management for C-suite leaders, strategically prioritizing requests, resolving conflicts, and protecting executives’ focus time.
Travel & Logistics: End-to-end coordination of complex domestic and international travel itineraries, including flights, lodging, ground transportation, and detailed agendas.
Expense & Admin Management: Take full ownership of monthly expense tracking, reconciliation, invoice processing, and associated administrative reporting for leadership.
Meeting Strategy & Support: Prepare leaders for daily meetings, presentations, and board reviews by gathering briefing materials, tracking action items, and ensuring seamless execution.
External Communication: Manage external correspondence with high professionalism and discretion.
Special Executive Projects: Partner with leadership on ad hoc projects, which may include coordinating executive leadership offsites, board dinners, or high-priority team logistics.
Cross-Functional Collaboration: Partner closely with the People and Finance teams to align leadership schedules with company-wide initiatives, internal milestones, and strategic hiring needs.