Executive Assistant to Co-CEO (Insurance Tech)

About the role

The Executive Assistant will play a critical role as a strategic partner to our Co-CEO & Co-Founder. In this role, you will act as a force multiplier, managing complex schedules, anticipating leadership needs, and streamlining operations to maximize our Co-CEO’s time and impact.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• Pet friendly: Enjoy being around dogs and are happy to help support a dog-friendly office environment (including our Co-CEO’s dog).

Benefits

• Compensation: Competitive base salary in the $90-100K range, with flexibility depending on a candidate’s background and experience. An annual bonus plan is also included in our compensation package.
• Well-Being: Medical, dental, vision, short & long-term disability, life insurance and AD&D, and 401k matching. Additional family, wellness, and pet benefits.
• Home & Family: Paid time off and sick leave, 100% paid parental leave (16 weeks for primary caregivers and 12 weeks for secondary caregivers). We offer a flexible schedule for new parents returning to work.
• Office Life: Catered lunches, happy hours, pet-friendly spaces, and monthly technology stipend.
• Growth & Training: $1,000/year for each employee for professional development, as well as opportunities for tuition reimbursement.
• Sponsorship: We are open to sponsoring candidates currently in the U.S. who need to transfer their active visa. Please check with our Recruiting team if your visa is applicable for transfer.