Executive Assistant

Behind every great company is a powerhouse of organization, anticipation, and execution. At Ledgebrook, our Executive Assistant isn’t just a calendar wrangler—they’re a strategic partner who helps keep us aligned, focused, and driving forward. You bring the foresight, agility, and attention to detail—we’ll provide the fast-paced, high-impact environment to help you thrive.

Ledgebrook is a tech-enabled E&S MGA on a mission to modernize specialty insurance. The industry is burdened with legacy technology and inefficient processes, preventing innovation at scale. We are changing that. Our goal is to become the best-in-class, full-stack insurance and re/insurer, leveraging AI and data-driven insights to revolutionize underwriting, pricing, and risk selection. To help us get there, we’re looking for an Executive Assistant to support our leadership and provide exceptional administrative and operational support.

As our Executive Assistant, you’ll be the right hand to our leadership team, managing schedules, coordinating events, and ensuring high-priority initiatives stay on track. You’ll serve as a trusted gatekeeper and problem-solver, enabling our leaders to focus on what matters most. This is not your typical EA role—at Ledgebrook, you’ll have a front-row seat to how a high-growth startup is built and have a real impact in shaping our culture, operations, and success.

What You’ll Do:

• Calendar and Travel Management: Help coordinate and manage complex schedules, meetings, and travel for our CEO and executive team across time zones
• Drive Special Projects and Events: Lead and support a variety of high-impact projects across operations, culture, events, and executive priorities
• Uphold Confidentiality & Trust: Handle sensitive information with discretion, judgment, and professionalism. Your integrity and reliability will be second to none
• Support Culture & People Ops: Help organize team events, onboarding logistics, and internal communications. Be a culture ambassador that keeps the team connected and engaged
• Keep Us Running Smoothly: Anticipate needs and remove roadblocks before they arise. Assist with meeting prep, follow-ups, action items, and cross-functional coordination

Here at Ledgebrook we’re passionate about creating a team that thrives on continuous learning and shares our excitement about building a company from the ground up. We’re looking for people to join us with:

• A passion for delivering world-class customer service to our internal and external customers
• Intellectual curiosity and a strong desire for innovation, rather than following the status quo
• A hunger for continuous learning and opportunities to grow 
• Agile prioritization skills coupled with a keen sense of urgency - we balance getting it right with getting it done right now
• A strong drive and desire to win together as a high-performing team
• A moral compass to "do the right thing, period." We have zero tolerance for toxic behaviors
• An eagerness to actively participate and connect with the whole team, across remote locations
• An honest, transparent communication style

A proactive, solution-oriented mindset. We don’t look for blame, we look for the solution

Must Haves:

• 3+ years of experience in an Executive Assistant or similar role supporting senior executives
• Strong organizational and project management skills with a demonstrated ability to manage competing priorities
• Proven track record of handling confidential information with discretion
• Confidence working with leadership team, investors, board members, or senior stakeholders

Nice to Haves:

• Proficiency with Google Workspace (Docs, Sheets, Calendar), Slack, and Zoom
• Experience coordinating across multiple time zones in a remote or hybrid team
• Previous experience in a high-growth startup or tech-enabled environment
• Background in People Ops, Recruiting, or Internal Comms

• Competitive salary and meaningful equity
• Full remote flexibility and asynchronous work culture
• Unlimited PTO and fully paid sick leave
• Autonomy, purpose, and the chance to shape something from the ground up

At Ledgebrook, we’re building something truly special. If you thrive in a dynamic environment, take pride in helping others operate at their best, and want to be part of a team that care, strive, and thrive together, we’d love to hear from you.