Executive Assistant to the CEO

Behind every high-performing company is exceptional operational support. At Ledgebrook, we’re hiring an Executive Assistant to the Founder & CEO—a highly visible, high-impact role at the center of a fast-growing business.

This is a rare opportunity to work directly alongside our Founder and CEO as a trusted partner, helping manage priorities, protect focus, and drive operational excellence across the business. We’re looking for someone with exceptional judgment, discretion, adaptability, and attention to detail who thrives in fast-paced environments and enjoys bringing structure to complexity.

In return, this role offers far more than traditional executive support. You’ll gain front-row exposure to company building at a high-growth startup, with visibility into leadership decision-making, board and investor interactions, strategic initiatives, and the day-to-day realities of scaling a business from the ground up. If you’re energized by being close to the action, solving problems proactively, and making a meaningful impact, this is an opportunity to grow alongside an ambitious company and leadership team.

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 that limit innovation at scale - we’re changing that. Our goal is to become a best-in-class, full-stack insurance and re/insurer, leveraging AI and data-driven insights to transform underwriting, pricing, and risk selection.

As Executive Assistant to the CEO, you’ll serve as a true right hand and strategic partner, helping our CEO navigate the demands of building and scaling a high-growth company. You’ll manage complex scheduling, coordinate internal and external communications, and ensure key priorities stay organized and moving forward.

You’ll act as a gatekeeper, anticipating needs before they arise, optimizing workflows, and protecting the CEO’s time and focus on high priority items. 

What You’ll Do:

• Own Calendar & Time Management: Manage a highly dynamic and complex calendar for the CEO, including scheduling internal and external meetings, prioritizing competing demands, and ensuring time is aligned with company priorities.
• Coordinate Travel & Logistics: Own all travel arrangements, including flights, accommodations, itineraries, and logistics for business travel, offsites, conferences, and leadership meetings.
• Act as Strategic Gatekeeper: Manage inbound requests, communications, and meeting requests with strong judgment and prioritization. Help protect the CEO’s focus while ensuring critical stakeholders are supported. 
• Drive Executive Operations: Prepare meeting agendas, briefing materials, notes, and follow-up action items. Ensure key meetings are productive and next steps are clearly tracked to completion.
• Support Board, Investor & Leadership Engagement: Assist with board meeting logistics, investor coordination, leadership offsites, and executive communications.
• Manage Special Projects: Own or support high-priority cross-functional initiatives on behalf of the CEO, ranging from operational improvements to internal events, culture initiatives, and ad hoc strategic projects. 
• Handle Sensitive Information with Discretion: Manage confidential company, employee, and investor information with exceptional professionalism, judgment, and integrity.
• Keep the CEO & Business Running Smoothly: Anticipate needs, identify bottlenecks, solve problems proactively, and create systems that improve efficiency across the CEO’s day-to-day operations.

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 supporting a CEO, founder, or senior executive in an Executive Assistant or Chief of Staff support capacity
• Experience managing highly complex calendars, travel, and shifting priorities in a fast-paced environment
• Strong organizational and project management skills with exceptional attention to detail
• Excellent written and verbal communication skills
• Demonstrated ability to handle highly confidential information with discretion and sound judgment
• Experience interacting confidently with senior leadership, board members, investors, and external stakeholders
• Ability to operate independently, anticipate needs, and solve problems proactively

Nice to Haves:

• Experience supporting a founder or C-level executive at a high-growth startup
• Proficiency with Google Workspace (Docs, Sheets, Calendar), Slack, Zoom, and project management tools
• Experience coordinating across multiple time zones in a remote or hybrid environment
• Interest in Insurtech or technology-driven businesses

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer visa sponsorship at this time

• 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