Chief of Staff

United States
Hybrid âś…
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Apply before: 
Jun 24, 2023

Pathpoint is looking for a Chief of Staff with exceptional analytical, planning, writing, synthesis, and project leadership skills to partner with our CEO and leadership team. You’ll drive strategic outcomes, implement critical business decision-making processes, and execute successful company communications.

This position will have visibility and leverage over functions across the business and is set up to embed further within the company. This role is a unique opportunity to have an outsized impact on the future of the E&S industry.

This role reports directly to the CEO.

What you'll do:

  • Ensure the CEO is working on the most important priorities (i.e. evaluate prior periods and set out goals for upcoming week, month, quarter, etc.)
  • Administer the leadership meeting by helping the CEO craft the agenda as well as tracking action items and follow-ups
  • Lead the creation of critical presentations including weekly All Hands, monthly Investor Updates, and quarterly Board Meetings (e.g. help the CEO compose a narrative, collate content, constructing slides)
  • Become an extension of the CEO through visibility into and integration across all parts of the business
  • Initiate and execute special projects and strategic initiatives across the organization
  • Identify opportunities and lead workstreams that will enable the organization to execute better and faster
  • Synthesize data from various sources into easy to understand briefings to settle on important priorities
  • Give leaders time leverage by running high-value projects such as searches for various senior roles, setting the agenda for leadership and company off-sites, compiling research and analyses, and operationalizing key cadences and planning processes
  • Pinch hit on business operations and across teams as needed

What we look for:

  • 3-7 years of experience in professional services (e.g. consulting, investment banking, corporate law) or strategy/operations at technology startups
  • Good at data analysis and great at making arguments with data
  • A broad knowledge of business frameworks, strategic planning, financial modeling, and project management
  • Ability to instill order into chaotic situations using rigorous thinking and can persuade others to agree with proposed actions
  • A diplomatic facilitator who can manage complex meetings and reconcile parties in conflict
  • A great listener and coach, able to form alliances with junior individual contributors as well as senior leaders
  • Spectacular storytelling capabilities across formats, including email, video / phone, written memos, slide decks, and spreadsheets
  • Caring about our business and our team as much as the CEO does
  • A “there is no job beneath me” attitude
  • Exhibition of extreme discretion with privileged materials
  • Exceptional honesty and forthrightness
  • A servant leader who takes pride in helping others succeed
  • Experience with the insurance, insurtech, and/or fintech industries is a plus but not required

Pathpoint is an equal opportunity employer that values diversity, inclusion, and belonging. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

About Pathpoint:

Businesses and individuals around the world rely on the surplus lines insurance market to mitigate risk. Global commercial P&C premiums eclipsed $920 billion in 2022, with over $100 billion written in the surplus lines market. Yet insureds, brokers, and carriers lose countless dollars on slow processes, terrible technology, high commissions, and fees. We’ve created a new way to place and service excess and surplus lines risk that’s faster, cheaper, and easier for everyone. Learn more at

Pathpoint's Values:

Hard Problems Drive Us: We believe the insurance industry hasn’t kept up with changing times and fixing that is a hard problem worth solving.

We Start with Why: Seek to understand what customers care about. Use data to challenge assumptions and figure out the problem.

We Take Ownership and Accountability: We think people are their happiest when they have high ownership and accountability over the problems confronting them and are empowered to move decisively to work on them.

We Work Together: Nothing happens without the individual efforts of our team members, but effective teamwork is how we build and maintain customer value.

We Move Forward: We value the ability to persist through adversity to achieve goals and believe speed plays an important role.

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