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Chief of StaffCoverdash • New York, NY, US
Chief of Staff

Chief of Staff

Coverdash • New York, NY, US
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Chief of Staff Location :

  • Hybrid - New York, NY Department : Platform - Executive Reports to : CEO Compensation : $125,000-$150,000 Interview Process : Recruiter Screen → CEO Interview → Head of Partnerships → Leadership Team Presentation   About Coverdash Coverdash is the fastest-growing startup and SMB-focused insurtech agency, powered by the industry’s most advanced embedded technology and partnership strategies.
  • Powering 150+ embedded partners and 25k+ customers, our mission is to help growing businesses purchase and manage business insurance from the places they trust most.
  • Our simple and powerful embedded technology helps partners offer insurance to existing customers with a single line of code.
  • Coverdash was founded by a team with deep fintech and financial services experience and is the first insurance-as-a-service platform.
  • We have raised over $16 million to date from top investors including NYCA (Affirm, Fundbox, Acorns, Gemini), Bling Capital (Lyft, Square, Instacart, Palantir), World Insurance Labs (HubSpot, DocuSign, Twitter), and Expansion VC (Postmates, AngelList, Lemonade).
  • Our rapidly growing team is a smart, dynamic, and fun-loving group privileged to be collaborating with some of the world’s most innovative embedded partners.
  • The Opportunity At Coverdash, we are a high-growth startup, constantly iterating on how we organize and operate.
  • We’re looking for a Chief of Staff to the CEO who will help us scale from 50 to 150 employees and turn high-level strategy into reality.
  • This is a unique opportunity for someone who thrives in a high-growth environment, can translate vision into structure, and wants to build toward a future operational leadership role.
  • You’ll be a key connective tissue across Sales, Operations, Product, and People - driving clarity, accountability, and impact.

You will “wear many hats,” but success in this role will depend on your ability to :

  • Design and redesign the organization to support scale.
  • Lead change in a sales-centric environment.
  • Drive alignment and execution through exceptional project management.
  • Key Responsibilities Strategic & Operational Leadership Partner closely with the CEO and leadership team to define and operationalize company strategy, ensuring alignment across revenue, operations, and talent.
  • Establish and refine company operating cadence (OKRs, business reviews, and exec syncs) to ensure focus and accountability across teams.
  • Be a force multiplier for the CEO through clear communication, insight, and execution support.
  • Translate high-level goals into clear operating plans, structures, and decision frameworks.
  • Continuously evaluate organizational effectiveness and recommend changes to improve speed, accountability, and outcomes.
  • Org Design and Change Management Support org design for the GTM organization (team structures, roles, capacity planning, levelling, compensation, etc).
  • Help drive change management efforts to ensure smooth adoption of new structures, processes, and responsibilities across teams.
  • Partner with the CEO and People team to proactively design for scale - anticipating talent needs, revisiting org structure quarterly, and ensuring alignment between GTM and operational capacity.
  • Project Management Manage and prioritize high-impact, cross-functional initiatives from idea through execution.
  • Align stakeholders, resources, and timelines to ensure projects ship on time and achieve outcomes.
  • Track progress, remove roadblocks, and hold teams accountable.
  • Operational Organization & Systems Mastery Build and maintain a highly organized central operating system for the company across Google Workspace, Notion, and internal tools.
  • Own documentation hygiene and ensure key company knowledge (projects, org charts, playbooks, processes) is easily accessible and version-controlled.
  • Design repeatable workflows and templates that create clarity and consistency across departments.
  • Manage meeting cadences, agendas, and follow-ups to ensure decisions and action items are tracked to completion.
  • Serve as the “systems glue” connecting information, accountability, and execution across leadership and teams.
  • Executive Communication Own communications from the CEO’s office to internal and external stakeholders.
  • Synthesize complex information into clear narratives for leadership, board meetings, and company-wide updates.
  • Draft and prepare materials for investor updates, Board meetings, and strategic partner discussions.
  • Who You Are 3-5 years of experience in a mix of strategy, operations, or Chief of Staff roles - ideally in high-growth startups, consulting, or finance.

    • Strong operator :

  • can take a fuzzy problem, clarify it, and drive it to execution across multiple teams.
  • Exceptional communicator and relationship-builder, able to influence without authority.
  • Thrives in a fast-paced, ever-changing environment, and is comfortable shifting from tactical to strategic daily.
  • Ambitious and humble - eager to learn directly from the CEO and grow into a senior leadership role Why Us?
  • Competitive compensation with uncapped growth potential as we continue to expand and capture market share ($125,000-150,000 USD Annually) We’re the fastest-growing Insurtech in the U.S., building the largest embedded insurance distribution network in the market.
  • Operating at break-even, we’re growing rapidly from a position of stability.
  • We’re playing the long game.
  • A benefits package designed to support you inside and outside of work.
  • Join a high-performing, innovative team that’s as focused on delivering impact as it is on building a fun, collaborative environment.
  • We review every candidate manually.
  • We look forward to reviewing your application and exploring how you can contribute to our continued success!
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