Chief of StaffCoverdash • New York, NY, US

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.

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