Chief of Staff

About WithCoverage

WithCoverage revolutionizes traditional insurance brokerage by integrating AI-driven risk management tailored for today's dynamic economy. Our clientele includes cutting-edge, high-growth companies such as GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. They represent sectors like iconic consumer brands, hospitality, manufacturing, and defense contractors operating within complex risk landscapes that demand agile partnerships.

Our proprietary Agency Management System empowers our elite risk advisory team with comprehensive insights into policies, risks, claims, billing, and commissions, enabling deep automation and superior service standards.

Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), WithCoverage has secured over $43M in investments from leading firms like Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. Our goal extends beyond improving brokerage—it redefines risk management across industries.

Why Join Us

• Accelerated growth with opportunities to develop leadership and influence the company’s trajectory.
• Meaningful impact protecting innovative brands across diverse industries.
• Industry transformation by leveraging proprietary technology, automation, and AI.
• Attractive financial packages including competitive salaries, equity, and benefits, with clear career advancement paths emphasizing internal promotion.

Role Overview

The Chief of Staff serves as a direct multiplier for the CEO, balancing strategic oversight with direct customer engagement. This hybrid role involves driving early revenue efforts, aligning organizational goals, accelerating decision processes, supporting sales, and ensuring exceptional client experiences. You will manage diverse responsibilities ranging from operations to go-to-market strategies and customer success in a high-visibility capacity.

Key Responsibilities

• Focus entirely on rapid and efficient growth of WithCoverage, owning critical company initiatives.
• Operate as the CEO’s representative to ensure alignment, accountability, and execution throughout the organization.
• Lead project management for cross-departmental projects such as launches, partnerships, and implementations to maintain seamless operations.
• Assist and potentially lead sales functions including participating in discovery calls, pipeline management, follow-ups, and closing deals.
• Organize CEO priorities, prepare essential materials for meetings, and translate decisions into actionable business strategies.

Candidate Profile

• Possess 2 to 6 years of experience in operations, chief of staff, sales, consulting, or similar generalist roles.
• Excellent communication skills, capable of representing leadership with clarity and professionalism both internally and externally.
• Comfortable engaging in sales conversations by asking insightful questions, managing objections, and driving next steps.
• Experienced in building processes and systems, particularly in early-stage or zero-to-one environments.
• Highly organized with strong follow-through and keen attention to detail.
• Capable of thriving in ambiguous environments and adept at balancing strategic planning with practical execution.
• Exemplify a high ownership mentality—proactive, resourceful, and capable of operating with minimal supervision.
• Familiarity with data analysis, dashboards, CRM software, and basic go-to-market metrics.
• Trustworthy with the discretion to handle sensitive information and accurately represent executive leadership.

Compensation and Benefits

The anticipated on-target earnings (OTE) for candidates based in the United States range from $150,000 to $200,000 annually, varying based on factors such as location, expertise, and role scope. Compensation includes base salary along with potential variable pay linked to performance targets. Additionally, the package encompasses equity participation and a comprehensive benefits suite.

Employee Benefits

• Competitive salary coupled with equity offerings.
• Extensive medical, dental, vision, life, and disability insurance plans.
• Pre-tax benefits including FSA, HSA, dependent care FSA, and commuter savings accounts.
• 401(k) retirement plans through Human Interest.
• Flexible paid time off, sick leave, family and medical leaves, and recognition of major national holidays.
• A thoughtfully designed in-office environment fostering community, connection, and innovation.
• A culture that values transparency, collaboration, and enjoyment.

Location

This position is based onsite in New York, NY.