About WithCoverage:

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy. 

We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed.

Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service.

WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $43M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners. 

Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy.

Why Join Us:

• Grow Faster – We’re scaling quickly, giving you significant opportunities to learn, lead, and shape your career and the company's future.
• Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
• Redefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.
• Financial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth.

About The Role:

As our Executive Assistant, you will work directly with our co-founders. This is an opportunity to work alongside individuals who are driven by excellence and a passion for technology. The ideal candidate is a team player with exceptional communication skills, meticulous attention to detail and creative problem-solving skills. This role requires the ability to juggle competing responsibilities while prioritizing. Daily responsibilities include calendar management, coordinating meetings, travel and logistics, and prioritizing across multiple leaders. We are looking for someone with strong experience working with executive teams in fast-paced environments, and the ability to handle sensitive information with excellent judgment, diplomacy and discretion. This role will be based in our brand new Hudson Square office 5 days per week.

What You'll Do

• Own and defend multiple executive calendars, including recurring meetings, resolving complex conflicts and exercising judgment about what gets time and what gets moved
• Coordinate high-stakes meetings end to end, board meetings, investor updates, client and carrier meetings, executive offsites, and leadership staff meetings — including attendee communications, venue coordination, A/V setup, catering, and preparation of program materials
• Proactively manage inbound communication and respond to urgent inquiries from internal and external stakeholders on the executives' behalf
• Prepare executives for what's next: assemble briefing materials, pull background on the people and companies in the room, and make sure they walk in ready
• Organize and compile data and content to support executive presentations, board decks, and investor materials
• Build and improve the administrative infrastructure, templates, workflows, and system, that lets executive support scale as the company grows
• Contribute to a curated in-office experience: office management, team events, offsites, client hosting

Who You Are

• 5+ years supporting senior executives, ideally multiple at once, in a fast-paced and ambiguous environment
• Exceptionally detail-oriented. You catch the wrong time zone, the misspelled name, the flight that connects too tightly. Details are not a task for you; they are a reflex
• A strong communicator, written and verbal. You write clearly and quickly, and you adapt your tone whether you're emailing a board member, a client's CFO, or a candidate
• Discreet and trustworthy. You have a high degree of integrity around confidential and sensitive information, and sound judgment about what to share, with whom, and when
• Proactive and resourceful. You do not wait to be asked. You identify what needs doing, propose a solution, and close the loop
• Calm under pressure and resilient. Priorities change, meetings collapse, flights get canceled, you re-plan without drama
• A genuine team player who thrives in a collaborative setting and works well with people at every level
• Systems-minded. You build the repeatable process instead of solving the same problem twice, and you're comfortable adopting new tools, including AI, to work faster
• Excited by an early-stage environment where the scope of the role will expand as the company does

You likely come from one of these backgrounds:

• Executive Assistant or Chief of Staff at a high-growth startup, supporting founders or C-suite through a period of rapid scaling
• Executive Assistant at a venture capital, private equity, or investment firm, supporting partners and managing board and LP-facing logistics
• Executive Assistant supporting VP-level or above at a large technology, financial services, or professional services firm
• Executive support in consulting, banking, or law, where precision, confidentiality, and long hours of high-stakes coordination are the norm
• Hospitality, events, or high-touch client service, where you learned to anticipate needs and manage complex logistics flawlessly — and have since moved into executive support

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $140,000 – $160,000/year. Actual compensation will vary based on individual factors, including market location, relevant experience, and role scope. In addition to base salary, this role is eligible for variable compensation tied to performance or quota attainment, where applicable. WithCoverage’s Total Rewards package for full-time employees also includes equity participation and comprehensive benefits. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.

What We Offer:

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
• Human Interest: 401(k) provider
• Time Off: Flexible time off, sick leave, family and medical leave, and major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture