Executive Assistant

WithCoverage; New York (NY); On-site; USD 140,000 - 160,000; Full time

Benefits offered by this job

Equity

Benefits package

Pre-tax accounts

401(k) provider

Flexible time off

In-office culture

Team events

Job summary

WithCoverage is transforming risk management with AI-powered tools and elite advisory services. As Executive Assistant, you will directly support the co-founders, managing calendars, travel, meetings, and sensitive information with excellence.

You will help prepare briefing materials, coordinate board and investor meetings, and streamline administrative workflows to scale with the company’s rapid growth. This role is based in our Hudson Square office, five days a week.

Qualifications

• 5+ years supporting senior executives in fast-paced environments.
• Exceptional attention to detail is essential.
• Strong written and spoken communication skills.
• Discretion and trust with confidential information.
• Proactive, resourceful, and able to close the loop.
• Calm under pressure with flexible prioritization.
• A collaborative team player who thrives in small teams.
• Comfortable building repeatable processes and adopting new tools.

Responsibilities

• Own and defend multiple executive calendars, resolving conflicts and prioritizing meetings.
• Coordinate high-stakes meetings end to end, including board/investor updates and offsites.
• Inboxes and inquiries: respond on executives' behalf with discretion.
• Prepare briefing materials and background on attendees for meetings.
• Assemble content for presentations, decks, and investor materials.
• Improve administrative infrastructure, templates, and workflows.
• Support curated in-office experiences, events, and client hosting.

Skills

5+ years

Attention to detail

Strong communicator

Discreet

Proactive

Calm under pressure

Team player

Systems-minded

Job description

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

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self‑identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in WithCoverage's Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Voluntary Self-Identification of Disability

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp .

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

• Alcohol or other substance use disorder (not currently using drugs illegally)
• Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
• Blind or low vision
• Cancer (past or present)
• Cardiovascular or heart disease
• Celiac disease
• Cerebral palsy
• Deaf or serious difficulty hearing
• Diabetes
• Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
• Epilepsy or other seizure disorder
• Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
• Intellectual or developmental disability
• Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
• Missing limbs or partially missing limbs
• Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
• Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
• Neurodivergence, for example, attention‑deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
• Partial or complete paralysis (any cause)
• Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
• Short stature (dwarfism)
• Traumatic brain injury