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Salary: USD 140,000 - 160,000 / annual
WithCoverage is an AI-powered risk management platform replacing traditional insurance brokerages. Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), the company has raised $43M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. WithCoverage partners with high-growth companies including GoPuff, Eight Sleep, Bombas, and Blank Street Coffee, serving consumer brands, hospitality leaders, general contractors, advanced manufacturers, and defense contractors.
As Executive Assistant, you will work directly with the co-founders in a fast-paced, high-growth environment. You will own and manage multiple executive calendars, resolving complex scheduling conflicts and exercising judgment about prioritization. You will coordinate high-stakes meetings end-to-end, including board meetings, investor updates, client and carrier meetings, executive offsites, and leadership staff meetings—handling attendee communications, venue coordination, A/V setup, catering, and preparation of program materials.
Key responsibilities include proactively managing inbound communication and responding to urgent inquiries from internal and external stakeholders on behalf of the executives; preparing executives for meetings by assembling briefing materials, researching attendees and companies, and ensuring they are fully prepared; organizing and compiling data and content to support executive presentations, board decks, and investor materials; building and improving administrative infrastructure, templates, workflows, and systems to enable executive support to scale; and contributing to a curated in-office experience through office management, team events, offsites, and client hosting.
The role is based in WithCoverage's Hudson Square office, 5 days per week. You will work in a collaborative environment with people at every level, handling sensitive and confidential information with discretion and sound judgment. This is an opportunity to shape the company's administrative infrastructure during a period of rapid scaling and to work alongside founders driven by excellence and a passion for technology.
**Requirements:**
- 5+ years supporting senior executives, ideally multiple at once, in fast-paced and ambiguous environments
- Exceptionally detail-oriented; ability to catch errors in time zones, names, flight connections, and other logistics
- Strong written and verbal communication skills; ability to adapt tone for board members, clients, candidates, and internal teams
- High degree of integrity and discretion around confidential and sensitive information
- Proactive and resourceful; ability to identify needs, propose solutions, and close the loop without being asked
- Calm under pressure and resilient; ability to re-prioritize and adapt when plans change
- Genuine team player who thrives in collaborative settings
- Systems-minded; ability to build repeatable processes and adopt new tools, including AI
- Excitement about early-stage environments where role scope expands with company growth
Ideal candidates come from backgrounds such as: Executive Assistant or Chief of Staff at high-growth startups supporting founders or C-suite through scaling; Executive Assistant at venture capital, private equity, or investment firms managing board and LP-facing logistics; Executive Assistant supporting VP-level or above at large technology, financial services, or professional services firms; Executive support in consulting, banking, or law; or hospitality, events, or high-touch client service backgrounds with transition into executive support.
