Founders' Office, Special Projects

About WithCoverage:

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

We partner with over one thousand 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

We're looking for an exceptional operator to join our Founders' Office and work directly with our co-founders on some of WithCoverage's most ambitious commercial initiatives.

As we scale, we're pursuing opportunities that don't fit neatly within an existing team. These might include launching a new business line, validating a strategic partnership, entering a new market, or bringing an entirely new commercial model to life. Many of these opportunities have the potential to generate millions of dollars in revenue and materially change the trajectory of the company.

You'll take these ideas from concept to execution. That means assessing the opportunity, developing a strategy, building the right relationships, and doing whatever it takes to get something off the ground.

This is not a traditional strategy or Chief of Staff role. You won't research opportunities, prepare recommendations, or coordinate execution. You'll own initiatives from start to finish and be accountable for delivering results.

The ideal candidate combines exceptional problem-solving ability with strong commercial instincts, creativity, and relentless follow-through. You can operate comfortably with senior executives, but you're equally willing to get into the details and do the work yourself.

What You'll Do

• Own high-impact special projects end to end. Take ambitious ideas from the founders, evaluate their potential, develop a plan, and independently drive execution through launch.
• Build new commercial opportunities. Identify and pursue new markets, business models, strategic partnerships, and distribution channels with meaningful revenue potential.
• Launch zero-to-one initiatives. Validate demand, develop business models, secure initial customers or partners, and build the infrastructure necessary to bring new opportunities to market.
• Build strategic external relationships. Represent WithCoverage with founders, executives, investors, and prospective partners. Develop relationships that create meaningful commercial opportunities.
• Drive cross-functional execution. Work across Growth, Risk, Product, Engineering, Finance, and Legal to navigate complex initiatives and bring them to completion.
• Solve ambiguous problems independently. Build context quickly in unfamiliar industries, develop practical solutions, and find creative ways to make progress without an established playbook.
• Validate early successes: Validate and hand off new opportunities. Test ambitious ideas, prove their commercial viability, and establish the initial operating model. Once validated, transition ownership to the appropriate team to scale.

Who You Are

• You have 2+ years of experience in a high-performance environment, such as founding or operating at a startup, management consulting, investing, or strategic business development.
• You have exceptional commercial instincts and can evaluate opportunities based on their strategic importance, economics, and potential to create meaningful business value.
• You are highly entrepreneurial and energized by building something from zero to one.
• You have extremely high agency. You can take an ambiguous objective, define the path forward, and drive progress without constant direction.
• You are a strong relationship builder who can establish credibility with senior executives, negotiate effectively, and represent WithCoverage externally.
• You combine strategic thinking with hands-on execution. You're as comfortable building a business case as you are making calls, closing a partnership, or solving an operational problem.
• You have excellent judgment, a strong sense of urgency, and an exceptionally high bar for the quality of your work.
• You are motivated by ownership and outcomes rather than titles, organizational boundaries, or narrowly defined responsibilities.

Compensation

For candidates based in the United States, the expected pay range for this position at the start of employment is $140,000 – $170,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. This role may also be eligible for additional variable compensation, including quota-based incentives where applicable. WithCoverage offers a comprehensive Total Rewards package for full-time employees, which includes equity grants and a robust suite of benefits.

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