{"schemaVersion":"jobsearcher.job.v1","id":"0ed9f44ae7e6257f4df4f1b3","url":"https://jobsearcher.com/jobs/0ed9f44ae7e6257f4df4f1b3","canonicalUrl":"https://jobsearcher.com/jobs/0ed9f44ae7e6257f4df4f1b3","title":"Lead Risk Advisor","description":"Location: New York, NY, Philadelphia, or Chicago\nJob Type: Full-Time\n\nWithCoverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—100's of brands like GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee—so they can move fast without compromise.\n\nInstead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.\n\nFounded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), WithCoverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.\n\nWe’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.\n\nWhy Join Us:\n\nGrow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.\n\nWork That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.\n\nRedefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.\n\nFinancial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.\n\nAbout The Role:\n\nWe’re looking for a Lead Risk Advisor to own client relationships end-to-end and help scale a risk vertical. You’ll work directly with business leaders to assess exposures, lead Risk Analyses, and deliver tailored solutions that drive measurable impact.\n\nWhat You’ll Do:\n\nOwn and manage a portfolio of client accounts end-to-end, driving strong relationships and delivering exceptional service.\n\nLead client-facing Risk Analyses with senior executives, diagnosing coverage gaps and presenting tailored insurance solutions.\n\nBuild and refine playbooks for your vertical to create repeatable, scalable best practices for future advisors.\n\nCollaborate closely with the Growth, Product, and Ops teams to ensure seamless execution and a differentiated client experience.\n\nTranslate client needs into actionable insights for underwriting, operations, and product improvements.\n\nTrack and report key client metrics to identify opportunities for expansion, efficiency, and impact.\n\nContribute to the culture of excellence, curiosity, and accountability that defines our team.\n\nWho You Are:\n\n4–7 years into your career, ideally with experience in commercial insurance, risk management, or client advisory roles.\n\nConfident leading high-stakes client conversations and comfortable presenting analyses or proposals.\n\nDeeply curious about how businesses operate and motivated to become a trusted advisor to their leaders.\n\nStrong communicator who thrives in fast-moving, collaborative environments.\n\nHighly detail-oriented and accountable — you own outcomes, not just tasks.\n\nCoachable and eager to learn; open to feedback and committed to growth.\n\nDrawn to environments where performance is rewarded with real upside and autonomy.\n\nHardworking, kind, and humble — the type of teammate others want to work with.\n\nFor candidates based in the United States, the pay range for this position at the start of employment is expected to be between $140,000 – $190,000year. Your exact offer may vary depending on multiple individualized factors, including market location, job‑related knowledge, skills, and experience. Total compensation for this position may also include equity, quota incentives (for sales roles), and employee benefits.\n\nIn addition to cash compensation, WithCoverage offers full‑time employees a comprehensive Total Rewards package that includes equity grants.\n\nWhat We Offer:\n\nCompetitive compensation that may include equity\n\nFlexible paid time off\n\nComprehensive benefit plans for medical, dental, vision, life, and disability\n\nFlexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA\n\nCommuter Savings Account\n\nHuman Interest: 401(k) provider\n\nTime Off: Sick Leave, Family and Medical Leave, Flexible Time Off\n\nPaid Holidays: Observance of all major national holidays\n\nA curated in‑office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in‑office workers\n\nCollaborative, transparent, and fun culture\n\n#J-18808-Ljbffr","company":"Withcoverage","rawCompany":"withcoverage","city":"Chicago","state":"IL","isRemote":false,"isActive":false,"createdAt":"2026-04-11T03:06:06.468Z","occupations":[{"code":"13-2054.00","title":"Financial Risk Specialists","slug":"financial-risk-specialists"},{"code":"41-3021.00","title":"Insurance Sales Agents","slug":"insurance-sales-agents"},{"code":"13-2053.00","title":"Insurance Underwriters","slug":"insurance-underwriters"}],"industries":[{"code":"524298","title":"All Other Insurance Related Activities","slug":"all-other-insurance-related-activities"},{"code":"524126","title":"Direct Property and Casualty Insurance Carriers","slug":"direct-property-and-casualty-insurance-carriers"},{"code":"524210","title":"Insurance Agencies and Brokerages","slug":"insurance-agencies-and-brokerages"}],"jobPosting":{"@context":"https://schema.org","@type":"JobPosting","title":"Lead Risk Advisor","description":"Location: New York, NY, Philadelphia, or Chicago\nJob Type: Full-Time\n\nWithCoverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—100's of brands like GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee—so they can move fast without compromise.\n\nInstead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.\n\nFounded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), WithCoverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.\n\nWe’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.\n\nWhy Join Us:\n\nGrow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.\n\nWork That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.\n\nRedefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.\n\nFinancial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.\n\nAbout The Role:\n\nWe’re looking for a Lead Risk Advisor to own client relationships end-to-end and help scale a risk vertical. You’ll work directly with business leaders to assess exposures, lead Risk Analyses, and deliver tailored solutions that drive measurable impact.\n\nWhat You’ll Do:\n\nOwn and manage a portfolio of client accounts end-to-end, driving strong relationships and delivering exceptional service.\n\nLead client-facing Risk Analyses with senior executives, diagnosing coverage gaps and presenting tailored insurance solutions.\n\nBuild and refine playbooks for your vertical to create repeatable, scalable best practices for future advisors.\n\nCollaborate closely with the Growth, Product, and Ops teams to ensure seamless execution and a differentiated client experience.\n\nTranslate client needs into actionable insights for underwriting, operations, and product improvements.\n\nTrack and report key client metrics to identify opportunities for expansion, efficiency, and impact.\n\nContribute to the culture of excellence, curiosity, and accountability that defines our team.\n\nWho You Are:\n\n4–7 years into your career, ideally with experience in commercial insurance, risk management, or client advisory roles.\n\nConfident leading high-stakes client conversations and comfortable presenting analyses or proposals.\n\nDeeply curious about how businesses operate and motivated to become a trusted advisor to their leaders.\n\nStrong communicator who thrives in fast-moving, collaborative environments.\n\nHighly detail-oriented and accountable — you own outcomes, not just tasks.\n\nCoachable and eager to learn; open to feedback and committed to growth.\n\nDrawn to environments where performance is rewarded with real upside and autonomy.\n\nHardworking, kind, and humble — the type of teammate others want to work with.\n\nFor candidates based in the United States, the pay range for this position at the start of employment is expected to be between $140,000 – $190,000year. Your exact offer may vary depending on multiple individualized factors, including market location, job‑related knowledge, skills, and experience. Total compensation for this position may also include equity, quota incentives (for sales roles), and employee benefits.\n\nIn addition to cash compensation, WithCoverage offers full‑time employees a comprehensive Total Rewards package that includes equity grants.\n\nWhat We Offer:\n\nCompetitive compensation that may include equity\n\nFlexible paid time off\n\nComprehensive benefit plans for medical, dental, vision, life, and disability\n\nFlexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA\n\nCommuter Savings Account\n\nHuman Interest: 401(k) provider\n\nTime Off: Sick Leave, Family and Medical Leave, Flexible Time Off\n\nPaid Holidays: Observance of all major national holidays\n\nA curated in‑office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in‑office workers\n\nCollaborative, transparent, and fun culture\n\n#J-18808-Ljbffr","datePosted":"2026-04-11T03:06:06.468Z","dateModified":"2026-04-11T03:06:06.468Z","hiringOrganization":{"@type":"Organization","name":"Withcoverage","sameAs":"https://jobsearcher.com"},"jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"Chicago","addressRegion":"IL","addressCountry":"US"}},"identifier":{"@type":"PropertyValue","name":"JobSearcher","value":"0ed9f44ae7e6257f4df4f1b3"},"url":"https://jobsearcher.com/jobs/0ed9f44ae7e6257f4df4f1b3"}}