Lead Risk Advisor

Location: New York, NY, Philadelphia

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:

We’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.

What You’ll Do:

• Own and manage a portfolio of client accounts end-to-end, driving strong relationships and delivering exceptional service.
• Lead client-facing Risk Analyses with senior executives, diagnosing coverage gaps and presenting tailored insurance solutions.
• Build and refine playbooks for your vertical to create repeatable, scalable best practices for future advisors.
• Collaborate closely with the Growth, Product, and Ops teams to ensure seamless execution and a differentiated client experience.
• Translate client needs into actionable insights for underwriting, operations, and product improvements.
• Track and report key client metrics to identify opportunities for expansion, efficiency, and impact.
• Contribute to the culture of excellence, curiosity, and accountability that defines our team.

Who You Are:

• 4–7 years into your career, ideally with experience in commercial insurance, risk management, or client advisory roles.
• Confident leading high-stakes client conversations and comfortable presenting analyses or proposals.
• Deeply curious about how businesses operate and motivated to become a trusted advisor to their leaders.
• Strong communicator who thrives in fast-moving, collaborative environments.
• Highly detail-oriented and accountable — you own outcomes, not just tasks.
• Coachable and eager to learn; open to feedback and committed to growth.
• Drawn to environments where performance is rewarded with real upside and autonomy.
• Hardworking, kind, and humble — the type of teammate others want to work with.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $140,000 – $190,000/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.

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, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture

Client Service Manager

Location: Philadelphia, PA or Salt Lake City, UT

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:

Partner with Risk Advisors on assigned book of business, manage day-to-day service processes and outputs, support a variety of strategic, client-facing initiatives, and run point on each client’s renewal cycle, ensuring a positive and productive client experience.

What You’ll Do:

• Maintains effective and positive relationships with clients. Serves independently in a client-facing capacity on matters of moderate importance and complexity. 
• Facilitates the timely and accurate flow of information between clients, and Risk team members, keeping all parties informed. 
• Handles client open items lists and responds to client ad-hoc requests. 
• Gathers and analyzes data and drafts assigned elements of stewardship reports and other convincing presentations tailored to the needs of the audience and the circumstances of the presentation.
• Actively supports and monitors the renewal process, engaging with account team members as necessary. May draft quote comparisons and is responsible for saving down binders, policies, and endorsements.
• Receives and handles routine and sophisticated coverage inquiries.
• Serves as key client liaison for items such as certificates, auto IDs, location additions, invoices, Worker’s Compensation posting notices, allocations, premium finance agreements, summaries of insurance, and policy transmittals.
• Monitors and follows-up on invoice generation, fee agreements, receivables, and collections. Addresses and resolves problems. 
• Ensures tools are understood and used. Performs related duties as assigned.

Who You Are:

• 2+ years of commercial insurance experience required (preferably in an Account Management role)
• Property & Casualty broker’s license strongly preferred, or to be obtained within 120 days of start date
• High school diploma or equivalent required 
• Associates degree preferred 
• Experience supporting complex clients is preferred

For candidates based in the United States, the expected pay range for this position at the start of employment is $100,000 – $140,000/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, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture

Risk Team Lead / Director

Location: New York, NY or Philadelphia, PA

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 the Director of Risk Management, you’ll lead our strategy and execution for client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. You’ll partner closely with advisors, service teams, and executive leadership to deliver world-class risk solutions that drive retention, growth, and operational excellence.

What You’ll Do:

• Directly responsible for client retention, client servicing, and oversight on new client placements across WithCoverage’s Risk Advisory Team
• Manage a growing team of Risk Advisors to ensure all conversion, execution, and servicing timelines are met
• Monitor and address performance metrics with Risk Team to ensure performance expectations are met across a rapidly growing client base.
• Maintain a culture of excellence across the Risk Team as it pertains to day to day work, client engagement, and internal operational execution.
• Lead the design and implementation of client risk management programs across multiple industries and lines of business (P&C, Workers Comp, Auto, Cyber, etc.)
• Partner with Risk Advisors to deliver comprehensive renewal and risk mitigation strategies
• Partner with Risk Advisors to oversee loss analysis, benchmarking, and claims trends to guide client decision-making and carrier negotiations
• Partner with Risk Advisors to evaluate client operations, exposures, and contractual risks to propose proactive solutions
• Support internal education and development of best practices across the risk team
• Collaborate with leadership to enhance processes, tools, and technology for risk advisory delivery

Who You Are:

• 8–12 years of experience in commercial insurance or risk management, ideally within a brokerage or consulting environment
• 2+ years of quota carrying-people management experience, ideally in a fast paced and high ownership environment
• Deep understanding of commercial lines (GL, Property, Auto, WC, Umbrella, and Specialty)
• Proven ability to communicate complex insurance concepts to executive-level clients in a clear, advisory tone
• Strong analytical and strategic thinker, comfortable working across clients and industries
• Leadership mindset with a desire to mentor others and build scalable systems for growth
• Designations (CPCU, ARM, CIC, CRM) preferred but not required

For candidates based in the United States, the expected pay range for this position at the start of employment is $200,000 – $300,000/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, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture

Risk Advisor

Location: New York, NY or Philadelphia, PA

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:

We’re looking for a 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, partake in Risk Analyses, and deliver tailored solutions that drive measurable impact.

What You’ll Do:

• Own and manage a portfolio of client accounts end-to-end, driving strong relationships and delivering exceptional service.
• Build and refine playbooks for your vertical to create repeatable, scalable best practices for future advisors.
• Collaborate closely with the Growth, Product, and Ops teams to ensure seamless execution and a differentiated client experience.
• Translate client needs into actionable insights for underwriting, operations, and product improvements.
• Track and report key client metrics to identify opportunities for expansion, efficiency, and impact.
• Contribute to the culture of excellence, curiosity, and accountability that defines our team.

Who You Are:

• 2+ years into your career, ideally with experience in commercial insurance, risk management, or client advisory roles.
• Confident leading high-stakes client conversations and comfortable presenting analyses or proposals.
• Strong critical thinking skills, with experience evaluating complex coverage programs, synthesizing risk, coverage, and cost considerations, and translating analysis into actionable strategies.
• Deeply curious about how businesses operate and motivated to become a trusted advisor to their leaders.
• Strong communicator who thrives in fast-moving, collaborative environments.
• Highly detail-oriented and accountable — you own outcomes, not just tasks.
• Coachable and eager to learn; open to feedback and committed to growth.
• Drawn to environments where performance is rewarded with real upside and autonomy.
• Hardworking, kind, and humble — the type of teammate others want to work with.

For candidates based in the United States, the expected pay range for this position at the start of employment is $85,000 – $125,000/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, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture