WithCoverage
Set The New Standard For The Insurance Brokerage Industry
Build the future of Risk Management and join a team of insurance experts, software engineers, product designers, business operators, and insurance attorneys.
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Lead Risk Advisor
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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
Ready to apply?
Apply to WithCoverage
Recruiter
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Recruiter (Founding Talent team member)
Location: Preference for this team member to be based near one of our hubs in New York, NY, Chicago, or Philadelphia, but open to considering a remote US-based hire.
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 our early joiner End-to-End Recruiter, you will play a critical role in building the teams that power WithCoverage’s growth. You’ll own the full recruiting lifecycle—partnering closely with leadership to attract, engage, and hire top-tier talent across Sales, Growth, Product, Engineering, Risk, and other critical functions.
This is an exciting opportunity as a founding Talent team member to join a fast-growing startup where your work will have a direct impact on the company’s success. You’ll help shape hiring strategy, build scalable recruiting processes, and act as a trusted advisor to hiring managers as we grow.
What You’ll Do:
- Own the end-to-end recruiting lifecycle for roles across Sales, Growth, Product, Engineering, Risk, and other business-critical teams, from intake through offer and close
- Partner closely with the Head of Talent and hiring managers to define hiring needs, role requirements, and ideal candidate profiles
- Proactively source and engage candidates using LinkedIn Recruiter, Juicebox, and other creative sourcing strategies
- Manage and optimize candidate pipelines in Greenhouse, ensuring an excellent candidate experience
- Coordinate and drive interview processes, including scheduling, feedback collection, and decision-making
- Act as a brand ambassador for WithCoverage, clearly communicating our mission, culture, and value proposition to candidates
- Use Slack to collaborate cross-functionally and keep stakeholders informed throughout the hiring process
- Track recruiting metrics and continuously improve hiring efficiency, quality, and speed
- Support the evolution of recruiting processes and best practices as the company scales
Who You Are:
- 3-5+ years of experience as an end-to-end recruiter, with a strong focus on outbound sourcing for roles across Sales, Growth, Product, Engineering, Risk, and similar functions. Ideally, having a blend of high volume (agency) and internal corporate recruiting experience.
- Proven experience sourcing and hiring in a startup or high-growth environment
- Hands-on experience with LinkedIn Recruiter, Greenhouse, Juicebox, and Slack (or similar tools)
- Comfortable managing multiple roles and priorities in a fast-paced environment
- Strong stakeholder management skills -- you know how to partner with leaders and influence hiring decisions
- Data-driven, organized, and process-oriented, while still being flexible and scrappy
- Passionate about building diverse, high-performing teams
- Excited to work within a startup company and help build recruiting foundations from the ground up
For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $70,000 – $120,000/year. 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, a performance tied annual bonus, and employee 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
Ready to apply?
Apply to WithCoverage
Risk Team Lead / Director
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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
Ready to apply?
Apply to WithCoverage
Risk Advisor
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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
Ready to apply?
Apply to WithCoverage
Growth Lead
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Growth Lead
Location: New York, NY
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:
Join With Coverage as a Growth Lead on the Growth team - you’ll own and scale one of our fastest-growing verticals end-to-end. This is a sales-driven leadership role where you’ll drive growth of the vertical across the full conversion cycle, build deep industry relationships, and lead all aspects of deal execution.
We’re looking for someone who wants ownership, thrives in high-performance environments, and is eager to accelerate their career by building something meaningful. You’re motivated by results, comfortable operating with autonomy, and willing to put in the work required to achieve outsized outcomes as you directly shape the growth of one of our key business verticals.
What You’ll Do:
- Own the vertical’s growth. Become the true owner of a key business line as the Vertical Lead responsible for pipeline generation, relationship development, and deal execution.
- Drive execution. Generate demand through targeted outreach, manage the pipeline, and guide prospects through the full conversion cycle with clear communication and follow-through.
- Develop industry relationships. Develop a deep understanding of your vertical and build deep relationships with industry C-suite leaders, associations, and connectors.
- Shape the GTM playbook. Shape the sales playbook in partnership with an Insurance Lead and give product feedback to address the needs of your customers
- Build pipeline. Expand referral networks and identify new go-to-market opportunities to consistently grow qualified opportunities.
Who You Are:
- 4+ years in relevant fields (high-growth startups, management consulting, or investment banking/PE/VC)
- Expert relationship manager and networker, with capacity to excel in B2B sales closing 6-7 figure deals
- Excellent communication and executive presence – you will represent the brand
- Quick learner
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $200,000 – $250,000/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
Ready to apply?
Apply to WithCoverage