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Community & Events Associate
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:
About The Role:
As our Community & Events Associate, you'll help operate and scale one of our most important GTM channels: a community-driven events engine that builds brand, generates pipeline, accelerates deals, and turns clients into champions. You'll work directly with our Community Lead to build out and operate this function — partnering with our Growth Team, running high-volume programs, and helping turn our community work into a predictable pipeline channel.
This is a rare chance to join a community-driven events ecosystem being built from the ground up, contribute to standing up our early in-house business development and marketing capabilities, and scale awareness across the operators shaping the modern economy. If you're excited by building communities, running high-volume events, and taking a systems-driven approach to turn creative GTM ideas into measurable pipelines, we'd love to chat.
What You'll Do
Event strategy & execution
Pipeline & relationship building
Community management & onboarding
Content & storytelling
Who You Are
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $85,000 – $150,000/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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
Ready to apply?
Apply to WithCoverage
Community & Events Manager / Community Lead
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:
Why This Role
You will be our first dedicated Workplace and People Operations hire, helping shape how our company runs and how it feels to work here. This is not just about keeping things organized.
You will build the foundation for our employee experience as we scale, from how the office operates to how every new hire starts their journey.
Role Overview
This is a high-impact role based in our NYC office at the center of the company. You will own the day-to-day workplace experience while supporting core People Operations workflows across onboarding, systems, and employee lifecycle processes. You will partner across teams to ensure things run smoothly, people feel supported, and processes scale with the business. If you enjoy building from the ground up and being the person who makes everything work, this role will be a great fit.
What You’ll Own
Workplace and Office Operations
Onboarding and Employee Experience
People Operations
Equipment and Systems
What Success Looks Like
You Might Be a Fit If
For candidates based in the United States, the expected pay range for this position at the start of employment is $60,000 – $75,000/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:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
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. We grew more than 10x last year while cash-flow positive, and we are very early in the opportunity.
Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy.
Why Join Us:
About The Role:
We are looking for a strategic, hands on Demand Generation Lead to architect and execute our digital lead generation strategy.
This is a foundational hire. You will partner closely with our Growth Leads, BDR, and Community teams to generate high quality inbound pipeline and create repeatable, scalable acquisition channels.
You will own digital marketing end to end, from strategy and experimentation to execution and optimization, with a clear focus on pipeline generation and revenue impact.
If you are excited about building from zero, testing fast, and driving measurable growth at a scaling company, this role is for you.
What You’ll Do:
Build the Digital Demand Engine
Own Performance and Optimization
Launch and Optimize Campaign Infrastructure
Establish Scalable Foundations
Who You Are:
Experience
Skills
Mindset
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $150,000 – $200,000/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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
Ready to apply?
Apply to WithCoverage
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:
About The Role:
Trusted referrals is one of the most impactful growth levers for WithCoverage today. As Partnerships Lead, you will own and grow our connector ecosystem of hundreds of key clients, investors, and industry relationships. You will manage and optimize our existing connector program while identifying and activating new high-value partners.
This is a highly external, relationship-driven role that sits at the intersection of sales, brand, and community. If you are energized by meeting people, building trust quickly, and turning relationships into real outcomes, this role will have a direct impact on company growth. You'll work directly with leadership and own scaling one of our most critical channels today.
What You’ll Do:
Manage our Existing Affiliate Network
Source and Activate New Connector Partners
Run Partnership Operations and Systems
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $150,000 – $220,000/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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
Ready to apply?
Apply to WithCoverage
Growth Associate (Account Executive)
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:
About The Role:
Join WithCoverage as a Growth Associate (Account Executive) on the Growth team, based out of our NYC office. The Growth Associate will be responsible for onboarding new mid-market accounts, identifying and addressing client needs, developing and maintaining strong client relationships, and executing sales strategies. This role requires close collaboration with the BDR and Risk Management Teams throughout the full sales funnel. The Growth Associate will also contribute to sourcing new prospects, driving deals to close, and maintaining a high standard of client satisfaction.
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.
What You’ll Do:
Who You Are:
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $250,000 – $300,000/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:
Ready to apply?
Apply to WithCoverage
Senior Manager - Business Development
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:
About The Role:
As Senior Manager of Business Development, you will own the strategy, performance, and evolution of WithCoverage’s outbound motion. We are currently booking hundreds of meetings with a small team and seeing tremendous success. This is a senior leadership role responsible for building a world-class BDR organization across multiple centers of excellence (currently Salt Lake and Denver) that consistently generates high-quality pipeline for the sales team. We’ve built the tools to move quickly and effectively, now we need to build the processes that allow us to scale from 10 to 25 to 50 BDRs, ideally by this time next year.
You will move beyond day-to-day management and instead focus on scaling systems, developing leaders, refining GTM strategy, and aligning outbound efforts with company-wide growth goals. While you’ll stay close to execution, your primary mandate is to design a repeatable, data-driven outbound engine that can scale with the business.
You’ll partner closely with Sales, Growth, Marketing, and Leadership to ensure outbound is tightly integrated into the broader go-to-market strategy.
What You’ll Do:
Own Outbound Strategy & Pipeline Generation
Who You Are:
Teacher, Trainer, and Coach: Giving feedback gives you energy. You love teaching people how to do what you do and you’re able to articulate your success in a way that other people can execute on as well
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $175,000 – $225,000/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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
Business Development Representative
Location: These roles will be work-from-home, with a preference for Salt Lake City, UT, and Denver, CO, as we build out hubs in these cities. As these hubs grow, we plan to have our teams operate on a hybrid in-office structure as we open office spaces in the future.
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:
About The Role:
As a Business Development Representative (BDR), your primary responsibility is to drive top-of-funnel activity by booking calls with qualified prospects. You'll be the first voice many of our future clients hear, reaching out via cold calls to introduce WithCoverage and spark interest. This is a high-output, high-impact role where success is measured by conversations started and meetings set. You’ll be equipped with a strong list of pre-qualified leads and supported by a collaborative growth team that’s focused on results. High performers in this role will have the opportunity to advance into closing or managerial positions over time. Schedule: Monday to Friday, 9am – 5pm EST (weekends off).
What You’ll Do:
Who You Are:
For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $65,000 – $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, quota incentives (for sales roles), and employee benefits.
What We Offer:
Ready to apply?
Apply to WithCoverage
Location: New York, NY
Job Type: Full-Time
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:
About The Role:
As a software engineer on the product team, you’ll build AI-native products that help us serve our clients’ complex risk needs. You’ll work at the intersection of large language models, complex business workflows, and real production systems. You’ll turn manual, expertise-heavy processes into reliable, autonomous capabilities.
You’ll ship agents that parse dense policy documents, automate email workflows, build knowledge representations of client risk profiles, and handle real client work end to end. You’ll architect the systems that make these agents trustworthy, observable, and extensible so they can be deployed across workflows by the rest of the team.
You’ll craft APIs used by both the UIs you design and the AI agents you build. You’ll solve hard AI problems, including task decomposition, tool use, memory, error recovery, human-in-the-loop patterns, and evaluation frameworks.
What You’ll Do:
Who You Are:
This role is on-site in our New York office. The expected cash compensation range for this position at the start of employment is $180,000 – $275,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. WithCoverage offers a comprehensive total rewards package for full-time employees, which includes equity grants and a robust suite of benefits.
What We Offer:
Ready to apply?
Apply to WithCoverage
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:
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:
Who You Are:
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:
Ready to apply?
Apply to WithCoverage
Claims Support Specialist
Location: Remote
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:
About The Role:
As our Claims Specialist, you will be the primary advocate for our clients, ensuring a seamless claims process by providing expert guidance, proactive communication, and strategic claims resolution. You’ll work closely with insurers, adjusters, and internal teams to manage claims efficiently, resolve coverage issues, and optimize outcomes for our clients. This role is ideal for someone who thrives in a fast-paced, tech-enabled environment, has a deep understanding of claims advocacy, and enjoys problem-solving within the evolving landscape of commercial insurance.
What You’ll Do:
Who You Are:
For candidates based in the United States, the expected pay range for this position at the start of employment is $60,000– $75,000/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
Ready to apply?
Apply to WithCoverage
Claims Counsel
Location: Preference for New York, NY, Philadelphia, Chicago, or Austin, but open to Remote
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:
What You’ll Do:
Who You Are:
For candidates based in the United States, the expected pay range for this position at the start of employment is $150,000 – $190,000/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:
Ready to apply?
Apply to WithCoverage
BDR Manager
Location: Remote, with future potential to be hybrid in-office (Denver, CO)
Job Type: Full-Time
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:
About The Role:
As a Business Development Manager, you’ll be a player-coach: leading a team of 5+ BDRs while also carrying an individual quota. You’ll be responsible for driving top-of-funnel performance personally and across your team — owning outbound execution, coaching, performance management, and continuous improvement.
This is a hands-on leadership role for someone who thrives in high-output environments, leads by example, and knows how to turn outbound activity into a consistent, qualified pipeline. You’ll work closely with Growth, Sales, and Leadership to refine messaging, improve conversion rates, and scale a repeatable outbound engine.
Schedule: Monday–Friday, 9am–5pm EST (weekends off)
Location: Denver, CO, to start as work from home, with the potential to be in office hybrid as we build out a team hub.
What You’ll Do:
Who You Are:
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $160,000 – $180,000/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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
Ready to apply?
Apply to WithCoverage
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