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

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

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:

• 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 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:

• Claims Advocacy & Resolution
• Serve as the main point of contact for clients throughout the claims process, providing clear guidance and updates.
• Evaluate policy coverage and advocate for the best possible outcomes for clients.
• Challenge adjusters when necessary to ensure fair and timely settlements.
• Proactively anticipate and present strategic solutions to clients for resolving claims.
• Claims Management & Communication
• Oversee the full lifecycle of claims, from initial report to final resolution.
• Conduct new business claims audits for newly acquired clients.
• Collaborate with insurers, underwriters, and external adjusters to negotiate claims settlements.
• Facilitate client meetings, claims reviews, and carrier discussions to ensure alignment and transparency.
• Maintain meticulous documentation of claims activity in our proprietary agency management system.
• Client Education & Risk Mitigation
• Educate clients on claims administration, coverage nuances, and proactive risk management.
• Offer guidance on reducing claim exposure and improving policy language to prevent disputes.
• Prepare and deliver quarterly claims reviews with key insights and recommendations.
• Process Optimization & Technology Integration
• Leverage technology to streamline claims handling, improving efficiency and accuracy.
• Partner with product team to identify opportunities to enhance internal claims processes using tech-driven solutions.
• Provide data-driven insights to clients on claims trends, risk mitigation strategies, and best practices.

Who You Are:

• Industry Experience
• 3-7 years of experience in claims handling and claims advocacy.
• Strong knowledge of commercial lines claims, including non-admitted experience with complex coverage nuances
• Significant experience in policy interpretation and claims negotiation.
• Skills & Competencies
• Exceptional problem-solving and strategic thinking abilities.
• Strong communication and negotiation skills, with the ability to advocate for clients.
• Ability to work autonomously while collaborating with internal teams and external stakeholders.
• Familiarity with claims technology platforms and data analytics tools.
• Tech-Savvy Mindset
• Comfortable working in a digital-first brokerage environment.
• Ability to leverage claims management software and automation tools to improve processes.
• Licensing & Certifications (Preferred, Not Required)
• Adjuster’s License (a plus, but not required).
• Certifications related to claims management or risk mitigation (e.g., AIC, CPCU) are a bonus.

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

• 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

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:

• 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.

What You’ll Do:

• Own complex claims end-to-end across GL, Cyber, D&O, Property, and Marine/Cargo lines—triaging new matters, confirming coverage, coordinating carrier notices, and driving resolution strategies through to closure.
• Serve as the primary client advocate, translating coverage and litigation issues into clear guidance, managing expectations, and aligning carriers, counsel, and vendors around the client’s best outcome.
• Analyze and negotiate coverage positions, drafting demand and rebuttal letters, challenging denials, and securing optimal defense and indemnity contributions from insurers.
• Oversee litigation and recovery efforts, ensuring defense and coverage counsel strategies align with policy recovery, and leading loss quantification for property, cyber, and other first-party claims.
• Manage external partners and internal team members, setting standards for claims handling, mentoring analysts, and maintaining high-quality, audit-ready files and documentation.
• Deliver insights and reporting through claims data, dashboards, and renewal narratives—identifying trends, coverage gaps, and opportunities to improve client programs and outcomes.
• Continuously improve processes and tools, partnering with Operations and Product to streamline claims workflows, automate documentation, and enhance the client experience.

What success looks like:

• Shortened claim cycle times and increased recovery/indemnity percentages (especially in the first‑party).
• Fewer coverage disputes/denials through early positioning and escalations that stick.
• High client satisfaction (clear communication, predictable updates, strong outcomes).

Who You Are:

• Experienced claims professional with 5–10 years managing complex commercial insurance claims—ideally across GL, Cyber, D&O, Property, and Marine/Cargo—within a carrier, law firm, or brokerage environment.
• Coverage-driven mindset with a J.D. and active bar membership; skilled in analyzing policy wording, drafting coverage positions, and advocating for insureds in high-stakes matters.
  Full-lifecycle operator comfortable owning claims from first notice through resolution, including coverage analysis, litigation oversight, negotiation, and first-party recovery.
• Client-focused communicator who can translate complex coverage and litigation issues into clear business guidance, maintaining calm and credibility with executives during live incidents and negotiations.
• Hands-on leader and mentor able to review and elevate team output, establish standards, and help build playbooks, templates, and scalable claims processes.
• Analytical and process-minded, leveraging data, metrics, and technology to manage performance, improve consistency, and drive efficiency.
• Collaborative and entrepreneurial, thriving in a fast-moving startup setting with strong judgment, humility, and a bias toward action and continuous improvement.

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:

• 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