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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Director of Channel Partnerships
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Director of Channel Partnerships
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:
Channel partnerships are one of the most significant untapped growth levers at WithCoverage. As Channel Partnerships Lead, you will build our channel motion from the ground up, creating a durable pipeline through firms whose clients overlap directly with our buyers across finance, legal, and the executive suite. Think accounting firms, fractional CFOs, payroll providers, and any other trusted advisor or partner that sits next to the major decisions our clients are making.
This is a builder role with direct pipeline accountability. You will identify the right partners, get in front of them, and show them why WithCoverage's expert team paired with our technology is a step function improvement for their clients (then show them the path to making it happen). You'll work directly with leadership, own a critical new growth channel end-to-end, and have clear upside and a fast promotion path as the channel scales.
What You’ll Do:
Build the B2B Channel Motion from Scratch
- Identify and prioritize partner segments where buyer overlap is highest (accounting, fractional CFO, payroll, legal, executive advisors)
- Source, qualify, and close new channel partners through targeted outreach, events, and warm introductions
- Develop a sharp value prop for each partner type and "show the path": why their clients need WithCoverage and how the partnership works in practice
Drive Pipeline and Revenue
- Own pipeline directly attributable to channel-sourced opportunities
- Build trusted relationships with partner principals and front-line referrers to ensure consistent, high-quality referral flow
- Partner closely with sales to convert referrals and feed insights back into partner strategy
Run Channel Operations and Systems
- Implement systems to track, measure, and performance-manage partners against pipeline targets
- Build SOPs, enablement materials, and onboarding workflows that let the channel scale without breaking
- Represent WithCoverage at partner-facing events and industry functions
Who You Are:
- 5-12 years of experience in Sales, BD, or GTM; 3+ years minimum directly in a partnerships role
- Startup experience preferred but not required
- Track record of building or meaningfully scaling a channel (you've sourced partners from scratch and turned them into real revenue)
- Ruthlessly organized; you can run hundreds of relationships in parallel without dropping balls, and you have the systems to prove it
- Relationship-driven with strong commercial instincts; people trust you quickly and you know how to turn that trust into outcomes
- High-ownership operator; you want real accountability, real upside, and a clear path to expanded scope
For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $175,000 – $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. 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:
- 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
Demand Generation Lead
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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:
- 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 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
- Identify, test, and scale high performing acquisition channels including paid search, paid social, display, and retargeting
- Build a structured experimentation roadmap with clear hypotheses and success metrics
Own Performance and Optimization
- Manage paid media budgets and optimize for CPL, SQLs, and pipeline contribution
- Implement and improve tracking, attribution, and reporting frameworks
- Use data to inform targeting, creative, messaging, and landing page improvements
Launch and Optimize Campaign Infrastructure
- Build and optimize landing pages and conversion funnels
- Partner with design to develop high performing creative assets including case studies, webinars, Risk Analysis benchmarking, and more
- Improve website conversion rates and implement cutting-edge solutions to optimize SEO/AEO
Establish Scalable Foundations
- Select and manage marketing technology stack as needed
- Create dashboards and reporting for leadership
- Define benchmarks and growth targets for digital acquisition
Who You Are:
Experience
- 5-8+ years in digital marketing, demand generation, or growth marketing
- Experience at a high growth startup, Series A to C preferred
- Proven track record of driving pipeline and revenue, not just traffic
- Experience owning paid channels with meaningful budget responsibility
Skills
- Deep expertise in performance marketing including Google Ads, LinkedIn, and Meta
- Strong understanding of B2B funnel metrics including MQL, SQL, CAC, LTV, and conversion rates
- Data driven mindset with strong analytical skills
- Experience with attribution and marketing analytics tools
- Ability to operate both strategically and tactically
Mindset
- Builder mentality and comfortable creating structure from scratch
- Highly collaborative and thrives in cross functional partnership
- Experimentation driven and hypothesis oriented
- Accountable for outcomes, not just activity
- Bias toward action in fast paced environments
What Success Looks Like in the First 12 Months
- Established a clear digital acquisition strategy tied to pipeline goals
- Launched and optimized multiple paid channels
- Increased qualified inbound pipeline contribution by a meaningful percentage
- Built scalable reporting and attribution infrastructure
- Became the central glue to orchestrate lead engagement across Paid Ads, Outbound, Direct Mail, and other channels
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:
- Competitive compensation that may include equity
- Flexible paid time off
- Comprehensive benefit plans for medical, dental, vision, life, and disability
- Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA
- Commuter Savings Account
- Human Interest: 401(k) provider
- Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
- Paid Holidays: Observance of all major national holidays
- A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
- Collaborative, transparent, and fun culture
Ready to apply?
Apply to WithCoverage
Workplace and People Operations Associate
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Workplace and People Operations Associate
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.
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
- Make our NYC office run smoothly and feel like a great place to work
- Manage vendors including facilities, cleaning, snacks, and supplies
- Plan and coordinate team events and in-office moments
- Support seating and workspace planning as the team grows
- Handle day-to-day logistics including mail, access, and inventory
Onboarding and Employee Experience
- Own onboarding logistics for all new hires
- Ensure every new hire is set up for success on day one
- Partner with Recruiting and hiring managers to deliver a strong onboarding experience
- Run onboarding sessions and continuously improve the experience
People Operations
- Manage employee data and workflows in Rippling
- Support onboarding and offboarding processes and documentation
- Handle employee requests and employment verifications
- Partner with Finance or vendors to support payroll and bonus inputs
- Maintain employee records including agreements and policies
- Support training programs and track completion
Equipment and Systems
- Coordinate laptop setup and inventory management
- Partner with IT vendors to ensure employees are fully set up
- Maintain clean, organized systems and process documentation
What Success Looks Like
- The NYC office runs smoothly and feels organized, welcoming, and high quality
- New hires have a seamless and thoughtful onboarding experience
- People Operations processes are reliable, clear, and easy to follow
- Employees know where to go for support and get help quickly
You Might Be a Fit If
- You have 2 to 5 years of experience in office operations, HR coordination, or People Ops
- You are highly organized and detail-oriented
- You are a strong communicator and enjoy working with people across teams
- You are comfortable using systems like HRIS platforms and Google Suite
- You are proactive, resourceful, and comfortable in a fast-paced environment
- You have experience with Rippling or a similar HR system
- You have supported onboarding or employee lifecycle processes
- You have worked in a startup or high-growth environment
- If you are the type of person who takes pride in making things run smoothly and creating a great experience for others, you will have a meaningful impact here from day one
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
Ready to apply?
Apply to WithCoverage
Technical Recruiter
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Technical Recruiter
Location: New York
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 first dedicated Technical Recruiter, you will own full-cycle hiring for Engineering, Product, and Data roles, the teams building the proprietary technology that sets WithCoverage apart. You’ll partner directly with engineering and product leaders to attract and close top-tier technical talent in a competitive market, while helping shape scalable recruiting foundations as a key early member of our Talent function.
What You’ll Do:
- Own end-to-end recruiting for Software Engineering, Product Management, Data Science/Engineering, and adjacent technical roles, from intake through offer and close
- Partner with the Head of Talent and technical hiring managers to define role requirements, leveling, and ideal candidate profiles
- Proactively source and engage passive technical candidates using LinkedIn Recruiter, GitHub, Juicebox, and other creative sourcing strategies
- Manage and optimize candidate pipelines in Greenhouse, ensuring an exceptional candidate experience at every stage
- Drive structured interview processes, including scheduling, calibration sessions, feedback collection, and hiring decisions
- Serve as a brand ambassador for WithCoverage, translating our technical roadmap and mission into a compelling narrative for candidates
- Track and report on recruiting metrics (time-to-fill, offer acceptance rate, pipeline health) to continuously improve hiring quality and speed
- Support the development of recruiting processes, scorecards, and best practices as the engineering org scales
Who You Are:
- 3–5 years of full-cycle technical recruiting experience, with a strong focus on Software Engineering, Product, and/or Data roles
- Proven ability to source and close passive technical candidates in a competitive market
- Hands-on experience with LinkedIn Recruiter, Greenhouse, Gem, and Juicebox (or comparable tools)
- Solid understanding of the technical landscape, enough to assess candidate profiles and hold credible conversations about engineering roles and stacks
- Comfortable managing multiple technical requisitions simultaneously in a fast-paced, startup environment
- Strong stakeholder management skills with the ability to influence and partner with engineering and product leaders
- Data-driven and process-oriented, while still being scrappy and adaptable when the situation calls for it
- Passionate about building diverse, high-performing technical teams
- Excited to help build recruiting infrastructure from the ground up at an early-stage company
Preferred (not required):
- Prior recruiting experience within insurtech, fintech, or other regulated industries
- Familiarity with private company equity, building SOPs, and creating ICPs
- Experience using AI or automation tools to improve sourcing or recruiting workflows
This role will be expected to be in our NYC office 4-5 days/week. For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $115,000 – $140,000/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 quota tied annual bonus, and employee benefits.
In addition to cash compensation, WithCoverage offers full-time employees a comprehensive Total Rewards package that includes equity grants.
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
Community & Events Associate
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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:
- 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 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
- Work with our Growth Team to design and execute multi-format events for our core communities
- Own end-to-end event execution: venues, vendors, budgets, production, timelines, RSVPs, and on-site logistics
- Travel from time to time to host, connect, and build relationships in person — serve as a WithCoverage ambassador
Pipeline & relationship building
- Drive event RSVPs and attendance through proactive outbound: cold email, LinkedIn, warm intros, conference outreach
- Build and maintain relationships with prospects, connectors, and partners to grow our event audiences over time
- Coordinate with co-hosts and partners on joint events to extend reach
Community management & onboarding
- Work directly with our Community Lead to build out executive communities focused on our ICP
- Own day-to-day community operations and member experience
- Run new member onboarding end-to-end
- Partner with Growth Team to execute new member growth strategies
Content & storytelling
- Help stand up the early marketing layer for our communities — newsletters, content, social, lifecycle automation
Who You Are
- 2-6 years of relevant experience in community, events, partnerships, field marketing, or BD — ideally at a startup or high-growth B2B company
- Operator first. Diligent, executional, ownership-driven — you run things to completion and don't need to be told twice
- Highly organized project manager. You juggle multiple events in flight, manage vendors and RSVPs, and ensure nothing falls through the cracks
- Polished, articulate, and a natural connector. You're comfortable in rooms with executives, operators, and investors — they should leave feeling welcome and impressed by the caliber of the team behind WithCoverage
- Comfortable with outbound and a sales mentality — cold outreach, prospecting, and treating events as a sales channel
- Experience using a CRM for tracking and reporting; HubSpot a plus
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:
- 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
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
Partnerships Lead
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Partnerships 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:
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
- Own and manage our network of 300+ connectors and key executive relationships as the primary point of contact across the network
- Implement a rigorous process to track, optimize, and performance manage existing connector partners
- Build strong, ongoing relationships to drive consistent introductions and top-of-funnel
Source and Activate New Connector Partners
- Identify high-potential connectors from existing clients, conference attendees, and event networks
- Build pipeline through industry events, conferences, and targeted outreach
- Onboard new connectors and shorten time from first conversation to first referral
Run Partnership Operations and Systems
- Build and implement a structured partnerships workflow
- Set up SOPs including outreach templates, tracking systems, and a central inbox
- Create a repeatable process for managing inbound and outbound partner activity
- Represent WithCoverage at partner-facing events and industry functions
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:
- 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 Associate (Account Executive)
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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:
- 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 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:
- Own the full mid-market sales cycle (discovery → close), partnering closely with a BDR to qualify opportunities and a Risk Management Advisor to drive deals forward with urgency and precision
- Own deep, consultative discovery that goes beyond surface-level needs - diagnosing operational challenges, key risk management exposures, and partnering to form a risk mitigation plan that earns trust and drives conviction
- Lead onboarding for new accounts and set the foundation for long-term success by aligning expectations, mapping timelines, and building trust early
- Nurture and manage your pipeline by proactively sourcing and engaging new prospects through outbound efforts, warm intros, referrals, and strategic networking
- Develop compelling proposals and deal narratives that communicate value, anticipate objections, and move decision-makers toward action
Who You Are:
- 3-8 years of experience in a Sales/AE role
- Client Relationship Management and Sales skills
- Experience in Mid-Market or Enterprise Account Management
- Excellent Communication and Presentation skills
- Ability to work collaboratively and in a team environment
- Experience in the insurance industry is a plus
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:
- 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
Senior Manager - Business Development
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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:
- 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 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
- Define and execute the company’s outbound strategy across segments, industries, and ICPs
- Own top-of-funnel pipeline targets and ensure consistent, high-quality pipeline generation
- Continuously refine targeting, messaging, and channel mix to improve efficiency and conversion
Build & Scale the BDR Organization
- Hire, develop, and lead a team of BDR managers and individual contributors
- Design org structure, capacity planning, and career progression frameworks
- Establish a strong leadership bench and scalable coaching infrastructure
Drive Performance & Operational Excellence
- Set and manage KPIs across the funnel (activity, conversion, pipeline, and revenue contribution)
- Implement reporting systems and dashboards to track performance and inform decisions
- Identify gaps and implement process improvements to increase output and efficiency
Partner Cross-Functionally
- Work closely with Sales leadership to align pipeline quality and revenue goals
- Collaborate with Growth/Marketing on messaging, campaigns, and ICP refinement
- Provide feedback loops from outbound to inform product positioning and GTM strategy
Elevate Messaging & Outbound Effectiveness
- Develop and iterate best-in-class outbound messaging frameworks and playbooks
- Leverage data and experimentation to continuously improve outreach performance
- Ensure consistent execution quality across all outbound channels
Who You Are:
- Experienced leader: Capable Leader: demonstrated excellence in executing top of funnel motions, experience leading BDRs or BDR managers
- Builder mindset: You don't just lead by what the spreadsheets tell you, you get in the weeds and figure things out to develop a scalable, repeatable system and process
- Metrics driven: You understand the KPIs that drive an outbound BDR organization. Strong command of pipeline analytics, funnel metrics, and what great looks like
- Cross-functional influencer: Experience working closely with Sales, Marketing, and executive teams
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
- High standards: You set a high bar for performance, accountability, and culture
- Adaptable & fast-moving: Thrive in high-growth, ambiguous environments
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:
- 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
Software Engineer - Product
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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:
- 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 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:
- Build AI-powered workflows. Design and ship automations that solve real problems using LLMs, our internal agent platform, and whatever tools get the job done. Own the full lifecycle, from prototype to production deployment to ongoing improvement.
- Build for extensibility. Design systems that others can build on top of. Create the abstractions, APIs, and patterns that let risk advisors ship workflow solutions quickly without reinventing the plumbing. Your infrastructure should multiply the team’s output.
- Ship fast, iterate faster. You’re not building a roadmap six months out. You’re identifying problems this week and shipping solutions next week. Move quickly, measure impact, and iterate based on what is actually working for the team.
- Engineer reliable AI systems. Architect agentic systems that work at scale, including multi-step reasoning, structured extraction from unstructured data, and multi-agent coordination. Build evaluation frameworks to measure agent quality, catch regressions, and iterate with confidence.
Who You Are:
- 4+ years of experience building software in production environments, with hands-on experience applying LLMs to real-world problems.
- 2+ years at the same company in a prior role, with demonstrated promotions and recognition.
- You’ve built AI-powered solutions that real users depend on. You understand prompt engineering and the challenges of making AI reliable in production.
- Strong software engineering fundamentals: you write clean code, design sensible systems, and ship consistently.
- High EQ and strong communication skills. You can work closely with non-technical teams, understand their workflows deeply, and translate that understanding into practical solutions.
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:
- 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