Job Description

Technical Recruiter (Founding technical TA hire)

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, Gem, 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, Gem, 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 $100,000 – $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 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

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