Sr. Recruiter

Location: New York, NY (Hudson Square, in office 4 to 5 days/week)

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.

As a Sr. Recruiter, you will own full-cycle hiring for Sales, Growth, Product, Risk, and other critical functions. You'll act as a true talent partner to our leaders, bringing the judgment, market knowledge, and closing ability that comes from years of in-house recruiting at high-growth companies. You'll carry our most critical searches, including senior and leadership roles, while helping shape how hiring scales at WithCoverage.

• Own end-to-end recruiting for Sales, Growth, Product, Risk, and other business-critical teams, from intake through offer and close, including senior IC and leadership searches
• Serve as a strategic advisor to the Head of Talent and hiring managers on role design, leveling, compensation, and ideal candidate profiles, pushing back with market data when needed
• Lead proactive, creative sourcing of passive talent using LinkedIn Recruiter, GitHub, Gem, Juicebox, and your own networks, with a focus on candidates from top startups and growth-stage companies
• Pitch and close candidates with confidence, including walking candidates through startup equity (options, vesting, strike price, and how to think about upside) and navigating competing offers
• Manage and optimize candidate pipelines in Greenhouse, ensuring an exceptional candidate experience at every stage
• Design and run structured interview processes, including calibration sessions, interviewer training, feedback collection, and hiring decisions
• Serve as a brand ambassador for WithCoverage, translating our roadmap and mission into a compelling narrative for candidates
• Track and report on recruiting metrics (time-to-fill, pass-through rates, offer acceptance rate, pipeline health), and use them to drive improvements in hiring quality and speed
• Build and refine recruiting processes, scorecards, SOPs, and best practices as the engineering org scales
• Mentor and raise the bar for other members of the Talent team as the function grows

• 5 to 10 years of full-cycle recruiting experience, with the majority spent in-house
• Experience at a startup or growth-stage company, ideally through a period of rapid scaling
• A proven track record of sourcing and closing passive, senior talent in a competitive market
• Comfortable and credible pitching equity, explaining how startup compensation works, and helping candidates evaluate offers
• A sourcer at heart: you enjoy the hunt and don't rely solely on inbound
• Hands-on experience with LinkedIn Recruiter, Greenhouse, Gem, and Juicebox (or comparable tools)
• Strong skillset fluency, enough to assess candidate profiles, hold credible conversations about roles, and earn the trust of candidates and leaders
• Able to manage multiple requisitions simultaneously in a fast-paced environment
• Strong stakeholder management skills with the ability to influence, advise, and push back with hiring managers and executives
• 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

Preferred (not required):

• Recruiting experience within insurtech, fintech, or other regulated industries
• Experience hiring leadership (Manager, Director, or Head of level)
• Experience using AI or automation tools to improve sourcing or recruiting workflows

This role will be expected to be in our Hudson Square office in NYC 4 to 5 days/week. For candidates based in New York City, the pay range for this position at the start of employment is expected to be between $140,000 and $170,000/year. Your exact offer may vary depending on multiple individualized factors, including job-related knowledge, skills, and experience. Total compensation for this position may also include equity, an annual bonus, and employee benefits.

In addition to cash compensation, WithCoverage offers full-time employees a comprehensive Total Rewards package that includes equity grants.

• 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)
• 401(k) through Human Interest
• 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
• A collaborative, transparent, and fun culture