Sr. Recruiter

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.

About The Role

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.

What You'll Do

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

Who You Are

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

Compensation

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.

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)

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