Head of Sales

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.

Why Join Us:

• Grow Faster – This role is for someone who wants to build a generational revenue organization in a $1T market and is comfortable being held accountable for outcomes. You will be responsible for building a team that can close a 9-figure total contract value book and add thousands of accounts per year.
• Frontlines of Applied AI – Rewrite the playbook of one of the largest, slowest-moving markets, insurance. Sell and scale a product where human risk advisors and AI agents work together. Build a sales org that is AI-native from day one: instrumentation, call intelligence, pipeline analytics, automated follow up, and agent-assisted prospecting.
• Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
• Financial Rewards – We hire the best and invest in you. That means compelling comp, meaningful equity, and great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.

About The Role:

As our Head of Sales, you will own the next stage of growth for our sales org while helping close the largest opportunities (player + coach role). We partner with mid-market and enterprise businesses as their AI-Enabled Risk Management Team. This requires developing a deep level of trust, showing a relentless amount of care for our prospective clients, handling their objectives, outlining thoughtful implementation plans etc. You’ll lead by example, developing best practices and then leveling up the entire team. 

You’ll set up systems to oversee the rest of the team, train them, and be consistently joining their most complex deals to help support. If you love high-stakes selling, enjoy building teams, and want a seat at the table shaping GTM, this role is for you.

What You’ll Do:

Close Big Deals (Player, First)

• Personally lead and close our largest, most complex opportunities.
• Understand how we win by doing it yourself. Then productize the processes and playbooks so you can coach the team. 

Level Up the Team (Coach, Second)

• Coach the team in live deals—not after the fact—through call participation, real-time feedback, and structured deal reviews.
• Build a culture of elite execution: high standards, crisp follow-through, and “how we win” discipline.
• Run weekly pipeline / forecast reviews focused on improving deal quality and closing behavior.

Scale the Sales Engine

• Build a world class growth team – you’ll be responsible for recruiting, training, and execution. You’ll partner directly with the CEO.
• Set the standard for excellence in all our communications with prospective clients.

Who You Are:

• 6+ years in B2B sales with a proven record of closing large, complex deals (mid-market or enterprise).
• A true player-coach: you’ve led teams and carried a number where you were still one of the top closers.
• Systems-minded: you’ll set up clear protocols across a fast growing team and constantly improve processes
• Strong executive presence with CFO/CEO-level buyers; credible, sharp, and consultative.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $250,000 - $350,000. 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