GM, Outbound

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:

WithCoverage has 1,000+ customers and has built that almost entirely on word of mouth, warm introductions, and events. That engine works — but it only reaches as far as our network does. The next order of magnitude comes from accounts that have never heard of us.

This role owns Outbound at WithCoverage, end to end: the strategy, the system, and the number. But the mandate is bigger than running channels well. We want to build an AI-first outbound engine — one always-on system that warms our entire TAM, reads intent signals off that engagement, and routes every account into the right conversion motion automatically. Cold email, cold calling, cold social, gifting, and our named-account ABM program stop being five separate programs and become surfaces that one engine acts through.

We're looking for the operator who builds it. Today outbound is several motions at different stages of maturity: a BDR team that produces our largest share of top-of-funnel but hasn't yet cracked cold conversion economics, a young cold email program, and an early ABM push against our top-tier targets. All of it is run by humans, campaign by campaign. Your job is to make them one system, get the funnel math to work, and then let the system scale in a way headcount can't. When this converts profitably, we will invest behind it aggressively.

This is a senior, hands-on role. You own the strategy, the system, and the outcome — and you carry the number.

What You'll Do

• Build the engine, not just the campaigns. Own the architecture above and the roadmap to get there from where we are today. You'll partner closely with Growth Product & Engineering on tooling, signal infrastructure, and data — and you'll be specific about what you need from them.
• Own the always-on awareness layer. The content, the offers, and the cadence that keep our full TAM warm — including the personalized-audit and event-invite plays that earn a reply from accounts with no reason to know us.
• Build the signal layer. Define what counts as intent for a company buying insurance, instrument it, and turn it into account scoring that actually predicts conversion. Getting the signal taxonomy right for our market is the hardest and highest-leverage piece of this job.
• Own conversion end to end. Signal-specific sequences through to closed revenue — tuning conversion at every stage of the funnel, not just the top.
• Run the channels as surfaces of the system. Cold email, cold calling and how the BDR motion plugs in, cold social, gifting, direct mail, and closed/lost re-engagement.
• Run ABM. The high-touch play against named, top-tier target accounts — where the engine's intelligence meets human judgment.
• Put AI agents to work. Decide what gets automated, where a human stays in the loop, and how the system learns from every touch. Push the automation frontier deliberately rather than defaulting to more headcount.
• Integrate with the rest of marketing. Outbound doesn't run in a vacuum — you'll coordinate with brand, paid, events, and lifecycle so targeted accounts get hit from multiple directions.

How You'll Be Measured

ACV of intro calls booked (demos), and the conversion from those calls down the pipeline to closed revenue within our ICP.

Incremental ARR from driving better conversion through existing sales touchpoints.

Engine maturity: share of TAM under always-on nurture, signal → conversion rates by signal type, and how much of our pipeline comes from pre-warmed accounts versus true cold.

Who You Are

• 8+ years in growth, outbound, demand generation, lifecycle or ABM — and you've owned a number, not just a program.
• You've built an outbound or account-based engine from the ground up and scaled it. You know what breaks at each stage and you've fixed it before.
• You think in systems, not campaigns. You've built the thing that runs the plays, not just the plays — and you're energized by an architecture-first mandate.
• You're fluent across channels — email, phone, social, gifting, direct mail, ABM — and opinionated about which ones earn investment and when.
• You've put AI to real work in GTM: personalization, content generation, signal enrichment, agentic sequencing. You have a clear view on where it's genuinely better than a human and where it isn't.
• You think in unit economics. You can build the funnel model, find where conversion is leaking, and tell the difference between a channel that's broken and one that's underfunded.
• You're technical enough to work with Growth Product & Engineering on signal infrastructure and tooling, and specific about what you need from them.
• Senior enough to own strategy, hands-on enough to write the sequence, listen to the calls, and rebuild the play yourself.
• You want the mandate that comes with a channel the company is willing to put real money behind if you make it work.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $200,000 – $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. 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 including equity
• Flexible paid time off
• Comprehensive benefits: medical, dental, vision, life, and disability
• FSAs: Health Care and Dependent Care
• Commuter Savings Account
• 401(k) via Human Interest
• Paid holidays and family/medical leave
• Catered Friday lunches in-office
• Collaborative, transparent, and ambitious culture