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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.

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:

We are looking for a strategic, hands on Digital Marketing Lead to architect and execute our digital lead generation strategy.

This is a foundational hire. You will partner closely with our Growth Leads, BDR, and Community teams to generate high quality inbound pipeline and create repeatable, scalable acquisition channels.

You will own digital marketing end to end, from strategy and experimentation to execution and optimization, with a clear focus on pipeline generation and revenue impact.

If you are excited about building from zero, testing fast, and driving measurable growth at a scaling company, this role is for you.

What You’ll Do:

Build the Digital Demand Engine

• Develop and execute our digital marketing strategy aligned to pipeline and revenue goals Identify, test, and scale high performing acquisition channels including paid search, paid social, display, and retargeting.
• Build a structured experimentation roadmap with clear hypotheses and success metrics

Drive Pipeline for Growth Teams

• Partner with Growth Leads to align campaigns to ICPs, verticals, and priority segments
• Support BDR with campaign driven lead flows and nurture strategies
• Collaborate with Community to amplify programs, events, and partnerships digitally

Own Performance and Optimization

• Manage paid media budgets and optimize for CPL, SQLs, and pipeline contribution
• Implement and improve tracking, attribution, and reporting frameworks
• Use data to inform targeting, creative, messaging, and landing page improvements

Launch and Optimize Campaign Infrastructure

• Build and optimize landing pages and conversion funnels
• Partner with content to activate high performing assets including case studies, webinars, and thought leadership
• Improve website conversion rates through CRO best practices

Establish Scalable Foundations

• Select and manage marketing technology stack as needed
• Create dashboards and reporting for leadership
• Define benchmarks and growth targets for digital acquisition

Who You Are:

Experience

• 5-8+ years in digital marketing, demand generation, or growth marketing
• Experience at a high growth startup, Series A to C preferred
• Proven track record of driving pipeline and revenue, not just traffic
• Experience owning paid channels with meaningful budget responsibility

Skills

• Deep expertise in performance marketing including Google Ads, LinkedIn, and Meta
• Strong understanding of B2B funnel metrics including MQL, SQL, CAC, LTV, and conversion rates
• Data driven mindset with strong analytical skills
• Experience with attribution and marketing analytics tools
• Ability to operate both strategically and tactically

Mindset

• Builder mentality and comfortable creating structure from scratch
• Highly collaborative and thrives in cross functional partnership
• Experimentation driven and hypothesis oriented
• Accountable for outcomes, not just activity
• Bias toward action in fast paced environments

What Success Looks Like in the First 12 Months

• Established a clear digital acquisition strategy tied to pipeline goals
• Launched and optimized multiple paid channels
• Increased qualified inbound pipeline contribution by a meaningful percentage
• Built scalable reporting and attribution infrastructure
• Became a trusted strategic partner to Growth Leads, BDR, and Community

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $150,000 – $200,000/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 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