Founding Account Executive

The Mission

The E&S insurance market is a $100B+ industry running on systems designed before the internet. Every policy requires dozens of complex decisions and hundreds of steps. While others try to patch the existing system with basic automation, we're building something fundamentally different: an intelligent system where humans and AI seamlessly collaborate to execute complex workflows at unprecedented speed, turning two-week processes into hours.

You're Our Person If

• You're a hardcore closer who can sell ice to an eskimo, but you're also obsessed with building scalable, automated sales systems
• You transform sales processes rather than follow them, making teams 10x more effective
• You excel at leveraging AI for sales - from crafting the perfect pitch with AI assistance to building automated lead generation and qualification workflows
• You bridge the gap between manual sales efforts and automation, using AI strategically while permanent solutions are developed
• You measure success by deals closed and revenue generated, not hours worked
• You think in first principles and build complex sales systems in one-third the normal time
• You're comfortable throwing everything away and starting from scratch when needed
• You can look at complex sales workflows that "experts" say can't be improved, see through to the core problems, and build solutions at a speed that makes others uncomfortable
• Ex-founders with experience building and scaling sales teams are a huge plus
• While you will be selling insurance products to businesses, you are not expected to be an insurance expert on Day 1. The qualities we’ve listed here are the core of the role - we will teach you the rest

Hard Requirements

• Must be in San Francisco during YC W25 batch (Jan-March 2025)
• Long term: Based in San Francisco or New York
• Proven track record of building and running high-performance sales at unprecedented speed
• Experience turning sales intuition and decision-making into scalable automated systems
• Comfort with high-velocity environments where everything changes daily
• Working in insurance requires certain licenses you will be expected to obtain within the first 90 days

In Your First Two Weeks, You'll

• Master our core sales playbook by end of week 1 - you'll be the closer driving our revenue
• Use AI to eliminate 95% of friction from lead-to-close workflow
• Identify critical sales bottlenecks and launch first AI-human workflow for throughput improvement
• Take ownership of key accounts while testing new AI-assisted sales techniques
• Be ready to adapt or rebuild the playbook from scratch as we learn

By weeks 3-4, You'll

• Design sales systems for rapid expansion into new insurance lines
• Create and deploy AI-human sales workflows that transform conversion rates
• Build scalable sales processes that don't require additional headcount
• Work closely with engineering to test AI solutions and provide rapid feedback
• Bridge the gap with AI sales tools until permanent automation is built

Your Domain & Impact

You'll both close deals tactically and transform the core of our sales engine:

• Sales Strategy: Design and run intelligent workflows that optimize how we sell and collaborate with insurance carriers
• Sales Playbooks: Build and continuously enhance our sales playbooks, leveraging AI to make them smarter and more efficient
• Sales Automation: Create and manage scalable AI-assisted sales systems that allow us to close more deals faster

How We Execute

• Make Requirements Less Dumb: Question everything. If someone says "that's how insurance sales works," that's exactly where we start
• Delete the Process Step: The fastest sales process is no process. Every step must justify its existence
• Optimize: Make it smarter. If AI can help close the deal better, it should
• Accelerate: Speed compounds. What can be closed in a day should be closed in an hour
• Automate: Transform sales intuition into AI systems that scale

Our Operating Philosophy

• "Move fast. Break things. Fix them faster."
• "Strong opinions, loosely held"

Join as an Owner, Not an Employee

But here's what really matters - we're building something that could transform a $100B+ industry, and we want the person who takes this role to be a true architect and owner of this transformation. Your equity package will reflect your role as a core builder who's fundamentally reshaping how insurance is sold.

We're looking for someone who sees this role not as a job, but as an opportunity to build and own the future of insurance sales. If you're comparing base salaries at tech companies, you're thinking too small. This role is for someone who understands that the real upside comes from building and owning revolutionary sales systems that could transform an entire industry.

Think like an owner because you will be one. If you're primarily optimizing for cash compensation, we're probably not the right fit. If you're excited about building something massive, seeing your sales innovations drive real change, and owning a meaningful piece of what we're building - let's talk.