Founding Operations Lead

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 both an operator and architect - running today's processes while building tomorrow's systems
• You transform processes rather than follow them, making teams 10x more effective
• You excel at AI integration - from prompt engineering for tactical operations to working with engineering to build AI agent workflows
• You bridge the gap between manual operations and automation, using AI strategically while permanent solutions are developed
• You measure success by problems eliminated, not hours worked
• You think in first principles and build complex systems in one-third the normal time
• You're comfortable throwing everything away and starting from scratch when needed
• You can look at complex workflows that "experts" say can't be improved, see through to the core problems, and build solutions at a speed that makes others uncomfortable

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 complex systems at unprecedented speed
• Experience turning human decision-making into scalable automated systems
• Comfort with high-velocity environments where everything changes daily

Indicative Weekly Targets

In your first two weeks, you'll:

• Master our core operations by end of week 1 - you'll be the operator driving our business
• Use AI to eliminate 95% of friction from lead-to-binding workflow
• Identify critical bottlenecks and launch first AI-human workflow for throughput improvement
• Take ownership of sales and payment operations while testing new AI solutions
• Be ready to adapt or rebuild from scratch as we learn

By weeks 3-4, you'll:

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

Your Domain & Impact

You'll both operate tactically and transform the core of our brokerage:

• Sales Operations: Design and run intelligent workflows that optimize both how we sell and how we work with insurance carriers
• Payment Operations: Build and operate frictionless payments for the complex flow of insurance premiums
• Customer Operations: Create and manage scalable systems that turn us into a true risk manager for our clients providing near instant customer service

How We Execute

1. Make Requirements Less Dumb: Question everything. If someone says "that's how insurance works," that's exactly where we start
2. Delete the Process Step: The fastest process is no process. Every step must justify its existence
3. Optimize: Make it smarter. If AI can do it better, it should
4. Accelerate: Speed compounds. What can be done in a day should be done in an hour
5. Automate: Transform human expertise 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

Base compensation for the Operations Lead role ranges from $75-150K depending on your experience:

• Early Career (1-2 years): $75-100K
• Mid-Level (3-5 years): $100-125K
• Senior (6+ years): $125-150K

But here's what really matters - we're building something that could transform a $100B+ industry, and we want our Operations Lead 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 operations work.

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 operations. 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 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 operational innovations drive real change, and owning a meaningful piece of what we're building - let's talk.