Special Projects Lead
Job description
About the role
This position works directly with the CEO on the hardest problems in the business, embedding within every substantive layer of the organization including business operations, growth initiatives, strategic projects, investor materials, M&A diligence, and emergent crises that define the weekly agenda. The hire owns the undefined and volatile workstreams where success is not prescribed by a manual but discovered through rigorous judgment and rapid experimentation. They are responsible for converting opaque founder intent into coordinated execution across underwriting, operations, and commercial teams while maintaining clarity for external stakeholders. The role is designed for someone who thrives on extreme ownership, where the problems are ambiguous, the stakes are existential, and the pace mirrors the growth trajectory of a company compressing years of evolution into months. Performance in this position materially accelerates the transition from a startup mode to a scaled commercial insurance powerhouse, directly influencing the company's trajectory from tens of millions to hundreds of millions in premium. The successful candidate will develop a deep, systemic understanding of the entire business, gaining exposure to strategy, finance, product, and carrier relationships that is rare even at much more senior levels. If the work is performed at the expected level, the role will organically evolve, potentially into running a critical function, acting as a true right-hand to leadership, or providing the foundation to launch a new venture.
Key facts
What you'll do
Take the CEO's hardest problems directly, with unrestricted access to every critical domain where the company's success is determined, adapting to a shifting weekly agenda that reflects immediate business needs.
Build 0-to-1 systems from scratch, specifically reimagining underwriting operations, customer experience, and risk evaluation by leveraging AI to automate and replace historically manual brokerage workflows.
Conduct deep analysis of customer interactions, underwriting requirements, and operational workflows to identify systemic patterns that lift conversion rates and increase throughput efficiency.
Bridge the gap between engineering, operations, and growth by translating raw customer needs and market realities into precise product requirements and iterative improvements.
Own problems end-to-end, moving from initial data gathering and system mapping through constraint identification, solution proposal, experimentation, and driving the work to a completed state.
Coordinate and lead cross-functional initiatives that require rapid alignment and high-quality output from engineering teams, carrier partners, underwriters, and direct customer feedback.
Construct the intelligence layer of the business, creating dashboards, metrics frameworks, and reporting systems that surface the truth about throughput, efficiency, and commercial viability.
Operate with extreme ownership in a high-intensity environment, managing early morning starts and late finishes to navigate the complex reality of building a company that is replacing a trillion-dollar industry.
Maintain clarity and communication under conditions of constant change, where the scope is intentionally undefined and the ability to adapt determines the value delivered to the company.
Act as the primary integrator of information, distilling complex, ambiguous situations into clear narratives and decisions that allow the executive team to move with speed and confidence.
Requirements
Possess raw analytical horsepower, demonstrating the ability to think in systems and deconstruct complex problems into manageable, actionable components.
Exhibit a bias toward action, consistently choosing movement and execution over hesitation, particularly when facing incomplete information or high-stakes uncertainty.
Display resilience and comfort with complexity, remaining energized and focused when navigating intricate operational and commercial challenges rather than becoming rattled.
Bring a background forged in high-intensity analytical or operational roles within investment banking, management consulting, private equity, or equivalent high-growth startup environments where performance is relentlessly measured.
Thrive under pressure with a proven track record of delivering critical outcomes even when resources are constrained and timelines are aggressive.
Be based in San Francisco or be prepared to relocate immediately to meet the on-site, five-day-a-week schedule that defines the company's operating rhythm.
Demonstrate exceptional written and verbal communication skills, essential for coordinating across carriers, underwriters, engineers, and C-suite stakeholders.
Show the capacity to operate autonomously, managing multiple shifting priorities and context-switching effectively without sacrificing the quality of output.
Nice to have
Prior experience within insurance, fintech, or other regulated industries where complex compliance and commercial dynamics intersect.
Previous work directly alongside founders or C-suite executives in fast-paced, high-stakes environments.
Familiarity with AI and automation tooling that can be leveraged to rapidly prototype and deploy solutions.
Hands-on prior startup experience or a track record of building something from a blank slate (0-to-1).
Practical notes
The schedule requires Monday-Friday work with very early morning start times and in-office presence five days a week in San Francisco.
Travel is not a formal requirement of the role, though the position may involve engagement with carriers, partners, and customers as dictated by critical business initiatives.
Visa sponsorship is not indicated in the provided source information; candidates must confirm eligibility to work in the United States.
The day-to-day reality involves banking-analyst intensity with higher stakes, requiring resilience and adaptability to a scope that never fully settles.
Candidates who romanticize working with the CEO should understand that this involves accountability, ownership of outcomes, and exposure to the full complexity of running a business at speed.
The compensation package includes salary, performance bonuses, and equity, aligned with the expectation of exceptional contribution and impact.
The successful candidate will have the opportunity to define the future of the company's operations and strategy, with the potential to transition into roles of greater scope and responsibility as the business scales.
The intellectual reward of solving deeply intertwined business problems with direct influence on a trillion-dollar industry transition is the primary motivator for this position.