Pibit.ai is an SF-based insurtech company reconstructing the art and science of commercial underwriting for carriers and MGAs.
At the heart is the CURE™ platform, the industry's only centralized underwriting risk
environment powered by agentic underwriting services that deliver decision ready outcomes.
It converts submissions into decisions by automating intake, triage, and data enrichment
from documents and external sources while surfacing risk insights that help customers win
the right accounts faster, scale throughput, and reduce loss ratios.
Backed by Y Combinator, our proprietary platform serves dozens of clients across the U.S.,
enabling 85% faster underwriting, a 32% increase in GWP per underwriter, and up to 700
basis points improvement in loss ratios.
For details, visit pibit.ai.
Role Overview
The Chief of Staff to the CEO is a high leverage, high visibility role designed to serve as the extended arm of the CEO across all critical company functions - AI,Technology, Product, Sales, Operations, Marketing
This is not a coordination only role. You will be a hands on problem solver, strategic thinker, cross functional orchestrator, and enabler of founder alignment. You will operate with the authority and context of the CEO, diving deep into business challenges, driving execution discipline, and ensuring organizational clarity and momentum
This is the first Chief of Staff role at Pibit.AI, making it a unique opportunity to shape the Founder's Office function from the ground up and become a critical architect of our operational excellence as we grow
Key Responsibilities
- Act as the CEO's problem solving arm on complex, multi team challenges.
- Convert CEO priorities into task clarity, execution plans, and measurable outcomes.
- Prepare the CEO for high leverage decisions with analysis, insights, briefs, and recommendations.
- Represent the CEO in selected internal/external conversations when required.
- Run leadership syncs, founder reviews, and company wide OKR check ins.
- Build systems for tracking execution, accountability, risks, and blockers.
- Design processes, cadences, and mechanisms that keep teams aligned, fast, and focused.
- Own high stakes problems end to end (hands on).
- Work with functional heads to clarify priorities and accelerate outcomes.
- Drive alignment between Sales, Product, Tech, AI, Ops
- Identify operational bottlenecks and design solutions that scale.
- Ensure decisions, priorities, and blockers flow smoothly across geographies.
- Drive asynchronous execution culture with clarity and speed.
iExperience & Background
- 5–8 years of professional experience in high-growth B2B startups, management consulting (Tier 1 firms), or strategic operations roles or Ex - founders
- Proven track record of operating in fast-paced, ambiguous, 0-to-1 or scaling environments.
- Direct experience working closely with founders or C-suite executives in a strategic capacity (Chief of Staff, Strategic Operations, Founder's Office, or similar).
- Business acumen: Strong understanding of B2B SaaS business models.
- Cross-functional fluency: Comfortable navigating and contributing across Sales, Product, Engineering, Operations, Marketing, and Finance.
- Problem-solving mindset: Ability to take on complex, multi-dimensional problems, break them down, and drive to resolution without handholding.
- Execution excellence: Track record of owning initiatives end-to-end, driving accountability, and delivering results on time
- Insurance or InsurTech domain experience: Familiarity with commercial insurance, underwriting workflows, carriers, MGAs, or broker ecosystems is a strong advantage.
