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Chief of Staff to the Founder & CEO

Outmarket.AI

Outmarket.AI

People & HR, Operations
San Francisco, CA, USA
Posted on Jun 3, 2025

At Outmarket, we’re transforming how the $1T commercial insurance industry works. Our AI-powered platform helps brokers, MGAs, and carriers unlock insights from messy data and automate complex workflows. We’re backed by top investors, already serving forward-thinking agencies, and on track for rapid growth.
We’re now hiring a Chief of Staff to work directly with our Founder & CEO, Vishal —a repeat entrepreneur and product leader from Uber, Meta, and Ethos. This is a rare opportunity to operate at the heart of a high-growth company and help scale strategy, execution, and impact from day one.Why This Role Is Special

  • Work side-by-side with the Founder & CEO across product, GTM, fundraising, hiring, and ops

  • Serve as the connective tissue across leadership, investors, customers, and partners

  • Step into a high-trust role that gives you unmatched visibility into every part of the business

  • Learn how a fast-scaling startup is built from the inside, with exposure to top-tier investors and strategic customers

What You’ll Own

  • Drive high-priority strategic initiatives from concept to execution

  • Prepare materials for investors, board meetings, and enterprise customers

  • Partner with Vishal on fundraising, investor updates, and external communication

  • Coordinate across product, sales, and ops to ensure the right things get done

  • Build internal processes to scale a 0 to 1 to 100 company

  • Be a trusted thought partner on critical decisions

What We’re Looking For

  • 3–6 years of experience in founder’s office, strategy, consulting, venture, or startup operating roles

  • Exceptional project management and communication skills

  • Bias for action, clear thinking, and ruthless prioritization

  • Ability to quickly learn and context-switch across domains

  • Hungry to grow fast, take on new challenges, and operate without ego

Bonus If You Have

  • Startup or SaaS operating experience

  • Exposure to insurance, fintech, AI, or data platforms

  • Experience supporting GTM, fundraising, or customer strategy

What You’ll Get

  • A seat at the table on the founding team

  • Daily exposure to top investors, customers, and executives

  • Competitive compensation and meaningful equity

  • A front-row view into how a high-growth AI startup is built

  • Remote-friendly, high-trust culture focused on outcomes, not politics

How to Apply
Email your resume or LinkedIn profile to careers@outmarket.ai
Include a short note on why you want to be Chief of Staff at Outmarket and how you can help scale the business.