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.