Chief of Staff to the Founder & CEO

About our client

At Outmarket, they are transforming how the $1T commercial insurance industry works. Their AI-powered platform helps brokers, MGAs, and carriers unlock insights from messy data and automate complex workflows. They are backed by top investors, already serving forward-thinking agencies, and on track for rapid growth.

They are now hiring a Chief of Staff to work directly with their 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 They’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
• Salary: $120k - $140k + performance
• Benefits: Great gear, equity plan, team retreat, modern tools, flex schedule, unlimited PTO and growth budget