Temporary Challenger 350 Pilot Jobs (NOW HIRING)

Gumloop is seeing massive enterprise adoption — Shopify, Instacart, DoorDash, and Ramp are rolling out company-wide, all through pure word of mouth. We’re bringing on a seasoned Account Executive to navigate our largest enterprise deals and go after hundreds of product-qualified leads. This is a greenfield opportunity at a category-defining moment in AI automation.

• Own the entire sales process from prospecting to close for Fortune 1000 companies with deal sizes in the six to seven figure range, navigating complex multi-stakeholder environments across procurement, legal, security, and executive functions to drive deals forward with urgency and precision.

• Build and maintain a healthy pipeline of strategic opportunities by outbounding to target accounts, partnering with SDRs to develop account strategies and execute outreach, and qualifying opportunities rigorously to ensure only the right prospects enter the funnel.

• Run high-converting pilots and POCs that clearly demonstrate business value and create the foundation for enterprise-wide rollouts, experimenting continuously with tactics and approaches to remove friction, accelerate deal velocity, and close with confidence.

• Forecast consistently and accurately to give leadership clear visibility into the pipeline, while acting as a brand ambassador and trusted advisor who evangelizes Gumloop and brings automation best practices and strategic insights to every customer conversation.

• Help build the sales machine from the ground up — developing playbooks, processes, materials, and templates — while capturing customer feedback and partnering closely with product to help shape Gumloop’s roadmap.

• 5+ years of enterprise SaaS sales experience with a consistent track record of closing large deals.

• Experience selling into complex organizations with long sales cycles.

• Consultative approach — you listen first, understand the problem, then solve.

• Comfort operating in a fast-moving, early-stage environment with limited process.

• Experience selling developer tools, automation platforms, or AI products.

• Existing relationships in enterprise technology or IT leadership.

• Highly competitive salary and meaningful equity.

• Generous paid time off: 24 days for SF employees and 20 days globally, use them as you need.

• $350/month wellness benefit to spend on gym, spa, equipment, or whatever keeps you at your best.

• 15 days of temporary remote work flexibility per year.

• 401k match up to 6%.