Enterprise Account Executive

About Us Gumloop is the multiplayer AI agent builder. We believe the people who know the work best should be able to automate it, and use what they build to help their whole team do more. Anyone at a company can build, share, and optimize agents with any AI model and any integration. Teams can orchestrate those agents across their business, while IT keeps full control over data, access, and spend. We're a small team building as fast as humanly possible. Gusto, Ramp, Shopify, Samsara, Instacart, and Opendoor are running agents on Gumloop across their company. We've raised over $70M from Benchmark, First Round Capital, Y Combinator, Nexus Ventures to scale and are looking for people who care as much as we do to join the team. Here’s what life at Gumloop is like: Our beliefs – The Handbook Our adventures – Wall of Photos What our users are saying - Wall of Love What we’re working on – Changelog Role Overview 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. What You'll Do 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 What You Bring 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 Bonus Experience selling developer tools, automation platforms, or AI products Existing relationships in enterprise technology or IT leadership Benefits 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/RRSP match up to 6%