Founding Account Executive (AI Cloud)

Title: Founding Account Executive (AI Cloud) Location: Remote (US & Canada) ABOUT FEATHERLESS Featherless.ai is building the world's most reliable open-model inference platform — a serverless foundation for deploying and scaling AI without infrastructure overhead. Backed by AMD, Airbus Ventures, 500 Global, Kickstart Ventures, HF0 Residency, Panache Ventures, and Oakseed Ventures, we're a well-funded team of researchers and engineers on a mission to democratize AI through performance and accessibility. Our cloud provides instant access to 40,000+ open-source AI models and the research innovations powering next-generation efficiency, reliability, and model optimization. ABOUT THE ROLE We're looking for an experienced Account Executive (AI Cloud) — someone who owns deals end-to-end, builds lasting relationships with technical buyers, and thrives in the early-stage chaos of a fast-moving AI company. This is a full-cycle sales role. You'll carry quota, close enterprise and scale-up deals, and help shape the commercial motion at a company that's redefining how AI teams deploy open-source models. You'll work directly with the CRO and founders, engage deeply with developers, ML engineers, and CTOs, and play a central role in building a repeatable GTM engine. If you're a self-starter who loves technical sales, enjoys working at the frontier of AI infrastructure, and wants outsized impact and ownership at a Series A company — this is for you. WHAT YOU'LL OWN IMMEDIATELY - Build and close a pipeline of scale-up and high-growth startup accounts - Own deals from first contact through signed contract — discovery, demo, proposal, negotiation, close - Build and maintain executive-level relationships with CTOs, ML leads, and infrastructure decision-makers - Work with the CRO to refine acquisition and expansion playbooks - Partner with BDR and DevRel on pipeline generation - Maintain CRM rigor and deliver accurate forecasting and pipeline reporting - Represent Featherless at industry events and conferences to generate and advance deals CORE RESPONSIBILITIES - Run full-cycle sales across mid-market and enterprise segments - Lead high-quality discovery and technical demo calls tailored to each buyer's stack and use case - Develop custom proposals and business cases that connect model inference needs to Featherless capabilities - Negotiate and close complex, multi-stakeholder deals - Expand revenue within existing accounts — identify upsell and cross-sell opportunities - Use AI tools extensively to automate research, outreach personalization, and workflow efficiency - Maintain clean CRM hygiene in HubSpot — all activity logged, pipeline stages accurate - Collaborate with product and engineering to share feedback from the field - Mentor BDRs and help define what great pipeline looks like WHAT YOU BRING - 3–6 years in a closing role in Cloud Infrastructure, MLOps, or AI/developer tooling - Proven track record closing deals with technical buyers (developers, ML engineers, CTOs) - Comfortable navigating multi-stakeholder enterprise sales cycles - Strong written and verbal communication — concise, credible, technically literate - Entrepreneurial and self-driven — you build your own process and don't wait for a playbook - Disciplined forecaster with clean CRM habits and a data-driven approach to pipeline management - Familiar with HubSpot, Clay, Claude/ChatGPT or equivalent tools WHY FEATHERLESS - Build out the AE function at a company growing in one of the fastest-moving spaces in AI - Work directly with the CRO — your wins shape the company's trajectory - Be part of a small, high-performing team making open weight AI accessible to everyone - Competitive base + commission