Founding Account Executive (AI Cloud)

Founding Account Executive (AI Cloud) Featherless AI Boston, MA Job Details Full-time 12 hours ago Qualifications Deal closing Pricing Sales revenue Forecasting Sales proposal development Sales reporting Upselling Enterprise selling Client relationship development Cross-selling Proposal writing Entrepreneurship Sales experience within tech Mentoring Product demos Sales pipeline management CRM system proficiency Senior level AI Go-to-market strategy Communication skills MLOps Stakeholder relationship building Cloud services Stakeholder management Full Job Description 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 30,000+ 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 pre-Series A company — this is for you. What You'll Own Immediately Carry and close a pipeline of enterprise, 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 develop pricing strategies, deal structures, and expansion playbooks Partner with BDR and DevRel on pipeline generation and ecosystem-driven sourcing 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 DevRel and Product on feedback loops 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, n8n, 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 founders and 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