Founding Account Executive (AI Cloud)

Featherless AI; Orlando (FL); On-site; USD 90,000 - 150,000; Full time

Benefits offered by this job

Competitive base salary

Commission

Small, high‑performing team

Job summary

Featherless AI is seeking an Account Executive (AI Cloud) in Orlando to own deals end‑to‑end, build relationships with CTOs and ML leads, and drive growth for an open-model inference platform. You’ll work closely with the CRO and founders in a fast‑moving startup, closing enterprise and scale‑up opportunities.

You will manage discovery, demos, proposals, and negotiations while shaping the commercial motion. This role offers ownership, quota responsibility, and a competitive base plus commission.

Qualifications

• 3–6 years closing role in Cloud Infrastructure, MLOps, or AI tools
• Proven track record closing with technical buyers (developers, ML engineers, CTOs)
• Comfort navigating multi-stakeholder enterprise sales cycles
• Strong written and verbal communication, technically literate

Responsibilities

• Run full‑cycle sales across mid‑market and enterprise segments
• Lead discovery and technical demos tailored to buyer’s stack
• Develop custom proposals and business cases for model inference needs
• Negotiate and close complex multi‑stakeholder deals
• Expand revenue within existing accounts with upsell opportunities
• Maintain CRM rigor and accurate pipeline reporting
• Represent Featherless at industry events to advance deals

Skills

Closing deals

Enterprise sales

Technical buyers

CRM proficiency

Forecasting

Tools

HubSpot

Clay

Claude/ChatGPT

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 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.

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