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 outstanding 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

📌 Founding Account Executive (AI Cloud) (Winnipeg)
🏢 Featherless AI
📍 Winnipeg