Founding Account Executive (AI Cloud)

Featherless AI; Toronto; On-site; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Competitive base + commission

Job summary

Featherless AI is hiring an Account Executive (AI Cloud) to own deals end-to-end—from discovery to closing—with CTOs, ML leads, and infrastructure decision-makers. You'll shape the commercial motion at a fast-moving Series A AI company and build a repeatable GTM engine.

You will run full-cycle sales across mid-market and enterprise segments, negotiate complex agreements, and partner with CRO and founders to scale growth. Competitive base + commission, open-model AI platform.

Qualifications

• 3–6 years closing in Cloud Infrastructure, MLOps, or AI tooling.
• Proven track record closing deals with developers, ML engineers, CTOs.
• Experience navigating multi-stakeholder enterprise sales cycles.
• Strong written and verbal communication, technically literate.
• Entrepreneurial and self-driven with data-driven pipeline management.

Responsibilities

• Run full-cycle sales across mid-market and enterprise segments.
• Lead discovery and technical demos tailored to buyer's stack and use case.
• Develop proposals and business cases connecting model inference needs to Featherless capabilities.
• Negotiate and close complex, multi-stakeholder deals.
• Expand revenue within existing accounts with upsell/cross-sell opportunities.
• Maintain CRM rigor and accurate forecasting and pipeline reporting.
• Collaborate with product/engineering to share field feedback.

Skills

Cloud sales

Enterprise sales

MLOps

Technical buyers

CRM

HubSpot

Forecasting

Tools

HubSpot

Clay

Claude/ChatGPT

Job description

About FeatherlessFeatherless.ai is building the world's most reliable open-model inference platform — a serverless foundation for deploying and scaling AI without infrastructure overhead.

About FeatherlessFeatherless.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 RoleWe'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

Compensation Range: $180K - $240K