AI Cloud Enterprise Account Executive (Founding Role)

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

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.