Founding Account Executive (AI Cloud)

Featherless AI; Toronto; On-site; CAD 250,000 - 333,000; Full time

Benefits offered by this job

Competitive base + commission

Job summary

Featherless.ai is building a premier AI cloud platform and seeks an Account Executive to own deals end-to-end. You will engage developers, ML engineers, CTOs, and executives, closing enterprise and scale-up opportunities while shaping the commercial motion at a Series A company.

You will work directly with the CRO and founders, build lasting executive relationships, and help define repeatable GTM motions in a fast-moving open-model AI space.

Qualifications

• 3–6 years closing enterprise deals in cloud or AI tooling.
• Proven track record closing deals with technical buyers.
• Experience navigating multi-stakeholder enterprise cycles.

Responsibilities

• Run full-cycle sales across mid-market and enterprise segments.
• Lead discovery and technical demo calls tailored to buyer's stack and use-case.
• Develop custom 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 opportunities.
• Use AI tools to automate research, outreach and workflow efficiency.
• Maintain clean CRM hygiene in HubSpot with accurate pipeline.
• Collaborate with product and engineering to share field feedback.
• Mentor BDRs and help define pipeline quality.

Skills

Closing deals

Technical buyers engagement

Enterprise sales cycles

CRM forecasting

Technical communication

Self-driven

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 are 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 is 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