Founding Account Executive (AI Cloud)

Featherless AI•Toronto, ON

About The Position

Featherless.ai is seeking an experienced Account Executive (AI Cloud) to own deals end-to-end, build relationships with technical buyers, and contribute to the growth of a fast-moving AI company. This full-cycle sales role involves carrying a quota, closing enterprise and scale-up deals, and shaping the commercial strategy. The position reports directly to the CRO and founders, requiring deep engagement with developers, ML engineers, and CTOs. The ideal candidate is a self-starter passionate about technical sales, AI infrastructure, and making a significant impact at a Series A company.

Requirements

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

Responsibilities

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
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