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Featherless AI

Founding Account Executive (AI Cloud)

Reposted 21 Days Ago
In-Office or Remote
Hiring Remotely in Canada
Mid level
In-Office or Remote
Hiring Remotely in Canada
Mid level
The Account Executive will manage the full sales cycle for enterprise and scale-up accounts, building relationships with technical buyers and collaborating closely with senior leadership to drive revenue and shape sales strategies.
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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 30,000+ 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.

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
  • Carry and close a pipeline of enterprise, 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 develop pricing strategies, deal structures, and expansion playbooks

  • Partner with BDR and DevRel on pipeline generation and ecosystem-driven sourcing

  • 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 DevRel and Product on feedback loops 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, n8n, 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 founders and 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

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