About Featherless
Featherless.
Ai is building the world U2019s 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 U2019re a well-funded team ofresearchers 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 U2019re 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 quick-moving AI company.
This is a full-cycle sales role. You U2019ll carry quota, close enterprise and scale-up deals, and help shape the commercial motion at a company that U2019s redefining how AI teams deploy open-source models. You U2019ll 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 U2019re 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 U2019ll Own Immediately
Build and close a pipeline of scale-up and high-growth startup accountsOwn deals from first contact through signed contract — discovery, demo, proposal, negotiation, closeBuild and maintain executive-level relationships with CTOs, ML leads,



and infrastructure decision-makersWork with the CRO to refine acquisition and expansion playbooksPartner with BDR and DevRel on pipeline generationMaintain CRM rigor and deliver accurate forecasting and pipeline reportingRepresent Featherless at industry events and conferences to generate and advance dealsCore Responsibilities
Run full-cycle sales across mid-market and enterprise segmentsLead high-quality discovery and technical demo calls tailored to each buyer U2019s stack and use caseDevelop custom proposals and business cases that connect model inference needs to Featherless capabilitiesNegotiate and close complex, multi-stakeholder dealsExpand revenue within existing accounts — identify upsell and cross-sell opportunitiesUse AI tools extensively to automate research, outreach personalization, and workflow efficiencyMaintain clean CRM hygiene in HubSpot — all activity logged, pipeline stages accurateCollaborate with product and engineering to share feedback from the fieldMentor BDRs and help define what great pipeline looks likeWhat You Bring
3–6 years in a closing role in Cloud Infrastructure, MLOps, or AI/developer toolingProven track record closing deals with technical buyers (developers, ML engineers, CTOs)Comfortable navigating multi-stakeholder enterprise sales cyclesStrong written and verbal communication — concise, credible, technically literateEntrepreneurial and self-driven — you build your own process and don U2019t wait for a playbookDisciplined forecaster with clean CRM habits and a data-driven approach to pipeline managementFamiliar with HubSpot, Clay, Claude/ChatGPT or equivalent toolsWhy Featherless
Build out the AE function at a company growing in one of the fastest-moving spaces in AIWork directly with the CRO — your wins shape the company U2019s trajectoryBe part of asmall, high-performing team making open weight AI accessible to everyoneCompetitive base + commissionCompensation Range: $180K
- $240K
#J-18808-Ljbffr

📌 Founding Account Executive (Winnipeg)
🏢 Featherless AI
📍 Winnipeg