Founding Account Executive (AI Cloud)
At a glance
Mid-level Account Executive role at Featherless AI. Remote, Canada · full-time · $180,000–$240,000 base.
Growth Roles summary, based on the employer's posting.
What you'll do
- Build and close a pipeline among scale-ups and high-growth startups
- Guide each deal from initial outreach through discovery, demos, proposals, negotiation, and signature
- Sell to CTOs, ML leaders, developers, and infrastructure decision-makers across complex buying groups
- Create tailored business cases that connect model inference requirements with platform capabilities
- Keep HubSpot records current, forecast accurately, and use AI tools to improve research and outreach
What you bring
- Three to six years closing sales in cloud infrastructure, MLOps, or AI and developer tooling
- A record of winning business with developers, ML engineers, CTOs, and other technical buyers
- The ability to manage enterprise purchases involving several stakeholders
- Strong concise communication and enough technical fluency to earn buyer credibility
- Working familiarity with HubSpot, Clay, and Claude, ChatGPT, or comparable tools
Who this fits
You’ll suit a self-directed mid-level seller who can create process, manage a full sales cycle, and work closely with the CRO and founders. The role combines new business, expansion within existing accounts, BDR mentoring, and collaboration with product and engineering. It is remote and based in Toronto, Canada, with industry events and conferences part of the work.
From the employer
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 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'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
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
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