Founding Sales Engineer

Featherless AI; Montreal (administrative region); On-site; CAD 150,000 - 190,000; Full time

Benefits offered by this job

Competitive base

Commission

Job summary

Featherless AI in Montreal is seeking an accomplished Enterprise Sales professional to own the full sales cycle from discovery to contract.

You will run mid-market and enterprise deals, tailor proposals to buyer stacks, negotiate complex terms, and expand revenue within existing accounts. The role requires 3–6 years closing experience in cloud/ML tooling, strong communication, and a data-driven approach. Hybrid work possible.

Qualifications

• 3–6 years in closing role in Cloud Infrastructure, MLOps, or AI/developer tooling.
• Proven track record closing deals with technical buyers.
• Experience navigating multi-stakeholder enterprise sales cycles.
• Strong written and verbal communication — concise and credible.
• Entrepreneurial and data-driven with CRM discipline.
• Familiar with HubSpot, Clay, Claude/ChatGPT or equivalent tools.

Responsibilities

• Run full-cycle sales across mid-market and enterprise segments.
• Lead high-quality discovery and technical demo calls tailored to buyers’ stacks.
• Develop custom proposals and business cases linking model inference needs to Featherless capabilities.
• Negotiate and close complex, multi-stakeholder deals.
• Expand revenue within existing accounts and identify upsell opportunities.
• Use AI tools to automate research, outreach, and workflow efficiency.
• Maintain CRM hygiene in HubSpot with accurate pipeline reporting.
• Collaborate with product/engineering to share field feedback.
• Mentor BDRs and help define pipeline quality.

Skills

Closing deals

Enterprise sales

Multi-stakeholder

CRM hygiene

Forecasting

HubSpot

AI/ML knowledge

Tools

Claude/ChatGPT

Clay

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.

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.

• 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: $150K - $190K