Founding Sales Engineer

Featherless AI; Toronto; On-site; CAD 208,000 - 263,000; Full time

Benefits offered by this job

Competitive base + commission

Job summary

Featherless AI is seeking a Senior Account Executive in Toronto to close enterprise AI deals and build strategic relationships with CTOs, ML leads and infra decision-makers. You will own the full sales cycle from discovery to close, tailoring proposals to customer stack and use case, and collaborating with product and engineering to feed the field.

You’ll forecast pipeline, maintain clean CRM in HubSpot, and mentor BDRs while expanding revenue within existing accounts in a fast-moving AI

Qualifications

• 3–6 years of closing experience in Cloud Infrastructure, MLOps, or AI/developer tooling.
• Proven track record closing deals with developers, ML engineers, CTOs.
• Comfortable navigating multi-stakeholder enterprise sales cycles.
• Strong written and verbal communication with technical literacy.
• Entrepreneurial and self-driven approach to building process.

Responsibilities

• Run full-cycle sales across mid-market and enterprise segments.
• Lead discovery calls and technical demos tailored to buyer stacks.
• Develop custom proposals and business cases connecting model inference needs to Featherless capabilities.
• Negotiate and close complex, multi-stakeholder deals.
• Expand revenue within existing accounts via upsell/cross-sell opportunities.
• Use AI tools to automate research, outreach, and workflow efficiency.
• Maintain CRM hygiene in HubSpot with accurate pipeline
• Collaborate with product and engineering to relay field feedback.
• Mentor BDRs and shape pipeline expectations.

Skills

Closing deals

Enterprise sales

Multi-stakeholder sales

CRM (HubSpot)

Technical buyer communication

Tools

HubSpot

Clay AI

Claude/ChatGPT

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