Founding Sales Engineer — AI/Cloud Enterprise Growth

Featherless AI; Chicago (IL); On-site; USD 150,000 - 190,000; Full time

Benefits offered by this job

Competitive base + commission

Job summary

Featherless AI in Chicago is seeking an enterprise sales professional to own the full-cycle closing process for mid-market and enterprise opportunities. You will tailor discovery and demos to buyers’ stacks and use cases, and develop compelling proposals that connect model inference needs to Featherless capabilities.

You will negotiate complex multi-stakeholder deals, expand revenue within existing accounts, mentor BDRs, and collaborate with product and engineering to relay field feedback.

Qualifications

• 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 data-driven pipeline management.

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.

Skills

Close enterprise deals

Technical buyer engagement

Multi-stakeholder selling

Written communication

Entrepreneurial drive

CRM forecasting

HubSpot/CRM tools

Tools

HubSpot

Clay

Claude/ChatGPT

Job description

Featherless AI in Chicago is seeking an enterprise sales professional to own the full-cycle closing process for mid-market and enterprise opportunities. You will tailor discovery and demos to buyers’ stacks and use cases, and develop compelling proposals that connect model inference needs to Featherless capabilities.

You will negotiate complex multi-stakeholder deals, expand revenue within existing accounts, mentor BDRs, and collaborate with product and engineering to relay field feedback.