Founding AI Cloud Account Executive: Enterprise Deals

Featherless AI; Tampa (FL); On-site; USD 180,000 - 240,000; Full time

Job summary

Featherless.ai is seeking an experienced Account Executive (AI Cloud) to own deals end-to-end, close enterprise and scale-up accounts, and build a repeatable GTM engine in the US. You’ll work directly with the CRO and founders, engaging CTOs, ML leads, and developers to shape commercial motion.

You’ll run full-cycle sales across mid-market and enterprise segments, craft tailored proposals, and negotiate multi-stakeholder deals while maintaining CRM rigor in HubSpot.

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.

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

Closing deals

Technical buyers

Multi-stakeholder sales

CRM discipline

HubSpot familiarity

Tools

HubSpot

Clay

Claude/ChatGPT

Job description

Featherless.ai is seeking an experienced Account Executive (AI Cloud) to own deals end-to-end, close enterprise and scale-up accounts, and build a repeatable GTM engine in the US. You’ll work directly with the CRO and founders, engaging CTOs, ML leads, and developers to shape commercial motion.

You’ll run full-cycle sales across mid-market and enterprise segments, craft tailored proposals, and negotiate multi-stakeholder deals while maintaining CRM rigor in HubSpot.