Strategic Account Executive (AI)

TL;DR

Strategic Account Executive (AI Enterprise Sales): Drive enterprise sales cycles for LLM-agnostic AI platform enabling secure, scalable deployments with an accent on $1M+ ACV deals in regulated industries like FinServ, Healthcare, Manufacturing, Retail. Focus on building pipeline from scratch, translating AI/ML capabilities into C-suite business outcomes, and shaping GTM strategy with founders.

Location: Chicago, Remote

Company

Stealth AI startup with $50M Series A from top VCs, building LLM-powered platform for enterprises to deploy customized AI apps without fine-tuning or data sharing.

What you will do

• Lead complex multi-stakeholder sales cycles into regulated industries leveraging on-premises AI capabilities.
• Build pipeline from zero and close strategic $1M+ ACV enterprise accounts.
• Translate AI/ML solutions into business outcomes for CIOs and C-suite, positioning buy-vs-build advantages.
• Architect multi-year account expansion and deep relationships across IT, product, innovation teams.
• Partner with VP of Sales and founders to refine enterprise GTM and influence product roadmap.

Requirements

• 8+ years enterprise software sales with consistent quota over-achievement at Fortune 500 companies
• Proven track record closing $1M+ ACV deals in early-stage environments
• Experience selling complex technical solutions to CIO organizations
• Background in AI/ML platforms, digital transformation, enterprise data platforms, or management consulting
• Entrepreneurial mindset thriving in ambiguity, owning outcomes, building from scratch
• Success in highly regulated industries with complex compliance requirements

Nice to have

• Regulated industry experience
• Early-stage success

Culture & Benefits

• Uncapped compensation with aggressive accelerators rewarding over-performance on large deals.
• Work directly with VP of Sales and founders in high-performance culture.
• Equity in Series A company with institutional backing and momentum.
• Free POC for buyers, no data sharing or upfront costs.