8h ago

Enterprise Sales Director

Chicago

$150k-$250k / yearest.

full-timesenior Remoteai-ml

💼 About This Role

You'll own and expand relationships with Giga's largest enterprise accounts, driving complex sales cycles across Fortune 1000 organizations. You'll collaborate with leadership and engineering to shape custom solutions and unlock expansion opportunities. This is a foundational role at a high-growth AI startup backed by a $61M Series A.

🎯 What You'll Do

  • Develop deep trusted partnerships with executive stakeholders across CX, Operations, and Product.
  • Drive expansion within largest customers, converting POCs into multi-year partnerships.
  • Lead enterprise negotiations and coordinate technical validation through close.
  • Execute tailored account plans to deepen engagement and expand into new lines of business.

📋 Requirements

  • 5+ years in strategic or enterprise SaaS sales.
  • Proven record of closing 6 or 7-figure deals.
  • Skilled at navigating large complex organizations and building executive-level relationships.
  • Thrives in early-stage, fast-paced environments where process is still being written.

✨ Nice to Have

  • Experience selling AI, automation, or CX transformation solutions.
  • Familiarity with large-scale deployments in telecom, logistics, or e-commerce.
  • Early GTM or founding sales experience at a fast-growing startup.

🎁 Benefits & Perks

  • 💰 Competitive base + commission + equity
  • 🍽️ Catered lunch daily + dinner stipend
  • 💪 $150/month wellness benefit
  • 🏥 Medical, dental, and vision coverage
  • 👶 Paid parental leave (12 weeks maternal, 6 weeks paternal)
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