10h ago

Account Executive (Enterprise)

Chicago, IL

$130k-$150k / year

full-timeseniorAI-powered training software

🛠 Tech Stack

💼 About This Role

You'll own full-cycle enterprise sales for Yoodli, an AI roleplay simulator revolutionizing communication training. You'll drive consultative sales cycles using value-based selling and a Challenger mindset. This high-autonomy role lets you shape the sales playbook at a mission-driven Series B startup with $40M funding.

🎯 What You'll Do

  • Own full-cycle sales for enterprise accounts
  • Run deep discovery to connect buyer challenges to Yoodli's value
  • Lead multi-threaded sales motions across stakeholders
  • Deliver ROI-driven narratives focused on transformation
  • Partner with RevOps, SEs, and CS for smooth handoffs

📋 Requirements

  • 8+ years in B2B SaaS sales with consistent quota attainment
  • High emotional intelligence to detect buyer apathy and adapt
  • Skilled in objection handling and managing next steps with discipline
  • Experience with MEDDIC, Challenger, or similar value-based methodologies

✨ Nice to Have

  • Experience selling to GTM leaders (enablement, L&D, RevOps)
  • Familiarity with Gong, Outreach, Clay, or HubSpot
  • Incorporating AI into sales workflows

🎁 Benefits & Perks

  • 💰 Competitive Base Salary: $130K-$150K
  • 📈 Variable OTE: $130K-$150K
  • 🧩 Equity: Meaningful early-stage options
  • 🏥 Full benefits: healthcare, dental, vision, 401k
  • 🏖️ Unlimited PTO
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