Account Executive (Enterprise)

Yoodli AI RoleplaysChicago, IL

About The Position

We’re hiring an Enterprise Account Executive to help drive Yoodli through this next inflection point. You’ll lead consultative sales cycles across mid-market and enterprise segments. You’ll own the full sales process - from first conversation to signed contract - using deep discovery, value-based selling, incredible demo skills and a Challenger mindset. Your passion for helping others grow through communication is evident throughout. You’ll work closely with Leadership, Solutions Engineering, Marketing, and Customer Success to land and expand accounts that shape the future of our platform. This is a high-trust, high-autonomy role ideal for someone who blends curiosity, grit, and a mission-driven mindset.

Requirements

  • 8+ years in B2B SaaS sales with a track record of consistent quota attainment
  • High emotional intelligence—you can detect buyer apathy and adapt quickly
  • Skilled in signal recognition, objection handling, and managing next steps with discipline
  • Experienced in MEDDIC, Challenger, or similar value-based methodologies
  • Comfortable respectfully challenging buyer assumptions to create urgency
  • Treats pipeline and forecast like an operator, not a speculator
  • Team-first mindset—you're coachable, iterative, and eager to help others win

Nice To Haves

  • Experience selling to GTM leaders (enablement, L&D, revops)
  • Familiarity with tools like Gong, Outreach, Clay, or HubSpot, and incorporating AI into your sales workflows

Responsibilities

  • Own full-cycle sales for enterprise accounts
  • Run deep, rigorous discovery to understand buyer challenges and connect to Yoodli’s differentiated value
  • Lead multi-threaded sales motions across economic, technical, and operational stakeholders
  • Deliver compelling, ROI-driven narratives that shift focus from product to transformation
  • Partner with RevOps, SEs, and CS to ensure smooth handoffs and long-term customer success
  • Build pipeline via outbound, partnerships, and demand follow-up
  • Contribute to a high-performing, collaborative sales culture that lives our values

Benefits

  • Full benefits: healthcare, dental, vision, 401k, unlimited PTO
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