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Head of Sales Academy

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Groupon

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Location:
United States , Chicago

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Category:
Sales

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Contract Type:
Not provided

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Salary:

110000.00 - 155000.00 USD / Year
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Job Description:

Groupon is seeking an innovative Sales Training Leader to revolutionize how we develop and scale our marketplace sales organization. This role will architect and lead a modern, AI-enhanced training ecosystem that transforms sales performance across our US operations. You'll build scalable systems that leverage technology, people, and proven methodologies to drive sales excellence.

Job Responsibility:

  • Design and implement a comprehensive sales training framework that leverages AI tools (AI Co-Pilot, SaltedCX) to deliver personalized, scalable learning experiences
  • Create a train-the-trainer model that empowers managers and team leads to deliver consistent, high-impact training across the organization
  • Develop automated training workflows, AI-powered coaching tools, and data-driven performance improvement systems
  • Design behavioral interviewing frameworks, onboarding curricula, and early-tenure success programs that reduce time-to-productivity
  • Create ongoing skill development programs, AI-enhanced coaching systems, and performance improvement pathways for existing sales teams
  • Partner with HR, RevOps, and business leaders to integrate training into existing systems and drive organization-wide sales effectiveness
  • Implement SaltedCX and AI Co-Pilot to create conversational intelligence, call coaching, and automated training experiences
  • Build dashboards and analytics to measure training effectiveness, skill development, and business impact
  • Continuously optimize training content and delivery based on performance data

Requirements:

  • 5+ years of sales training/enablement experience in marketplace, on-demand, or technology companies (e.g., GrubHub, Uber, DoorDash, Delivery Hero, Instacart)
  • Proven track record designing training programs that improved sales metrics (conversion rates, ACV, quota attainment)
  • Experience with AI-powered sales tools (conversational intelligence, AI coaching platforms, LMS systems)
  • Demonstrated ability to build scalable training systems with small teams by leveraging technology and distributed trainers
  • Strong understanding of marketplace/local commerce sales dynamics and challenges
  • Excellent instructional design skills with ability to create engaging, multimedia training content

Nice to have:

  • Experience with SaltedCX, Gong, Chorus, or similar conversational intelligence platforms
  • Background in sales operations, revenue enablement, or sales leadership
  • Familiarity with adult learning theory, competency frameworks, and performance consulting
  • Experience managing training teams or cross-functional training initiatives
  • Data analysis skills (SQL, Tableau, or similar tools a plus)
What we offer:
  • Medical
  • Dental
  • Vision
  • EAP
  • 401(k) Match
  • ESPP
  • Life and Disability Insurance
  • FSAs
  • Flexible PTO

Additional Information:

Job Posted:
February 13, 2026

Employment Type:
Fulltime
Work Type:
Hybrid work
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