Head of Sales Academy

Groupon is a marketplace where customers discover new experiences and services everyday and local businesses thrive. To date we have worked with over a million merchant partners worldwide, connecting over 16 million customers with deals across various categories. In a world often dominated by e-commerce giants, we stand out as one of the few platforms uniquely committed to helping local businesses succeed on a performance basis.

Groupon is on a radical journey to transform our business with relentless pursuit of results. Even with thousands of employees spread across multiple continents, we still maintain a culture that inspires innovation, rewards risk‑taking and celebrates success. The impact here can be immediate due to our scale and the speed of our transformation. We’re a "best of both worlds" kind of company.

We’re big enough to have the resources and scale, but small enough that a single person has a surprising amount of autonomy and can make a meaningful impact.

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.

• Design and implement a comprehensive sales training framework that leverages AI tools (AI Co‑Pilot, Salted
  
  CX) 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

• Selection & Onboarding – Design behavioral interviewing frameworks, onboarding curricula, and early‑tenure success programs that reduce time‑to‑productivity
• Performance Acceleration – Create ongoing skill development programs, AI‑enhanced coaching systems, and performance improvement pathways for existing sales teams
• Cross‑Functional Collaboration – Partner with HR, Rev Ops, and business leaders to integrate training into existing systems and drive organization‑wide sales effectiveness

• Implement Salted
  
  CX 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

• 5+ years of sales training/enablement experience in marketplace, on‑demand, or technology companies (e.g., Grub Hub, Uber, Door Dash, 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

• Experience with Salted
  
  CX, 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)

• Extreme Ownership – One owner per outcome, no passengers, no excuses. We avoid accountability theater; we don’t blame teams or create shared ownership that diffuses responsibility. When something goes wrong, we look in the mirror first. We escape early, make trade‑offs explicit, and ensure everyone knows who owns what.
• Speed Over Comfort – We ship…