Head of Sales Training

About the Role:

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.

What You'll Do:

Build & Scale Training Infrastructure

• 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

Drive Sales Excellence Through Three Pillars

• 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, RevOps, and business leaders to integrate training into existing systems and drive organization-wide sales effectiveness

Leverage Technology & Data

• 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

What You Bring:

Required

• 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

Preferred

• 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)

How We Operate:

At Groupon, we're building a culture of extreme ownership, speed, impact, simplicity, and discipline. These aren't aspirational values - they're how we expect everyone to show up every day:

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 escalate early, make trade-offs explicit, and ensure everyone knows who owns what.

Speed Over Comfort – We ship fast and learn faster. Perfect is too slow. We make fast, reversible decisions, normalize iteration, encourage early demos and prototypes, and admit mistakes openly. Bureaucracy and endless debate are the enemy. We clear bottlenecks and accelerate decisions across functions.

Impact Obsessed – We focus only on what moves the metrics that matter. We set metric-first goals, direct effort to high-value work, avoid feel-good activity, and use data and customer/merchant stories to guide decisions. We don't confuse effort with impact or tolerate low-ROI work that erodes trust. We drive team ROI and raise the quality bar by prioritizing ruthlessly.

Simplify to Scale – Complexity kills; simplicity scales. We build lean, scalable processes, remove noise, champion clarity and efficient ways of working. We drive cross-org simplification, push automation and tooling, question every layer, and ensure systems work for diverse voices - especially those closest to customers and merchants.

Disciplined – We do more with less; constraints breed creativity. We make ROI-based decisions, enforce resource discipline, set clear priorities, make durable decisions, and uphold integrity in data and commitments. We use constraints to drive innovation, build efficient operating rhythms, lift team productivity, and protect trust in trade-offs. We prioritize long-term value and create organizational leverage that scales efficiently.

In this role, these principles mean:

• You own outcomes, not activities - if a program stalls, you fix it, no finger-pointing
• You ship imperfect solutions fast, iterate based on data, and don't wait for consensus
• You kill projects that don't move core metrics and reallocate resources to high-impact work
• You eliminate complexity ruthlessly - every process, dashboard, and meeting must justify its existence
• You make every dollar of ops spend count and build systems that scale without proportional headcount growth

Why You’ll Love Working Here:

• Lead training innovation at a company serving millions of customers and thousands of local merchants
• Opportunity to build from the ground up with cutting-edge AI tools
• Chicago-based role with hybrid flexibility
• Competitive compensation including base + bonus + equity
• Collaborative culture that values experimentation and continuous improvement

Location: Chicago, IL (Hybrid - 3 days/week in office)

Salary Range: 110K to 155K + bonuses

Benefits: Medical, Dental, Vision, EAP, 401(k) Match, ESPP, Life and Disability Insurance, FSAs, Flexible PTO, and more 

Ready to Make an Impact?
If you’re looking for the best of both worlds — the influence of a large public company and the energy of a nimble, entrepreneurial culture — we’d love to hear from you.