Sales AI Enablement Associate

Groupon • Chicago, IL

6h • $90,000 - $120,000 • Hybrid

About The Position

Groupon is a marketplace connecting customers with experiences and services and local businesses. It has worked with over a million merchant partners and connects over 16 million customers. Groupon is transforming its business with AI, specifically Project Foundry's autonomous agent fleet handling outbound motions and lead ranking. The Sales AI Enablement Associate role focuses on improving the quality of what sales representatives do with the intelligence provided by Foundry, aiming to close the gap between AI-delivered leads and conversion. This role is not a training role but owns the content infrastructure, determining what content is built, how it's informed by data, and how it continuously improves based on rep performance signals. The associate reports directly to the CSO and works at the intersection of AI, data, and commercial execution. The North Star for this role is to build an AI-powered content system that translates Groupon’s sales data into practical rep capability, ensuring every rep performs closer to the top of the team every quarter.

Requirements

• A degree from an Ivy League or equivalent top-tier university — communications, education technology, data science, psychology, or any field that trained you to translate complex information into clear, actionable content.
• Up to 2 years of professional experience.
• Demonstrated ability to create content using AI tools — you have used LLMs to generate, structure, and refine learning or enablement material, and you know how to apply judgment to the output rather than accepting it wholesale.
• Data literacy strong enough to read a Salesforce report and draw a content conclusion — you don’t need to be a data scientist, but you need to be comfortable sitting in a dataset and extracting a signal.
• Strong written and verbal communication — the content you build needs to land with a rep who has 30 seconds between calls.
• Intellectual curiosity about how people learn and what makes commercial training actually stick — not theory, but a genuine instinct for what works in a fast-moving sales environment.

Nice To Haves

• Builder before curator.
• Data-driven by default.
• AI-native, not AI-decorated.
• A communicator who can motivate.
• Comfortable being the person behind the scenes.
• Extreme Ownership — If reps aren’t using the content you built, or it isn’t moving their performance, that’s your problem to diagnose and fix — not the trainer’s, not the manager’s.
• Speed Over Comfort — You ship a module with the data you have, gather signal from real usage, and iterate. You don’t wait six weeks for a perfect dataset before producing anything.
• Impact Obsessed — The metric isn’t content published. It’s rep performance improvement, measured against the Salesforce data you used to justify building it in the first place.
• Simplify to Scale — A training asset that only works when you explain it in person hasn’t been built well. Everything you create must stand alone.
• Disciplined — Every piece of content is tied to a performance hypothesis. You define what success looks like before you ship, not after.

Responsibilities

• Own the AI-powered content library — Design and build the enablement content reps use to work leads, handle objections, and close deals.
• Mine sales data to identify capability gaps — Pull signal from Salesforce, Salted CX, and call data to understand where rep performance breaks down. Turn that into a prioritised content roadmap.
• Iterate content based on performance outcomes — Track whether content actually changes behaviour. If conversion doesn’t move after a module goes live, you go back into the data, find out why, and rebuild.
• Embed AI tools into the sales workflow — Identify where AI can reduce rep effort or sharpen rep judgment — call prep, objection handling, pitch sequencing — and build the content that makes adoption practical and sticky.
• Build for scale, not for yourself — Everything you create can be updated, used, and adapted by a rep or manager without your direct involvement.

Benefits

• Base salary: 90k-120k base + 10% ABP Bonus
• Benefits start the 1st of the month after your start date — Medical, Dental, Vision, Life Insurance, Disability, FSAs, EAP, 401(k) match, ESPP, flexible PTO, and more
• Employee Resource Groups & inclusive team culture

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level