Sales AI Enablement Associate Chicago (35 W. Wacker Dr.); Remote - United States 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. About the Role: Groupon is rebuilding its sales motion with AI at the centre. Project Foundry's autonomous agent fleet handles the outbound motion, ranks the queue through predictive intelligence, and brings warm leads to the rep's desk. That fleet is running. The question now is what happens at the handoff — the quality of what reps do with the intelligence Foundry delivers is what determines whether it converts. The Sales AI Enablement Associate exists to close that gap... This is not a training role. The existing onboarding function handles live delivery and new hire ramp. This role owns the content infrastructure behind it — what gets built, how it’s informed by data, and how it improves continuously as rep performance signals change. You report directly to the CSO and work at the intersection of AI, data, and commercial execution. North Star Build the AI-powered content system that turns Groupon’s sales data into practical rep capability — so every rep performs closer to the top of the team, every quarter. What You’ll Do: - Own the AI-powered content library — Design and build the enablement content reps use to work leads, handle objections, and close deals. Every asset is AI-assisted, data-informed, and built to be updated as performance signals evolve — not a static deck that ages out in three months. - 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. You don’t guess what reps need — you read it in the data. - 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. Every asset has a before/after record. - 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. You are building a system, not running a program. What You Bring: - A degree from an Ivy League or equivalent top-tier university strongly preferred — 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. You write for that person, not for a slide deck reviewer. - 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. Who You Are: - Builder before curator. Your instinct is to create something new and test it, not to catalogue what already exists. - Data-driven by default. You don’t build content because it feels right — you build it because the numbers point to a gap, and you measure whether it closed it. - AI-native, not AI-decorated. You use AI to do in an hour what would otherwise take a week. You know the difference between using AI as a shortcut and using it as a genuine capability multiplier. - A communicator who can motivate. The content you create needs to make a rep want to use it — not feel like they’re being lectured. You understand the difference between informing someone and engaging them. - Comfortable being the person behind the scenes. The existing onboarding team delivers live. You build what they deliver and what reps come back to. That’s a different kind of ownership, and you’re good at it. How We Operate: At Groupon, we build on five principles: Extreme Ownership, Speed Over Comfort, Impact Obsessed, Simplify to Scale, and Disciplined. These aren’t values on a wall — they’re how we expect everyone to show up. In this role, these principles mean: - 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. How We Measure Your Success: - Rep adoption rate of AI tools and workflows introduced through enablement content — tracked monthly. - Measurable improvement in rep conversion metrics correlated with content consumption — reported to CSO level. - Content library coverage — percentage of core rep workflows backed by a current, data-informed AI-assisted asset. - Iteration cadence — how quickly content is updated when rep performance data signals a gap. - First AI-powered training asset in production and in use by the rep population by day 90. Compensation & Benefits: - Base salary: 90k-120k base + 10% ABP Bonus - Location: Downtown Chicago (hybrid, 3 days a week in-office) - Alternate locations: Can be remote for the right fit, NYC strongly encouraged - 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 Groupon is an AI-First Company We’re committed to building smarter, faster, and more innovative ways of working—and AI plays a key role in how we get there. We encourage candidates to leverage AI tools during the hiring process where it adds value, and we’re always keen to hear how technology improves the way you work. If you’re passionate about AI or curious to explore how it can elevate your role—you’ll be right at home here. Groupon’s purpose is to build strong communities through thriving small businesses. To learn more about the world’s largest local e-commerce marketplace, click here. You can also find out more about us in the latest Groupon news as well as learning about our DEI approach. If all of this sounds like something that’s a great fit for you, then click apply and join us on a mission to become the ultimate destination for local experiences and services. Beware of Recruitment Fraud: Groupon follows a merit-based recruitment process without charging job seekers any fees. We've noticed an increase in recruitment fraud, including fake job postings and fraudulent interviews and job offers aimed at stealing personal information or money. Be cautious of individuals falsely representing Groupon's Talent Acquisition team with fake job offers. If you encounter any suspicious job offers or interview calls demanding money, recognize these as scams. Groupon is not responsible for losses from such dealings. For legitimate job openings (and a sneak peek into life at Groupon), always check our official career website at Groupon Careers