Enterprise B2B Sales Closer – National Brands (AI)

Groupon; Chicago (IL); On-site; USD 60,000 - 95,000; Full time

Benefits offered by this job

Medical

Dental

Vision

401(k) Match

ESPP

Life & Disability

FSAs

EAP

Job summary

Groupon’s Things To Do Enterprise team in Chicago seeks an ambitious Enterprise Business Development Representative to close national, multi-market deals with high-value brands. You’ll own the full sales cycle, negotiate at the C-suite, and drive revenue that activates across Groupon’s experience platform.

You’ll leverage AI daily to accelerate prospecting, structure win-ready deals, and partner with Merchant Success to ensure smooth activation.

Qualifications

• 2+ years of enterprise B2B sales closing complex, multi-stakeholder deals — Things To Do preferred; SaaS, digital media, or marketplace experience also strong.
• Track record of beating New Revenue / Gross Profit targets with strong close rates on time-sensitive deals.
• Fluency in deal structuring and comfort being measured on revenue outcomes, not effort.
• Familiarity with ticketing/reservation platforms and connectivity APIs (or the curiosity to get up to speed fast — we'll train you on vouchers, API connectivity, tax, and reconciliation).
• Working AI fluency — AI tools are your default for prospecting and deal prep, not a novelty.

Responsibilities

• Run the full sales cycle solo — prospect, pitch, negotiate, close — against a targeted list of high-value nationwide and multi-market accounts, built from your network, your research, and our pipeline.
• Structure complex deals: pricing, margin, availability, contract terms. You'll know when to hold the line and when flexing wins the logo.
• Negotiate from insight, not scripts — you'll understand each prospect's business model, consumer base, and profit drivers before the first call.
• Use AI daily to compress the time from first contact to signed contract — prospecting, research, outreach, deal prep. We run Claude Cowork and Claude Code; if you've built automations or agents to scale your own work, you'll fit right in.
• Hand off cleanly to Merchant Success so the deals you close activate on strategy, without renegotiation.
• Bring industry intel back to leadership — your read on the TTD market shapes our roadmap.

Skills

Enterprise B2B sales

Deal closing

AI fluency

Tools

Claude Cowork

Claude Code

Job description

Groupon’s Things To Do Enterprise team in Chicago seeks an ambitious Enterprise Business Development Representative to close national, multi-market deals with high-value brands. You’ll own the full sales cycle, negotiate at the C-suite, and drive revenue that activates across Groupon’s experience platform.

You’ll leverage AI daily to accelerate prospecting, structure win-ready deals, and partner with Merchant Success to ensure smooth activation.