Enterprise Business Development Representative - Things To Do (TTD)

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

Enterprise Business Development Representative - Things To Do (TTD)

Chicago (35 W. Wacker Dr.)

Groupon connects 42 million customers with local experiences - restaurants, events, wellness and travel - and the million-plus merchants who deliver them. Our mission is to get people offline and into the real world at prices that make it possible. We're an AI-native company in the middle of a platform transformation, moving from a deals marketplace to an experience discovery platform that works for customers and merchants at the same time.

Enterprise Business Development Representative

The Role

Groupon's Things To Do vertical is scaling nationwide, and we need a closer who can land the brands that move the needle. You'll own new-logo enterprise acquisition — signing nationwide chains and multi-market operators in Local Activities, Tours & Attractions that have never worked with Groupon or lapsed years ago.

This is a hunter role with real teeth: you'll carry genuine discretion on deal structure, margin, and contract terms, sell at the C-suite level, and get paid on signed, activated revenue — not activity metrics.

What You'll Do

• 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.

What You Bring

• 2+ years of enterprise B2B sales closing complex, multi-stakeholder deals — Things To Do preferred; SaaS, digital media, or marketplace experience also strong.
• A 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.

Who Thrives Here

• Closers who treat "no" as a data point, not a stop sign.
• Reps who build their own playbook when the standard one doesn't fit the account.
• Owners — your pipeline, your number. You don't wait on marketing-sourced leads; you build your own path to close.
• People who send the outreach before the deck is perfect. Cold nationwide accounts don't wait for polish.

How We Measure Success

New enterprise TTD logos signed per quarter (GP-weighted), Gross Profit delivered against target, close rate on time-critical deals, and clean handoffs that activate without renegotiation.

Why You'll Love It

• Real upside: $60K–$95K base (depending on experience) + 60% bonus target, paid on outcomes you control.
• Full benefits: Medical, Dental, Vision, 401(k) Match, ESPP, Life & Disability, FSAs, EAP, and more.
• Autonomy and visibility: a high-priority category, direct influence on how major national brands show up on Groupon, and the freedom to run your book your way.

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.