Outbound Sales Representative

Groupon • Chicago, IL

4d • $40,000 • Onsite

About The Position

Groupon is growing and we’re looking for ambitious, energetic Outbound Sales Representatives to join our sales team in Chicago’s River North. If your background includes sales or other customer-facing roles where you regularly pitched, upsold, or handled objections, you’ll be well prepared to succeed here.
As an Outbound Sales Rep, you’ll be on the front lines helping local businesses grow. You’ll introduce them to Groupon, uncover their goals, and craft solutions that bring new customers through their doors.

Requirements

• A confident and engaging communication style — you enjoy talking to people and know how to listen.
• An outgoing personality and a love for tackling goals and challenges.
• Ability to work in-office 3 days/week in downtown Chicago (4 days/week during onboarding is required).
• Comfort with tech and sales tools; Salesforce experience is a plus.
• Strongly Preferred: 6+ months of relevant sales experience — cold calling, telesales, or any customer-facing role where persuasion and rapport mattered.

Nice To Haves

• Familiarity with Chicago or local business communities is a bonus.

Responsibilities

• Discover and connect with local businesses that could shine with Groupon.
• Make outbound calls to introduce our platform and spark curiosity in business owners.
• Deliver compelling pitches by tailoring solutions to each merchant’s goals.
• Own your targets and celebrate your wins.
• Build trust and long-term relationships with merchants.
• Partner with internal teams to launch successful campaigns.

Benefits

• Base Salary: $40,000/year
• Commission: Uncapped, based on gross profit you deliver.
• Last year’s median total earnings for BDRs hitting or exceeding their targets: $60-70k+
• Benefits starting the 1st of the month after your start date: Medical, dental, vision, life insurance, disability, FSAs, EAP, 401(k) match, ESPP, and more.
• Learning & Development: Comprehensive training, ongoing coaching, and a supportive team committed to your success.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees