Outbound Sales Representative

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.

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.

• 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.

• 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.
• Familiarity with Chicago or local business communities is a bonus.
• Strongly Preferred
  : 6+ months of relevant sales experience – cold calling, telesales, or any customer‑facing role where persuasion and rapport mattered.
• Please note: Our hiring process may include a background check.

• 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.

Groupon is evolving – and our Sales team is at the heart of that transformation. This is more than a role where you just make calls; it’s an opportunity and a place where your energy, curiosity, and voice can shape real success stories for local businesses.

If you’re ready to level up, we’d love to hear from you.

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.