Full-Time

Regional Sales Director

Posted on 9/18/2025

Groupon

Groupon

10,001+ employees

Online marketplace for discounted local deals

Compensation Overview

$128k - $170k/yr

+ 60% OTE

Chicago, IL, USA

Hybrid

Hybrid, 3 days in office.

Category
Sales & Account Management (1)
Required Skills
Financial analysis
Requirements
  • 7+ years of extensive experience leading Sales Teams and Sales Managers
  • Experience in leading by influence in matrixed organizations
  • Experience leading big teams (4-6 direct reports DSM level, 12 REPs each, around 50 employees in total)
Responsibilities
  • The Business Performance of your region against its defined supply input metrics
  • Engagement of the teams (employee feedback scores, attrition rates, resourcing)
  • Establishing a high performance culture with clear development and succession plans in place for the team
  • Leadership & representation of the teams in cross functional collaborations that drive and support the key deliverables
  • Contributing to the shaping and delivery of the Sales Operational Plan and OKR’s
  • Coaching & mentoring regional divisional sales managers, and sales reps
  • Establishes short- and long-range objectives and criteria for monitoring progress and measuring success
  • Understanding the financial expectations of the business to deliver/exceed against agreed targets
  • Developing the sales strategy and tactics for growth
  • Developing, sharing and adopting best practice ways of working to maximize business outputs for your region
  • Ensuring you are meeting or exceeding the Input Metric benchmarks for your region focused on Supply and Supply Quality.
  • Setting and managing to performance standards and management routines to ensure key business input metrics are being met
  • Setting goals for your region and cross functional team & regularly reviewing performance and coaching and guiding your team to achieve against those goals
  • Be the inspirational figurehead for your region - being the trusted leader that is guiding the growth your region and your teams
  • As a Leader, support in shaping the strategic direction of the sales organization in order to achieve its vision and contribute to the development of the organization’s strategic and annual business plans.

Groupon operates an online marketplace that connects consumers with local merchants by offering discounted deals on goods and services, plus a Groupon Goods section for direct product sales. Deals are listed by partners, presented to subscribers, and purchased through Groupon; the company earns revenue by taking a percentage of each deal and through direct product sales. The service helps local businesses attract new customers by driving traffic and sales with discounted offers, while giving shoppers access to savings in their area. Its differentiator is its strong focus on local deals and partnerships, combining marketplace discounts with direct goods, and personalized deal notifications to encourage repeat use.

Company Size

10,001+

Company Stage

IPO

Headquarters

Chicago, Illinois

Founded

2008

Simplify Jobs

Simplify's Take

What believers are saying

  • North America Local billings reaccelerated in April 2026 after Q1 pressures.
  • Full-year guidance of 3-5% billing growth and $70-75M adjusted EBITDA reaffirmed.
  • International local revenue grew 10% in Q1 2026, offsetting North America decline.

What critics are saying

  • Q1 2026 returned to $12.9M net loss; goods revenue collapsed 40.9%.
  • Project Foundry's 15% Q2 headcount reduction destroys merchant relationships and deal quality.
  • Expedia partnership termination eliminates Groupon Getaways' 25,000+ travel offers and fastest-growing segment.

What makes Groupon unique

  • AI voice agents targeting merchant outreach at scale through Project Foundry initiative.
  • Integrated local deals, goods, and cashback within single platform ecosystem.
  • Active customer base of 16.2 million with established merchant relationships.

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Your Connections

People at Groupon who can refer or advise you

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Company Match

Employee Stock Purchase Plan

Health Savings Account/Flexible Spending Account

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
The Associated Press
Mar 10th, 2026
Groupon returns to revenue growth after decade-long decline with North America local billings up 14%

Groupon reported fourth quarter and fiscal year 2025 results, marking its first return to growth in both billings and revenue in a decade. North America local revenue grew 4% in Q4 and 5% for the full year, whilst local billings increased 9% in Q4 and 14% for 2025. The company generated $64.5 million in trailing twelve-month operating cash flow from continuing operations and $49.9 million in free cash flow. CEO Dusan Senkypl described the results as a "landmark achievement" in Groupon's multi-year transformation, citing momentum in its core local category and improved platform velocity. The company aims to position itself as the trusted destination for quality local experiences. Groupon filed its Form 10-K with the Securities and Exchange Commission and posted earnings materials on its investor relations website.

Yahoo Finance
Mar 10th, 2026
Groupon posts $7.3M Q4 profit but revenue misses forecasts at $132.7M

Groupon reported fourth-quarter net income of $7.3 million, or 17 cents per share, meeting Wall Street expectations. However, the online daily deal service's revenue of $132.7 million fell short of analyst forecasts of $137.2 million. For the full year, the Chicago-based company reported a loss of $83.5 million, or $2.08 per share, with total revenue of $498.4 million.

TechLi
Sep 18th, 2025
Breaking news: Andrew Mason Announces Grouspawn

Just now on stage at TechCrunch Disrupt in San Francisco, Andrew Mason of Groupon took the stage and announced a new launch called, "Grouspawn."

Refresh Miami
Jul 30th, 2025
Yung Sidekick is building an AI-powered bridge between therapists and their patients

When Alexander Anastasin left his career in venture capital and corporate leadership at Groupon, he wasn't sure what would come next.

The Wall Street Journal
Jun 29th, 2025
CityDeal Founders Cash in on Groupon

Two of the big winners in Groupon's forthcoming IPO are likely to be Oliver and Marc Samwer, the brothers who founded CityDeal, the European company Groupon bought in May 2010 to expand overseas.

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