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Regional Sales Leader- Chicago

Popmenu

Popmenu

Sales & Business Development
Chicago, IL, USA
USD 150k-160k / year + Equity
Posted on Mar 2, 2026

The Opportunity

We're hiring a proven sales leader to own the Chicago market and build the team that wins it. 🔥

Popmenu powers 14,000+ restaurants with technology that drives real revenue, and Chicago is one of our highest-priority markets. You won't just be leading a team. You'll be shaping how we compete, hire, and scale in one of the most dynamic restaurant cities in the country.

Our product delivers clear ROI, fast. Short sales cycles. Frequent wins. A motivated team hungry to close. Your job is to make them sharper, faster, and better every single day, and to build a culture where that standard becomes the norm.

Your team is selling directly to decision-makers who care about revenue, guest experience, and survival in a crowded market. Popmenu is not a nice-to-have. It is a revenue-driving platform restaurants rely on to compete, and you'll lead the people who bring that message to Chicago every day.

What You'll Own

Team Performance:

  • Develop elite sales talent for the Chicago market
  • Coach reps to be great for themselves, their customers, and this team
  • Drive urgency, accountability, and disciplined pipeline management daily
  • Lead from the front. This looks like co-sell with your reps, stay close to the deals, and never hide behind a dashboard
  • Build a team culture where high standards and high energy coexist

Revenue:

  • Own monthly targets and blow past them
  • Maintain tight forecast accuracy and pipeline visibility
  • Jump into deals strategically to accelerate and close
  • Identify friction in the sales process and remove it fast

Culture and Growth:

  • Create an environment where reps compete hard, win together, and keep getting better
  • Level up consistently -- through coaching, industry knowledge, podcasts, peer learning, and staying sharp on what's happening in restaurant tech
  • Become a genuine expert in Popmenu's product and the restaurant industry so you can lead your team to advise operators with credibility and trust
  • Be the kind of leader people follow because you make them better

Strategic Impact:

  • Deliver clear, data-driven reads to executive leadership
  • Surface market intel directly to Product and Leadership
  • Find new growth pockets in Chicago's dense, ever-evolving restaurant scene

What You Bring

  • 4-6+ years in sales, 2+ years leading a team
  • Track record of exceeding targets as both a rep and a manager
  • High-velocity sales experience (1--30 day cycles preferred)
  • Strong SaaS background -- restaurant tech or hospitality is a plus
  • Fluent in Salesforce, Salesloft, and AI-driven sales tools
  • A coaching framework you can install, replicate, and scale
  • Chicago restaurant market knowledge? Even better.

High-performing ICs ready to step into leadership are encouraged to apply.

Compensation

  • Base: $150,000 to $160,000
  • OTE: $320,000+
  • Uncapped earnings
  • Equity included for every employee

What We're Serving

  • Remote- Chicago
  • Genuine Core Values with quarterly peer recognition through our Super Booms
  • Visible Growth and Development in a scaling SaaS company where your impact is seen and rewarded
  • Company Ownership with meaningful equity at a company built for long-term growth
  • Comprehensive Benefits including medical, dental, vision, 401(k), and Wagmo Wellness Plan for your pets

Build the team. Drive the revenue. Win big. 🚀