Regional Sales Leader- Chicago
About The Position
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.
Requirements
- 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
Nice To Haves
- Chicago restaurant market knowledge? Even better.
- High-performing ICs ready to step into leadership are encouraged to apply.
Responsibilities
- 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
- 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
- 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
- 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
Benefits
- Equity included for every employee
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
