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Senior Director of Product & AI

SpotOnChicago, Illinois, United States
On-site Full-time $220K/yr - $260K/yr

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Experience Level

Senior Level Manager

Qualifications

Qualifications:Proven experience in product management and AI integration within technology-focused environments. Strong leadership skills with a history of building and managing high-performing teams. Excellent communication and interpersonal skills, with a customer-centric approach. Ability to analyze market trends and customer feedback to inform strategic decisions. Advanced problem-solving skills and a proactive mindset.

About the job

About SpotOn

SpotOn supports independent restaurants with technology designed to help them compete and grow. The company’s point-of-sale system and AI-powered profit tools aim to help operators improve margins, simplify daily operations, and retain staff. Every solution comes with support from a team that cares about restaurant success.

  • #1 Restaurant POS by G2 (Fall 2025), based on real user reviews
  • Top-rated POS for restaurants, bars, retail, and small businesses by Capterra users
  • Multiple years recognized as a Great Place to Work and on Built In’s Best Workplaces lists

SpotOn values agility, empathy, and a strong commitment to helping independent operators thrive. The team is driven to make a real impact for restaurants every day.

Role Overview: Senior Director of Product & AI

This Chicago-based leadership role blends product strategy with organizational growth. The Senior Director of Product & AI will guide product teams and drive the integration of AI into business processes. Success in this role requires experience leading teams, understanding customer needs, and delivering results that matter.

Key Responsibilities

  • Lead and develop the Marketing, Guest Data, Labor, and Shared Value product teams. Set direction, shape roadmaps, and work closely with the C-suite to align on strategy and execution.
  • Advance efficiency across the company by integrating AI into workflows for Product, Engineering, Operations, Support, Sales, Marketing, and General Administration.
  • Prototype new AI workflows quickly and build long-term product visions that turn emerging technology into practical solutions for customers and teams.
  • Navigate ambiguity, create structure, and translate new technologies into business results.

Product Leadership

  • Direct Product Managers in developing strategy for their focus areas (Marketing, Guest Data, Labor, Shared Value) while helping shape SpotOn’s broader product vision.

About SpotOn

SpotOn is at the forefront of providing innovative solutions for independent restaurants. Our commitment to empowering these businesses with technology ensures they can not only compete but excel in a challenging market. With accolades for our products and workplace culture, we prioritize our clients' success and our team's well-being.

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