Senior Director of Product & AI

SpotOn • Chicago, IL

3d • $220,000 - $260,000

About The Position

We’re not just building restaurant tech, we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sht about helping restaurants succeed.
Named the #1 Restaurant POS by G2 (Fall 2025), based on ratings from real users
Rated the top-rated point-of-sale (POS) for restaurants, bars, retail, and small businesses by Capterra users
Awarded Great Places to Work and Built In’s Best Workplaces for multiple years running
We move fast, care hard, and fight for independent restaurant operators to do what they love, and love doing it. If you’re looking to make an impact with heart and hustle, SpotOn is the place for you.
SpotOn is seeking a Senior Product and AI leader who can operate at the intersection of customer-facing product strategy and internal organizational acceleration. This person is (and will be) a team leader. This person has a demonstrated ability to listen to and drive outcomes for customers. Most importantly, this person
In this role the ideal hire will:
Lead and grow our Marketing, Guest Data, Labor, and Shared Value product teams—driving strategy, roadmap, and execution in close partnership with the C-Suite.
Dramatically increase organizational throughput by intelligently embedding AI into high-leverage workflows across Product, Engineering, Operations, Support, Sales, Marketing, and G&A.
The ideal candidate is a builder-operator who can lead a team, zoom in to prototype an AI workflow that ships this week, and zoom out to craft multi-year product vision.
This person moves quickly, can bring order and execution to ambiguity, and knows how to translate emerging technology into measurable business impact for our customers and our teams.

Requirements

• 6+ years of relevant product management experience, with at least 2 years managing and coaching a team of Product Managers.
• Demonstrated experience building and deploying AI-powered workflows in real-world environments.
• Strong understanding of the product development lifecycle and experience designing and delivering quality products.
• Experience and comfort operating in metrics-driven environments that leverage data to make informed decisions.
• Strong communication and presentation skills—this role requires presenting to audiences ranging from SMB operators to seasoned investors and executives.
• Demonstrated ability to put yourself in the customer’s shoes to understand their needs and how they interact with your products.
• Comfort managing teams through ambiguity, complexity, and imperfect information.

Nice To Haves

• Startup or founder experience.
• Experience building internal tools or automation systems.
• Real product examples you can share that you’ve built with AI.
• A track record of reducing cycle times or materially increasing team output.
• Past restaurant experience—especially working in one. A serious plus, but not a hard requirement.

Responsibilities

• Be the team leader for a group of PMs helping define the product strategy for the areas your direct reports own (Marketing, Guest Data, Labor, Shared Value). You will also be a major influencer in SpotOn’s overall product direction.
• Manage and coach a team of Product Managers as they investigate market opportunities, build roadmaps, and make strategic adjustments based on client needs, data, and business priorities.
• Assess market competition, client preferences, emerging technologies, and industry trends to identify what’s needed to maintain a competitive advantage.
• Be creative in your approach to product vision and design. SpotOn’s goal is not to chase what’s already out there—it’s to author the future of the industry we love.
• Work with cross-functional teams—Engineering, Design, Sales, and Support—to elicit, rationalize, and prioritize requests for new functionality.
• Build relationships with key business partners and serve as the internal and external evangelist for your product portfolio.
• Collaborate with product marketing on positioning and go-to-market strategies for your products.
• Audit workflows across departments to uncover repetitive, high-friction, and high-volume processes ripe for AI-driven improvement.
• Quantify impact in terms of time saved, output increased, or decision cycles shortened—and maintain a living AI opportunity roadmap aligned to company goals.
• Rapidly build and deploy functional AI-powered tools and automations using APIs, workflow orchestration platforms, and lightweight scripting. Launch pilots in days or weeks—not quarters.
• Partner with Engineering to productionize successful AI initiatives and define guardrails, governance, data handling standards, and monitoring processes.
• Create internal AI playbooks and best practices, run enablement workshops, and elevate AI fluency across teams.
• Track adoption, cycle time reductions, and measurable throughput improvements—and report impact to executive leadership.
• Continuously test and leverage insights—both customer feedback and AI experiment results—to inform decisions across your entire scope.
• Serve as a cross-functional advisor to leaders seeking to accelerate their functions, whether through better product or smarter AI deployment.
• Present to multiple audiences ranging from groups of SMBs to seasoned investors and executives.

Benefits

• Medical, Dental and Vision Insurance
• 401k with company match
• RSUs
• Paid vacation, 10 company holidays, sick time, and volunteer time off
• Employee Resource Groups to build community and inclusion at work
• Monthly cell phone and internet stipend
• Tuition reimbursement for up to $2,000 per calendar year to assist with your professional development

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees