Senior Director of Product & AI, SpotOn

• 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
• 6+ years of relevant product management experience, with at least 3 years managing and coaching a team of Product Managers
• Demonstrated experience building and deploying AI-powered workflows in real-world environments
• Technical fluency with LLM platforms, agents, automation/orchestration tools, and lightweight scripting
• 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

Desirable

• We’re looking for a Senior Product and AI leader who can operate at the intersection of customer-facing product strategy and internal organizational acceleration
• This is not just a team management role, and it’s not just an innovation lab experiment
• It’s a high-agency position that spans two critical mandates:
• You'll 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
• You'll 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
• 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
• Assess market competition, client preferences, emerging technologies, and industry trends to identify what’s needed to maintain a competitive advantage
• 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
• What Success Looks Like
• Within 90 Days
• Product team relationships established; initial roadmap reviews completed for Marketing, Guest Data, Labor, and Shared Value
• Top 10 AI leverage points identified across the organization
• Multiple AI pilots launched; at least one visible, high-impact workflow accelerated
• Within 6 Months
• Clear product strategy defined for all four product areas with executive alignment
• AI embedded in several cross-functional workflows with documented velocity improvements
• Internal AI enablement framework established
• Within 12 Months
• Product portfolio is driving measurable business outcomes for SpotOn’s restaurant operators
• Measurable increase in organizational throughput attributable to AI initiatives
• AI embedded as a default tool across critical operations, with a clear roadmap for continued scaling