SpotOn

Senior Director of Product, AI

SpotOn

full-time

Posted on:

Location Type: Hybrid

Location: Chicago • Illinois • Missouri • United States

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Salary

💰 $220,000 - $260,000 per year

Job Level

Senior

About the role

  • 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.

Requirements

  • 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.
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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
product managementAI-powered workflowsLLM platformsautomation toolsorchestration toolslightweight scriptingproduct development lifecycledata-driven decision makingroadmap buildingmarket analysis
Soft Skills
team leadershipcoachingcommunicationpresentationcustomer empathystrategic thinkingcollaborationcreativityadaptabilityproblem-solving