Director of Product

Company Name: tastytrade 
Role: Director of Product 
Location: Chicago, IL -- Hybrid (3 days/week in office) 

Our Product Team manages the portfolio of features and enhancements that power tastytrade, guiding each initiative from initial concept through discovery, build, deployment, and continuous improvement. As the Director of Product, you'll oversee multiple product lines and major platform components while establishing scalable delivery frameworks that drive innovation and significant business growth. You'll lead a team of product managers, develop organizational product strategy, and play a pivotal role in shaping the future of our retail brokerage and trading technology. 

What You'll Do: 

• Lead strategic product portfolio: Oversee multiple product lines with direct accountability for the impact of the 18-24 month strategic roadmap which you’ll jointly develop with our business leadership. Establish commercial frameworks that align product strategy with company financial objectives while creating new business models and revenue streams with measurable market impact. 
  
  
• Drive organizational transformation: Establish scalable delivery frameworks, KPI dashboards, and governance structures for predictability and efficiency. Lead the organization through complex product transformations while fostering a culture of innovation and continuous improvement across teams. Pioneer adoption of agent-augmented product development lifecycle workflows.  
  
  
• Deliver significant business outcomes: Create measurement systems that track how product initiatives impact company goals, using clear metrics and KPIs that everyone can understand. Build compelling business cases with financial projections to secure executive buy-in for major investments. Make data-driven decisions about which products to prioritize, expand, or sunset based on their contribution to revenue and strategic objectives. 
  
  
• Build high-performing teams: Develop future product leaders through comprehensive coaching programs and stretch assignments. Establish organizational standards for PM methods and tools while creating knowledge sharing frameworks that disseminate product expertise across the entire organization. 
  
  
• Master stakeholder relationships: Communicate product vision to diverse stakeholders from engineers to C-suite executives in ways that inspire action and alignment. Oversee strategic vendor management and partnership development while establishing frameworks for portfolio-level priority decisions across competing initiatives. 

Who You Are: 

• Demonstrable product management experience with proven ability to lead product organizations, make decisions grounded in commercial sensibility, and drive significant business outcomes through new business models and revenue streams
   
• Deep expertise in consumer-facing fintech or an adjacent regulated industry (e.g. insurance, gaming). Experience in retail trading, brokerage operations, or financial markets technology is a significant advantage – comprehensive understanding of trading platform capabilities, market microstructure, order execution, market data, and regulatory requirements including FINRA and SEC compliance frameworks 
  
  
• Strong technical and commercial leadership – ability to establish NFR standards across product lines, inform architecture decisions balancing innovation with business objectives, and develop sophisticated financial models with ROI projections 
  
  
• Mastery of strategic product methods – expert in establishing measurement frameworks, OKRs/KPIs, advanced analytics, and leveraging AI and emerging technologies to create competitive advantages while maintaining operational excellence 
  
  
• Exceptional executive communication – ability to translate complex technical concepts into compelling business narratives, navigate high-stakes organizational discussions, and build strategic partnerships with external vendors and partners 
  
  
• Proven team builder and change agent