Senior Product Manager

Company: tastytrade

Role: Senior Product Manager I

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 a Senior Product Manager, you'll lead complex product initiatives spanning multiple teams while driving strategic vision for a significant area of our trading platform. You'll mentor other product managers, develop deep subject matter expertise in your domain, and play a pivotal role in shaping the future of our retail brokerage and trading technology.

• Lead strategic product initiatives: Own complex, multi‑team projects from conception through delivery, developing 12‑18 month roadmaps that balance innovation with execution. Partner with engineering leadership to anticipate technical challenges and establish collaborative frameworks for technology innovation.
• Drive measurable business outcomes: Develop comprehensive product strategy that translates business vision into executable plans, implementing data‑driven frameworks to measure impact through OKRs and KPIs. Create sophisticated business cases with ROI projections and lead market research initiatives to inform strategic direction, with particular focus on trading platform capabilities.
• Navigate complexity and stakeholder relationships: Communicate confidently with executive stakeholders while effectively translating between technical and business perspectives. Resolve complex conflicts through structured negotiation and lead priority decisions that balance multiple business units and regulatory requirements.
• Leverage emerging technologies: Use AI and emerging technologies to enhance product capabilities and solve customer problems more effectively. Establish monitoring strategies to ensure ongoing adherence to performance, security, and reliability requirements post‑launch.
• Mentor and elevate the team: Coach Product Managers and Associate Product Managers on strategic thinking, stakeholder management, and domain expertise. Establish scalable ways of working and facilitate discovery sessions that improve team capabilities across the organization.

• 7‑10 years of product management experience with demonstrated success leading complex product initiatives, managing stakeholder relationships, and delivering products that drove significant business outcomes and revenue growth
• Deep expertise in retail trading, brokerage operations, or financial markets technology – you understand order execution, market data, trading workflows, account management, and regulatory requirements in the retail brokerage space
• Strong technical and commercial acumen – you can define comprehensive NFR requirements and work in lockstep with engineering teams while creating business cases, developing pricing models, and tracking financial metrics tied to product performance
• Mastery of advanced PM methods and emerging technologies – expert with prototyping, A/B testing, advanced analytics, and road mapping platforms, with experience leveraging AI and machine learning to optimize product capabilities
• Exceptional communication and leadership skills – able to tailor messaging to diverse stakeholders from engineers to executives, with experience mentoring junior product managers and establishing scalable ways of working across teams
• Passion for empowering individual traders and improving the trading experience through data‑driven insights and strategic decision‑making

• Performance bonuses
• Stock purchase options
• Annual educational / conference stipend
• Sustainable workday with minimal on‑call responsibilities
• 401(k) plan
• 20 paid vacation days (plus an additional paid vacation day the month of your birthday!)
• 10 paid sick days
• Pet insurance
• Wellness & mental health programs
• Charitable donation matching
• Daily catered lunch when in the office
• Full kitchen with snacks and beverages
• Shuttle to/from Metra
• Office located in the West Loop – Chicago’s growing center of tech, great cuisine, and high‑end bars

Base Salary: $155,000
The actual salary offered will be…