Director of Product

tastylive•Chicago, IL

11d•$195,000 - $235,000•Hybrid

About The Position

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.

Requirements

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).
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 – track record of developing high-performing product organizations, mentoring product managers, and leading organizations through complex transformations
Passion for empowering individual traders and democratizing access to financial markets through innovative trading technology and exceptional user experiences

Nice To Haves

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

Responsibilities

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.

Benefits

Performance Bonuses
Stock Purchase Options
401k Plan
Medical/Dental/Vision Benefits
20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!)
10 Paid Sick Days
Gym Membership Reimbursement
Commuter Benefits
Pet Insurance
Wellness & Mental Health Programs
Charitable Donation Matching
Two Paid Volunteer Days Off
Daily catered lunch when in the office
Full kitchen with snacks and beverages
In-building gym
Shuttle to/from Metra