Head of Product (VP-Level)

tastytrade•Chicago, IL

12d•$275,000 - $325,000•Hybrid

About The Position

IG North America is seeking a Head of Product to define and execute product strategy across our North American trading platforms. As Head of Product, you will own the product roadmap for the entire organization, reporting directly to the North America CEO. This is a defining leadership role - you'll lead the evolution of our product management practice; establishing product as a standalone function separate from technology and elevating its strategic importance within the organization. You will lead and develop a team of 9 Product Managers and 9 Product Designers (including a Head of Design), while also having oversight of CRM journeys and internal tooling. This role offers the opportunity to shape the future of retail trading technology while building contemporary products that broaden our reach.

Requirements

A seasoned product leader with a track record of leading and scaling product organizations, with demonstrated success setting strategy, building teams, and driving business outcomes at the company level
A confident and credible cross-functional leader who can represent product in the senior leadership team, earn the trust of engineering and design partners, and bring stakeholders across the organization into alignment around a shared vision
Deep expertise in consumer-facing fintech or an adjacent regulated industry (e.g. insurance, gaming).
A skilled operator who can translate strategic ambition into structured execution — establishing OKRs, delivery cadences, and measurement frameworks that scale across a growing team and portfolio
Technically and commercially fluent — able to inform architecture decisions, set non-functional requirement standards across product lines, and develop sophisticated financial models with ROI projections that inform executive-level investment decisions
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 financialmarkets 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

Develop and steward an 18-24 month roadmap that directly reflects CEO and board-level priorities.
Serve as the authoritative voice of product strategy across the organization — translating high-level business objectives into clear, actionable, and efficiently executed plans that create measurable market impact.
Design customer-centric product experiences that balance sophisticated trading capabilities with intuitive usability, supporting customer progression from basic investing to active trading in multiple asset classes.
Own CRM journey strategy and executive product decisions on internal tooling solutions.
Develop and maintain a deep understanding of active traders’ needs, psychology, and decision-making processes.
Identify the unmet needs of traders and translate them into category-defining products.
Lead the product team in conducting user research via multiple channels - including platform usage data, customer support interactions, industry research, targeted surveys, user analytics - to build a holistic understanding of customer needs and lead teams in designing experiences customers love.
Develop an ecosystem of trading tools, educational content, community, and engaging market awareness features to provide active traders with opportunity to succeed.
Represent the product organization in the leadership team, partnering with the CEO, CTO and other tastytrade and IG Group leadership on business strategy execution, market expansion priorities, and investment decisions while maintaining tastytrade's independent culture and trader-first focus.
Facilitate portfolio-level trade-off decisions across competing initiatives and build the organizational trust that keeps product at the center of company decision-making.
Create measurement systems that track how product initiatives impact company goals, using clear metrics and KPIs that everyone can understand.
Build a robust understanding of brokerage economics including transactional revenue, payment for order flow, credit and debit interest, regulatory capital requirements, and operating expense structure.
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.
Recruit, coach, and develop product managers at every level - establishing career paths, mentorship programs, and stretch assignments that grow the next generation of product leaders.
Set the bar for PM craft and foster a culture of curiosity, rigor, and continuous improvement.
Build the frameworks, standards, and culture that make product management a recognized center of excellence at tastytrade.
Design and implement the governance structures, rituals, and KPI dashboards that drive predictability, accountability, and efficiency across the portfolio.
Drive AI integration both within the product experience (personalization, trading tools, education) and across team workflows to accelerate delivery.

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