Tastylive
Strategic Operations Leader
$150,000 – $175,0001w ago
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.
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). 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 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
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
Salary Range: $275,000 - $325,000 The actual salary offered will be based on the candidate's level of experience and qualifications Discretionary performance bonus: 15-20% of base salary based on individual and company performance + eligibility to participate in company long term incentive equity plan. About IGNA + tasty IG North America is home to tastytrade, tastylive, tastyfx, and tastycrypto—a family of brands built to democratize trading and empower individual investors. Founded in Chicago by the creators of thinkorswim, acquired by London-based IG Group in 2021, we combine startup innovation with the backing of a global fintech leader with 50+ years of experience. From our headquarters in Chicago's Fulton Market, our team builds award-winning trading platforms, produces live financial education content daily, and creates technology that makes complex markets accessible. tastytrade is our retail brokerage for self-directed investing and trading, with tastylive providing content to educate our customers. tastyfx is the fastest-growing forex broker in the US. tastycrypto provides self-custody digital wallets for decentralized finance. We're a lean, collaborative team that values autonomy, pragmatism, and impact. Whether you're building technology, creating content, serving customers, or supporting operations, you'll work alongside people who are passionate about disrupting traditional finance and genuinely care about helping traders succeed. Our culture rewards initiative, embraces experimentation, and measures success by the value we create for our users. Location: Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars. tastytrade | tastylive | tastyfx | tastycrypto 1330 W Fulton Market, Chicago, IL 60607 *Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they have every single qualification. Our team is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role but your experience doesn't align perfectly, we encourage you to apply anyway. You may be just the right candidate for this or other roles!