Lead Product Manager

tastylive • Chicago, IL

19h • 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. We're hiring a Lead Product Manager to own the foundation every tastytrade customer touches — the core platform experience across mobile, web, and desktop including onboarding, discovery, and the connections between our vertical trading products. This is a high-visibility role with real platform authority and a team to lead.

Requirements

• 8+ years of product management experience with demonstrated success leading complex, cross-functional product initiatives — including experience setting direction for other PMs or operating in a lead capacity on a multi-PM team
• Deep expertise in consumer-facing experiences that span mobile and web, with a strong point of view on navigation, information architecture, onboarding, and product discovery and design. You've thought hard about how customers progress through a product over time, not just how they use it in a single session
• Strong technical and commercial acumen — you can define comprehensive non-functional 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 a track record of influencing without authority across teams with competing priorities
• Passion for empowering individual traders and improving the trading experience through data-driven insights and strategic decision-making

Nice To Haves

• Experience in fintech or an adjacent regulated industry (e.g. insurance, gaming) or retail trading, brokerage operations, or financial markets technology is a meaningful advantage — you understand that platform decisions carry compliance and operational weight, not just UX tradeoffs

Responsibilities

• Own the customer journey: Drive the end-to-end experience from onboarding and first funding through account management and dashboard, optimizing for the progressions that matter: first funded account, first trade, first options position.
• Set platform standards: Establish the design conventions, navigational frameworks, and shared components that vertical product teams build within, ensuring the full tastytrade experience feels coherent across products and platforms.
• 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 — with particular focus on activation rates, funding conversion, feature discoverability, and cross-sell. Create sophisticated business cases with ROI projections and lead market research initiatives to inform strategic direction. Define the metrics that matter for platform health and customer progression and hold yourself accountable to them.
• Navigate complexity and stakeholder relationships: Operate as the connective tissue between vertical product teams (equities, options, futures, FX etc.) and the broader organization — resolving prioritization conflicts, establishing shared conventions, and ensuring that platform-level decisions serve both the business and end customers well. Communicate confidently with executive stakeholders while effectively translating between technical and business perspectives. 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 — from smarter onboarding personalization to intelligent cross-sell surfaces and proactive account management tools. Establish monitoring strategies to ensure ongoing adherence to performance, security, and reliability requirements post-launch.
• Mentor and elevate the team: This role carries real leadership responsibility - You'll coach Product Managers and Associate Product Managers on strategic thinking, stakeholder management, and domain expertise — helping them grow into increasingly senior roles. Establish scalable ways of working, run effective discovery sessions, and model the standard for product craft across the organization.

Benefits

• Performance Bonuses
• Stock Purchase Options
• Medical/Vision/Dental Benefits
• 401k Plan
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed