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tastytradetastytradeChicago, IL

Lead Product Manager

Lead Product Manager owning the core platform experience across mobile, web, and desktop for a fintech trading platform. Sets platform standards, drives activation metrics, mentors PMs, and leverages AI to improve onboarding, discovery, and cross-sell.

190k – 220k/yr
Hybrid8+ YOEProduct Management

About the role

What You’ll Do

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:

  • 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.

Who You Are

  • 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
  • Strong technical and commercial acumen — able to 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
  • 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

Compensation & Benefits

  • Base Salary Range: $190,000 - $220,000
  • Discretionary Performance Bonus: 15-20% of base salary
  • 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

Skills

Product ManagementMobileWebOnboardingNavigationInformation ArchitectureProduct DiscoveryA/B TestingAnalyticsRoadmappingAIMachine LearningPrototypingStakeholder ManagementOkrs
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