Remote Position - must reside in Florida, Texas, Illinois, New York, New Jersey, Colorado, Idaho, Massachusetts, Michigan, Minnesota, Missouri, North Carolina, South Carolina, Utah or Virgina

Who We Are:

TradeStation is an online brokerage firm seeking to level the playing field for self-directed investors and traders, empowering them to claim their individual financial edge.  At TradeStation, we're continuously pushing the boundaries of what's possible, encouraging out-of-the-box thinking and relentless search for innovation.

What We Are Looking For:
 

We’re seeking a Senior Director who is a product leader to architect and deliver the future of AI at TradeStation — from the ground up. The Senior Director will define what an AI platform means for our business, identify the highest-impact use cases, and lead the design, selection, and deployment of the tools, APIs, and guardrails that will power next-generation trading experiences and operational efficiency.

This is a builder-operator role which means  designing, developing, and running early AI automations, agents, and prompting systems that immediately enhance product management workflows and decision-making, while laying the foundation for enterprise-scale AI adoption.

This role will drive AI at TradeStation by owning and leading the operational AI & automation process as well as building the Customer AI Platforms & Tools.

This leader will think in systems — data, guardrails, workflows — not just features. The Sr. Director will be fluent in brokerage across equities, options, and futures, and measure success in hard business metrics, not flashy demos. This role will know how to navigate SEC/FINRA frameworks, align InfoSec, Legal, and Compliance, and carve a repeatable path to market for AI products — from vision to hands-on execution.

What You’ll Be Doing:

• Operational AI & Automation – Partner with the Sr. Director of AI Implementation & Automation to embed AI into high-impact workflows, reducing manual effort, improving accuracy, and delivering measurable efficiency gains
• Customer AI Platforms & Tools – Build and operate the AI platforms, APIs, and guardrails that enable product teams to deliver AI-powered trader capabilities with speed, clarity, control, and compliance — directly increasing engagement, trade volume, and retention
• Define, Build, and Own the AI Product Platform: Lead discovery of platform requirements, evaluate build vs. buy, select core technologies, and stand up the initial platform with security, compliance, and scalability in mind. Operate AI tools, LLM integrations, agents, and automations during the build phase to deliver immediate business impact.
• Identify and Deliver High-Value AI Initiatives: Map, prioritize, and execute AI opportunities across customer experiences and brokerage operations, with clear ROI, KPIs, and measurable outcomes.
• Automate and Enhance the Product Management Function: Design and deploy AI automations, agents, and prompt libraries to accelerate research, analysis, and product delivery.
• Enable AI-Powered Customer and Operational Solutions: Partner with product, data, and operations leaders to embed AI into trading platforms, workflows, and analytics pipelines — improving trader performance, operational accuracy, and efficiency.
• Commercialize Winning AI Proofs-of-Concept: Rapidly assess AI POCs for technical and business viability, scaling the most impactful into production.
• Ensure Compliance and Remove Bottlenecks: Collaborate with InfoSec, Legal, and Compliance to navigate SEC/FINRA frameworks, streamline approvals, and maintain governance.
• Report and Iterate: Communicate AI progress to senior leadership, tie milestones to tangible business impact, and adjust strategy based on results.
• Shape and Evolve the Role: Take ownership of defining what this role becomes over time. As AI adoption expands, proactively identify new opportunities, responsibilities, and areas of ownership — carving a path that grows the role’s scope and influence within the organization.

The Skills You Bring:

• Hands-on AI Builder: Skilled at designing, prototyping, and deploying AI automations, agents, and prompt-based workflows without waiting on large engineering builds
• Platform Strategist: Able to define multi-year AI platform strategy while delivering near-term wins in a greenfield environment
• Executive-Level Leadership: Strong cross-functional influence across Product, Engineering, Data, Operations, Legal, and Compliance — bringing structure to ambiguity, driving urgency, and delivering measurable results
• Technical and Regulatory Execution: Proven ability to set up, configure, and operate AI platforms, LLMs, and agent frameworks while navigating SEC/FINRA compliance requirements
• Outcome-Driven Operator: Defines clear KPIs for all AI initiatives, tracks progress, and holds teams accountable for delivering measurable business impact
• POC Triage and Scaling: Skilled at rapidly assessing AI proofs-of-concept for technical and commercial viability and scaling the winners to production
• Mentorship & Enablement: Capable of upskilling product teams in AI tools, frameworks, and delivery processes without direct reporting lines
• Comfortable operating in high-urgency, high-visibility environments with competing priorities
• Deep domain expertise in brokerage operations — equities, options, and/or futures — OR equivalent expertise in broker-dealer technology, market structure, and regulatory reporting
• Technical execution skills to set up, configure, and operate AI platforms, LLMs, and AI agent frameworks (e.g., LangChain, AutoGen, Haystack, semantic search pipelines) in a production environment
• Regulatory navigation skills with demonstrated ability to work within SEC/FINRA frameworks (e.g., Reg BI, 2210, 15c3-5, 17a-4) to deliver compliant AI solutions
• Track record of scaling AI initiatives — including POC evaluation, commercialization, and cross-functional delivery — in complex, regulated environments
• KPI-driven leadership with the ability to prioritize based on business impact and hold teams accountable for measurable outcomes
• Greenfield AI platform experience — launching shared AI infrastructure from scratch in a regulated environment preferred
• Hands-on expertise with LLM configuration, AI agent frameworks, and prompt engineering for both operational automation and customer-facing applications preferred
• Experience delivering AI-powered capabilities for self-directed trading or active trader platforms preferred
• Familiarity with U.S. brokerage back-office and middle-office workflows (onboarding/KYC, funding, ACATS, margin, surveillance, corporate actions) and how to automate them preferred
• Track record of accelerating AI delivery by creating repeatable playbooks for InfoSec, Legal, and Compliance approvals preferred
• Background in AI safety, governance, and explainability frameworks for financial products preferred
• Strong fintech and AI partner network with proven ability to evaluate and integrate third-party solutions preferred

Minimum Qualifications:

• 10–15 years of progressive product management experience, including 5+ years at the Senior Director level or above in fintech, trading technology, or other heavily regulated financial services.
• Proven record of delivering AI/ML-powered products or large-scale workflow automation from concept to production with quantifiable business impact (e.g., multi-million-dollar revenue growth, double-digit efficiency gains, major risk reduction)

Desired Qualifications:

• Advanced degree in a relevant field (e.g., Computer Science, Financial Engineering, Data Science, MBA).

What We Offer:

• Collaborative work environment
• Competitive Salaries
• Yearly bonus
• Comprehensive benefits for you and your family starting Day 1
• Unlimited Paid Time Off
• Flexible working environment
• TradeStation Account employee benefits, as well as full access to trading education materials
• Pay Range (US) $250-280K (Countries outside of the US have differing ranges in accordance with local labor markets)

TradeStation provides equal employment opportunities to current and prospective employees, without regard to race, color, religion, sex, national origin, ancestry, sexual orientation, age, pregnancy, disability, handicap, citizenship, veteran or marital status, or any other legally recognized status entitled to protection under federal, state, or local anti-discrimination laws.

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