Sr. Director - Brokerage Services AI and Automation

[Link available when viewing the job] 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: As the Senior Director of AI Implementation and Automation for Brokerage Operations, you will be the strategic and operational leader responsible for designing, deploying, and optimizing advanced AI and intelligent automation solutions across our brokerage ecosystem. This role requires deep expertise in financial markets and brokerage operations, paired with a strong technical foundation in artificial intelligence and process automation. You will champion end-to-end transformation of trading, post-trade, compliance, and client-facing processes, ensuring measurable impact, compliance, and exceptional client experience. What You’ll Be Doing:

• Develop and execute a comprehensive AI and automation strategy aligned with organizational, operational, and regulatory goals
• Lead large-scale AI initiatives, from proof-of-concept to production, ensuring performance, scalability, and compliance
• Oversee intelligent automation architecture using AI/ML, RPA, NLP, and decision engines across core brokerage workflows (clearing, settlements, surveillance, onboarding, fraud detection, client advisory, and others)
• Partner with Product, Technology, Compliance, Legal, Risk, and Data Science teams to identify business opportunities and drive seamless implementation
• Direct the project planning, budgeting, staffing, vendor selection, and performance monitoring for all AI/automation initiatives
• Communicate strategy, progress, and outcomes to senior executives, board members, regulators, and business stakeholders
• Ensure alignment with regulatory standards (SEC, FINRA) and support data governance, model explainability, and audit readiness
• Build, mentor, and grow a high-performing, cross-disciplinary team, fostering innovation and a continuous-improvement culture
• Drive operational excellence and measurable outcomes (speed, accuracy, cost, efficiency, client experience)

The Skills You Bring:

• Proven track record of implementing AI/ML and automation (RPA) solutions within trading, brokerage, or wealth management contexts
• Deep understanding of financial markets, trading systems, broker-dealer operations, and regulatory environments
• Technical expertise with AI/ML development (Python, TensorFlow, Scikit-learn, LLM APIs), automation tools (UiPath, Blue Prism), and cloud platforms (AWS, Azure, GCP)
• Strong cross-functional collaboration, communication, and stakeholder management skills
• Experience with regulatory compliance, audit support (JSOX, 3120 testing), and risk frameworks
• Preferred: Background with generative AI, NLP, real-time data processing, middle-office modernization, margin systems, and vendor management

Minimum Qualifications:

• 10 years of experience in financial services or brokerage operations, with 5+ years in senior leadership roles focused on AI, automation, or digital transformation

Desired Qualifications:

• Advanced degree in Computer Science, Finance, Data Science, or related field preferred

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) $250K+ (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. Apply Job! Apply to this Job