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tastytrade Logo tastytrade · Finance

Head of Trade Surveillance and Best Execution

United States, Chicago Employment contract 170000.00 - 190000.00 USD / Year · Job Posted April 24, 2026
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Job Description

Come join a cross-functional team dedicated to protecting clients and the firm by ensuring trades are supervised, fairly executed, and accurately reported. You will own the end-to-end best execution and trade surveillance program for the broker-dealer, helping the business meet regulatory expectations while supporting scalable growth. You will work closely with Trading Desk, Operations, Compliance, Technology, and Finance to design controls, analyze execution quality, and resolve complex trading issues. Your work will turn trading data, venue analytics, and surveillance outputs into clear actions, reports, and process improvements that directly influence senior management decisions.

Job Responsibility

  • Lead the best execution program while continuously improving the firm's trade surveillance and best execution frameworks, policies, and procedures including venue analysis, routing reviews, and regular execution quality assessments and reports under FINRA Rule 5310
  • Manage trade management operations across the trade lifecycle (capture, allocation, corrections, breaks), ensuring accurate and timely processing and recordkeeping
  • Leveraging automated surveillance systems, data analytics, and emerging technologies to monitor and analyze trading activity more effectively including tuning alert logic, managing surveillance platforms, and working closely with engineering
  • Own trade-and execution-related regulatory reporting (e.g., CAT/CAIS, FINRA trade reporting facilities, and, where applicable, Rules 605/606 disclosures)
  • Coordinating across compliance, legal, and trading desks and reporting to senior management and regulators, while managing a Market Structure and Order Routing Specialist
  • Ensuring the firm's written supervisory procedures (WSPs) reflect current regulatory expectations and actual practice
  • Maintain and enhance written supervisory procedures, management reports, and committee materials that document reviews, decisions, and remediation
  • Partner on projects and system changes involving OMS/EMS, surveillance platforms, and data feeds, including testing, calibration, and control design

Requirements

  • Bachelor's degree in Economics, Business, Finance, Accounting, or related field (or equivalent work experience)
  • FINRA Series 4,7,24, and 63 (or equivalents)
  • 7-10 years of experience in broker-dealer trade surveillance, best execution, trading operations, or trade compliance
  • Strong working knowledge of FINRA Rules 5310 and 3110, SEC execution and reporting rules, and broker-dealer supervisory frameworks
  • Experience with trade surveillance and reporting platforms and OMS/EMS systems, plus strong data skills using tools such as Tableau and SQL or similar analytics
  • Experience with managing relationships with market managers and counterparties
  • Ability to interpret complex trading and venue data, communicate findings clearly in writing and verbally, and influence stakeholders across trading, operations, risk, legal, and compliance
  • High integrity, attention to detail, and a control mindset, with comfort working in a fast-paced, regulated trading environment and managing competing priorities

What we offer

  • 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
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