Head of Trade Surveillance and Best Execution

Company Name: tastytrade
Role: Head of Trade Surveillance and Best Execution
Location: Chicago, IL - Hybrid (3 days/week in office)
Licensure: FINRA Series 4,7,24, and 63 (or equivalents)

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. 

What You’ll Do:  

• Program Ownership: 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. 

• Trade Management Operations: Manage trade management operations across the trade lifecycle (capture, allocation, corrections, breaks), ensuring accurate and timely processing and recordkeeping. 

• Technology & Systems: Leveraging automated surveillance systems, data analytics, and emerging technologies to monitor and analyze trading activity more effectively. This would include tuning alert logic, managing surveillance platforms, and working closely with engineering. 

• Regulatory Interface: Own trade-and execution-related regulatory reporting (e.g., CAT/CAIS, FINRA trade reporting facilities, and, where applicable, Rules 605/606 disclosures). 

• Team Leadership: Coordinating across compliance, legal, and trading desks and reporting to senior management and regulators, while managing a Market Structure and Order Routing Specialist. 

• Policy & Procedure: 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. 

• Projects: Partner on projects and system changes involving OMS/EMS, surveillance platforms, and data feeds, including testing, calibration, and control design. 

Who You Are: 

• 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. 

Company Perks + Benefits:

• 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

Salary Range: $170,000 - $190,000
The actual salary offered will be based on the candidate's level of experience and qualifications

Discretionary performance bonus: 15-20% of base salary based on individual and company performance

About IGNA + tasty
IG North America is home to tastytrade, tastylive, tastyfx, and tastycrypto—a family of brands built to democratize trading and empower individual investors. Founded in Chicago by the creators of thinkorswim, acquired by London-based IG Group in 2021, we combine startup innovation with the backing of a global fintech leader with 50+ years of experience.

From our headquarters in Chicago's Fulton Market, our team builds award-winning trading platforms, produces live financial education content daily, and creates technology that makes complex markets accessible. tastytrade is our retail brokerage for self-directed investing and trading, with tastylive providing content to educate our customers. tastyfx is the fastest-growing forex broker in the US. tastycrypto provides self-custody digital wallets for decentralized finance.

We're a lean, collaborative team that values autonomy, pragmatism, and impact. Whether you're building technology, creating content, serving customers, or supporting operations, you'll work alongside people who are passionate about disrupting traditional finance and genuinely care about helping traders succeed. Our culture rewards initiative, embraces experimentation, and measures success by the value we create for our users.

Location: Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars.

tastytrade | tastylive  | tastyfx | tastycrypto
1330 W Fulton Market, Chicago, IL 60607  

*Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they have every single qualification. Our team is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role but your experience doesn't align perfectly, we encourage you to apply anyway. You may be just the right candidate for this or other roles!