Management & Leadership Jobs in Chicago, IL (Now Hiring) — 8,169 open — Page 388

Company Name: tastytrade
Role: Director of Trade Management Operations
Location: Chicago, IL - Hybrid (3 days/week in office)
Licensing: FINRA Series 3, 4, 7, 24, and 63 licenses (or equivalents)

We are seeking a dynamic and experienced Director of Trade Management Operations to lead and transform our back-office function across our Broker-Dealer and non-clearing Futures Commission Merchant (FCM) businesses. This role carries broad ownership of post-trade operations — including trade settlement, clearing, custody, corporate actions, and reconciliation — while spearheading a firm-wide initiative to automate and modernize key back-office processes. The ideal candidate is an operational leader with deep capital markets expertise, a hands-on management style, and a proven ability to drive process improvement and build high-performing teams.  

What You’ll Do:  

Leadership & Team Building 

• Recruit, build, and develop a high-performing back-office team spanning reconciliation, settlement, clearing, and custody operations 
• Define team structure, roles, and responsibilities; establish clear performance standards and career development pathways 
• Provide day-to-day management, coaching, and mentorship to staff at all levels 
• Partner with HR on headcount planning, hiring, and workforce development as the business grows 
• Serve as the primary escalation point for operational breaks, settlement failures, and counterparty disputes

Back Office Operations 

• Oversee all post-trade operations across asset classes including equities, options, exchange-traded derivatives, and FX 
• Manage trade confirmation, settlement, and fail management across custodians, prime brokers, and clearing firms 
• Coordinate give-up processing and submission workflows between executing brokers and the firm's designated clearing FCM, ensuring accurate and timely allocation of futures and options trades 
• Supervise corporate actions processing, including voluntary and mandatory events, elections, and entitlement reconciliation 
• Oversee margin and collateral tracking in coordination with the clearing FCM, Prime Brokerage, and Treasury 
• Ensure all back-office functions adhere to strict settlement deadlines and operational SLAs

Reconciliation 

• Own end-to-end reconciliation across all business lines, including trade, position, cash, and asset reconciliation 
• Oversee daily reconciliation of internal books and records against prime broker, custodian, and clearing FCM statements 
• Manage position and cash reconciliation across exchange-traded products, ensuring alignment between the firm's records and clearing FCM-reported balances 
• Ensure compliance with broker-dealer customer protection obligations under SEC Rule 15c3-3 and applicable FINRA rules
• Drive root cause analysis on recurring breaks and implement sustainable corrective actions to reduce break volumes over time

Automation & Process Transformation 

• Lead a strategic initiative to automate back office and reconciliation workflows, reducing manual processing and operational risk across the function 
• Evaluate, select, and implement technology solutions including reconciliation platforms (e.g., AutoRek GMI, Broadridge) and back-office processing systems 
• Define the target operating model for a scalable, automated back office and drive execution of the transformation roadmap 
• Partner with Technology and Data teams to design automated break detection, exception management, and reporting workflows 
• Establish KPIs and management dashboards tracking settlement efficiency, break aging, fail rates, and STP rates, with regular reporting to senior leadership 
• Champion data quality and standardization initiatives to improve straight-through processing across the trade lifecycle

Risk, Controls & Compliance 

• Maintain a strong control environment consistent with SEC, FINRA, CFTC, and NFA requirements applicable to a non-clearing FCM 
• Develop and maintain policies, procedures, and desktop guides for all back-office functions 
• Partner with Internal Audit, Compliance, and Risk Management on control assessments, regulatory examinations, and audit responses 
• Monitor regulatory developments impacting back-office obligations and proactively update processes and controls accordingly

Who You Are:

• 6-10 years of progressive experience in back-office operations at a broker-dealer, FCM, prime broker, or clearing firm
• FINRA Series 3, 4, 7, 24, and 63 licenses (or equivalents)
• Broad operational knowledge spanning settlement, clearing, custody, corporate actions, and reconciliation across multiple asset classes 
• Familiarity with non-clearing FCM operations, including give-up processing, allocation workflows, and coordination with clearing FCMs
• Demonstrated experience managing and developing operational teams 
• Proven track record leading process improvement or automation initiatives within a financial services environment
• Strong working knowledge of DTCC (DTC, NSCC, FICC) settlement processes and exchange-traded derivatives workflows
• Familiarity with regulatory requirements applicable to broker-dealers and non-clearing FCMs, including SEC Rule 15c3-3, FINRA rules, and baseline CFTC/NFA obligations
• Experience with reconciliation or back-office platforms (SmartStream, Broadridge, Duco, AutoRek, or comparable)
• Strong analytical, communication, and organizational skills with the ability to present to senior management and regulators     

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: $150,000 - $175,000
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, and tastyfx—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 FTSE 100 fintech operating across five continents serving over 1.3m customers and handling billions of dollars in transactions – built on scale, trust, and proof. 

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.

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. The bar is high – bring a curious and forward-thinking mindset and we'll give you the platform to define what comes next. Join us at IG|tasty – the future gets built here. 
 
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!