Director, OTC Operations

PEAK6•Chicago, IL

16h•Hybrid

About The Position

We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets. ABOUT THIS ROLE We are a proprietary trading firm building and scaling an OTC equity derivatives platform. We are seeking a Director of OTC Operations to architect and lead the full operational infrastructure across OTC trading, documentation, collateral, and counterparty management. This individual will operate as the senior operational authority and a strategic partner to executive leadership. As the Director of OTC Operations, you will be an experienced operator with a deep understanding of OTC products and can design scalable systems, controls, and workflows from the ground up while serving as a strategic partner to trading and senior leadership. To be successful, the candidate must be an independent, hands-on, solutions-oriented leader with the ability to identify gaps, implement institutional-grade processes, and operate without relying on day-to-day direction.

Requirements

5+ years in OTC derivatives operations at a bank, hedge fund, or prop firm
Director level or senior individual contributor with demonstrated ownership
Strong operational experience required across: E quity Index & Single Name Options Variance Options & Variance Swaps Volatility, Dividend, Total Return / Price Return, Dispersion & Basket Swaps
Hands-on experience with Markitwire/OSTTRA, ISDA & CSA frameworks, and S&P Counterparty Manager
Strong understanding of margin, collateral, and treasury flows related to OTC transactions

Nice To Haves

Experience with Credit Default Swaps preferred, but not required

Responsibilities

Lead end-to-end OTC trade lifecycle management (execution through settlement lifecycle events, and unwind)
Own confirmation workflows via Markitwire (OSTTRA) and ensure timely matching and affirmation with bank counterparties
Oversee ISDA, CSA, and confirmations governance in partnership with Legal & the Head of Operations
Manage counterparty onboarding and relationships, including ISDA’s, using tools such as S&P Counterparty Manager
Build and manage collateral and margin processes (IM/VM, disputes, treasury coordination)
Establish operational support across complex OTC equity derivatives and structured products
Design scalable systems, reconciliation controls, and reporting infrastructure
Act as operational advisor to senior leadership on new products, counterparties, and capital efficiency
Build and lead an operations team over time