Head Of Operations - OTC Prop Trading Firm

PEAK6 • Chicago, IL

1d • Hybrid

About The Position

We are a proprietary trading firm building and scaling an OTC equity derivatives platform. We are seeking a Head of 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 Head 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: Equity Index & Single Name Options Variance Options & Variance Swaps Volatility, Dividend, Total Return / Price Return, Dispersion & Basket Swaps
• Experience with Credit Default Swaps preferred, but not required
• 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

Benefits

• We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match.
• We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits.
• As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed