Director - OTC Hedging & Monetization

Fort Point is seeking a Director of OTC Hedging & Monetization who will serve as a senior subject matter expert responsible for structuring, evaluating, and executing sophisticated hedging and monetization strategies for ultra-high-net-worth individuals, founders, executives, family offices, and institutional clients.

The successful candidate will combine institutional OTC equity derivatives market-making experience, advanced quantitative modeling capabilities, and deep expertise in the tax, legal, regulatory, and operational considerations surrounding concentrated equity transactions. Working closely with senior leadership, financial advisors, dealer banks, and clients' legal and tax professionals, the ideal candidate will develop customized solutions that optimize downside protection, liquidity, diversification, financing, and tax efficiency while maintaining the highest standards of execution and regulatory compliance.

Primary Responsibilities/Expertise

Transaction Structuring & Execution

• Evaluate client objectives, tax considerations, financing costs, liquidity needs, and market conditions to develop customized transaction recommendations.
• Execute transactions from initial structuring through pricing, negotiation, documentation, and settlement.
• Exercise sound judgment in balancing transaction economics against tax, legal, regulatory, operational, and reputational considerations.
• Structure sophisticated concentrated equity solutions which shall include (i) Prepaid Variable Forwards, (ii) Equity Collars, (iii) Delayed Draw Forwards, (iv) Customized OTC Option Strategies, and (v) other bespoke hedging and monetization solutions.

Institutional OTC Derivatives Expertise

• Apply institutional OTC equity derivatives market-making experience to evaluate pricing, volatility, financing costs, dealer hedging strategies, and transaction economics.
• Negotiate pricing and transaction terms with major dealer banks to achieve optimal client outcomes.
• Review, analyze and negotiate ISDA agreements, confirmations, pledge agreements, collateral provisions, and other OTC documentation.
• Understand dealer balance sheet constraints, capital considerations, funding costs, inventory management, and hedge execution in order to effectively evaluate transaction structures and negotiate with counterparties.

Tax, Legal & Regulatory Expertise

Serve as an internal technical resource regarding the legal, tax, and regulatory considerations surrounding concentrated stock hedging and monetization strategies, including:

• IRC Sections covering hedging and monetization
• Qualified Covered Call Rules
• Wash Sale Rules
• Rule 144
• Rule 10b5-1
• Section 16 Reporting
• Exchange Act disclosure requirements
• Insider trading restrictions
• FINRA and SEC regulatory requirements

Partner closely with clients' attorneys and tax advisors to ensure transaction structures appropriately reflect applicable legal and tax considerations.

Quantitative Modeling & Platform Development

• Develop sophisticated pricing, valuation, and risk models supporting concentrated equity transactions.
• Build, calibrate, and maintain implied volatility surfaces, volatility skew models, and term structure analytics used in pricing and evaluating bespoke OTC equity derivatives.
• Design advanced financial models utilizing Excel, VBA, Power Query, Power Pivot, Python, SQL, or similar technologies to support transaction analysis, pricing, financing, tax optimization, and risk management.
• Develop scalable analytical tools and automate workflows that improve transaction efficiency, pricing transparency, and advisor decision-making.

Cross-Functional Collaboration

• Coordinate with external law firms, accounting firms, custodians, and dealer counterparties to facilitate transaction execution.
• Assist in developing transaction standards, analytical tools, and educational resources supporting the firm's concentrated equity platform.

Advisor & Client Support

• Serve as a technical resource for clients regarding sophisticated concentrated equity solutions.
• Participate in client meetings involving hedging and monetization transactions.
• Develop educational materials and provide training on evolving market structures, tax developments, regulatory changes, and transaction strategies.

Qualifications

Experience

• 10+ years of institutional equity derivatives experience.
• Direct OTC equity derivatives market-making experience at a major investment bank or institutional dealer.
• Significant experience pricing, structuring, negotiating, and executing bespoke OTC equity derivative transactions.
• Demonstrated experience advising on concentrated stock hedging and monetization strategies.

Technical Expertise

• Deep understanding of equity options, volatility markets, financing, securities-based lending, collateral management, and dealer hedging methodologies.
• Extensive knowledge of the tax, legal, and regulatory framework governing concentrated equity hedging and monetization strategies.
• Expert-level financial modeling and quantitative analysis skills.
• Demonstrated experience building and calibrating implied volatility surfaces, modeling volatility skew and term structure, and applying advanced option pricing methodologies.
• Advanced Excel skills, including VBA, Power Query, Power Pivot, and dynamic financial modeling.
• Programming experience in Python, SQL, C#, or similar languages used for financial analytics and automation.
• Strong understanding of stochastic processes, option pricing, risk modeling, and quantitative finance.
• Experience with ISDA documentation, OTC confirmations, pledge agreements, and collateral mechanics.