Director of Strategy & Transaction

Reporting to the CEO, the Director will lead Leeward’s digital asset and Web3 business, with full accountability for strategy, business origination, profitability, client delivery and risk management. Responsibilities and performance expectations

• Deliver annual revenue, new business, operating margin and client retention targets, reporting against budgets and agreed KPIs.
• Personally originate and convert mandates, maintain a measurable referral pipeline and expand relationships across international client markets.
• Lead advisory engagements for founders, boards and special councils covering structuring, token launches, treasury governance, restructuring and distressed situations.
• Lead multidisciplinary teams against utilization, productivity, service delivery and control standards.
• Oversee onboarding, AML/CFT compliance, financial reporting, banking, custody and wallet controls.
• Undertake frequent international travel, including at short notice, for client engagements, business development and industry events.
• Work across client time zones, including early mornings, evenings and weekends as required for international meetings, transactions and urgent client matters.

Essential qualifications and experience

• At least 16 years’ relevant professional experience, including substantial experience within a Big Four accounting or advisory firm and at least five years directly within digital assets and Web3.
• Bachelor’s degree in Economics, Finance or a related discipline, together with completed specialist programmes, diplomas or professional certifications in blockchain, digital assets and decentralized finance.
• Demonstrable executive responsibility for building and scaling a business or practice, with ownership of its P&L, budgets and commercial performance.
• Proven experience leading teams across corporate administration, treasury operations, accounting, governance and compliance, including recruitment, performance management and succession planning.
• Verifiable record of personally originating revenue, converting complex mandates and meeting growth and profitability targets.
• Substantial practical experience with Cayman foundation companies, DAO structures, BVI token issuers, token generation events, vesting arrangements and on-chain governance.
• Detailed working knowledge of multi-signature and MPC wallets, custody arrangements, signer policies, stablecoin treasury management and the Cayman VASP framework.
• Direct experience advising distressed Web3 businesses on restructuring, creditor negotiations, recovery processes and orderly wind-downs.