Jack Ashford is a legal professional at Cleveland & Co, advising across the firm’s client base on financial regulation, commercial contracts, and corporate matters. With a strong foundation in contentious work and financial mis-selling claims, Jack brings a disciplined, detail-driven approach to complex legal issues, supporting clients with clear, practical advice in fast-moving environments.
Jack has developed experience in contentious financial regulation, including financial mis selling claims, supporting large scale and document intensive matters under demanding time pressures. He assists with legal research, evidence analysis, disclosure review, and the preparation of materials across the dispute lifecycle, contributing to the effective management of complex regulatory and litigation driven workstreams.
Prior to joining Cleveland & Co, Jack worked in the Financial Mis-Selling Department at Hugh James, where he managed matters from onboarding and early case assessment through to settlement and trial preparation. His experience included analysing evidence and documentation, preparing detailed risk assessments, and drafting key correspondence throughout the dispute lifecycle, strengthening his ability to operate effectively under pressure and handle complex, document-heavy matters with care and accuracy.
Jack’s approach reflects Cleveland & Co’s core values of clarity, responsiveness, and excellence. He is known for his calm and organised working style, strong attention to detail, and collaborative mindset, which enable him to support colleagues and clients across fast moving and evolving legal matters. Alongside his client work, Jack contributes to the firm’s thought leadership and client communications, supporting newsletters and assisting with articles on legal and regulatory developments.
Outside of work, Jack enjoys playing football and training at the gym, interests that reflect the same resilience, energy, and discipline he brings to his legal practice.
Jack is developing technical skills in:
- AML
- Financial Services regulation
- Broker Agreements
- Broker Services
- Business Formation
- Civil Litigation
- Collective Investment Schemes
- Compliance
- Commercial Contracts
- Corporate Agreements
- Corporate and Commercial
- Pension Funds
- Legal Strategy
- Financial Regulation
- Regulatory & Compliance
- Regulatory Developments
- Regulatory Investigation
- Regulatory Obligations
Public Markets & Investment Management Advisory
Support for investment managers and listed entities on a broad range of corporate and commercial matters within the financial services sector. Advise on contractual arrangements, governance frameworks, and operational issues impacting regulated firms, applying a practical understanding of market conduct and regulatory expectations developed through prior contentious financial services work.
Financial Regulation & Regulatory Risk
Provide regulatory advisory support to investment managers, drawing on a strong foundation in FCA principles, FSMA 2000, and Conduct of Business obligations. Assist with interpreting and applying regulatory requirements to day-to-day business operations, fund structures, and client communications, with a litigation-informed focus on identifying conduct risk, evidential vulnerabilities, and enforcement exposure at an early stage.
Commercial Contracts & Cross-Disciplinary Insight
Experience in advising on general commercial matters for financial services clients, including supplier agreements, services contracts, and advisory arrangements. Leverage experience from complex financial mis-selling litigation to assess risk allocation, liability caps, and termination provisions through a contentious lens, ensuring documentation is robust, commercially balanced, and defensible in the event of dispute or regulatory scrutiny.
Data Protection & Information Governance
Advising investment managers on data protection and information governance issues, including contractual data protection provisions, data sharing arrangements, and compliance with UK GDPR requirements. Apply a risk-based approach shaped by prior litigation exposure to disclosure disputes and evidential management, helping clients mitigate regulatory, reputational, and operational risk associated with personal and confidential data.
Client-Focused Delivery & Commercial Judgment
Worked closely with senior lawyers and clients to deliver clear, concise, and commercially grounded support. Known for bringing a dispute-aware mindset to advisory work, anticipating how advice and documentation may be scrutinised by regulators, counterparties, or courts, and contributing to pragmatic solutions aligned with clients’ commercial objectives.
- Bachelors Degree of Law, LLB – Cardiff University, September 2019 to June 2022.
- English
