Trust Associate Director – Winchester

Trusts Senior Manager - Winchester

Ref: 534Thursday 27 August 2026

Competitive Salary + Benefits

Trust Associate Director – Winchester

Winchester, Hampshire | Hybrid Working | Permanent | Competitive Salary + Benefits

Keywords: Trust Associate Director, Trust Director, Trusts & Estates, Private Client Tax, Trust Tax, Trust Manager, Inheritance Tax, IHT, Estate Planning, STEP, CTA, HNW, High Net Worth, Accountancy Practice, Winchester

We're recruiting a Trust Associate Director for a leading accountancy practice in Winchester.

This is a senior specialist opportunity for an experienced Trusts & Estates professional looking to take a leading role in developing a specialist service line, managing complex private client relationships and providing high-level technical advice.

Key Responsibilities

  • Lead and grow a complex portfolio of Trusts & Estates clients
  • Act as a trusted adviser on highly technical and sensitive matters
  • Provide specialist advice across trust taxation, estate planning and IHT
  • Oversee complex trust compliance, including trust accounts, tax returns and IHT returns
  • Build strong relationships with HNW clients and professional referrers
  • Act as a technical authority, supporting colleagues across the wider business
  • Help shape and develop the firm's Trusts & Estates offering
  • Identify new business opportunities and contribute to winning new work
  • Develop relationships with solicitors, financial advisers and other professional referrers
  • Maintain high technical, compliance and risk management standards
  • Support, mentor and develop members of the wider team

About You

  • STEP and/or CTA qualified
  • Minimum 8 years' post-qualified experience in Trusts & Estates
  • Extensive technical knowledge across trust taxation, IHT and estate planning
  • Strong experience advising HNW clients on complex and sensitive matters
  • Proven ability to manage and develop a high-value client portfolio
  • Strong leadership and team development experience
  • Commercially aware with a proven interest in business development
  • Excellent communication and relationship-building skills
  • Experience overseeing complex trust compliance work
  • Strong technical judgement and attention to detail
  • Professional, credible and confident dealing with senior clients and professional advisers

What's on Offer

  • Hybrid and flexible working
  • Senior leadership position within a growing Trusts & Estates team
  • High-quality HNW and private client portfolio
  • Significant technical and advisory exposure
  • Opportunity to help shape and grow a specialist service line
  • Strong business development and networking opportunities
  • Career progression towards Director / Partner
  • Supportive and collaborative working environment
  • Competitive salary and benefits

Location

Winchester, Hampshire, commutable from Southampton, Eastleigh, Romsey, Basingstoke, Andover, Fareham and surrounding areas.

Apply today for a confidential discussion with Jack Wood on 07817 796391 or jack@oscar-wood.co.uk.

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