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Orla Gilligan

@orlagilligan

I review complex real estate, property finance, and AI-generated legal work.

United Kingdom
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What I'm looking for

I'm looking to apply my commercial real estate, property-finance and legal work-product review experience to complex legal, infrastructure or AI-evaluation work where independent judgement, accuracy and clear written reasoning matter.

I work across commercial real estate, property finance, secured lending and refinancing, with a focus on testing complex legal work for accuracy, risk and practical usefulness.

At Wessex Internet, I analyse statutory infrastructure issues, title information, contracts and evidential material, translating detailed legal requirements into concise operational advice. I also challenge unsupported positions and explain reasoned alternatives where legal, technical, cost and delivery considerations compete.

As a remote consultant at Woodstock Legal Services, I advise on acquisitions, disposals, leases, development and complex title matters. My work includes identifying gaps and contradictions, assessing solutions, and drafting and revising agreements for legal accuracy and commercial effect.

My experience also includes energy and infrastructure work for a national electricity and gas statutory undertaker, development work at Taylor Wimpey, and earlier litigation involving complex evidence and competing legal arguments. I’m particularly interested in applying substantive property expertise to evaluating and improving AI-generated legal content.

Experience

Work history, roles, and key accomplishments

WL
Current

In-House Solicitor - Telecommunications Infrastructure

Wessex Internet Limited

Oct 2025 - Present (11 months)

Analyse legislation, case law, title information, contractual documents and factual material within a technical statutory infrastructure regime, testing propositions against the underlying legal framework and identifying errors, inconsistencies and practical risk. Review and draft complex agreements and evidential material for accuracy, completeness, clarity and practical effect.

WL
Current

Consultant Senior Commercial Property Solicitor

Woodstock Legal Services LLP

Sep 2023 - Present (3 years)

Work autonomously in a remote consultancy model on commercial property matters, undertaking detailed title and document review and providing clear, reasoned advice. Advise on acquisitions, disposals, leases, development and complex title issues; identify gaps, contradictions and material risks and assess proposed solutions for legal and practical usefulness.

FL

Technical Property Associate Solicitor

Farnfields Solicitors LLP

Jan 2022 - Sep 2023 (1 year 8 months)

Advised on complex commercial property and development matters, including secured lending and refinancing, agricultural property, SIPP/SSAS transactions and difficult Land Registry issues. Reviewed lender, title, planning, development and transactional documentation, identifying legal and factual issues and producing practical, risk-based advice.

KL

Solicitor & Office Head

Kitson & Trotman LLP

Aug 2020 - Dec 2021 (1 year 4 months)

Managed a broad property caseload alongside office responsibility, reviewing complex transactional material, identifying risk and maintaining consistent professional standards.

GS

Locum Solicitor / Head of Conveyancing

Gales Solicitors

Jan 2020 - Jul 2020 (6 months)

Led a busy property function during a time-limited appointment, applying consistent quality standards while managing deadlines, risk and stakeholder expectations.

HL

Commercial Property Solicitor - Energy & Infrastructure

Harper Macleod LLP

Jul 2017 - Dec 2019 (2 years 5 months)

Acted exclusively for a national electricity and gas statutory undertaker, analysing complex title and infrastructure documentation within statutory and regulatory frameworks. Drafted and negotiated leases, easements, wayleaves and associated land-rights documentation; undertook title due diligence and assessed issues affecting legal rights and project delivery.

TL

Property & Development Paralegal

Taylor Wimpey UK Limited

Jan 2015 - Jan 2017 (2 years)

Worked client-side within a major residential developer, reviewing legal, title, planning and development material and collaborating with legal, planning and technical teams to resolve issues affecting delivery.

RC

Associate Solicitor

Richard Sedgley & Co

Mar 2002 - Dec 2005 (3 years 9 months)

Practised across clinical negligence, personal injury and property litigation, critically analysing pleadings, witness and expert evidence, documentary material and competing legal arguments. Prepared statements, pleadings, Schedules of Loss and court bundles; instructed experts and Counsel; assessed liability, quantum and litigation risk; and negotiated settlements.

SH

Assistant Solicitor

Shoosmiths

Aug 2001 - Feb 2002 (6 months)

Worked on high-value catastrophic injury and clinical negligence matters involving adults and children, requiring meticulous review of complex factual and medical evidence and careful testing of causation and liability arguments.

Education

Degrees, certifications, and relevant coursework

CL

College of Law

Professional Skills Certificate, Legal Practice

2000 - 2001

Completed the Professional Skills Certificate at the College of Law from 2000 to 2001.

Bournemouth University logoBU

Bournemouth University

Post Graduate Diploma in Legal Practice, Legal Practice

1998 - 1999

Completed a Post Graduate Diploma in Legal Practice at Bournemouth University from 1998 to 1999.

University of Southampton logoUS

University of Southampton

LLB (Hons), Law

1995 - 1998

Completed an LLB (Hons) in Law at the University of Southampton from 1995 to 1998.

King's College London logoKL

King's College London

Degree in Paediatric Nursing, Paediatric Nursing

1990 - 1993

Completed a Degree in Paediatric Nursing at King's College London from 1990 to 1993.

Tech stack

Software and tools used professionally

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