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Diann Cannon

Diann is a Partner in the Corporate and Commercial Department, advising on mergers and acquisitions, private equity and venture capital investments, corporate restructurings, succession planning, and commercial contracts.
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She works closely with business owners, founders, investors, and management teams, providing clear, commercially focused advice on transactions across the full spectrum; from early-stage fundraisings, commercial contracts, and mid-market transactions to complex, high-value corporate transactions.

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Experience

Diann joined Flynn O'Driscoll LLP in 2012, having previously worked in the legal department of the Irish concentrates division of The Coca-Cola Company.

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She has extensive experience in domestic and cross-border mergers and acquisitions (both buy-side and sell-side), private equity and venture capital investments, and other strategic corporate transactions. She regularly advises on high-value, complex transactions that demand commercial judgment, technical expertise, and practical execution.

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Beyond transactional work, Diann advises on business structuring and formation, succession and exit planning, joint ventures and shareholder arrangements, and a wide range of commercial contracts that support her clients’ strategic objectives.

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Diann brings a strategic, commercially focused approach. She advises companies at every stage of their development, from high-growth companies to established companies, and across various sectors including healthcare, technology, food and beverage, telecommunications, renewable energy, hospitality, manufacturing, and financial services.

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Clients value Diann’s ability to translate complex legal structures into clear business decisions and to focus on what will matter most when deals close and beyond.

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Recent

Representative matters across a broad range of transactions and values include:

Mergers & Acquisitions
  • Acquisition of a €26m hospitality company
  • Sale of a €15m personal protective equipment business
  • Acquisition of a €98m motor insurance business
  • Sale of a €13m concrete manufacturing business
  • Acquisition of a €10m wealth management business
  • Sale via auction of a €50m Medtech business
  • Acquisition of a €9m commercial property insurance business
  • Sale of a €48m consumable food packaging business
  • Acquisition of a €7m HR business
  • Sale via auction of a €37m renewable electricity and natural gas company
Private Equity & Venture Capital
  • €30m Series A investment in a Medtech company
  • €8.7m combined Seed and pre-Series A equity and convertible debt fundraising for an early-stage IT company
  • €8.5m Series A investment in a Medtech company
  • €4.3m equity fundraising for a mental health and wellbeing support services HR IT company
  • €2m Seed investment in an IT company
  • Pre-Seed and Seed fundraising for a food company
Corporate Restructuring & Succession Planning
  • Group restructuring and corporate advice to companies and groups across the following sectors:
    - Meat processing and distribution
    - Telecommunications
    - Fitness
    - Brewing
    - AI technology
  • Management incentive schemes and corporate reorganisations for companies across the following sectors:
    - Plant hire
    - Construction and civil engineering
    - Precast concrete manufacturing
    - Aviation software and IT
  • Reorganisation and succession planning for companies across the following sectors:
    - Pub and hospitality (approx. €250m)
    - Food and property (approx. €60m)
Debt Finance & Commercial Contracts
  • Multiple equity and debt financing rounds for a property development group
  • Debt fundraising and secured lending transactions for private companies and groups
  • Commercial contracts in the energy sector
  • Commercial contracts in the hospitality sector
  • Commercial contracts in the food sector

Education

  • Solicitor, Law Society of Ireland
  • Solicitor, England & Wales
  • Masters in Commercial Law, University College Dublin
  • Bachelor of Laws, NUI Galway
Professional Development
  • Artificial Intelligence - online course, Law Society of Ireland
  • GDPR - online course, Law Society of Ireland

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Memberships

  • Member of the Law Society of Ireland
  • Member of the Law Society of England & Wales

Testimonials

“Diann has been an excellent solicitor to work with across a number of our angel investment deals each year. She is highly proactive, thorough, and consistently adds value throughout the process, from legal due diligence through to investment documentation review, particularly identifying potential issues early and working constructively to resolve them before they become problems. Her advice is clear, commercial, and pragmatic, and she is a trusted part of our investment process, helping deals progress smoothly and efficiently. I would highly recommend Diann for any investment work.”

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Emily Ryan, Irrus Investments

“Diann advises us on corporate advisory/governance matters as we scale, from shareholder agreements and share schemes to consents and governance requirements. She balances legal precision with commercial reality, which is exactly what a growing company needs, and she is always available when we need her.”

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Bill Blake, Cloudcards

“Diann takes a real interest in understanding how ComOp think about our investments. This means the advice is not just top notch legal advice, but it is delivered tailored to our way of thinking. Across 11 investments and 37 rounds of investment, CLNs and all manner of investments the advice is considered, researched and always excellent. We feel protected and that is key.”

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Derek Delaney, ComOp

"Diann is technically excellent, commercially minded, and solution focused. Diann consistently delivers value for her clients. Highly recommended."

Paul Morris, PWC

“Having worked with Diann for a number of years across multiple transactions and corporate matters, she is easy to work with, very responsive, and her advice is always clear and well thought through. She’s efficient, reliable, and gives advice we trust."

John Vaughan, Jennings Meats

"The team is knowledgeable and experienced, and has the capability and willingness to work around any problem."

Chambers Global 2025

"Exceptionally commercial in their approach. Make an effort to understand the underlying operations of the businesses we acquire and tailor their advice accordingly."

Legal 500 EMEA 2025

'There is a “spring in the step” at Flynn O’Driscoll — very competent professionals focused on supporting and delivering for clients engaged in wide-ranging commercial activities with diverse legal requirements.'

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Legal 500 EMEA 2024

'Flynn O'Driscoll is a very pragmatic and commercial law firm.'

Chambers Global, 2025

'The law firm has good breadth and depth across a wide range of legal activities. The department works well to access required skill sets and experience among the team.'

Chambers Global, 2024

‘Solution driven team, providing strong support and guidance to clients. Problem solvers, commercially focused and very reliable.’

Legal 500 EMEA

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Expertise

Commercial Agreements
Corporate Advisory
Restructuring & Insolvency
Investments & Capital Raising
Mergers & Acquisitions
Private Businesses
Private Equity
Start-ups
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