"Scaling and exiting your business can be challenging, frustrating and costly. We focus on what actually creates value."
Hugh Simpson
Entrepreneur, Investor and Founder of Headmark Advisory.
To help amazing entrepreneurs realise life-changing outcomes by investing in and scaling their businesses to successful exits. We believe that by bringing together our experience, people, capital and ideas we create opportunity to grow and build value.
Most entrepreneurs we work with want three things... to build a thriving business, create a future for their families and unlock the wealth they deserve from their business!

99% of all businesses in the UK are considered small-to-medium sized enterprises with less than 50 employees. Over 65% of these businesses are looking to exit in the next 2-3 years yet only 1:1000 actually successfully achieve this whilst the rest exit by shutting down.

For businesses turning over less than £5 million per annum, many of the founders are either nearing retirement age or are traditional small businesses where the venture capital and private equity approaches are not the best fit.

That's why we started Headmark Advisory.

We're passionate about building great businesses and know how to leverage data, AI and other technologies to grow the business, optimise operations and maximise the possibility for a life-changing exit.

Our team is made up of accomplished entrepreneurs, not bankers. We are open to flexible win-win deals that get you closer to your target exit without undue pressure from outside investors.

We are your transformational partners helping you to identify untapped potential, navigate complexity and nurture positive relationships in order to unlock meaningful growth...together!
Our ways of working...
  • No bullshit! Ready to get hands dirty.
  • Customised solution built for you.
  • Results matter most.
  • We are partners working together.
Hugh Simpson
Managing Director / Founder of Headmark Advisory
Hugh started out as a warfare officer in the Navy before working in the insurance sector (special risks + insurtech). Whilst completing his MBA at the University of Sydney (Australia's #1), Hugh joined EY where he became a specialist Data & AI Product Manager in Sydney and London building cutting edge products in TMT, sports, utilities and government sectors.

In 2019, Hugh launched Headmark Advisory and started working with investment firms to grow and scale their assets as a senior leader embedded in the business working alongside senior executives.

Key roles have included being interim COO for a $20m regional marketing and communications group with 200 staff helping scale for a retirement exit, co-founder of a start-up outsourcing firm scaling to 7-figure revenue from scratch before a successful exit, and VP Data & AI an outsourcing firm driving 33% growth p.a. leading to a successful exit for the PE fund.

Throughout his career Hugh has worked with founders of SME's (<250 staff) and scale-ups as they look to an exit. Headmark Advisory is currently working with an insurance brokerage, disability fitness app, Web3 scale up and a fast-growth service provider.
Our diverse team of experts...
  • Alex Herlihy
    Alex is a former Oggin client and Private Equity Associate who joined Oggin having successfully scaled and exited multiple businesses over the last 15 years. His successful exits have included an e-commerce platform, digital agency, hospitality venues and property.
  • Hanna Podopryhora
    Talent Advisor
    Business is all about people and Hanna is our talent expert having been an HRBP and recruiter for over 10 years. As an experienced HR professional Anna brings a unique perspective to solving the talent challenges many businesses face.
  • Luther Poier
    Start-Up and Exit Strategy Advisor
    Luther is also a former Navy officer with over 30 years' experience in working in wealth management, venture capital and start-up mentoring having successfully invested in over 100 companies helping coach them to multi-million pound exits.
  • Sergii Gerasimov
    Financial Engineering Advisor
    Sergii is our in-house financial engineering expert having work with SME's and multi-national companies for over 20 years. As a former CFO specialising in cross-border operations, Sergii will work closely with our clients to optimise operations.
Let's talk!
Grow and sell your business successfully with Headmark Advisory. Get in touch to arrange an intro call with our specialist team.