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We connect the dots to consistently deliver.
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We are operators,
not just advisors.
Headmark Advisory bridges the gap between mid-market potential and institutional-grade realisation as your AI-native Operating Partner. We were founded to bridge the gap between mid-market potential and institutional-grade realisation.

We act as your Operating Partner to enable you to scale with predictability by deploying elite "strike teams" to rewire your business for the AI-native economy. By aligning operational efficiency, product innovation, and financial performance, we prepare businesses for high-velocity growth and premium exits.
Are you ready to create value?
Our leads have built, scaled and exited businesses with a collective value of over $1bn. Your free discovery call could accelerate your value realisation.
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Scaling a tech talent platform
Guided the product lifecycle from PoC to MVP to $1m ARR for an RPA-enabled B2B PaaS platform for technology talent.
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Exit transformation for global IT firm
Increased the EBITDA by 5pts with a transformed AI-enabled operating model for a 1,600 person global IT engineering powerhouse prior to exit.
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Accelerated product growth & funding
Supported the founders to accelerate cross-border growth through product innovation and securing funding from Google for Start-Ups.
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Scaled Data & AI service line prior to exit
Redefined the line of business GTM strategy, expanded offerings into new verticals and grew revenue by 33% and gross margin by 6%.
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Post-merger operational turnaround
Managed a £40m P&L and 200+ staff, delivering a 60% Gross Margin and 9% EBITDA while driving commercial rigor that increased average day rates by 18%.
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OUR APPROACH

Our AI-powered value creation operating system.

HeadmarkOS is an AI decision-engine, transforms businesses into AI-native assets. Supported by AI-enabled proprietary diagnostic tools such as the Founder Dependability Index Exit Simulator, and Services Architecture, the operating system bridges legacy data silos with autonomous intelligence for scale and institutional valuation.
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Our team are strategists, creatives, data nerds, and technologists. We connect the dots to consistently deliver.
  • Hugh Simpson
    Managing Partner
    Hugh uses his Royal Australian Navy and 20+ year tech leadership experience to drive value for PE-backed SaaS and services firms (£40m–£160m revenue). He transforms businesses, delivering rapid results: EBITDA growth through AI, 42% OpEx reduction, and scaling ventures from 0 to $1.2M ARR within 6 months.
  • Charlie Robinson
    Partner
    Charlie uses his British Army and 20+ year tech leadership experience to fix execution problems for SaaS companies (£15m–£75m revenue). He transforms businesses, delivering rapid results: EBITDA up 6–10 points, pipeline coverage from 1.2x to over 3.0x, and CAC payback dropping from 24 to 14–16 months.
The future is yours to create.
Come and make a real impact on our clients, their customers. And in turn we’ll make an impact on you.
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Unlock Your Rapid Exit Diagnostic
Maximise your company’s value with our Rapid Exit Diagnostic, a swift and strategic review of your business to identify potential deal-breakers and opportunities.
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