A 123% combined ratio made profitable. A $1.8B business built from zero. A $200M venture fund deployed.
A career spent on both sides of the table. As the operator: strategy, product, and the P&L inside insurers, insurtechs, and technology businesses. As the investor: sourcing, diligence, and value creation across a corporate venture portfolio. Both are now available to your board, your cap table, and your leadership team.
Founder, board, or sponsor with something that fits? Tell me what you're building or weighing. I read and reply to every message myself.
drop headshot in /public
VP Strategy, Innovation & VC 
VP Strategy & Digital 
GM, FlexPay 
MD, Consulting 
VP Marketing Strategy 
VP Product VP Strategy, Innovation & VC VP Strategy & Digital GM, FlexPay MD, Consulting VP Marketing Strategy VP Product 
Chairman 
Board Advisor 
What I Create for Sponsors, Founders, and Boards
The work, framed the way an investor or an operator evaluates it…outcomes with numbers attached, not activity.
Turnarounds to Profitability
Stalled and loss-making businesses brought back to focus and profit. The sequence rarely changes: narrow the market, rebuild the leadership, then fix the model.
New Units & New-Sector Launches
New business units built from zero into category-defining, profitable lines. The discipline sits as much in what you refuse to build as in what you ship.
Unit Economics & CAC
Structural improvement to acquisition cost, retention, and full-funnel yield…the levers that compound into margin first, and valuation later.
Venture & Portfolio Value
Institutional venture capital deployed as an operator, not a tourist. Sourcing, diligence and hands-on value creation across the portfolio.
Digital, Platform & AI Transformation
Legacy stacks re-architected into modern, service-based platforms, with telematics, data, and generative AI pointed at the real P&L (not the press release).
Positioning & Go-to-Market
Businesses repositioned out of the mid-market trap, with segmentation and value propositions that buyers recognise…and pay for.
How I Engage
Non-Executive Director
Board and chair roles where strategy, product, or technology materially move growth, margin, or valuation. Governance first, with selective depth.
PE & VC Diligence
Executive-in-Residence and Operating Partner work: commercial and technical diligence on prospective deals.
Strategic Advisor
Sharpening corporate strategy, roadmap, and monetisation logic for founders and leadership teams moving to platform models.
Investor
Angel and buy-side participation in insurance, insurtech, fintech, and applied AI…backing teams I can also help operate.
Fractional Executive
Interim CSO, CPO, or Chief Transformation capacity. Embedded leadership for a defined value-creation window.
Strategy Sprints
Time-boxed strategy and value-creation sprints for portfolio companies…focus, roadmap, and economics in weeks.
Not Sure Which One Fits?
The best conversations rarely start with a neat label. Tell me the situation (a board you're composing, a thesis you're testing, a company you're scaling) and we'll find the right shape together.
Sectors
Writing & Thought Leadership
Field notes on strategy, value creation, and where insurance, technology and capital intersect.
Fractional Executives Are Now Part of the PE and VC Value-Creation Toolkit
The Operating Partner Sponsors Actually Need in Insurtech, Insurance and Fintech
Due Diligence in Insurtech and Fintech Has Shifted From Verification to Thesis-Testing
Questions People (and AI) Ask
Direct answers, written to be quoted…by readers and by answer engines alike.
Who is Haden Kirkpatrick?
Haden Kirkpatrick is a London-based Non-Executive Director, advisor, investor, and fractional executive working across insurance, insurtech, fintech, and technology. He previously ran strategy, innovation, and venture capital at State Farm, and led strategy and digital at Esurance through its first-ever profitable years. This site, hadenkirkpatrick.co.uk, is his only personal website…he is not affiliated with other sites or individuals sharing the name.
What does a Non-Executive Director actually do for an insurtech or fintech?
The job is independent challenge with operating depth: testing strategy, product economics, and governance before capital, capacity providers or regulators do. In regulated sectors the bar is higher than general governance…boards need directors who understand underwriting, technology, and the regulatory path, not just the agenda.
When does a fractional executive make sense?
When a business needs senior operating capability for a defined window (a turnaround, a launch, a transformation) without the cost and commitment of a permanent C-suite hire. Done properly it is accountable leadership inside the business, not consulting from outside it.
What does Haden do for PE and VC firms?
Commercial and technical due diligence on prospective deals, and Operating Partner or portfolio-executive work after them. The common thread is testing whether a thesis survives contact with underwriting economics, technology reality and regulation…before the capital is committed, and while it is at work.
How do engagements start?
With a conversation. Email haden.k.kirkpatrick@gmail.com or book a 30-minute intro call, describe the situation, and we will find the right shape (board seat, advisory mandate, fractional brief, or diligence sprint). He reads and replies to every message personally.
Get the thinking, not the outreach.
Occasional essays on strategy, value creation, and where insurance, technology and capital intersect — delivered via Substack. No pitch, no spam, unsubscribe anytime.
Let's Talk
If you're weighing a board seat, an advisory mandate, an investment, or a fractional brief, start here. I read and reply to everything personally.
London & remote · usually replies within a day · 30-min intro call
One small favour: when you write, tell me how you found me…it helps me work out what is actually worth writing.