Charlie Hollinrake for Anthropic
Enterprise Account Executive, Insurance · London

I sell to the industries that trust slowest.

Eight years selling risk, compliance and security software to the UK's most cautious enterprise buyers. Insurers buy the same way, and I'd like to help them adopt Claude safely and at scale.

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#1Ranked first internationally at KnowBe4, with four promotions in three years
122%Quota attainment at LogicGate, with a best quarter of 243%
£381kLargest deal in annual recurring revenue, selling enterprise risk management
8 yrsWinning new business from CROs, CISOs, risk, compliance, legal and procurement

Insurers buy like risk teams buy. That is the cycle I run every day.

An insurer will not adopt frontier AI on a demo. It gets there through vendor risk, security review, model governance, procurement and the board. I have spent my career inside exactly that cycle.

  • Currently lead UK go-to-market for Corporater, selling enterprise risk management to boards, risk and audit leaders at regulated organisations, including live cycles with UK insurers and reinsurers.
  • Open board-level conversations by leading with the UK Corporate Governance Code's Provision 29 on risk management and internal controls, so I speak the language the board and the regulator use.
  • Took the UK&I record for highest monthly sales at KnowBe4, self-sourcing most of my own pipeline, then ranked first internationally selling to organisations with over 1,000 employees.
  • Ran multi-stakeholder enterprise deals at LogicGate through risk, security, legal and procurement, finishing at 122% of quota.

"The buyers who trust slowest are the ones who stay longest. Earn them properly and they become your reference base."

Why Anthropic

Safety is not a feature insurers want. It is the condition of entry. Anthropic is the only frontier lab whose whole posture matches how a regulated buyer has to think, and that is the story I want to tell to underwriting, claims and distribution leaders.

I use Claude every day

I build my own prospecting workflows, account plans, pitch pages and pipeline tools with Claude and Claude Code. I know what the product does because I rely on it.

I sell outcomes, not models

Nobody in insurance buys a model. They buy faster claims decisions, cleaner underwriting files and lower loss-adjustment expense, with an audit trail. That is how I would frame every conversation.

I am built for the long cycle

My deals run through procurement frameworks, third-party assurance and board sign-off. I enjoy that work, and I am good at keeping momentum through it.

What I would do in the first 90 days

A plan I would expect to refine with the team in week one, not a script.

1

Map the market

Build the UK and EMEA insurance account map across insurers, reinsurers, brokers and MGAs. Rank by AI readiness and by the three use cases with the clearest value: claims handling, underwriting support and distribution.

2

Land design partners

Open conversations with the Chief Underwriting, Claims and Data Officers at the ten most ready firms. Run the vendor-risk and security reviews early, so procurement is a formality rather than a surprise.

3

Turn wins into a playbook

Feed what insurers ask for back to Product and Marketing, document the insurance sales motion, and build the first reference stories the rest of the sector will want to copy.

Let's talk

I am based in London, available from January 2027, and happy to be in the office well beyond 25% of the time.

cghollinrake@gmail.com +44 7840 489283 CV (PDF)