The senior management team comprises executives with an average of 20 years’ experience in the insurance and financial services industries, whilst also bringing rich experience from Telco, Retail & Energy.


David Mcmillan Chief Executive Officer

David McMillan

Chief Executive Officer +
David Mcmillan Chief Executive Officer

David McMillan

Chief Executive Officer

Appointed: July 2019
David chairs the Group Executive Committee. He attends the Risk, Audit and Remuneration Committees.

Background and experience

During his career, David has been responsible for leading different businesses through start-up, high growth, restructuring and turnaround phases. He holds a BA in Finance and Computer-Science from Heriot-Watt University, an executive MBA from the University of Chicago and is a Fellow of the Institute of Management Accountants. David is a non-executive director of Scottish Rugby Union plc.

Prior appointments

Prior to joining esure, David was Group Chief Operating Officer of QBE, one of the world’s top 20 insurance and reinsurance companies and was responsible for Strategy, Transformation, Digital, Technology and Operations. Before QBE, he was Chief Executive Officer, Europe and India and Chairman of Global Health Insurance for Aviva plc. Earlier in his career at Aviva, David was Chief Executive Officer of UK General Insurance & Group Transformation Officer. He joined Aviva in 2002 following almost 10 years with the management consulting arm of PricewaterhouseCoopers.

Peter Bole Chief Financial Officer

Peter Bole

Chief Financial Officer +
Peter Bole Chief Financial Officer

Peter Bole

Chief Financial Officer

Appointed: March 2020
Peter is a member of the Group Executive Committee. He attends the Risk Committee and Audit Committee.

Background and experience

Peter joined the business in January 2020 and was appointed Chief Financial Officer in March 2020. He is accountable for the leadership of the finance function, ensuring the effective delivery of all aspects of financial management of the business. Peter graduated with a 1st Class Honours degree from the University of Aberdeen and is a member of the Institute of Chartered Accountants of Scotland. He has over 25 years’ experience in finance leadership roles across several strong consumer businesses within the Banking and Insurance sectors.

Prior appointments

Prior to joining esure, Peter was Chief Financial Officer of Virgin Money having moved there from Tesco Bank where he was also the Chief Financial Officer. Earlier in his career Peter held senior financial roles at Direct Line Group, Standard Life and Deloitte.

Caroline Smith People Officer

Caroline Smith

Chief People Officer +
Caroline Smith People Officer

Caroline Smith

Chief People Officer

Joined: January 2020

Caroline is accountable for leading the HR Function, developing and implementing our people strategy and working alongside the Group Executive to create an organisation and culture that supports and enables our business strategy.

Background and experience

Previously, Caroline was accountable for the people strategy and the set-up of a new Transformation Division at Lloyds Bank and led HR support to over 25,000 employees within the Lloyd’s Banking Group.

Prior to her time at Lloyds, she held a variety of critical HR leadership and Change management roles in the Pearson group, BT, Pepsico and Accenture.

Caroline has a 1st class degree in Computer Science from the University of Bristol and has been very successful in enabling organisations to move to an agile way of working whilst building the right structure, culture and capabilities to support the journey to digitalisation.

Andy Burton Chief Technology Officer

Andy Burton

Chief Technology Officer +
Andy Burton Chief Technology Officer

Andy Burton

Chief Technology Officer

Joined: January 2021

Andy is accountable for leading the Technology function to ensure the security, stability and evolution of technical platforms, in addition to delivering technology change programmes.

Background and experience

Andy has over 30 years’ experience of working in and leading technology teams across multiple sectors including financial services, retail, gaming and telco. Prior to joining esure Group, Andy was the CTO at The Very Group, the UK’s largest integrated digital retailer and financial services provider. Before that he was the CTO at Sky Betting & Gaming for nine years and a member of the Executive team that led the business through substantial growth and international expansion. Andy has a wealth of experience in leading large-scale tech-led digital businesses and delivering agile transformations.

Andy has a degree in Mathematics from the University of Sheffield.

Kirsty Whitehead General Counsel and Company Secretary

Kirsty Whitehead

General Counsel and Company Secretary +
Kirsty Whitehead General Counsel and Company Secretary

Kirsty Whitehead

General Counsel and Company Secretary

Joined: January 2020

Kirsty is accountable for leading the Legal and Company Secretarial functions while ensuring the maintenance of healthy, legally compliant relationships with our partners, suppliers and industry regulators.

Background and experience

Prior to joining esure Group, Kirsty was General Counsel for Worldpay UK, joining the business after the demerger from RBS and working closely with Bain Capital prior to Worldpay’s IPO.

Kirsty graduated from Cambridge University before formally qualifying as a lawyer and has previously worked in senior legal roles for Visa Europe, Thomson Reuters and initially as a practising lawyer in the global law firm, Freshfields Bruckhaus Deringer.

Peter Martin-Simon Chief Customer Officer

Peter Martin-Simon

Chief Customer Officer +
Peter Martin-Simon Chief Customer Officer

Peter Martin-Simon

Chief Customer Officer

Joined: October 2021

Peter was appointed as Chief Customer Officer on 1 July 2022, responsible for our Underwriting, Pricing and Data & Analytics initiatives, building a world-class trading and underwriting ability, and driving our data capabilities across esure.  He is also accountable for leading the Customer, Marketing and Digital areas of the business, which are critical to the Company’s strategy of delighting our customers and successfully growing the business.  Peter joined esure in October 2021 as Chief Trading Officer.

Background and experience

Previously, Peter ran British Gas residential and small business energy supply at Centrica, including the set-up of its new energy platform business and brands. Prior to this, Peter was responsible for Centrica Home Solutions, including Centrica Hive, focusing on growing the Hive brand of smarthome products.

Before Centrica, Peter worked at Barclays across its retail, corporate and wealth businesses in a range of roles, including leading a turnaround of its unsecured lending business through digitisation and applied analytics, before becoming Managing Director for Marketing, Analytics and Innovation. He previously led strategy, transformation and commercial diligence projects at PricewaterhouseCoopers and Deloitte.

Peter has an MA in Physics & Philosophy from Oxford University and an MBA (distinction) from the London Business School.

Roy Jubraj Chief Strategy & Transformation Officer

Roy Jubraj

Chief Strategy & Transformation Officer +
Roy Jubraj Chief Strategy & Transformation Officer

Roy Jubraj

Chief Strategy & Transformation Officer

Joined: November 2019

Roy joined esure in a new role of Chief Strategy & Transformation Officer.

He is accountable for developing esure Group’s strategy and plays a role in integrating transformation programmes.

Background and experience

Roy led Accenture’s UK and Ireland Insurance strategy practice and was one of the key architects of Accenture’s cross-sector innovation, transformation and digital agenda. He has extensive experience working with financial service companies to drive new customer propositions, develop new IT platforms and manage their path to digital transformation.

Roy holds a BSc in Finance, Accounting and Economics from Fordham University.

Darren Boland Chief Risk Officer

Darren Boland

Chief Risk Officer +
Darren Boland Chief Risk Officer

Darren Boland

Chief Risk Officer

Joined: March 2013

Darren joined esure Group in March 2013 as Head of Risk and was promoted to Chief Risk Officer later that year.

Background and experience

Prior to esure Group, he spent three years at Aspen Insurance as Head of Insurance Risk leading a team he established, providing oversight, challenge and support across the global insurance and reinsurance operations for the underwriting, pricing and reserving processes. Darren also spent 12 years at PricewaterhouseCoopers, initially within the audit practice, then spending the last eight years within the actuarial team supporting the general insurance clients focusing on risk management, underwriting, pricing and claims.

Darren is a Fellow of the Institute of Chartered Accountants and has a degree in Mathematics from Imperial College, University of London.

Graham Hughes Chief Claims Officer

Graham Hughes

Chief Claims Officer +
Graham Hughes Chief Claims Officer

Graham Hughes

Chief Claims Officer

Joined: October 2015

Graham joined esure Group with over 25 years of claims and insurance sector experience.

He is accountable for esure’s 630 staff strong Claims and Financial Crime operations based across Reigate, Manchester and Glasgow leading Claims customer service, indemnity control and Financial Crime.

Background and experience

Graham’s previous roles include Commercial Claims Director, RSA and he held senior positions at Allianz and Aviva. Graham holds an ACII, and MBA and he sits on the Thatcham Board, Chairs the ABI Motor Committee and is a member of the ABI GIC.