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

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. Until March 2023, David was a non-executive director of Scottish Rugby Ltd.

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 ten years with the management consulting arm of PricewaterhouseCoopers.

Peter Bole Chief Financial Officer

Peter Bole

Chief Financial Officer & Company Secretary +
Peter Bole Chief Financial Officer

Peter Bole

Chief Financial Officer & Company Secretary

Appointed: March 2020

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.

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.

Anton Ossip

Chief Claims Officer +

Anton Ossip

Chief Claims Officer

Joined: October 2023

Anton joined esure Group in October 2023, in the role of Chief Claims Officer, responsible for leading Claims and Financial Crime operations. Anton has a wealth of general insurance experience and a passion for customer-first thinking, with an excellent track record of driving business transformation and growth.

Background and experience

Anton has over 20 years’ experience in the financial services industry. His most recent role was CEO of Discovery Insure in South Africa, the General Insurance division within the Discovery/Vitality Group of companies. There Anton grew the business from a startup to a global leader in telematics-based insurance. He was a Board member of Cambridge Mobile Telematics and remains an adviser. Before Discovery Insure, Anton held a variety of leadership roles at the Alexander Forbes Group, Investment Solutions and Commercial Union Life Insurance Company. He is a Fellow of the Institute of Actuaries (UK) and has a degree in Actuarial Science and Statistics.

Helen Cooper

Chief Risk Officer +

Helen Cooper

Chief Risk Officer

Joined: August 2022

Helen joined esure in August 2022 in the role of Chief Risk Officer. She is accountable for leading the Risk, Compliance, Legal and Company Secretariat function which are responsible for enterprise risk management, regulation, legislative requirements and corporate governance matters.

Helen is an experienced insurance professional with an excellent track record for change delivery. She has a blend of strong technical acumen and a detailed understanding of the UK insurance market and ecosystem.

Background and experience

Helen has invaluable industry experience, having previously been Group Chief Actuary at Hiscox Ltd with responsibility for managing the actuarial teams across Hiscox’s diverse insurance portfolio. Prior to this, Helen held the position of Director at KPMG. Throughout her time at KPMG Helen became recognised as a finance and actuarial transformation specialist as well as being the lead actuarial expert on a significant number of UK audits. She has also led large scale finance and systems change projects with Zurich Insurance, Aviva and Direct Line. This wealth of experience will be instrumental to esure in its continuation of growth and transformation.

Helen holds a BSc in Mathematics (First Class) from the University of Warwick and is a Fellow of the Institute of Actuaries.

Alan MacEwan

Director of Operations +

Alan MacEwan

Director of Operations

Joined: May 2015

Alan joined esure in 2015 as Head of Operations. He was promoted to Director of Operations in 2022 and appointed to the Executive team in 2023.

Alan leads the operations team across multiple locations to provide customers with the quality service they expect from esure’s insurance brands. This includes supporting customer interactions across telephony, live chat, the MyAccount digital portal, and social media channels. Alongside this, Alan is responsible for the digital-first transformation of our service journeys, creating effortlessly easy experiences and on-demand support for our customers. Alan is the Executive Sponsor of esure's ESG agenda.

Background and experience

During his 20-year career in operations, Alan has led customer service excellence for some of the insurance industry’s greats, including previous roles as Head of Intermediated Operations at RSA, and Head of Offshore Operations at Aviva UK and Aviva Europe. He has extensive experience of leading large-scale operations teams, driving operational efficiency, and implementing complex digital transformation programmes to improve the customer experience.

Alan has a BA Hons in Economics and English from Strathclyde University, holds a professional diploma in general insurance, and is a Certified Insurance Practitioner with The Insurance Institute.