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We are Simply Business

Meet the leadership team enabling big dreams

Meet the team

Our team is united in delivering our purpose: insuring small businesses and enabling big dreams.

That doesn’t just mean enabling big dreams for our customers – it means enabling big dreams for our people and communities, too.

By harnessing the power of data and technology, we’re improving the insurance experience for small business owners and landlords. Simplicity, choice and value are front and centre.

And we empower our 1,000-plus employees to pursue what’s meaningful – both in work and the communities they’re part of.

With offices in London, Northampton and Boston, USA, meet the team changing the way small businesses buy insurance.

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David Summers

David Summers – Group CEO

David leads the business, implementing its ambitious growth and innovation strategy to not only maintain a market-leading position, but to continually find new ways of delivering outstanding customer value.

At the heart of this is building a truly product-centric culture that gives all of our teams both the structure – and empowerment – to make things happen.

David joined Simply Business in 2006 from Accenture, where he was a Management Consultant. David previously held the position of Chief Operating Officer and prior to that led our Northampton contact centre, having also had roles in business development and product.

Alan Thomas

Alan Thomas – UK CEO

As UK CEO, Alan oversees the growth and culture of our UK business – keeping us focussed on our long-term vision and strategic priorities. Central to this is a belief in our unique values, and an emphasis on enabling the big dreams of our diverse customers and people.

No two people – or customers – are the same, and Alan’s role is to make sure our culture, proposition, and values evolve to reflect this. And as an accredited B Corp, this applies to our communities, and the impact we can have on those around us too.

Before taking on the role of UK CEO, Alan was our Chief Commercial Officer. Using his wealth of experience as a Chartered Insurer, he managed the relationships with our insurer partners and suppliers – working to create the best outcomes for our customers.

Joining Simply Business in 2016, Alan brings with him over 20 years’ experience, having previously worked for Hiscox and RSA.

Samantha Roady

Samantha Roady – US CEO

Samantha joined as our US CEO in August of 2023, bringing with her nearly 25 years of C Suite experience building, scaling, and managing highly complex, regulated global financial technology businesses.

A marketer by training, Samantha is highly knowledgeable in consumer and B2B marketing and building brand-driven businesses. Her passion for customer-centric innovation, along with her experience leading teams through periods of pivotal growth and change, perfectly align with Simply Business' growth ambitions and our core values of providing simplicity, choice, and value to our customers.

Prior to joining Simply Business, Samantha served as Chief Operating Officer at MoneyLion. Before that, she was president of GAIN Capital's (now StoneX) global retail brokerage business, responsible for commercial strategy and all revenue-generating activities including sales, marketing, partnerships, customer operations and regional management.

Beatriz Montoya

Beatriz Montoya – UK Chief Operating Officer

Bea is an expert in creating customer-centric marketing efforts, and products and services. She’s proud to be able to work closely with our Marketing, Product and Operations teams to build insurance products that really work for business owners and landlords.

Passionate about diversity at Simply Business, Bea also leads our #IamRemarkable program, which aims to empower women in the work place.

Before joining Simply Business in 2015, Bea spent time at Euromoney, and more recently, Time Inc.

Scott Gregory

Scott Gregory – Group Chief Financial Officer

Scott joined us as Group Chief Financial Officer in 2020, coming from Aviva. Bringing with him over 30 years of commercial finance experience – in the insurance and retail sectors, both in the UK and internationally – Scott's held a range of senior leadership roles at Aviva, Sainsbury’s, and a number of private equity-backed startups.

He originally trained as a chartered accountant with Coopers & Lybrand (now PwC), gaining his early experience in audit and transaction support advisory work, before moving from practice into industry. Scott has a strong track record of delivering growth and enhancing core business performance, and relocated back to the UK having previously been CFO of Aviva Italy.

Dana Edwards

Dana Edwards – Group Chief Technology Officer

As Global Chief Technology Officer, Dana is focused on designing and developing our digital products for the US and UK businesses. He has a track record of running product, technology, and data teams using the latest customer-centric, agile practices.

His passion is helping engineers, business teams, product teams, data teams, and enterprises work in a way that produces high quality products for customers. This drives him to create an environment of empowerment and inclusivity.

Dana joined Simply Business in 2022 with an extensive background in financial services. Previously, he held roles as Chief Technology Officer for firms such as PNC Financial Services and MUFG Union Bank. His career started with roles in product and technology development, and academics.

Alissa Stayn

Alissa Stayn – Chief People Officer

Alissa joined us as Chief People Officer in 2023. Throughout her career, Alissa has served as a trusted advisor and partner to C Suite and executive leadership teams in several large, global organisations.

She’s a strategic thinker with demonstrated success in driving business results through effective planning and analytics, organisational design, full lifecycle talent management, succession planning, performance management, and reward. She has a track record of success influencing change and culture to deliver an enhanced and inclusive employee experience.

Alissa has held a range of senior leadership roles at Gartner, CarGurus, and Iron Mountain, and she brings a passion for harnessing the power of People teams to attract, retain, and develop diverse talent in high-growth companies.

Julie Fisher

Julie Fisher – UK Chief Commercial Officer

With over 30 years of insurance experience when she joined Simply Business in 2019, Julie's an expert in creating data-driven digital journeys and services for customers.

Julie puts the customer at the heart of our insurance product decisions – whether that's collaborating with our insurer partners to build the best products, or with distribution partners to help even more customers get tailored insurance through Simply Business. She's also focussed on ensuring customers can get back on their feet quickly should the worst happen, working with our claims specialists to create the best experience possible.

Prior to Simply Business, Julie has held leadership roles at Churchill, RBS, and Tesco Personal Finance. Most recently, she was Money Commercial Director for MoneySuperMarket, developing lending and money management products for their customers, including 'Credit Monitor' – a credit score and report service.

Joanne Theodoulou

Joanne Theodoulou – UK General Counsel

Joanne joined us as General Counsel in 2018 and looks after all things legal and governance here at Simply Business, making sure that we do the right thing in the right way for our customers and our people.

She has a wealth of legal and leadership experience gained primarily at city law firm Linklaters, Spanish bank BBVA and fintech start up NetOTC.

As sponsor of the ‘Inclusion is Everything’ pillar of our Social Impact strategy, Joanne strives to make sure diversity is celebrated at Simply Business. She is also a passionate advocate for workplace wellbeing, and sits on the board of Mind, the mental health charity.

Jane Smith

Jane Smith – Chief Data Officer

As Chief Data Officer, Jane's focus is to manage our data as a corporate asset. Tasked with ensuring Simply Business has cutting edge data and analytics operations, Jane drives a mandate to create business value from our data to drive our growth.

Jane's worked in data and tech for 18 years, in both consulting and industry. She's held data leadership roles at Ipsos, GlaxoSmithKline, Ernst & Young, and Accenture, and is recognised as a thought leader in this space.

In Jane's own words, data is such an appealing domain because "it takes many different people and skills to build data tools and products. Everyone can contribute and shine as we look at the pieces of the puzzle, take them apart... and put them together in a new way."

Deborah Holland

Deborah Holland – US Chief Operations Officer

Joining us in 2010 from Hiscox, Deborah’s responsible for making sure we deliver best-in-class customer service through our contact centre in Northampton, reinforcing our company values – learning, empowerment, authenticity, pioneering, and simplicity – across a team of over 200 people.

In her previous role as Commercial Director, she used her vast insurance experience to work with our underwriting team – strengthening our MGA (managing general agent) offering.

Deborah focuses on embracing technology and the opportunities it provides for growth and customer satisfaction, ensuring innovation is at the forefront of our contact centre strategy.

Fiona McSwein

Fiona McSwein – VP Strategic Programs

Fiona’s focus is on helping us build our business in the US. She’s using her experience to work with our global shareholders and teams to share what makes us successful.

Fiona was previously our Chief Marketing Officer, tasked with spreading the Simply Business message to the UK’s small business and landlord community through customer-focused and data-driven marketing.

Having founded and run two small businesses of her own, Fiona knows more than most the challenges that our customers face. This is coupled with over 20 years’ experience in business, including Euromoney and

Laura Winter

Laura Winter – UK VP of Product

Laura joined Simply Business in 2008 from Ageas, taking on her role as Director of Insurance Product in 2016 and becoming UK VP of Product in 2022.

Managing a team of product specialists, Laura helps the business understand our customers’ needs through data and insight, before designing and building flexible, tailored products.

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