Beyond the Desk with Mark Thomas

In this episode of Beyond the Desk, Mark Thomas is joined by Gilbert Harrap, CEO and co-founder of InsurX, the technology business connecting brokers and insurers in the London Market. They talk about leaving a senior corporate role to start a business, how a moment during the pandemic turned a side project into a company, and what it takes to grow as a leader as that company scales.

Gilbert joined MS Amlin as a graduate and spent six years in treaty reinsurance, underwriting US property risk and working his way from underwriting assistant to underwriter. Wanting to see the bigger picture, he took a full-time MBA at INSEAD, sponsored by MS Amlin, before returning as a strategy manager tasked with turning data into better underwriting decisions, and later becoming Head of Strategy for the reinsurance division. That is where the idea for InsurX began. In April 2020, as the London Market was forced to trade remotely, he realised the market would never go back to how it was, and on 1 November 2021 he and his co-founder Will started full-time.

The conversation then turns to a question every founder has to answer: how do you turn a big idea into something customers will pay for today?

Gilbert explains how InsurX’s vision of data flowing seamlessly between brokers and insurers had to start with one specific, painful problem: event cancellation insurance after the pandemic. From $20 million of premium in its first full year of trading, the platform is on track for around $170 million this year, with 35 insurers signed up. He also shares why InsurX has raised from investors connected to the insurance market rather than venture capital, and the lessons that come with growing from two founders to a team of 35.

A candid conversation about career pivots, founding an insurtech, data and technology in the London Market, and growing as a leader as the business scales.

In this episode of Beyond the Desk, Mark Thomas is joined by Crispin Marsland-Roberts, Chief Operating Officer at Hive Underwriters, the London Market MGA specialising in aviation, marine and political violence and terrorism risks. They talk about one of the most unconventional routes into insurance leadership, what it takes to build and scale a specialist MGA, and how smaller businesses can use data and AI to move faster than the market’s biggest players.

Crispin’s career has taken him from a gilts desk and Manchester University, through importing fresh produce for Marks & Spencer and helping build the Tenderstem broccoli brand, to running the finances of a content agency and supporting small businesses as an independent operator. That work led him to DA Strategy, where he fell into delegated authority, helped get new MGAs off the ground and first met Hive founder Bruce Common. He later joined Hive full-time as COO. His approach throughout has been simple: don’t chase the money or the title, chase the opportunity.

The conversation then turns to a question at the heart of today’s MGA boom: what separates the MGAs that thrive from the ones that struggle?

Crispin explains why a clear point of difference, a strong data story and a charismatic leader matter far more than a fully staffed C-suite on day one. He also shares how Hive is putting data and AI to work, from its Sentinel flight-tracking database to automated slip comparison. The aim isn’t to replace underwriting judgement but to put the right information in front of underwriters so they can make better, faster decisions.

They discuss:

• Crispin’s early ambitions to play sport and join the army, and how dyslexia shaped the way he learns, writes and communicates
• Starting out on a gilts desk, and why it showed him what he didn’t want to do
• Running the Marks & Spencer desk at a fresh produce importer by his mid-twenties
• Stepping into operations and finance roles “because there was an absence of it”
• Bringing budgets and process to a content agency full of filmmakers with big ideas
• Going self-employed to give small business owners the skills they don’t have
• Falling into insurance through Charles Rowley and DA Strategy
• Why he often asks: “If we invented insurance today, what would it look like?”
• Streamlining delegated authority, and why a coverholder you’ve worked with for 15 years shouldn’t face 300 questions at every renewal
• Helping Bruce Carman launch Hive, and why a startup MGA doesn’t need a full C-suite on day one
• The move from consultant to COO, and how the role has evolved as Hive has doubled in size
• What surprised him about the London Market: slow-moving data, bordereaux and approval timelines

A candid conversation about career pivots, operational leadership, MGAs, data and AI, and building a culture that scales.

In this episode of Beyond the Desk, host Mark Thomas is joined by Jonathan Fletcher, currently an Operating Advisor for mid-market private equity firm Abri, and former Group CTO of both CFC and Hiscox.

Jonathan takes us right back to the beginning – from tinkering with a Commodore 64 as a kid, to a split degree in computer science and music, through early jobs at Saatchi & Saatchi and the London Stock Exchange, and on to seven years scaling Hiscox's technology function. He then shares what it was really like joining CFC as employee number 200, scaling its tech and data capability to nearly 200 people, and living through one of the biggest private equity valuations the insurance sector has seen.

Now working as an advisor across a portfolio of PE-backed businesses, Jonathan reflects on what value creation really means for technology, why resilience is the number one executive skill, and what it takes to make the leap from hands-on technologist to commercially-minded leader.

In This Episode You'll Learn

• Jonathan's unconventional route into tech – splitting his degree between computer science and music, and early jobs at Saatchi & Saatchi, a VC firm, and the London Stock Exchange
• The seven years he spent at Hiscox, rising from architect to Group CTO
• What it was like joining CFC as employee number 200, and the culture shock of moving from a FTSE 100 business to a founder-led, entrepreneurial scale-up
• How CFC's tech and data team grew from 18 people to nearly 200, building in-house capability from scratch
• What it's really like working inside a private-equity backed business, including being part of one of the biggest ever PE valuations for an insurer
• How his role evolved from hands-on engineering to a more product- and business-facing leadership position
• What his current advisory work with Abri and non-exec role at AA Ireland involves
• Where AI and automation are already reshaping specialty insurance, and why identifying 'who a company really is' remains one of the hardest unsolved problems
• His advice for technologists who want to move into senior leadership roles

If you enjoyed this episode, be sure to subscribe to Beyond the Desk, leave a review and share it with someone in your network.

Connect with Mark Thomas and Jonathan Fletcher on LinkedIn to continue the conversation.

In this episode of Beyond the Desk, Mark Thomas is joined by Usha Badrinath, Group Chief Data Officer at Mosaic Insurance, to explore her unconventional career journey, the rapidly changing role of technology in insurance, and what AI could mean for the industry over the coming years.

Usha’s career has taken her from computer science and coding in India, through an MBA and technology consulting, to catastrophe modelling, data products, insurtech and ultimately insurance leadership. Along the way, she has repeatedly followed opportunities rather than a fixed career plan — describing her approach as more about trying things, learning from them and deciding what to do next.

The conversation then turns to one of the biggest questions facing insurance today: how should the industry actually use AI?

Usha shares her experience building Mosaic’s data foundations and explains why she believes the real opportunity isn't simply putting AI on top of existing processes. Instead, insurers need to think about how data, technology and workflows can be redesigned together to solve problems from end to end.

They discuss:

• Usha’s unexpected journey from aspiring liver transplant surgeon to technology and insurance leader
• Why her career has been shaped more by experimentation than a fixed plan
• Moving from coding into business, consulting and leadership
• The lessons she learned from working across technology and insurance
• How the “floating casinos” problem highlighted the importance of data in catastrophe modelling
• Why insurance companies can struggle to build technology that scales across different clients and workflows
• Usha’s decision to move from consulting into an insurance company and join Mosaic
• Building a data foundation designed to support AI from the outset
• Why Usha believes insurers should focus on the 20% that AI cannot solve
• How AI can help capture and make use of institutional knowledge that currently sits inside people's heads
• Why AI should augment human judgement rather than simply be viewed as a tool for reducing headcount
• The importance of reskilling as technology continues to evolve
• How AI could help insurers identify patterns, correlations and emerging risks
• Why future technology leaders need to understand business outcomes, not just technology
• Usha’s approach to leadership and building teams through difficult periods of change
• Why she thinks people should push themselves outside their comfort zone early in their careers
• Her advice to aspiring Chief Data Officers and AI leaders
• Why careers don't need to follow a traditional upward trajectory
• And why Usha believes the constant evolution of insurance is one of the industry's greatest attractions

A wide-ranging conversation about technology, data, AI, leadership, careers and the future of insurance.

What does it take to build a successful career in underwriting when you don't follow the conventional route?

In this episode of Beyond the Desk: Underwriting Special, Sanj Vagad sits down with Jana Ratnajothy to explore her unconventional journey from law and claims into underwriting, and the experiences that have shaped her career along the way.

Jana shares how 36 rejection letters eventually led to a career in law, how an unexpected opportunity at Beazley opened the door to insurance, and why she made the leap from claims into underwriting despite never feeling fully ready for the next role.

The conversation covers the value of specialising, the importance of understanding the numbers behind a portfolio, navigating different stages of the insurance cycle, and why strong relationships with clients and brokers remain so important.

Jana also reflects on the role of curiosity, networking and sponsorship in career progression, how to recognise when it's time to stretch yourself, and why understanding your own strengths can be one of the most important things you do for your career.

• Her journey from a first-generation immigrant family into law and insurance
• Receiving 36 rejection letters before securing her legal training contract
• Moving from private practice into Beazley's claims team
• Making the transition from claims into underwriting
• Why you should take opportunities even when you don't feel ready
• The three core elements of underwriting: maths, product and distribution
• The benefits and challenges of becoming a specialist underwriter
• Why understanding how to run a portfolio is essential for career progression
• Building a specialist portfolio at Convex from the ground up
• Navigating the current insurance market and different market cycles
• Why understanding the numbers and your organisation's objectives matters
• Networking without making it transactional or uncomfortable
• The importance of curiosity and asking questions
• Recognising when you're no longer being stretched or challenged
• Why knowing yourself and playing to your strengths can build confidence
• What makes the London insurance market such a unique place to build a career
• Jana's advice for the next generation of insurance professionals

What does it really take to build a successful career in underwriting?

In this episode of Beyond the Desk Underwriting Special, Sanj Vagad is joined by Adam Curran, Chief Underwriting Officer - Specialty, HDI Global, to explore his career from an unexpected start in insurance to senior leadership within one of the market’s major specialty businesses.

Adam shares how an initial opportunity at Alexander Forbes led him from broking into underwriting, and how each stage of his career brought new challenges, experiences and opportunities to learn.

The conversation explores the importance of being open to opportunities, knowing when to move on, and taking ownership of your own career rather than waiting for someone else to create the next step for you.

Adam also discusses what changes as you move from being a specialist underwriter into broader leadership roles, including the importance of accepting that you cannot know everything, asking the right questions and surrounding yourself with the right people.

As the conversation turns to the current underwriting market, Adam shares his perspective on navigating a soft market, returning to the fundamentals of underwriting and understanding what makes a strong portfolio. He also discusses delegated authority, governance and the challenge of balancing efficiency with the depth of underwriting information needed to make good decisions.

The episode closes with some practical advice for the next generation of underwriters — from becoming known as someone who can be relied upon, to putting forward ideas, taking on challenges and building relationships across the market.

And Adam reveals the one skill he believes is becoming increasingly underrated in underwriting: picking up the phone and having a conversation.

What does it take to build a successful career in underwriting?

In this episode of Beyond the Desk Underwriting Edition, Sanj Vagad is joined by Charles Boorman to explore a career spanning broking, D&O, financial lines, underwriting leadership, turnarounds and the MGA market.

Charles shares how he first fell into insurance before discovering that specialising in D&O was the turning point that made him realise he could genuinely add value to clients. He talks through his move from broking into underwriting at QBE, taking on the leadership of an FI team outside his comfort zone, and the experiences that shaped his approach to building and turning around underwriting businesses.

The conversation also explores Charles' move into the MGA world and why an incubator-style model gave him the opportunity to focus on underwriting, building a team and growing a business without taking on the same level of risk as a traditional MGA start-up.

Sanj and Charles discuss the challenges of turning around an underwriting business, including managing people, maintaining broker relationships and communicating difficult decisions. Charles also shares his perspective on the current D&O and FI markets, the impact of increasing capacity and competition, and whether combining commercial D&O and FI underwriting makes sense.

Towards the end of the episode, Charles offers advice to underwriters looking to broaden their experience, emphasising the importance of taking baby steps, learning from experienced people and getting outside your comfort zone.

• How Charles accidentally fell into insurance
• Why specialising in D&O changed the trajectory of his career
• Making the move from broking into underwriting
• Taking on an FI leadership role outside his comfort zone
• The challenges of building and turning around underwriting businesses
• Why people are often the hardest part of a turnaround
• The importance of communication and broker relationships
• Charles' transition into the MGA market
• The advantages of an incubator-style MGA model
• Current dynamics across the D&O and FI markets
• Whether commercial D&O and FI should be brought closer together
• How underwriters can broaden their class experience
• Why taking "baby steps" matters when learning a new product
• The importance of concentrating on your strengths and managing your weaknesses
• Why getting outside your comfort zone is where you learn and grow

Charles also reflects on the career decisions that changed his own trajectory and why his biggest advice is simple: when an opportunity comes to step outside your comfort zone, put your hand up and say yes.

What can we learn from the people shaping the future of insurance?

In this special highlights episode of Beyond the Desk, Mark Thomas brings together some of the most insightful moments from conversations with senior leaders across the global insurance industry.

Across the series, guests have explored everything from leadership and career development to AI, underwriting, talent, culture and the changing insurance market.

This episode brings those conversations together, highlighting some of the biggest ideas, lessons and predictions from the people working at the forefront of the industry.

• Nigel Walsh: on the leap of faith it took to move his family to New York for an opportunity at Google and how AI is reshaping underwriting and claims.
• Christopher Barclay: Imposter syndrome stepping into a CEO role and the moment he realised that being himself was the key to leading successfully.
• Kirk Southern: on leadership, career development, the evolving role of the Chief People Officer and how businesses can use AI to empower their people.
• Carys Lawton-Bryce: sharing perspectives on people, culture and the changing world of work.
• John Wingate: exploring technology, AI and the opportunities emerging from rapid technological change.
• Sally Peace: discussing culture, leadership and building successful businesses as organisations grow.
• Simon Jackson: from the Underwriting mini-series, exploring the future of underwriting and the changing role of technology.
• Talbir Singh Banes: on underwriting leadership, talent and the evolution of the MGA market.
• Mark Fellows: sharing lessons from a career in underwriting, building teams and developing underwriting businesses.
• Scott Bailey: discussing underwriting, AI and why human expertise and relationships will continue to matter.

Leadership & career development

Why curiosity, humility and a willingness to learn can be more valuable than trying to accelerate your career too quickly. Kirk, for example, reflects on the importance of learning the foundations of a role and the people who helped shape his career.

The future of AI

How AI could transform the way insurance businesses operate, while still leaving human judgement, relationships and expertise at the heart of the industry.

Underwriting

What makes a great underwriter, what makes a great underwriting leader, and how technology can augment rather than replace underwriting expertise.

Talent & culture

How insurance businesses can attract, develop and retain the people they need as the skills required across the industry continue to change.

The changing insurance market

From the growth of MGAs and delegated authority to changing market cycles and the evolving role of technology, the series explores where the industry could be heading next.

Human expertise in an increasingly automated world

One recurring message throughout the conversations is that technology can remove repetitive work and enhance decision-making, but insurance remains fundamentally a relationship-driven business.

As technology transforms the way insurance works, what will remain uniquely human?

From leadership and culture to underwriting expertise and broker relationships, this episode brings together the ideas that could shape the next chapter of the insurance industry.

In this episode of Beyond the Desk, Underwriting Mini Series, host Sanj Vagad sits down with Scott Bailey, Head of Global Cyber Underwriting at CFC.

Scott looks back on a career spanning 25 years in cyber insurance, from joining Click for Cover (later CFC) as employee number two in 2001, through spells at CNA Hardy and Markel, to his return to CFC three and a half years ago. Along the way, he shares how the cyber market was built from scratch, why the SME protection gap remains so wide, where we are in the current pricing cycle, and why AI is both the biggest emerging threat and one of the industry's best defensive tools.

Whether you're an underwriter, broker or simply curious about how one of insurance's youngest classes of business came to be, this episode is packed with first-hand insight from one of the market's most experienced cyber leaders.

In This Episode You'll Learn

How Scott's career began in car insurance telesales before he joined Click for Cover (later CFC) as employee number two in 2001

What it was like building the cyber insurance product from scratch – before regulation, actuarial data, or even market awareness of the risk existed

The lessons learned moving between an MGA (CFC) and carrier platforms (CNA Hardy, Markel)

Why Scott returned to CFC after a decade away, and the difference between heading global cyber and heading global cyber underwriting

Why only 10–15% of SMEs in developed economies buy cyber insurance, and what the industry needs to do about it

Where we are in the cyber insurance pricing cycle, and why the market may need to firm up in certain geographies

Why AI is both the biggest emerging cyber threat and one of the sector's best defensive tools

Scott's advice for underwriters early in their career, and why curiosity is the most valuable skill in the market

Key Takeaways

Cyber insurance was built from scratch, with 25 years of data now one of CFC's biggest advantages – even though the fast-changing nature of the class limits how much any historical data set can really tell you.

MGAs and carriers each carry different risks and rewards; being nimble matters most in a fast-evolving class like cyber.

The SME cyber protection gap comes down to education, not price – the best policies offer far more value than indemnity alone.

Cyber pricing has softened for three years following the 2021/22 correction, but a well-diversified portfolio matters given the ongoing ransomware and AI threat.

AI is a double-edged sword for cyber insurance, a growing attack vector, but also a powerful underwriting and defensive tool.

Curiosity and a willingness to ask questions is, in Scott's words, one of the most valuable traits an underwriter can have.

If you enjoyed this episode, be sure to subscribe to Beyond the Desk, leave a review and share it with someone in your network.

Connect with Sanj Vagad and Scott Bailey on LinkedIn to continue the conversation.

In this episode of Beyond the Desk: Underwriting Edition, Sanjeev Vegad sits down with Mark Fellows, Divisional Director, Financial Lines, International at Westfield Specialty, to explore a career that spans claims, underwriting, leadership, and multiple successful business builds across the London insurance market.

Mark shares how he accidentally fell into insurance after university, why a move to Swiss Re completely changed the trajectory of his career, and what he has learned from building underwriting platforms from scratch. He also offers a candid view on the current financial lines market, the rise of broker facilities, and the opportunities and risks that AI presents for the next generation of underwriters.

This episode is packed with practical leadership advice, insights into market cycles, and a reminder that deep expertise, curiosity, and strong relationships remain the foundations of great underwriting.

• How Mark went from claims into underwriting almost by accident
• Why he believes leadership is about responsibility, not hierarchy
• What he looks for when hiring underwriters and building high-performing teams
• The realities of launching and growing an underwriting business from zero
• How Westfield Specialty has positioned itself in a highly competitive market
• His perspective on the current soft market and the impact of broker facilities
• Why AI will transform insurance—but shouldn't replace human judgement
• The biggest mistake young underwriters can make in their early careers
• Why reading, asking questions, and being in the office still matter
• The career advice he wishes he had taken himself

• Build deep expertise before chasing seniority.
• Great underwriting teams are built around culture, trust, and collaboration.
• Differentiation comes from people, service, and execution.
• AI should enhance underwriting, not replace relationships and judgement.
• The best opportunities often come from being willing to build something new.

Whether you're an underwriting assistant, an experienced underwriter, or a leader looking to build the next successful platform, this conversation offers a thoughtful and practical look at what long-term success in insurance really looks like.