When David Jack was appointed Hyperion Insurance CIO at the end of 2013 he said he would be "developing an innovative and disruptive vision and driving fundamental change for one of the world's leading insurance businesses".

The former thetrainline.com CIO has been at Hyperion over a period during which the insurer has been growing a rate which made them at the start of 2015 twice the size the were the previous year, and with an upcoming merger with RK Holdings.

What the judges said

"He has the ear of the CEO and a narrative of what technology can enable the business to do and you can see he is genuinely outside in. I like the fact that he really has a single view of the customer. Yet he has no luxury of time because he has a demanding organisation." Ian Cohen

"He's a bold risk taker, but he is also getting things done." Jayne Nickalls

"He shows more vision that the rest of the sector and its submissions." Mike Altendorf

"He's done a lot of the IT change and that is great as he only started there in December 2013." Ian Cox

"The positioning of his submission and the CIO role is very good," Matt Ballantine

Job title
Group CIO.

When did you start your current role?
December 2013.

What is your reporting line?
Group CEO.

Do you meet with and discuss business strategy with the CEO every week?
We have weekly one-to-ones, I also meet with the individual CEOs of the various operating businesses in the UK and around the world. Obviously not every meeting is about business strategy – there is often way more mundane stuff to talk about. But it does give me the opportunity to spot the shifts and what is urgent versus important. I have also made the point of hosting our technical boards from some of our other offices around the world – immersing myself in the local strategies and challenges. I also spend significant time with our private equity backers to ensure that their views on both strategy and vision match where we are taking things.

Are you a member of the board of directors?

What other executive boards do you sit on?
The executive board is made up of the group CEO, CFO, HRD, head of legal, CEOs of the broking and underwriting businesses and myself.

Does your organisation have a CDO?
No. By default I play the role of the CDO, with focus on delivering, enhancing and exploiting three things:

• Single view of the customer. 
• Single view of the product (range). 
• Single view of our (worldwide) workforce.

Additionally I am responsible for building and enhancing cyber/data security across our global organisation while delivering raw content, mapping and insight on a hugely complex business operation, customer and product portfolio.

What non-technology responsibilities do you have in the organisation?
I was hired to support organisational, operational and commercial transformation; a significant portion of this is not a technology activity (that's arguably the easy bit). I work hand in hand with the other key transformation agent (our group HR director) to build a common understanding and articulation of our purpose, values and (commercial) strategy, and develop the environment (and structures) so that we can fund, plan, monitor, deliver and evaluate the results. In the last year this has meant that I have:

• Established, funded and executed the first deliverables of a transformation programme. 
• Built a group-wide PMO function (not just for technology projects).
• Established a number of global forums for change and decision-making (especially for CRM, ECM, data and trading platforms).

Additionally, due to my previous roles (rightly or wrongly!) I am considered to be the authority on e-commerce and m-commerce, not just from the perspective of the technology platform but also what good looks like from an SEO, PPC and general online marketing perspective. I am here to transform the provision, delivery and support of commercial insurance products.

Rather more informally I am working with the various COOs on developing a sales and customer-centric proposition – something that is familiar to retailers but less so for high-margin, high-inertia markets. This is as much to do with organisation and culture as it is tech and systems.

How many employees does your organisation have?
With our latest acquisition, over 2,500 across more than 80 offices in over 33 countries.

Does your organisation carry out significant trade in the EU?

What number of users does your department supply services to?
All staff worldwide (2,500+), with a variety of services ranging from the simple (email, Citrix, networking) to the more challenging and complex (deliver new trading platforms, CRM ,ECM, security, etc).

How do you ensure that you have a good understanding of your business and how your customers use your business's products?
From the inside out:

Organisationally. At a macro level, we are organised around a global, federated, highly devolved operation. I specifically want local technical resources to work with local business teams. Additionally we take further steps to specifically embed technical resources into operational and commercial teams - they are the eyes and ears of the extended technology function. This is especially important for the evolution of our trading platforms (of which we have a significant number).

OperationallyTwo of the most significant deliverables during 2014 were our enterprise data warehouse and a new financial consolidation system (including FP&A). We are putting the details on our sales/product performance on the desktop (and tablet) of every relevant person in the organisation. This is not only trading data (how much we sell, renew, etc) but also managing the KPIs of how the policies are performing, claims made, etc. The bottom line is that the simplest way of understanding our business is simply delivering data in a trusted, relevant and accessible way.

SamplingOf course it is also super interesting to sample performance by the informal 1:1s with our “customers” – some of whom are essentially suppliers (the insurers) and some are partners (retail brokers) and some are end customers (e.g. an insured corporation)

At a micro level:

I am the technical monkey for my CEOs, COOs and boards. I don’t mind fixing a printer or being complained at about stuff. So much of the real trading issues are expressed in the informal moments when you are under a desk. I also attend some of the boards of my operational CEOs around the world, especially when they are focusing on product performance.

From the outside in:

I have built a network of like-minded insurance innovators over the last year who I am indebted to and have learnt a huge amount from. This community is a great source of what 'good looks like' and allows me to challenge the status quo with reference to real-life examples of better delivery, better products and better customer service.

Hyperion Insurance technology strategy and IT agenda

Is your organisation being disrupted by the internet, mobility or technology-oriented start-ups?

Are you empowered by your organisation to disrupt from the inside?

Describe a disruptive measure you’ve led or played a major part in
Simply hiring a group CIO can be seen as hugely disruptive, challenging the federated and siloed technical organisations around the world to collaborate, adapt and innovate. In the past year we have executed a significant number of disruptive and transformational measures around the world, ranging from the banal/simple (implementing a group-wide PMO) to the more exciting delivery of ECM to every member of staff (for the first time linking every member of our staff with mail, P2P video, chat and micro-blogging) and to the transformational aggregation and delivery of the data and insight of all our UK market trading systems.

What major transformation project has been recently completed or is under way at your organisation?
In the past year the HR director and I have evaluated the key presenting issues, formed the team and established a programme named 'One Company Two Brands' (We have an underwriting business called Dual and a broking business called Howden). Obviously the pithy title wasn’t accidental - we were programming our businesses to keep their individuality and levels of entrepreneurial behaviours with an overlay of collaboration and optimisation.

I joined in December 2013. We established the various themes and needs within three months, received board approval on the level of spend and started simply delivering. From a tech perspective, many of the deliverables were designed specifically to obscure the architectural blueprint that we had devised – every project was treated atomically and was sold on value rather than an esoteric future reference platform. In the background, however, we have built a converging coherent global architecture that will support numerous additional innovations.

The programme streams were:

Establish a global shared services structure.
Provide common, global and accessible platforms and tools.
Reduce the operational debt.
Single view of all operational and commercial data.
Build an even better M&A machine.
Invest and support an evolution in culture and leadership.

The resulting projects collectively reflect the rapid shift from local to global, slow to fast, and tactical to strategic (reusable platforms) with data – human, product and customers at the heart of every activity. All the projects were achieved by a tiny group function, modest investment and in an environment of significant inertia.

What impact will the above transformation have on your organisation?
Simply, consolidation (of activity/data and process), collaboration and insight. We have lowered risk, enabled faster acquisition of new business and provided transparency of operational and commercial data. We have also deployed a reference platform, with Salesforce, Anaplan, Microsoft Analytics (with Workday following), that enables huge levels of future collaboration, innovation and problem solving. The organisation is also now beginning to believe that if they ask for something then the technical function will deliver it.

How has your leadership style contributed to the outcomes of the transformation project?
I think I like ambiguity. I am certainly prepared to take huge risks and I seem to be able to wave my arms around convincingly enough that people buy in and follow. But I think that the critical aspect of my style (if I have such a thing) is the inability to wait to work out all the details or get approval! I’m happy to know that if I do the right things, then I’m doing my job; and if I don’t, I lose my job.

What key technologies do you consider enable transformation?

• Salesforce (including communities)
• Microsoft Analytics
• Workday
• Anaplan

Are you expanding the number of cloud applications or infrastructure in use at your organisation?

What is your information and data analytics vision for the organisation?
Simply to over-deliver data and insight. For instance, I haven’t attempted to optimise the ETL of legacy systems into Salesforce or into the EDW. I have knowingly encouraged duplication of effort to create tension and competition. I don’t lose points for delivering too much.

Additionally, to have no fear about the commercial and operational insights that I bring.

And lastly, we will review and revise everything we do on data every quarter and will continue to revise, reinvent and re-implement if we think we can do better.

How is mobile and social networking impacting operations and customer experience?
Our vision is simply mobile first for platform delivery, and with Salesforce communities we have brought the model of social networking to the day-to-day experience of all our staff.

As we grow our direct to consumer businesses we assume that more and more of our sales channel will be driven via social sites, and to maintain a high NPS score we expect much of our customer interaction will be via the same sites.

Describe your strategic vision towards shadow IT and BYOD. How do you influence and engage executives and employees around choice?
We have led from the top. As a highly regulated industry we have focused on opening up the systems to BYOD in a controlled and highly secure manner. All of our reference systems (Salesforce, Dundas, Workday) assume BYOD as the primary client.

What strategic technology deals have been struck and with whom?
• Microsoft
• Salesforce
• Anaplan
• Workday (soon) 

Who are your main suppliers?
Discounting the trading platform suppliers:
• Citrix
• Microsoft
• Salesforce
• Anaplan
• Workday (imminently)

Globally, we have a massive tail of other main suppliers.

Hyperion Insurance IT security and budget

Has your organisation detected a cyber intrusion in the last 12 months?

Has cyber-security risen up your management agenda?

Does your organisation understand the potential cyber-security threats it faces?

Has this led to an increase in your security budget?

What is the IT budget?
Globally in excess of £10m. Due to the sensitivity of a current £400m acquisition, I cannot give any more detail of this.

How much is the IT operational spend compared to the revenue as a percentage?

What is the strategic aim of the CIO and IT operations for the next financial year?
With the pending acquisition (and a couple of others in the pipe) we will grow by almost 1,000 people within a couple of months. My focus is to make this transformational deal work perfectly, merge the two technical operations from day 1 and exploit the economies of scale and talent that I will have. This will be done in parallel, and will supercharge our fundamental technical strategy.

Overall, the aim is to enable our uniquely entrepreneurial global organisation to solve the hardest insurance challenges for our customers, exploiting a simple, data and sales-centric culture.

We will have:

One view of the customer. We will know more about who we sell to. We will share every contact, every trade, every win, every loss.

One view of the product (range). We will have the best solution for our customer, and we will share every product, every variation, every innovation.

One view of our (worldwide) workforce. We will manage and develop our people with insight: every employee, every deal, recognising today’s stars and developing others for the future.

Uniquely, we have not started out with Salesforce for CRM, we have established it as a common application and data management framework alongside Anaplan (and shortly Workday). We have then used Salesforce communities and line of business applications (like training and risk systems) to get Salesforce onto every desktop, and then rolled out specific prospecting, CRM or full trading systems to the early adopters. Further exploitation of Salesforce, Anaplan and Workday will continue this year.

Now we have spent a year putting many of the architectural foundations in place, it’s time to move even faster, innovating and disrupting within the global organisation, showing what a small team can do with good tools and ambition. 

Specifically, we will over-deliver on data and insight, and continue bringing all trading platforms, line of business apps and enterprise systems together into the enterprise warehouse. In parallel, we will continue to expose insight through Salesforce communities and enable Salesforce to manage and expose live customer data for our legacy systems. This year will also see further exploitation of our Anaplan infrastructure, capturing and consolidating finer-grained global financial data, reducing the gap between financial and operational data, and removing the need to deploy a common global general ledger system.

This will all be done while materially improving our data security on a global scale and ensuring that data residency is strictly adhered to (especially sensitive in our cloud solutions).

We will also aim for trading platform convergence, actively encouraging 'natural selection' to decommission old systems and extend prospecting and CRM deployments made this year into full (Salesforce) trading applications.

Our consumer-facing websites will begin their technical convergence and be brought in line visually with the house look and feel of our new corporate websites.

There will also be one view of the employee. We will bring together every worldwide entity with a common set of tools while not losing what makes our unique federation of highly motivated, entrepreneurial businesses feel special. This is not just a management activity. We want every member of the family to be able to find, engage and collaborate with anyone, anywhere at any time. Workday plus Salesforce communities over-delivers these capabilities.

At an organisational level, we will grow very modestly and continue to strengthen our global federation of technology teams.

Are you finding it difficult to recruit the talent you need to drive transformation?

Has recruitment and retention risen up your agenda as a CIO?

Are you looking for recruits in the EU to fill the skills shortage you have?

Does your IT organisation operate an apprenticeship scheme?

Hyperion technology department

How would you describe your leadership style?
I would love people to think that I am courageous, impatient and charismatic with endless energy and resolve. In reality I think I move fast because I get bored with planning. I run between meetings because I talk too much and spend much of my time unsure what the right course of action is!

So style-wise, I think that I can be bold, sell a vision, and inject energy and passion, but my team and my board recognise that I need help. As a team we are definitely more than the sum of the parts. I'm a compelling but flawed leader, happy to stand up and try things without knowing whether they are the right answer and need a strong, detail-orientated team to deliver.

Explain how you’ve supported and developed your senior leadership team to support your overall objectives and vision
Fit. I've shown that I'm happy to move people out of jobs they can't do, move people into jobs that they have no experience of (but I'm sure that they can do), and overwork people rather than use bad people. I've hired the best people I could afford (showing the team what good looks like).

StretchEvery member of my nascent management team is doing things that they have no background in. They have more to do than they can possibly deliver. And they are working at a level of ambiguity and uncertainty that they have never experienced before.

Immersion. I've involved the team in every step of the evolving strategy and transformation programme. Even though our transformation programme is a business-wide initiative and isn’t just tech, it was founded by the technical teams, led by me (and our HR director) and is hugely influencing the strategy of the business. 

DeliveryEvery member of the team delivered hugely last year. They delivered more in one year than this business has ever seen and they were intimate with the strategic context – because they were instrumental in driving it!

Going forwardWe will change everything - new responsibilities, new scope, new job titles, and keep moving the goalposts.

How many employees are in your IT team?
Reporting to me and my directors - 80 in the UK/Singapore/US (including acquisition team).

What is the split between in-house/outsourced staff?
Overall, I retained much of our group operations in-house with local hires in regional offices to gain 24/7 and cost arbitrage. There are, however, a significant number of outsourced technical staff, especially in our global operations and development teams. I would estimate 50 to 100 worldwide.

Does your team include key skilled workers from the EU?