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CIO interview: Sasha Jory, Hastings Direct

Sasha Jory developed her IT leadership skills in a series of roles with blue-chip finance firms. She joined insurer Hastings Direct in 2019 and became CIO in January 2023. As a member of the company’s executive team, she reports to the chief executive and is responsible for technology strategy, delivery and operations.

“Hastings has provided me with a unique opportunity,” she says, reflecting on her time with the company. “I went in as chief digital and change director. And what that role offered me was the full end-to-end scope to manage and look after change across the business.”

Jory says that wide scope is unusual. Most of the companies she’s worked for split testing capabilities, business analysis and engineering. The cross-organisation nature of her digital leadership role meant she spent a lot of time managing stakeholders and negotiating with multiple parties to make things happen.

“The position spanned the whole gamut and I felt that was a structure I could use to make a big difference,” she says. “The structure meant we could focus on change, we could focus on efficiency, and we could make things happen really, really quickly.”

Jory says the ability to drive agile transformation is important because Hastings has a bold ambition to be the best and biggest digital insurer in the UK. As the company has grown, she says it has managed to hold onto its startup mentality.

“Our risk appetite for trying new things and being innovative is fantastic,” she says. “And so for somebody like me, Hastings provided an opportunity that just felt too good to pass by.”

Making decisions

As Jory began to exert her influence, so new openings emerged. In her first four years with Hastings, it became clear the organisation needed a clear focus on innovation to drive its digital agenda, and on customers to ensure they were at the heart of operational activity. That blended focus on innovation and customers had consequences for Jory.

“The decision was made to split the COO [operations] function into those two areas,” she says. “My colleague, Julie Taylor, became the chief customer and operations officer. And I became CIO, which meant I took on the data, CISO [security] and CTO [technology] worlds, and I kept going with the digital change world that I had previously managed.”

“You probably have to be slightly mad to love being in technology. It moves really quickly and it never switches off. You’re on 24/7/365, and have to be available and ready for whatever might occur. No two days are the same – and that’s possibly what I enjoy the most”
Sasha Jory, Hastings Direct

Almost a full year into the CIO role and Jory relishes her expanded position, despite the challenges it brings.

“You probably have to be slightly mad to love being in technology,” she says. “It moves really quickly and it never switches off. You’re on 24/7/365, and have to be available and ready for whatever might occur.”

However, Jory also recognises that the always-on nature of the CIO role means there’s a huge amount of workplace variety. “No two days are the same – and that’s possibly what I enjoy the most,” she says.

“I have a fantastic team. I love developing and growing them. And that’s critical, because technology changes so much that you need to invest in your people. It’s really important to show your people the opportunities and to help them grab them, because it can be quite scary to embrace change.”

One thing that remains true across all areas of Jory’s work is the persistent nature of transformation. Her team is responsible for delivering a lot of projects. As CIO, she gets to see all the initiatives, including those that are “red and stuck and broken”.

“You get to make lots of decisions to try to help people move things forward. We also do a lot of innovation. We have a lot of artificial intelligence [AI], which is the big thing everyone’s talking about. We’re also looking at automation and machine learning,” she says.

“This role gives me the opportunity to focus on people, on technology stability, on our service to our customers or our service to our colleagues, and then on innovation and how we keep up with what’s happening in the market.”

Driving change

While technological innovation can come in many forms, Jory says digital transformation for Hastings means being digital-centric above all else.

“We need to offer our customers the opportunity to transact with us in whichever manner they choose,” she says. “Whether they’re calling us or transacting with us via a digital channel, those journeys need to work – they need to be seamless and effortless for the customer.”

“We need to enable our people to be able to work in a digital way. We don’t want staff struggling to log in to multiple systems to find data in different places and then doing things in a slow, old-fashioned way”

Sasha Jory, Hastings Direct

Jory says effective digital transformation isn’t just about giving great services to external customers. Internal users need to be able to benefit from technology, too – especially if they’re going to be able to service customers in the best way possible.

“We need to enable our people to be able to work in a digital way,” she says. “We don’t want staff struggling to log in to multiple systems to find data in different places and then doing things in a slow, old-fashioned way. Success is about driving the right mentality internally and driving ourselves to be cloud-first, cloud-enabled and digital at the core.”

Significant progress has been made already. Jory says the journey she’s been on with her team at Hastings over the past four years has been “phenomenal”.

“We inherited a company that was pretty much on-premises and at the start of its journey on digital, where a lot of IT was outsourced to a third party,” she says.

“In that time, we’ve moved 100% to the cloud. We’ve migrated off all of our legacy technology, whether that’s our core platforms or data platforms. We’ve transformed our colleague experiences in terms of their desktop and their experience at work, and we’ve enabled them to be more digitally aware.”

Jory says her team has already brought in new capabilities around machine learning and automation, and is now looking at AI. “It’s been a great four years and we’ve driven a huge amount of change,” she says.

Consuming data

Of course, embracing digital transformation – and a whole new suite of systems and services – can be an expensive business. Going to the cloud brings flexibility to build IT on-demand, but it also comes with a new expenditure model. To allay some of these concerns, Jory says Hastings has a strategy to focus on “consuming healthy”.

“When you go to the cloud, it’s not the same as when you’re operating on-premises with a big infrastructure bill that you depreciate over multiple years, which usually involves known costs. When you go to the cloud, your costs can change quite dramatically because it’s all operating expenditure rather than capital spend,” she says.

Hastings, for example, doesn’t store any data on its legacy platforms and has moved 100% to Snowflake’s cloud-based data platform. Jory is running a proof-of-concept study with the open source framework Streamlit, and wants to embrace the Snowflake Marketplace, which brings third-party data directly into the insurer’s technology platform. The company continues to work closely with Snowflake to help its people consume data efficiently and effectively.

“If you don’t have control and understand how you’re consuming the cloud, you can get into trouble. The work we’ve done this year with Snowflake has been fantastic because we’ve had opportunities to look at how we’re running queries and using our warehouses,” she says.

“If you don’t have control and understand how you’re consuming the cloud, you can get into trouble. The work we’ve done this year with Snowflake has been fantastic because we’ve had opportunities to look at how we’re running queries and using our warehouses”
Sasha Jory, Hastings Direct

Jory’s team continues to work with Snowflake to consider some key data-consumption questions: “Are we using the right types of queries? Do we have queries that are non-performant? Are we writing queries in the most efficient way?” she says.

“We’ve been able to take 160 people in our pricing data and analytics community on that journey. And now we have a real culture of nurturing knowledge around costs as opposed to locking down and governing people. Our approach is about building a community of awareness and it’s really working.”

Embracing automation

Jory’s aim over the next 24 months is to use digitisation to give internal staff the same high-quality experiences as external customers.

Hastings employees use a system of record for key areas, such as policies, billing and claims. These systems are designed for call centre activity, which presents a challenge when most customers have instead interacted with the company via digital channels. Jory wants to bring all this insight together.

“What would be great is if we’re using the same digital journeys for our colleagues and our customers,” she says. “I think that would make the look and feel and the way of working modern and energised for our colleagues, and it would mean that the join-up between customers and colleagues is directly apparent.”

Jory is also keen to take advantage of emerging technology when opportunities arise. Rather than spending the IT budget on enterprise-wide services, such as large-scale robotic process automation, Jory and the Hastings board search for small-scale, tactical opportunities.

“That means bringing in AI where we need it and using automation to remove some of the more mundane tasks,” she says.

“We’ve done a lot of that activity in our technology operations world. And while initially people were probably a little bit afraid of what automation would mean, we’ve been able to demonstrate that the technology has enhanced their roles and given them opportunities.”

Jory expects to use more AI and machine learning in the future. Emerging technology, for example, could help to automate the checking and verification of photographic data from accidents. AI could be also used for fraud-detection processes. Hastings is working with Microsoft, EY and Snowflake to explore these opportunities.

“So far, we’ve been able to use AI to help people focus on more interesting work than the grunt work where you’re turning a handle, pushing a button and looking at a report,” she says. “Now, we’ve got machines doing that work for us. That transition has been great so far, and more of those benefits would be fantastic for our people.”

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